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0 Td 47.115385 Tz (specification ) Tj 3.888889 0 Td 49.691358 Tz (are ) Tj 1.069444 0 Td 55.632716 Tz (hereby ) Tj 51.428571 0 0 51.428571 0 1488.251557 Tm 6.358333 0 Td 51.041667 Tz (incorporated ) Tj 3.927778 0 Td 59.953704 Tz (by ) Tj 0.991667 0 Td 47.962963 Tz (reference. ) Tj 3.111111 0 Td 51.527778 Tz (Autotaxin, ) Tj 3.363889 0 Td 47.800926 Tz (also ) Tj 1.4 0 Td 66.111111 Tz (known ) Tj 2.255556 0 Td 46.990741 Tz (as ) Tj 0.836111 0 Td 64.814815 Tz (ATX, ) Tj 51.428571 0 0 51.428571 0 1447.423952 Tm 6.358333 0 Td 71.296296 Tz (ENPP2 ) Tj 2.352778 0 Td 51.851852 Tz (or ) Tj 0.836111 0 Td 62.222222 Tz (NPP2, ) Tj 2.1 0 Td 48.611111 Tz (short ) Tj 1.652778 0 Td 48.611111 Tz (for ) Tj 1.088889 0 Td 51.851852 Tz (Ectonucleotide ) Tj 4.530556 0 Td 54.660494 Tz (pyrophosphatase ) Tj 51.428571 0 0 51.428571 0 1406.746714 Tm 6.358333 0 Td 52.423747 Tz (phosphodiesterase ) Tj 5.483333 0 Td 58.333333 Tz (2 ) Tj 0.525 0 Td 38.888889 Tz (is ) Tj 0.641667 0 Td 55.092593 Tz (an ) Tj 0.836111 0 Td 63.194444 Tz (enzyme ) Tj 2.411111 0 Td 49.826389 Tz (secreted ) Tj 2.547222 0 Td 50.771605 Tz (within ) Tj 2.002778 0 Td 50.771605 Tz (the ) Tj 1.011111 0 Td 68.055556 Tz (human ) Tj 51.428571 0 0 51.428571 0 1364.610785 Tm 6.338889 0 Td 53.148148 Tz (body. ) Tj 1.711111 0 Td 53.472222 Tz (This ) Tj 1.419444 0 Td 55.092593 Tz (molecule ) Tj 2.761111 0 Td 52.932099 Tz (has ) Tj 1.069444 0 Td 57.523148 Tz (been ) Tj 1.477778 0 Td 66.111111 Tz (known ) Tj 2.1 0 Td 47.530864 Tz (for ) Tj 0.933333 0 Td 51.203704 Tz (generating ) Tj 3.188889 0 Td 58.738426 Tz (lysophos ) Tj 51.428571 0 0 51.428571 0 1324.64455 Tm 6.358333 0 Td 48.611111 Tz (phatidic ) Tj 2.527778 0 Td 51.041667 Tz (acid ) Tj 1.4 0 Td 60.277778 Tz (\(LPA\) ) Tj 1.983333 0 Td 53.703704 Tz (through ) Tj 2.430556 0 Td 52.5 Tz (conversion ) Tj 3.344444 0 Td 58.333333 Tz (of ) Tj 0.836111 0 Td 51.446759 Tz (lysophosphatidyl ) Tj 51.428571 0 0 51.428571 0 1281.752126 Tm 6.358333 0 Td 51.388889 Tz (choline ) Tj 2.352778 0 Td 60.925926 Tz (\(LPC\) ) Tj 2.002778 0 Td 48.148148 Tz (thereto ) Tj 2.255556 0 Td 47.530864 Tz (via ) Tj 1.069444 0 Td 52.614379 Tz (lysophospholipase ) Tj 5.580556 0 Td 84.259259 Tz (D ) Tj 0.719444 0 Td 44.560185 Tz (activity ) Tj 2.372222 0 Td 46.990741 Tz (\(the ) Tj 51.428571 0 0 51.428571 0 1239.866667 Tm 6.358333 0 Td 56.018519 Tz (removal ) Tj 2.488889 0 Td 58.333333 Tz (of ) Tj 0.777778 0 Td 51.388889 Tz (choline ) Tj 2.313889 0 Td 57.523148 Tz (from ) Tj 1.575 0 Td 48.611111 Tz (the ) Tj 0.991667 0 Td 55.092593 Tz (base ) Tj 1.438889 0 Td 64.814815 Tz (compound ) Tj 3.247222 0 Td 50.771605 Tz (generates ) Tj 2.916667 0 Td 56.388889 Tz (LPA\). ) Tj 51.428571 0 0 51.428571 0 1196.177083 Tm 6.377778 0 Td 71.296296 Tz (LPA ) Tj 1.536111 0 Td 55.092593 Tz (has ) Tj 1.244444 0 Td 57.523148 Tz (been ) Tj 1.711111 0 Td 46.990741 Tz (realized ) Tj 2.527778 0 Td 45.37037 Tz (to ) Tj 0.816667 0 Td 49.259259 Tz (contribute ) Tj 3.247222 0 Td 43.75 Tz (to ) Tj 0.836111 0 Td 58.333333 Tz (tumor ) Tj 1.963889 0 Td 43.75 Tz (cell ) Tj 1.341667 0 Td 52.314815 Tz (growth, ) Tj 51.428571 0 0 51.428571 0 1158.019002 Tm 6.338889 0 Td 48.37963 Tz (unfortunately, ) Tj 4.2 0 Td 48.611111 Tz (as ) Tj 0.738889 0 Td 48.611111 Tz (the ) Tj 1.011111 0 Td 45.046296 Tz (reactivity ) Tj 2.838889 0 Td 51.311728 Tz (within ) Tj 1.963889 0 Td 50.771605 Tz (the ) Tj 1.030556 0 Td 65.462963 Tz (human ) Tj 2.080556 0 Td 60.763889 Tz (body ) Tj 1.594444 0 Td 55.092593 Tz (of ) Tj 0.738889 0 Td 72.376543 Tz (LPA ) Tj 48.571429 0 0 48.571429 0 1114 Tm 6.711765 0 Td 54.901961 Tz (within ) Tj 2.182353 0 Td 49.509804 Tz (certain ) Tj 2.285294 0 Td 48.529412 Tz (tissues ) Tj 2.244118 0 Td 57.189542 Tz (has ) Tj 1.214706 0 Td 48.801743 Tz (resulted, ) Tj 2.820588 0 Td 49.754902 Tz (in ) Tj 0.802941 0 Td 49.509804 Tz (certain ) Tj 2.285294 0 Td 48.468137 Tz (studies, ) Tj 2.532353 0 Td 58.333333 Tz (of ) Tj 0.802941 0 Td 74.346405 Tz (can ) Tj 51.428571 0 0 51.428571 0 1072.2142 Tm 6.358333 0 Td 52.391975 Tz (cerous ) Tj 2.022222 0 Td 55.555556 Tz (growths ) Tj 2.488889 0 Td 64.814815 Tz (when ) Tj 1.672222 0 Td 50.925926 Tz (present ) Tj 2.255556 0 Td 45.37037 Tz (at ) Tj 0.661111 0 Td 46.759259 Tz (certain ) Tj 2.119444 0 Td 43.518519 Tz (levels. ) Tj 2.022222 0 Td 46.990741 Tz (In ) Tj 0.7 0 Td 43.75 Tz (this ) Tj 1.205556 0 Td 54.62963 Tz (manner, ) Tj 51.428571 0 0 51.428571 0 1030.063291 Tm 6.338889 0 Td 48.611111 Tz (then, ) Tj 1.691667 0 Td 34.027778 Tz (it ) Tj 0.602778 0 Td 55.092593 Tz (has ) Tj 1.225 0 Td 56.712963 Tz (been ) Tj 1.613889 0 Td 50.05144 Tz (theorized ) Tj 2.916667 0 Td 46.180556 Tz (that ) Tj 1.341667 0 Td 48.611111 Tz (the ) Tj 1.108333 0 Td 48.611111 Tz (greater ) Tj 2.236111 0 Td 50.771605 Tz (the ) Tj 1.127778 0 Td 51.851852 Tz (incidence ) Tj 3.013889 0 Td 58.333333 Tz (of ) Tj 51.428571 0 0 51.428571 0 990.07772 Tm 6.358333 0 Td 50.05144 Tz (autotaxin ) Tj 3.013889 0 Td 44.965278 Tz (activity ) Tj 2.469444 0 Td 51.311728 Tz (within ) Tj 2.177778 0 Td 49.691358 Tz (the ) Tj 1.186111 0 Td 66.111111 Tz (human ) Tj 2.294444 0 Td 52.5 Tz (body, ) Tj 1.886111 0 Td 50.771605 Tz (the ) Tj 1.225 0 Td 48.611111 Tz (greater ) Tj 2.333333 0 Td 49.691358 Tz (the ) Tj 51.428571 0 0 51.428571 0 950.542459 Tm 6.358333 0 Td 45.664983 Tz (possibility ) Tj 3.286111 0 Td 59.953704 Tz (of ) Tj 0.894444 0 Td 72.376543 Tz (LPA ) Tj 1.555556 0 Td 48.905724 Tz (generation. ) Tj 3.5 0 Td 84.259259 Tz (A ) Tj 0.797222 0 Td 49.691358 Tz (reduction ) Tj 3.013889 0 Td 43.75 Tz (in ) Tj 0.797222 0 Td 49.691358 Tz (the ) Tj 1.147222 0 Td 45.730453 Tz (catalytic ) Tj 51.428571 0 0 51.428571 0 905.638554 Tm 6.358333 0 Td 45.910494 Tz (capabilities ) Tj 3.441667 0 Td 58.333333 Tz (of ) Tj 0.777778 0 Td 50.05144 Tz (autotaxin ) Tj 2.858333 0 Td 46.990741 Tz (to ) Tj 0.719444 0 Td 51.388889 Tz (convert ) Tj 2.294444 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 72.376543 Tz (LPC ) Tj 1.477778 0 Td 55.497685 Tz (molecule ) Tj 2.8 0 Td 46.990741 Tz (to ) Tj 0.758333 0 Td 71.296296 Tz (LPA ) Tj 51.428571 0 0 51.428571 0 866.97136 Tm 6.338889 0 Td 61.574074 Tz (would ) Tj 2.002778 0 Td 46.367521 Tz (theoretically ) Tj 3.791667 0 Td 54.012346 Tz (permit ) Tj 2.080556 0 Td 58.333333 Tz (an ) Tj 0.894444 0 Td 49.421296 Tz (ultimate ) Tj 2.566667 0 Td 50.411523 Tz (reduction ) Tj 2.897222 0 Td 46.990741 Tz (in ) Tj 0.719444 0 Td 52.662037 Tz (possibil ) Tj 51.428571 0 0 51.428571 0 824.990385 Tm 6.358333 0 Td 42.12963 Tz (ity ) Tj 0.913889 0 Td 58.333333 Tz (of ) Tj 0.777778 0 Td 58.738426 Tz (unwanted ) Tj 2.975 0 Td 43.75 Tz (cell ) Tj 1.205556 0 Td 46.616809 Tz (proliferation ) Tj 3.811111 0 Td 53.240741 Tz (through ) Tj 2.430556 0 Td 54.166667 Tz (reduced ) Tj 2.469444 0 Td 70.216049 Tz (LPA ) Tj 1.438889 0 Td 59.953704 Tz (pres ) Tj 51.428571 0 0 51.428571 0 783.335878 Tm 6.358333 0 Td 55.902778 Tz (ence ) Tj 1.516667 0 Td 51.311728 Tz (within ) Tj 2.041667 0 Td 51.851852 Tz (a ) Tj 0.505556 0 Td 47.530864 Tz (subjects ) Tj 2.761111 0 Td 52.5 Tz (body. ) Tj 51.428571 0 0 51.428571 0 727.601467 Tm 7.097222 0 Td 62.654321 Tz (The ) Tj 1.263889 0 Td 60.853909 Tz (mechanism ) Tj 3.422222 0 Td 55.092593 Tz (of ) Tj 0.738889 0 Td 50.05144 Tz (autotaxin ) Tj 2.838889 0 Td 55.092593 Tz (interms ) Tj 2.45 0 Td 53.472222 Tz (of ) Tj 0.719444 0 Td 55.452675 Tz (enzymatic ) Tj 3.130556 0 Td 45.37037 Tz (activity ) Tj 51.428571 0 0 51.428571 0 688.091371 Tm 6.358333 0 Td 58.333333 Tz (and ) Tj 1.302778 0 Td 46.090535 Tz (catalysis ) Tj 2.761111 0 Td 43.75 Tz (to ) Tj 0.816667 0 Td 58.333333 Tz (form ) Tj 1.711111 0 Td 70.216049 Tz (LPA ) Tj 1.516667 0 Td 48.148148 Tz (resides ) Tj 2.275 0 Td 45.37037 Tz (in ) Tj 0.816667 0 Td 37.808642 Tz (its ) Tj 0.933333 0 Td 52.423747 Tz (phosphodiesterase ) Tj 51.428571 0 0 51.428571 0 646.394366 Tm 6.358333 0 Td 45.075758 Tz (capability. ) Tj 3.286111 0 Td 71.296296 Tz (LPA ) Tj 1.536111 0 Td 56.17284 Tz (can ) Tj 1.283333 0 Td 56.712963 Tz (be ) Tj 0.933333 0 Td 52.572016 Tz (generated ) Tj 3.111111 0 Td 56.712963 Tz (from ) Tj 1.652778 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 52.662037 Tz (cleavage ) Tj 2.780556 0 Td 59.953704 Tz (of ) Tj 0.875 0 Td 49.691358 Tz (the ) Tj 51.428571 0 0 51.428571 0 603.282667 Tm 6.358333 0 Td 53.347578 Tz (phophodiester ) Tj 4.394444 0 Td 58.333333 Tz (bonds ) Tj 2.041667 0 Td 59.953704 Tz (of ) Tj 0.952778 0 Td 61.574074 Tz (LPC, ) Tj 1.788889 0 Td 48.611111 Tz (as ) Tj 0.894444 0 Td 51.041667 Tz (well ) Tj 1.536111 0 Td 51.851852 Tz (as ) Tj 0.933333 0 Td 37.808642 Tz (its ) Tj 0.972222 0 Td 50.231481 Tz (function ) Tj 2.702778 0 Td 51.851852 Tz (as ) Tj 0.933333 0 Td 55.092593 Tz (a ) Tj 51.428571 0 0 51.428571 0 564.209302 Tm 6.358333 0 Td 53.596866 Tz (phospholipase ) Tj 4.375 0 Td 84.259259 Tz (D ) Tj 0.680556 0 Td 63.194444 Tz (enzyme ) Tj 2.45 0 Td 46.450617 Tz (\(as ) Tj 1.011111 0 Td 51.851852 Tz (presented ) Tj 2.975 0 Td 46.990741 Tz (in ) Tj 0.777778 0 Td 57.87037 Tz (Formula ) Tj 2.625 0 Td 34.567901 Tz (I\): ) Tj 30 0 0 30 0 2547 Tm 41.666667 0 Td 75 Tz (10 ) Tj 30 0 0 30 0 2339 Tm 41.666667 0 Td 72.222222 Tz (15 ) Tj 30 0 0 30 0 1923 Tm 41.6 0 Td 77.777778 Tz (25 ) Tj 30 0 0 30 0 1716 Tm 41.6 0 Td 80.555556 Tz (30 ) Tj 30 0 0 30 0 1507 Tm 41.6 0 Td 77.777778 Tz (35 ) Tj 30 0 0 30 0 1299 Tm 41.566667 0 Td 83.333333 Tz (40 ) Tj 30 0 0 30 0 1091 Tm 41.566667 0 Td 80.555556 Tz (45 ) Tj 30 0 0 30 0 883 Tm 41.6 0 Td 80.555556 Tz (50 ) Tj 30 0 0 30 0 675 Tm 41.6 0 Td 77.777778 Tz (55 ) Tj 30 0 0 30 0 467 Tm 41.633333 0 Td 77.777778 Tz (60 ) Tj 30 0 0 30 0 259 Tm 41.633333 0 Td 75 Tz (65 ) Tj 51.428571 0 0 51.428571 0 2969 Tm 33.775 0 Td 74.537037 Tz (2 ) Tj 40 0 0 40 0 2913 Tm 41.825 0 Td 66.666667 Tz (-continued ) Tj 37.142857 0 0 37.142857 0 2880.625 Tm 40.330769 0 Td 94.230769 Tz (O ) Tj 4.9 0 Td 96.474359 Tz (OH ) Tj 45.238095 0 0 45.238095 0 2837.243902 Tm 33.202105 0 Td 47.894737 Tz (| ) Tj 4.023158 0 Td 40.526316 Tz (s ) Tj 8.532632 0 Td 31.315789 Tz (-- ) Tj 65.714286 0 0 65.714286 0 2783.171429 Tm 21.471739 0 Td 102.971014 Tz (Ho--os-N-0 ) Tj 7.623913 0 Td 35.507246 Tz (C17H33 ) Tj 31.428571 0 0 31.428571 0 2752 Tm 47.663636 0 Td 111.363636 Tz (OH ) Tj 31.428571 0 0 31.428571 0 2719 Tm 58.990909 0 Td 111.363636 Tz (O ) Tj 31.428571 0 0 31.428571 0 2679 Tm 53.390909 0 Td 93.686869 Tz (LPA ) Tj 31.428571 0 0 31.428571 0 2638 Tm 68.536364 0 Td 111.363636 Tz (OH ) Tj 75.714286 0 0 75.714286 0 2557 Tm 25.503774 0 Td 88.050314 Tz (1 ) Tj 0.898113 0 Td 61.63522 Tz (\\ ) Tj 31.428571 0 0 31.428571 0 2501 Tm 64.336364 0 Td 64.393939 Tz (choline ) Tj 51.428571 0 0 51.428571 0 2385.75153 Tm 25.316667 0 Td 46.990741 Tz (In ) Tj 0.816667 0 Td 46.866097 Tz (extracellular ) Tj 3.830556 0 Td 43.055556 Tz (fluids, ) Tj 2.022222 0 Td 43.75 Tz (this ) Tj 1.283333 0 Td 55.092593 Tz (enzymatic ) Tj 3.208333 0 Td 46.090535 Tz (catalysis ) Tj 2.722222 0 Td 58.333333 Tz (removes ) Tj 2.683333 0 Td 49.691358 Tz (the ) Tj 51.428571 0 0 51.428571 0 2342.221411 Tm 25.297222 0 Td 51.388889 Tz (choline ) Tj 2.294444 0 Td 56.388889 Tz (group ) Tj 1.866667 0 Td 57.523148 Tz (from ) Tj 1.594444 0 Td 61.574074 Tz (LPC, ) Tj 1.633333 0 Td 50.925926 Tz (leaving ) Tj 2.313889 0 Td 59.953704 Tz (LPA, ) Tj 1.613889 0 Td 58.981481 Tz (which ) Tj 1.905556 0 Td 55.092593 Tz (has ) Tj 1.127778 0 Td 55.092593 Tz (a ) Tj 0.505556 0 Td 54.282407 Tz (tendency ) Tj 51.428571 0 0 51.428571 0 2298.869779 Tm 25.277778 0 Td 46.990741 Tz (to ) Tj 0.758333 0 Td 49.691358 Tz (stimulate ) Tj 2.858333 0 Td 42.939815 Tz (cell ) Tj 1.225 0 Td 56.17284 Tz (growth ) Tj 2.197222 0 Td 59.41358 Tz (and ) Tj 1.225 0 Td 46.866097 Tz (proliferation ) Tj 3.830556 0 Td 50.231481 Tz (as ) Tj 0.816667 0 Td 51.041667 Tz (well ) Tj 1.4 0 Td 50.231481 Tz (as ) Tj 0.797222 0 Td 65.895062 Tz (chemot ) Tj 51.428571 0 0 51.428571 0 2254.360153 Tm 25.297222 0 Td 44.074074 Tz (axis. ) Tj 1.594444 0 Td 63.194444 Tz (From ) Tj 1.75 0 Td 40.833333 Tz (this, ) Tj 1.438889 0 Td 34.027778 Tz (it ) Tj 0.583333 0 Td 52.777778 Tz (appears ) Tj 2.45 0 Td 45.37037 Tz (that ) Tj 1.283333 0 Td 49.691358 Tz (the ) Tj 1.108333 0 Td 47.395833 Tz (motility ) Tj 2.488889 0 Td 59.953704 Tz (of ) Tj 0.797222 0 Td 58.981481 Tz (tumor ) Tj 1.944444 0 Td 44.074074 Tz (cells ) Tj 1.555556 0 Td 38.888889 Tz (is ) Tj 51.428571 0 0 51.428571 0 2212.874109 Tm 25.297222 0 Td 50.771605 Tz (increased ) Tj 2.858333 0 Td 51.851852 Tz (as ) Tj 0.777778 0 Td 47.314815 Tz (well, ) Tj 1.575 0 Td 46.8107 Tz (resulting ) Tj 2.702778 0 Td 45.37037 Tz (in ) Tj 0.680556 0 Td 48.611111 Tz (properties ) Tj 3.052778 0 Td 59.41358 Tz (and ) Tj 1.186111 0 Td 58.333333 Tz (gene ) Tj 1.516667 0 Td 52.175926 Tz (expression ) Tj 51.428571 0 0 51.428571 0 2165 Tm 25.277778 0 Td 51.851852 Tz (within ) Tj 2.158333 0 Td 46.296296 Tz (certain ) Tj 2.216667 0 Td 51.388889 Tz (cancers ) Tj 2.430556 0 Td 51.851852 Tz (\(such ) Tj 1.808333 0 Td 44.290123 Tz (as, ) Tj 1.05 0 Td 49.691358 Tz (for ) Tj 1.127778 0 Td 47.170782 Tz (instance, ) Tj 2.780556 0 Td 49.151235 Tz (breast ) Tj 2.041667 0 Td 52.932099 Tz (cancer ) Tj 51.428571 0 0 51.428571 0 2123.637681 Tm 25.297222 0 Td 41.666667 Tz (cells\), ) Tj 1.925 0 Td 52.314815 Tz (causing ) Tj 2.372222 0 Td 47.222222 Tz (further ) Tj 2.1 0 Td 51.851852 Tz (processing ) Tj 3.247222 0 Td 46.990741 Tz (into ) Tj 1.263889 0 Td 58.333333 Tz (a ) Tj 0.505556 0 Td 57.523148 Tz (form ) Tj 1.536111 0 Td 45.37037 Tz (that ) Tj 1.263889 0 Td 38.888889 Tz (is ) Tj 0.622222 0 Td 48.971193 Tz (bioactive ) Tj 51.428571 0 0 51.428571 0 2083.001245 Tm 25.297222 0 Td 58.333333 Tz (and ) Tj 1.361111 0 Td 46.843434 Tz (potentially ) Tj 3.441667 0 Td 51.851852 Tz (dangerous. ) Tj 3.461111 0 Td 50.87963 Tz (Metastasis ) Tj 3.363889 0 Td 59.41358 Tz (and ) Tj 1.361111 0 Td 53.914141 Tz (oncogenesis ) Tj 3.888889 0 Td 56.712963 Tz (of ) Tj 51.428571 0 0 51.428571 0 2037.024081 Tm 25.297222 0 Td 53.472222 Tz (cancer ) Tj 2.119444 0 Td 44.074074 Tz (cells ) Tj 1.575 0 Td 54.552469 Tz (appear ) Tj 2.177778 0 Td 46.990741 Tz (to ) Tj 0.758333 0 Td 55.740741 Tz (occur ) Tj 1.847222 0 Td 51.851852 Tz (as ) Tj 0.875 0 Td 51.041667 Tz (well ) Tj 1.477778 0 Td 52.662037 Tz (with ) Tj 1.497222 0 Td 50.231481 Tz (elevated ) Tj 2.625 0 Td 46.450617 Tz (levels ) Tj 1.905556 0 Td 58.333333 Tz (of ) Tj 51.428571 0 0 51.428571 0 1999.218075 Tm 25.316667 0 Td 71.296296 Tz (LPA ) Tj 1.458333 0 Td 50.462963 Tz (present ) Tj 2.313889 0 Td 50.771605 Tz (within ) Tj 2.022222 0 Td 55.092593 Tz (a ) Tj 0.505556 0 Td 48.611111 Tz (targeted ) Tj 2.508333 0 Td 47.685185 Tz (region. ) Tj 51.428571 0 0 51.428571 0 1955.230179 Tm 26.036111 0 Td 37.268519 Tz (It ) Tj 0.563889 0 Td 54.012346 Tz (has ) Tj 1.127778 0 Td 50.231481 Tz (thus ) Tj 1.361111 0 Td 56.712963 Tz (been ) Tj 1.536111 0 Td 54.444444 Tz (determined ) Tj 3.402778 0 Td 45.37037 Tz (that ) Tj 1.244444 0 Td 48.611111 Tz (the ) Tj 0.991667 0 Td 44.907407 Tz (ability ) Tj 2.022222 0 Td 46.990741 Tz (to ) Tj 0.7 0 Td 49.016204 Tz (prevent, ) Tj 2.488889 0 Td 53.472222 Tz (or ) Tj 0.758333 0 Td 45.37037 Tz (at ) Tj 51.428571 0 0 51.428571 0 1911.751269 Tm 25.297222 0 Td 44.722222 Tz (least ) Tj 1.613889 0 Td 49.537037 Tz (reduce, ) Tj 2.313889 0 Td 49.691358 Tz (the ) Tj 1.108333 0 Td 61.574074 Tz (amount ) Tj 2.45 0 Td 58.333333 Tz (of ) Tj 0.855556 0 Td 71.296296 Tz (LPA ) Tj 1.555556 0 Td 50.771605 Tz (within ) Tj 2.061111 0 Td 66.111111 Tz (human ) Tj 2.236111 0 Td 59.953704 Tz (body ) Tj 1.691667 0 Td 51.851852 Tz (holds ) Tj 51.428571 0 0 51.428571 0 1875.089987 Tm 25.297222 0 Td 47.962963 Tz (great ) Tj 1.711111 0 Td 56.018519 Tz (promise ) Tj 2.625 0 Td 38.888889 Tz (at, ) Tj 0.991667 0 Td 47.170782 Tz (likewise, ) Tj 2.838889 0 Td 50.05144 Tz (reducing, ) Tj 2.994444 0 Td 42.12963 Tz (if ) Tj 0.719444 0 Td 50.771605 Tz (not ) Tj 1.147222 0 Td 49.494949 Tz (preventing, ) Tj 3.538889 0 Td 50.771605 Tz (the ) Tj 48.571429 0 0 48.571429 0 1830 Tm 26.785294 0 Td 54.901961 Tz (onset ) Tj 1.770588 0 Td 56.617647 Tz (of ) Tj 0.761765 0 Td 49.509804 Tz (certain ) Tj 2.223529 0 Td 51.041667 Tz (cancers. ) Tj 2.635294 0 Td 37.745098 Tz (It ) Tj 0.555882 0 Td 57.189542 Tz (has ) Tj 1.152941 0 Td 61.764706 Tz (been ) Tj 1.585294 0 Td 53.186275 Tz (theorized,as ) Tj 3.973529 0 Td 56.960784 Tz (noted ) Tj 1.832353 0 Td 54.901961 Tz (above, ) Tj 51.428571 0 0 51.428571 0 1788.622378 Tm 25.277778 0 Td 46.990741 Tz (that ) Tj 1.205556 0 Td 50.05144 Tz (autotaxin ) Tj 2.858333 0 Td 50.356125 Tz (modifications ) Tj 4.063889 0 Td 68.055556 Tz (may ) Tj 1.341667 0 Td 51.388889 Tz (prevent ) Tj 2.236111 0 Td 50.771605 Tz (the ) Tj 1.030556 0 Td 50.673401 Tz (undesirable ) Tj 3.461111 0 Td 71.296296 Tz (con ) Tj 51.428571 0 0 51.428571 0 1748.807169 Tm 25.297222 0 Td 50.925926 Tz (version ) Tj 2.313889 0 Td 57.523148 Tz (from ) Tj 1.594444 0 Td 73.45679 Tz (LPC ) Tj 1.516667 0 Td 43.75 Tz (to ) Tj 0.758333 0 Td 59.953704 Tz (LPA; ) Tj 1.652778 0 Td 49.691358 Tz (the ) Tj 1.05 0 Td 43.981481 Tz (ability ) Tj 2.061111 0 Td 45.37037 Tz (to ) Tj 0.7 0 Td 48.206019 Tz (actually ) Tj 2.508333 0 Td 55.416667 Tz (accomplish ) Tj 51.428571 0 0 51.428571 0 1703.977778 Tm 25.316667 0 Td 54.282407 Tz (Such ) Tj 1.458333 0 Td 58.333333 Tz (a ) Tj 0.505556 0 Td 45.37037 Tz (result ) Tj 1.769444 0 Td 54.012346 Tz (has ) Tj 1.127778 0 Td 56.712963 Tz (been ) Tj 1.536111 0 Td 46.180556 Tz (elusive, ) Tj 2.391667 0 Td 54.282407 Tz (however, ) Tj 2.741667 0 Td 46.990741 Tz (at ) Tj 0.719444 0 Td 44.722222 Tz (least ) Tj 1.477778 0 Td 46.990741 Tz (to ) Tj 0.738889 0 Td 50.771605 Tz (the ) Tj 1.069444 0 Td 53.472222 Tz (degree ) Tj 51.428571 0 0 51.428571 0 1663.520315 Tm 25.297222 0 Td 52.211934 Tz (necessary ) Tj 3.227778 0 Td 48.611111 Tz (for ) Tj 1.225 0 Td 46.450617 Tz (effective ) Tj 2.897222 0 Td 50.673401 Tz (broad-scale ) Tj 3.752778 0 Td 44.191919 Tz (utilization ) Tj 3.325 0 Td 59.953704 Tz (of ) Tj 0.991667 0 Td 55.092593 Tz (such ) Tj 1.730556 0 Td 55.092593 Tz (a ) Tj 52.857143 0 0 52.857143 0 1620.552826 Tm 24.613514 0 Td 54.054054 Tz (method. ) Tj 2.478378 0 Td 65.165165 Tz (Any ) Tj 1.418919 0 Td 49.136637 Tz (modification ) Tj 3.745946 0 Td 49.54955 Tz (thereof ) Tj 2.232432 0 Td 56.756757 Tz (must ) Tj 1.532432 0 Td 46.846847 Tz (exhibit ) Tj 2.156757 0 Td 55.18018 Tz (an ) Tj 0.851351 0 Td 43.243243 Tz (ability ) Tj 2.024324 0 Td 44.144144 Tz (to ) Tj 51.428571 0 0 51.428571 0 1581.632075 Tm 25.297222 0 Td 45.664983 Tz (drastically ) Tj 3.188889 0 Td 53.472222 Tz (reduce ) Tj 2.041667 0 Td 50.771605 Tz (the ) Tj 1.011111 0 Td 45.37037 Tz (activity ) Tj 2.333333 0 Td 55.092593 Tz (of ) Tj 0.738889 0 Td 49.691358 Tz (autotaxin ) Tj 2.858333 0 Td 54.444444 Tz (while ) Tj 1.711111 0 Td 49.421296 Tz (also ) Tj 1.302778 0 Td 54.62963 Tz (proving ) Tj 51.428571 0 0 51.428571 0 1539.771863 Tm 25.277778 0 Td 46.990741 Tz (to ) Tj 0.777778 0 Td 59.953704 Tz (be ) Tj 0.933333 0 Td 49.768519 Tz (non-cytotoxic, ) Tj 4.433333 0 Td 41.049383 Tz (or, ) Tj 0.933333 0 Td 45.37037 Tz (at ) Tj 0.758333 0 Td 41.049383 Tz (least, ) Tj 1.75 0 Td 50.771605 Tz (not ) Tj 1.088889 0 Td 51.851852 Tz (as ) Tj 0.855556 0 Td 53.472222 Tz (cancer ) Tj 2.080556 0 Td 56.532922 Tz (promoting ) Tj 3.266667 0 Td 50.231481 Tz (as ) Tj 40 0 0 40 0 1502 Tm 32.525 0 Td 93.055556 Tz (LPA ) Tj 1.925 0 Td 48.809524 Tz (itself. ) Tj 51.428571 0 0 51.428571 0 1456.959391 Tm 26.036111 0 Td 50.231481 Tz (Past ) Tj 1.380556 0 Td 62.384259 Tz (work ) Tj 1.613889 0 Td 55.092593 Tz (has ) Tj 1.147222 0 Td 57.523148 Tz (been ) Tj 1.536111 0 Td 53.652263 Tz (attempted ) Tj 3.072222 0 Td 43.75 Tz (at ) Tj 0.719444 0 Td 52.662037 Tz (reducing ) Tj 2.683333 0 Td 44.965278 Tz (activity ) Tj 2.352778 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 60.763889 Tz (alka ) Tj 51.428571 0 0 51.428571 0 1415.298201 Tm 25.297222 0 Td 45.37037 Tz (line ) Tj 1.419444 0 Td 53.914141 Tz (phosphatase ) Tj 3.888889 0 Td 56.712963 Tz (enzymes, ) Tj 3.052778 0 Td 55.092593 Tz (such ) Tj 1.652778 0 Td 50.231481 Tz (as ) Tj 0.952778 0 Td 61.574074 Tz (Myers ) Tj 2.177778 0 Td 58.333333 Tz (and ) Tj 1.380556 0 Td 54.372428 Tz (Widlanski ) Tj 51.428571 0 0 51.428571 0 1370 Tm 25.316667 0 Td 53.472222 Tz (\(1993\) ) Tj 2.391667 0 Td 58.549383 Tz (Mechanism-based ) Tj 5.755556 0 Td 47.800926 Tz (Inactivation ) Tj 3.908333 0 Td 59.953704 Tz (of ) Tj 1.030556 0 Td 48.251029 Tz (Prostatic ) Tj 3.013889 0 Td 57.523148 Tz (Acid ) Tj 51.428571 0 0 51.428571 0 1329.997503 Tm 25.297222 0 Td 54.012346 Tz (Phosphatase, ) Tj 4.277778 0 Td 49.826389 Tz (Science, ) Tj 2.780556 0 Td 53.148148 Tz (262\(5138\): ) Tj 3.286111 0 Td 54.444444 Tz (1451-1453, ) Tj 3.636111 0 Td 45.37037 Tz (in ) Tj 0.933333 0 Td 52.5 Tz (terms ) Tj 1.925 0 Td 59.953704 Tz (of ) Tj 51.428571 0 0 51.428571 0 1292.120381 Tm 25.297222 0 Td 49.016204 Tz (reacting ) Tj 2.566667 0 Td 53.269676 Tz (4-halomethylated ) Tj 5.347222 0 Td 52.662037 Tz (aromatic ) Tj 2.761111 0 Td 55.092593 Tz (phosphate ) Tj 3.188889 0 Td 45.910494 Tz (esters ) Tj 1.905556 0 Td 56.388889 Tz (there ) Tj 51.428571 0 0 51.428571 0 1247.543735 Tm 25.277778 0 Td 54.282407 Tz (with ) Tj 1.438889 0 Td 54.282407 Tz (Such ) Tj 1.477778 0 Td 51.203704 Tz (molecules. ) Tj 3.247222 0 Td 59.953704 Tz (Such ) Tj 1.555556 0 Td 52.932099 Tz (has ) Tj 1.069444 0 Td 55.632716 Tz (proven ) Tj 2.158333 0 Td 53.796296 Tz (moderately ) Tj 3.363889 0 Td 47.727273 Tz (successful, ) Tj 51.428571 0 0 51.428571 0 1205.04401 Tm 25.277778 0 Td 52.932099 Tz (but ) Tj 1.069444 0 Td 54.012346 Tz (has ) Tj 1.166667 0 Td 49.691358 Tz (not ) Tj 1.05 0 Td 49.789562 Tz (contributed ) Tj 3.422222 0 Td 46.990741 Tz (to ) Tj 0.719444 0 Td 56.17284 Tz (any ) Tj 1.186111 0 Td 50.411523 Tz (reduction ) Tj 2.877778 0 Td 46.990741 Tz (in ) Tj 0.738889 0 Td 71.296296 Tz (LPA ) Tj 1.438889 0 Td 50.87963 Tz (generation ) Tj 3.208333 0 Td 50.231481 Tz (as ) Tj 51.428571 0 0 51.428571 0 1164.02706 Tm 25.277778 0 Td 49.907407 Tz (these ) Tj 1.691667 0 Td 48.611111 Tz (prior ) Tj 1.613889 0 Td 48.148148 Tz (studies ) Tj 2.216667 0 Td 59.143519 Tz (were ) Tj 1.633333 0 Td 50.771605 Tz (not ) Tj 1.108333 0 Td 48.611111 Tz (directed ) Tj 2.488889 0 Td 46.990741 Tz (at ) Tj 0.738889 0 Td 60.648148 Tz (enzymes ) Tj 2.741667 0 Td 51.446759 Tz (involved ) Tj 2.683333 0 Td 48.611111 Tz (in ) Tj 51.428571 0 0 51.428571 0 1123.495541 Tm 25.316667 0 Td 71.296296 Tz (LPA ) Tj 1.594444 0 Td 50.378788 Tz (production, ) Tj 3.655556 0 Td 46.450617 Tz (particularly ) Tj 3.675 0 Td 45.37037 Tz (in ) Tj 0.894444 0 Td 52.5 Tz (terms ) Tj 1.905556 0 Td 59.953704 Tz (of ) Tj 0.952778 0 Td 72.376543 Tz (LPC ) Tj 1.613889 0 Td 52.824074 Tz (conversion ) Tj 51.428571 0 0 51.428571 0 1081.900645 Tm 25.277778 0 Td 45.775463 Tz (thereto. ) Tj 2.566667 0 Td 55.740741 Tz (Other ) Tj 1.983333 0 Td 53.292181 Tz (suggested ) Tj 3.247222 0 Td 48.070988 Tz (routes ) Tj 2.080556 0 Td 56.712963 Tz (have ) Tj 1.691667 0 Td 56.712963 Tz (been ) Tj 1.691667 0 Td 53.877315 Tz (provided ) Tj 2.955556 0 Td 53.472222 Tz (with ) Tj 51.428571 0 0 51.428571 0 1040.77804 Tm 25.297222 0 Td 51.311728 Tz (regard ) Tj 1.963889 0 Td 45.37037 Tz (to ) Tj 0.7 0 Td 49.691358 Tz (autotaxin ) Tj 2.819444 0 Td 45.868946 Tz (inactivation, ) Tj 3.733333 0 Td 53.472222 Tz (Such ) Tj 1.419444 0 Td 50.231481 Tz (as ) Tj 0.758333 0 Td 49.494949 Tz (carbacyclic ) Tj 3.402778 0 Td 63.425926 Tz (phospha ) Tj 51.428571 0 0 51.428571 0 996 Tm 25.277778 0 Td 43.425926 Tz (tidic ) Tj 1.516667 0 Td 46.666667 Tz (acid, ) Tj 1.594444 0 Td 50.231481 Tz (as ) Tj 0.875 0 Td 50.771605 Tz (discussed ) Tj 2.994444 0 Td 46.990741 Tz (in ) Tj 0.836111 0 Td 50.231481 Tz (Baker, ) Tj 2.080556 0 Td 51.851852 Tz (D. ) Tj 0.913889 0 Td 46.990741 Tz (L. ) Tj 0.797222 0 Td 45.37037 Tz (et ) Tj 0.758333 0 Td 36.458333 Tz (al., ) Tj 1.127778 0 Td 53.472222 Tz (\(2006\) ) Tj 2.138889 0 Td 60.925926 Tz (Carba ) Tj 51.428571 0 0 51.428571 0 957.896956 Tm 25.258333 0 Td 57.407407 Tz (Analogs ) Tj 2.586111 0 Td 51.851852 Tz (of ) Tj 0.7 0 Td 51.851852 Tz (Cyclic ) Tj 2.041667 0 Td 52.932099 Tz (Phosphatidic ) Tj 3.908333 0 Td 58.333333 Tz (Acid ) Tj 1.477778 0 Td 58.333333 Tz (Are ) Tj 1.186111 0 Td 48.251029 Tz (Selective ) Tj 2.780556 0 Td 47.314815 Tz (Inhibitors ) Tj 51.428571 0 0 51.428571 0 912 Tm 25.297222 0 Td 50.231481 Tz (of ) Tj 0.680556 0 Td 51.851852 Tz (Autotaxin ) Tj 2.936111 0 Td 62.654321 Tz (and ) Tj 1.244444 0 Td 59.953704 Tz (Cancer ) Tj 2.313889 0 Td 47.890947 Tz (Invasion, ) Tj 2.722222 0 Td 37.268519 Tz (J. ) Tj 0.641667 0 Td 45.37037 Tz (Biol. ) Tj 1.516667 0 Td 63.518519 Tz (Chem. ) Tj 2.080556 0 Td 61.574074 Tz (281:22786 ) Tj 51.428571 0 0 51.428571 0 872.768638 Tm 25.316667 0 Td 47.530864 Tz (93, ) Tj 1.088889 0 Td 39.969136 Tz (all ) Tj 0.952778 0 Td 46.990741 Tz (to ) Tj 0.836111 0 Td 55.092593 Tz (no ) Tj 0.875 0 Td 43.75 Tz (avail, ) Tj 1.808333 0 Td 53.877315 Tz (however, ) Tj 2.8 0 Td 51.851852 Tz (as ) Tj 0.855556 0 Td 49.907407 Tz (these ) Tj 1.691667 0 Td 61.934156 Tz (compounds ) Tj 3.577778 0 Td 48.148148 Tz (exhibit ) Tj 2.255556 0 Td 56.712963 Tz (no ) Tj 51.428571 0 0 51.428571 0 833.16 Tm 25.297222 0 Td 50.87963 Tz (propensity ) Tj 3.305556 0 Td 48.611111 Tz (to ) Tj 0.855556 0 Td 49.907407 Tz (covalently ) Tj 3.305556 0 Td 56.712963 Tz (modify ) Tj 2.313889 0 Td 47.638889 Tz (autotaxin. ) Tj 3.130556 0 Td 53.796296 Tz (Thus, ) Tj 1.905556 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 63.194444 Tz (auto ) Tj 51.428571 0 0 51.428571 0 790.884615 Tm 25.277778 0 Td 48.611111 Tz (taxin ) Tj 1.672222 0 Td 50.771605 Tz (modification ) Tj 3.888889 0 Td 42.12963 Tz (reliability ) Tj 2.955556 0 Td 59.953704 Tz (of ) Tj 0.836111 0 Td 54.282407 Tz (such ) Tj 1.497222 0 Td 50.87963 Tz (previously ) Tj 3.266667 0 Td 46.990741 Tz (tested ) Tj 1.847222 0 Td 84.259259 Tz (com ) Tj 51.428571 0 0 51.428571 0 749.191868 Tm 25.297222 0 Td 57.79321 Tz (pounds ) Tj 2.333333 0 Td 55.092593 Tz (has ) Tj 1.225 0 Td 57.523148 Tz (been ) Tj 1.652778 0 Td 48.611111 Tz (rather ) Tj 1.983333 0 Td 49.421296 Tz (low, ) Tj 1.438889 0 Td 47.916667 Tz (unfortunately. ) Tj 4.355556 0 Td 55.092593 Tz (Hence, ) Tj 2.255556 0 Td 45.37037 Tz (to ) Tj 0.836111 0 Td 45.37037 Tz (date, ) Tj 51.428571 0 0 51.428571 0 706.113801 Tm 25.277778 0 Td 49.259259 Tz (there ) Tj 1.633333 0 Td 45.37037 Tz (exists ) Tj 1.769444 0 Td 51.851852 Tz (a ) Tj 0.505556 0 Td 56.712963 Tz (need ) Tj 1.536111 0 Td 43.75 Tz (to ) Tj 0.680556 0 Td 53.240741 Tz (provide ) Tj 2.372222 0 Td 46.8107 Tz (effective ) Tj 2.683333 0 Td 50.356125 Tz (modifications ) Tj 4.102778 0 Td 45.37037 Tz (to ) Tj 0.680556 0 Td 63.194444 Tz (auto ) Tj 51.428571 0 0 51.428571 0 664.328302 Tm 25.277778 0 Td 48.611111 Tz (taxin ) Tj 1.672222 0 Td 61.111111 Tz (enzymes ) Tj 2.819444 0 Td 47.530864 Tz (for ) Tj 1.069444 0 Td 48.611111 Tz (the ) Tj 1.127778 0 Td 50.05144 Tz (reduction ) Tj 2.916667 0 Td 61.574074 Tz (of ) Tj 0.894444 0 Td 71.296296 Tz (LPC ) Tj 1.497222 0 Td 52.5 Tz (conversion ) Tj 3.402778 0 Td 45.37037 Tz (to ) Tj 0.816667 0 Td 71.296296 Tz (LPA ) Tj 51.428571 0 0 51.428571 0 623.291667 Tm 25.297222 0 Td 47.685185 Tz (readily ) Tj 2.177778 0 Td 60.493827 Tz (and ) Tj 1.302778 0 Td 42.12963 Tz (reliably. ) Tj 2.488889 0 Td 72.916667 Tz (No ) Tj 1.069444 0 Td 55.092593 Tz (such ) Tj 1.555556 0 Td 55.902778 Tz (need ) Tj 1.497222 0 Td 55.092593 Tz (has ) Tj 1.166667 0 Td 56.712963 Tz (been ) Tj 1.594444 0 Td 59.41358 Tz (met ) Tj 1.263889 0 Td 42.777778 Tz (until ) Tj 1.516667 0 Td 55.092593 Tz (now. ) Tj 38.571429 0 0 38.571429 0 550 Tm 35.544444 0 Td 105.432099 Tz (ADVANTAGES ) Tj 6.559259 0 Td 115.226337 Tz (AND ) Tj 2.359259 0 Td 89.012346 Tz (BRIEF ) Tj 2.981481 0 Td 94.668911 Tz (DESCRIPTION ) Tj 6.533333 0 Td 99.382716 Tz (OF ) Tj 38.571429 0 0 38.571429 0 509 Tm 41.637037 0 Td 105.144033 Tz (THE ) Tj 2.177778 0 Td 98.422497 Tz (INVENTION ) Tj 51.428571 0 0 51.428571 0 421.916449 Tm 26.036111 0 Td 37.268519 Tz (It ) Tj 0.641667 0 Td 37.268519 Tz (is ) Tj 0.641667 0 Td 49.421296 Tz (thus ) Tj 1.419444 0 Td 55.092593 Tz (an ) Tj 0.855556 0 Td 54.73251 Tz (advantage ) Tj 3.130556 0 Td 58.333333 Tz (of ) Tj 0.777778 0 Td 50.771605 Tz (the ) Tj 1.088889 0 Td 50.462963 Tz (present ) Tj 2.313889 0 Td 49.691358 Tz (invention ) Tj 2.877778 0 Td 46.990741 Tz (to ) Tj 0.758333 0 Td 52.777778 Tz (provide ) Tj 51.428571 0 0 51.428571 0 378.365135 Tm 25.297222 0 Td 45.775463 Tz (reliable ) Tj 2.294444 0 Td 50.411523 Tz (autotaxin ) Tj 2.877778 0 Td 46.720679 Tz (inactivators ) Tj 3.519444 0 Td 47.530864 Tz (for ) Tj 0.952778 0 Td 50.771605 Tz (the ) Tj 1.030556 0 Td 55.555556 Tz (purpose ) Tj 2.488889 0 Td 55.092593 Tz (of ) Tj 0.719444 0 Td 53.06713 Tz (reducing ) Tj 2.683333 0 Td 50.771605 Tz (the ) Tj 51.428571 0 0 51.428571 0 337.118501 Tm 25.297222 0 Td 52.175926 Tz (conversion ) Tj 3.286111 0 Td 58.333333 Tz (of ) Tj 0.777778 0 Td 73.45679 Tz (LPC ) Tj 1.458333 0 Td 46.990741 Tz (to ) Tj 0.738889 0 Td 71.296296 Tz (LPA ) Tj 1.419444 0 Td 53.703704 Tz (through ) Tj 2.411111 0 Td 49.691358 Tz (the ) Tj 1.05 0 Td 44.191919 Tz (utilization ) Tj 3.072222 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 55.092593 Tz (a ) Tj 0.486111 0 Td 47.685185 Tz (readily ) Tj 51.428571 0 0 51.428571 0 298.299304 Tm 25.297222 0 Td 48.251029 Tz (available ) Tj 2.702778 0 Td 59.41358 Tz (and ) Tj 1.147222 0 Td 47.530864 Tz (easily ) Tj 1.808333 0 Td 57.118056 Tz (produced ) Tj 2.877778 0 Td 63.599537 Tz (compound ) Tj 3.169444 0 Td 48.611111 Tz (\(or ) Tj 0.972222 0 Td 59.953704 Tz (compounds\) ) Tj 3.694444 0 Td 46.180556 Tz (that ) Tj 51.428571 0 0 51.428571 0 253.84264 Tm 25.297222 0 Td 55.092593 Tz (does ) Tj 1.633333 0 Td 50.771605 Tz (not ) Tj 1.147222 0 Td 56.712963 Tz (pose ) Tj 1.594444 0 Td 58.333333 Tz (any ) Tj 1.341667 0 Td 45.959596 Tz (significant ) Tj 3.305556 0 Td 64.814815 Tz (known ) Tj 2.197222 0 Td 49.151235 Tz (health ) Tj 2.080556 0 Td 42.12963 Tz (risks. ) Tj 1.788889 0 Td 57.407407 Tz (Another ) Tj 51.428571 0 0 51.428571 0 214.138272 Tm 25.297222 0 Td 54.372428 Tz (advantage ) Tj 3.169444 0 Td 37.268519 Tz (is ) Tj 0.661111 0 Td 50.771605 Tz (the ) Tj 1.108333 0 Td 44.444444 Tz (ability ) Tj 2.080556 0 Td 48.611111 Tz (for ) Tj 1.05 0 Td 51.49177 Tz (treatment ) Tj 2.994444 0 Td 52.662037 Tz (with ) Tj 1.497222 0 Td 55.092593 Tz (Such ) Tj 1.555556 0 Td 61.934156 Tz (compounds ) Tj 51.428571 0 0 51.428571 0 172.108844 Tm 25.297222 0 Td 48.611111 Tz (for ) Tj 1.030556 0 Td 53.472222 Tz (cancer ) Tj 2.061111 0 Td 51.203704 Tz (prevention ) Tj 3.286111 0 Td 51.131687 Tz (treatment ) Tj 2.936111 0 Td 51.851852 Tz (regimens. ) Tj ET Q endstream endobj 176 0 obj << /Length 1 >> stream q endstream endobj 177 0 obj << /Length 31254 >> stream Q q 0.24 0 0 0.24 0 0 cm BT /F1 1 Tf 3 Tr 62.857143 0 0 62.857143 0 3023 Tm 17.325 0 Td 83.522727 Tz (US ) Tj 1.240909 0 Td 58.333333 Tz (8,022,239 ) Tj 3.388636 0 Td 74.242424 Tz (B2 ) Tj 52.857143 0 0 52.857143 0 2968 Tm 14.454054 0 Td 72.522523 Tz (3 ) Tj 51.428571 0 0 51.428571 0 2918.326829 Tm 7.097222 0 Td 52.121914 Tz (Accordingly, ) Tj 3.869444 0 Td 43.75 Tz (this ) Tj 1.205556 0 Td 48.971193 Tz (invention ) Tj 2.819444 0 Td 57.449495 Tz (encompasses ) Tj 3.888889 0 Td 58.333333 Tz (a ) Tj 0.466667 0 Td 64.00463 Tz (compound ) Tj 3.188889 0 Td 71.296296 Tz (con ) Tj 51.428571 0 0 51.428571 0 2866.779412 Tm 6.358333 0 Td 56.018519 Tz (forming ) Tj 2.547222 0 Td 43.75 Tz (to ) Tj 0.719444 0 Td 50.771605 Tz (the ) Tj 1.088889 0 Td 46.8107 Tz (structure ) Tj 2.702778 0 Td 59.953704 Tz (of ) Tj 0.816667 0 Td 57.87037 Tz (Formula ) Tj 2.644444 0 Td 36.944444 Tz (\(II\): ) Tj 40 0 0 40 0 2647 Tm 29.725 0 Td 38.541667 Tz (\(II\) ) Tj 24.285714 0 0 24.285714 0 2607 Tm 24.211765 0 Td 68.627451 Tz (3 ) Tj 2.923529 0 Td 75.490196 Tz (2 ) Tj 80 0 0 80 0 2533 Tm 7.0125 0 Td 85.416667 Tz (/ ) Tj 51.428571 0 0 51.428571 0 2337.039422 Tm 7.077778 0 Td 55.555556 Tz (wherein ) Tj 2.547222 0 Td 74.537037 Tz (R ) Tj 0.641667 0 Td 37.268519 Tz (is ) Tj 0.622222 0 Td 98.302469 Tz (C2s ) Tj 1.944444 0 Td 47.962963 Tz (alkyl ) Tj 1.652778 0 Td 51.851852 Tz (or ) Tj 0.719444 0 Td 48.611111 Tz (alkenyl; ) Tj 2.508333 0 Td 84.259259 Tz (X ) Tj 0.719444 0 Td 37.268519 Tz (is ) Tj 0.641667 0 Td 62.87037 Tz (mono- ) Tj 2.041667 0 Td 53.472222 Tz (or ) Tj 0.777778 0 Td 53.472222 Tz (difluo ) Tj 51.428571 0 0 51.428571 0 2290.143219 Tm 6.358333 0 Td 63.464506 Tz (romethyl\(CHF ) Tj 4.744444 0 Td 53.472222 Tz (or ) Tj 0.797222 0 Td 71.296296 Tz (CHF\); ) Tj 2.294444 0 Td 60.493827 Tz (and ) Tj 1.263889 0 Td 87.5 Tz (X ) Tj 0.719444 0 Td 38.888889 Tz (is ) Tj 0.680556 0 Td 43.75 Tz (in ) Tj 0.7 0 Td 47.530864 Tz (either ) Tj 1.866667 0 Td 49.691358 Tz (the ) Tj 1.088889 0 Td 51.851852 Tz (2 ) Tj 0.505556 0 Td 55.092593 Tz (or ) Tj 0.797222 0 Td 58.333333 Tz (4 ) Tj 0.544444 0 Td 60.763889 Tz (posi ) Tj 51.428571 0 0 51.428571 0 2243.752381 Tm 6.338889 0 Td 47.800926 Tz (tion ) Tj 1.302778 0 Td 48.611111 Tz (\(ortho- ) Tj 2.197222 0 Td 51.851852 Tz (or ) Tj 0.738889 0 Td 46.8107 Tz (para-Substitution, ) Tj 5.25 0 Td 43.75 Tz (in ) Tj 0.680556 0 Td 48.971193 Tz (essence\). ) Tj 2.838889 0 Td 56.17284 Tz (For ) Tj 1.108333 0 Td 54.282407 Tz (purposes ) Tj 2.780556 0 Td 56.712963 Tz (of ) Tj 51.428571 0 0 51.428571 0 2196.102013 Tm 6.338889 0 Td 44.560185 Tz (this ) Tj 1.419444 0 Td 47.138047 Tz (disclosure, ) Tj 3.441667 0 Td 48.611111 Tz (as ) Tj 0.952778 0 Td 32.407407 Tz (it ) Tj 0.680556 0 Td 47.800926 Tz (pertains ) Tj 2.644444 0 Td 46.990741 Tz (to ) Tj 0.894444 0 Td 50.771605 Tz (the ) Tj 1.283333 0 Td 71.296296 Tz (R ) Tj 0.738889 0 Td 55.092593 Tz (groups ) Tj 2.294444 0 Td 47.727273 Tz (potentially ) Tj 51.428571 0 0 51.428571 0 2146.859355 Tm 6.358333 0 Td 50.925926 Tz (present ) Tj 2.372222 0 Td 59.953704 Tz (on ) Tj 1.011111 0 Td 48.611111 Tz (the ) Tj 1.147222 0 Td 57.87037 Tz (Formula ) Tj 2.722222 0 Td 37.268519 Tz (II ) Tj 0.719444 0 Td 60.133745 Tz (compound, ) Tj 3.519444 0 Td 49.691358 Tz (the ) Tj 1.205556 0 Td 48.611111 Tz (notation ) Tj 2.586111 0 Td 61.574074 Tz (of ) Tj 0.952778 0 Td 51.851852 Tz (18:0 ) Tj 51.428571 0 0 51.428571 0 2100.510328 Tm 6.358333 0 Td 61.574074 Tz (means ) Tj 1.983333 0 Td 49.259259 Tz (octadecyl, ) Tj 3.15 0 Td 51.851852 Tz (16:0 ) Tj 1.380556 0 Td 38.888889 Tz (is ) Tj 0.602778 0 Td 51.203704 Tz (hexadecyl, ) Tj 3.286111 0 Td 52.662037 Tz (14:0 ) Tj 1.380556 0 Td 38.888889 Tz (is ) Tj 0.622222 0 Td 45.37037 Tz (tetradecyl, ) Tj 3.208333 0 Td 51.041667 Tz (12:0 ) Tj 1.380556 0 Td 38.888889 Tz (is ) Tj 51.428571 0 0 51.428571 0 2049.727382 Tm 6.358333 0 Td 51.446759 Tz (dodecyl, ) Tj 2.566667 0 Td 60.493827 Tz (and ) Tj 1.186111 0 Td 56.17284 Tz (any ) Tj 1.166667 0 Td 49.016204 Tz (notation ) Tj 2.508333 0 Td 52.662037 Tz (with ) Tj 1.380556 0 Td 49.691358 Tz (the ) Tj 1.030556 0 Td 62.114198 Tz (number ) Tj 2.372222 0 Td 35.648148 Tz (1 ) Tj 0.447222 0 Td 49.826389 Tz (includes ) Tj 2.508333 0 Td 53.148148 Tz (\(such ) Tj 1.691667 0 Td 50.231481 Tz (as ) Tj 51.428571 0 0 51.428571 0 2003.986129 Tm 6.436111 0 Td 48.611111 Tz (16:1\) ) Tj 1.711111 0 Td 47.890947 Tz (indicates ) Tj 2.819444 0 Td 48.206019 Tz (alkenyl, ) Tj 2.605556 0 Td 52.662037 Tz (with ) Tj 1.536111 0 Td 50.771605 Tz (the ) Tj 1.147222 0 Td 55.092593 Tz (double ) Tj 2.216667 0 Td 60.763889 Tz (bond ) Tj 1.691667 0 Td 50.925926 Tz (present ) Tj 2.352778 0 Td 72.376543 Tz (any ) Tj 40 0 0 40 0 1961 Tm 8.15 0 Td 77.5 Tz (where ) Tj 2.575 0 Td 65.277778 Tz (within ) Tj 2.625 0 Td 62.5 Tz (the ) Tj 1.35 0 Td 70.138889 Tz (carbon ) Tj 2.775 0 Td 61.805556 Tz (chain. ) Tj 51.428571 0 0 51.428571 0 1895.093458 Tm 7.097222 0 Td 66.435185 Tz (As ) Tj 1.088889 0 Td 46.018519 Tz (well, ) Tj 1.672222 0 Td 43.75 Tz (this ) Tj 1.341667 0 Td 49.691358 Tz (invention ) Tj 2.955556 0 Td 57.744108 Tz (encompasses ) Tj 4.083333 0 Td 49.691358 Tz (the ) Tj 1.166667 0 Td 44.486532 Tz (utilization ) Tj 3.247222 0 Td 55.092593 Tz (of ) Tj 0.836111 0 Td 58.333333 Tz (a ) Tj 51.428571 0 0 51.428571 0 1849.915215 Tm 6.358333 0 Td 64.00463 Tz (compound ) Tj 3.208333 0 Td 51.131687 Tz (including ) Tj 2.858333 0 Td 55.092593 Tz (a ) Tj 0.427778 0 Td 53.009259 Tz (phosphodiester ) Tj 4.55 0 Td 58.333333 Tz (and ) Tj 1.166667 0 Td 49.537037 Tz (eithera ) Tj 2.255556 0 Td 62.384259 Tz (monofluo ) Tj 51.428571 0 0 51.428571 0 1804.53271 Tm 6.358333 0 Td 54.62963 Tz (romethylphenyl ) Tj 4.744444 0 Td 53.472222 Tz (or ) Tj 0.797222 0 Td 52.175926 Tz (difluoromethylphenyl ) Tj 6.416667 0 Td 51.311728 Tz (group, ) Tj 2.041667 0 Td 49.583333 Tz (preferably ) Tj 3.15 0 Td 55.092593 Tz (a ) Tj 51.428571 0 0 51.428571 0 1750.602028 Tm 6.358333 0 Td 64.00463 Tz (compound ) Tj 3.344444 0 Td 48.611111 Tz (as ) Tj 0.875 0 Td 50.925926 Tz (defined ) Tj 2.411111 0 Td 51.851852 Tz (within ) Tj 2.138889 0 Td 48.611111 Tz (the ) Tj 1.127778 0 Td 47.530864 Tz (structure ) Tj 2.819444 0 Td 59.953704 Tz (of ) Tj 0.913889 0 Td 57.407407 Tz (Formula ) Tj 2.702778 0 Td 36.944444 Tz (\(II\), ) Tj 51.428571 0 0 51.428571 0 1702.147287 Tm 6.358333 0 Td 52.391975 Tz (above, ) Tj 2.177778 0 Td 45.37037 Tz (to ) Tj 0.816667 0 Td 47.962963 Tz (effectuate ) Tj 3.130556 0 Td 55.092593 Tz (a ) Tj 0.641667 0 Td 50.05144 Tz (reduction ) Tj 2.994444 0 Td 45.37037 Tz (in ) Tj 0.816667 0 Td 44.965278 Tz (activity ) Tj 2.469444 0 Td 58.333333 Tz (of ) Tj 0.855556 0 Td 50.05144 Tz (autotaxin ) Tj 2.994444 0 Td 50.231481 Tz (in ) Tj 51.428571 0 0 51.428571 0 1656.070707 Tm 6.338889 0 Td 54.444444 Tz (terms ) Tj 1.886111 0 Td 59.953704 Tz (of ) Tj 0.894444 0 Td 47.170782 Tz (potential ) Tj 2.838889 0 Td 52.175926 Tz (conversion ) Tj 3.422222 0 Td 59.953704 Tz (of ) Tj 0.894444 0 Td 73.45679 Tz (LPC ) Tj 1.594444 0 Td 45.37037 Tz (to ) Tj 0.875 0 Td 59.143519 Tz (LPA, ) Tj 1.730556 0 Td 46.720679 Tz (particularly ) Tj 51.428571 0 0 51.428571 0 1607.178359 Tm 6.338889 0 Td 54.166667 Tz (through ) Tj 2.469444 0 Td 45.37037 Tz (structural ) Tj 2.916667 0 Td 50.356125 Tz (modifications ) Tj 4.102778 0 Td 46.990741 Tz (to ) Tj 0.719444 0 Td 51.851852 Tz (prevent ) Tj 2.333333 0 Td 47.138047 Tz (interaction ) Tj 3.305556 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 49.691358 Tz (the ) Tj 51.428571 0 0 51.428571 0 1558.586035 Tm 6.377778 0 Td 73.45679 Tz (LPC ) Tj 1.516667 0 Td 64.409722 Tz (compound ) Tj 3.325 0 Td 51.311728 Tz (within ) Tj 2.080556 0 Td 49.691358 Tz (the ) Tj 1.088889 0 Td 48.070988 Tz (active ) Tj 1.963889 0 Td 42.939815 Tz (site ) Tj 1.205556 0 Td 61.574074 Tz (of ) Tj 0.875 0 Td 48.611111 Tz (the ) Tj 1.127778 0 Td 53.06713 Tz (modified ) Tj 2.741667 0 Td 63.194444 Tz (auto ) Tj 51.428571 0 0 51.428571 0 1513.232503 Tm 6.338889 0 Td 47.962963 Tz (taxin ) Tj 1.613889 0 Td 56.944444 Tz (enzyme. ) Tj 2.488889 0 Td 87.5 Tz (A ) Tj 0.680556 0 Td 59.41358 Tz (method ) Tj 2.255556 0 Td 53.472222 Tz (of ) Tj 0.719444 0 Td 54.372428 Tz (producing ) Tj 3.072222 0 Td 55.092593 Tz (Such ) Tj 1.419444 0 Td 61.934156 Tz (compounds ) Tj 3.461111 0 Td 40.509259 Tz (is ) Tj 0.602778 0 Td 48.611111 Tz (also ) Tj 51.428571 0 0 51.428571 0 1465.831591 Tm 6.358333 0 Td 58.922559 Tz (encompassed ) Tj 4.005556 0 Td 50.771605 Tz (within ) Tj 1.944444 0 Td 43.75 Tz (this ) Tj 1.205556 0 Td 47.638889 Tz (invention, ) Tj 2.975 0 Td 55.092593 Tz (comprising ) Tj 3.383333 0 Td 49.691358 Tz (the ) Tj 1.030556 0 Td 48.611111 Tz (sequential ) Tj 51.428571 0 0 51.428571 0 1418.261261 Tm 6.377778 0 Td 47.314815 Tz (steps ) Tj 1.633333 0 Td 41.049383 Tz (of: ) Tj 51.428571 0 0 51.428571 0 1358.604167 Tm 7.097222 0 Td 45.37037 Tz (a\) ) Tj 0.738889 0 Td 49.016204 Tz (reacting ) Tj 2.527778 0 Td 55.740741 Tz (phosphorus ) Tj 3.538889 0 Td 52.73569 Tz (oxychloride ) Tj 3.655556 0 Td 53.472222 Tz (with ) Tj 1.477778 0 Td 55.092593 Tz (a ) Tj 0.525 0 Td 42.777778 Tz (fatty ) Tj 1.477778 0 Td 48.206019 Tz (alcohol; ) Tj 51.428571 0 0 51.428571 0 1297.424144 Tm 7.077778 0 Td 50.231481 Tz (b\) ) Tj 0.952778 0 Td 49.016204 Tz (reacting ) Tj 2.644444 0 Td 50.771605 Tz (the ) Tj 1.263889 0 Td 46.090535 Tz (resultant ) Tj 2.819444 0 Td 64.00463 Tz (compound ) Tj 3.402778 0 Td 56.712963 Tz (of ) Tj 0.913889 0 Td 48.611111 Tz (step ) Tj 1.516667 0 Td 53.472222 Tz (a ) Tj 51.428571 0 0 51.428571 0 1252.833944 Tm 6.338889 0 Td 55.092593 Tz (hydroxybenzaldehyde, ) Tj 7.038889 0 Td 51.388889 Tz (thereby ) Tj 2.566667 0 Td 56.481481 Tz (forming ) Tj 2.722222 0 Td 55.092593 Tz (a ) Tj 0.738889 0 Td 53.009259 Tz (phosphodiester ) Tj 51.428571 0 0 51.428571 0 1205 Tm 6.358333 0 Td 60.133745 Tz (compound; ) Tj 40 0 0 40 0 1301 Tm 28.1 0 Td 69.791667 Tz (with ) Tj 2.1 0 Td 75 Tz (a ) Tj 51.428571 0 0 51.428571 0 1143.310559 Tm 7.097222 0 Td 45.37037 Tz (c\) ) Tj 0.7 0 Td 49.016204 Tz (reacting ) Tj 2.527778 0 Td 47.800926 Tz (said ) Tj 1.302778 0 Td 52.777778 Tz (phosphodiester ) Tj 4.55 0 Td 64.409722 Tz (compound ) Tj 3.227778 0 Td 53.472222 Tz (with ) Tj 1.458333 0 Td 55.092593 Tz (a ) Tj 0.486111 0 Td 58.796296 Tz (cyanoet ) Tj 51.428571 0 0 51.428571 0 1094.306799 Tm 6.338889 0 Td 54.444444 Tz (hanol ) Tj 1.808333 0 Td 46.990741 Tz (to ) Tj 0.758333 0 Td 58.333333 Tz (form ) Tj 1.575 0 Td 58.333333 Tz (a ) Tj 0.505556 0 Td 50.339506 Tz (phosphotriester ) Tj 4.686111 0 Td 60.133745 Tz (compound; ) Tj 51.428571 0 0 51.428571 0 1034.432361 Tm 7.097222 0 Td 48.611111 Tz (d\) ) Tj 0.933333 0 Td 49.421296 Tz (reacting ) Tj 2.702778 0 Td 48.611111 Tz (said ) Tj 1.497222 0 Td 50.339506 Tz (phosphotriester ) Tj 4.861111 0 Td 63.599537 Tz (compound ) Tj 3.422222 0 Td 52.662037 Tz (with ) Tj 1.613889 0 Td 46.990741 Tz (bis\(2- ) Tj 51.428571 0 0 51.428571 0 984.038095 Tm 6.358333 0 Td 51.689815 Tz (methoxyethyl\)-sulfur ) Tj 6.397222 0 Td 42.669753 Tz (trifluoride, ) Tj 3.305556 0 Td 55.092593 Tz (wherein ) Tj 2.547222 0 Td 48.611111 Tz (said ) Tj 1.419444 0 Td 47.395833 Tz (reaction ) Tj 2.527778 0 Td 54.282407 Tz (with ) Tj 51.428571 0 0 51.428571 0 939.409195 Tm 6.338889 0 Td 50.854701 Tz (bis\(2-methoxyethyl\)-sulfur ) Tj 8.05 0 Td 44.191919 Tz (trifluoride ) Tj 3.091667 0 Td 37.268519 Tz (is ) Tj 0.622222 0 Td 48.935185 Tz (optionally ) Tj 3.072222 0 Td 55.902778 Tz (preceded ) Tj 51.428571 0 0 51.428571 0 890.636364 Tm 6.338889 0 Td 61.574074 Tz (by ) Tj 1.108333 0 Td 52.662037 Tz (reducing ) Tj 2.877778 0 Td 48.611111 Tz (said ) Tj 1.477778 0 Td 50.339506 Tz (phosphotriester ) Tj 4.861111 0 Td 63.599537 Tz (compound ) Tj 3.402778 0 Td 52.662037 Tz (with ) Tj 1.633333 0 Td 58.873457 Tz (sodium ) Tj 51.428571 0 0 51.428571 0 843.816492 Tm 6.338889 0 Td 52.121914 Tz (borohydride, ) Tj 3.869444 0 Td 52.314815 Tz (thereby ) Tj 2.313889 0 Td 55.092593 Tz (producing ) Tj 3.111111 0 Td 55.092593 Tz (a ) Tj 0.466667 0 Td 47.43266 Tz (fluorinated ) Tj 3.266667 0 Td 60.133745 Tz (compound; ) Tj 3.383333 0 Td 61.574074 Tz (and ) Tj 51.428571 0 0 51.428571 0 783.024969 Tm 7.097222 0 Td 45.37037 Tz (e\) ) Tj 0.719444 0 Td 50.501543 Tz (deprotecting ) Tj 3.791667 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 46.450617 Tz (resultant ) Tj 2.683333 0 Td 47.43266 Tz (fluorinated ) Tj 3.305556 0 Td 63.599537 Tz (compound ) Tj 3.247222 0 Td 55.092593 Tz (of ) Tj 0.758333 0 Td 47.800926 Tz (step ) Tj 51.428571 0 0 51.428571 0 735.030675 Tm 6.358333 0 Td 48.611111 Tz (d'. ) Tj 1.341667 0 Td 59.143519 Tz (Such ) Tj 1.575 0 Td 51.851852 Tz (a ) Tj 0.486111 0 Td 51.851852 Tz (novel ) Tj 1.75 0 Td 59.41358 Tz (method ) Tj 2.275 0 Td 38.888889 Tz (is ) Tj 0.622222 0 Td 51.49177 Tz (described ) Tj 2.936111 0 Td 43.75 Tz (in ) Tj 0.661111 0 Td 48.611111 Tz (greater ) Tj 2.197222 0 Td 43.75 Tz (detail ) Tj 1.730556 0 Td 51.851852 Tz (below. ) Tj 38.571429 0 0 38.571429 0 634 Tm 9.92963 0 Td 97.762346 Tz (DETAILED ) Tj 4.977778 0 Td 94.276094 Tz (DESCRIPTION ) Tj 6.533333 0 Td 99.382716 Tz (OF ) Tj 1.4 0 Td 106.584362 Tz (THE ) Tj 2.177778 0 Td 98.902606 Tz (INVENTION ) Tj 38.571429 0 0 38.571429 0 592 Tm 12.522222 0 Td 116.666667 Tz (AND ) Tj 2.385185 0 Td 101.303155 Tz (PREFERRED ) Tj 5.755556 0 Td 106.453423 Tz (EMBODIMENTS ) Tj 51.428571 0 0 51.428571 0 491.458276 Tm 7.116667 0 Td 46.666667 Tz (Basically, ) Tj 3.15 0 Td 30.787037 Tz (it ) Tj 0.661111 0 Td 54.012346 Tz (has ) Tj 1.283333 0 Td 57.523148 Tz (been ) Tj 1.691667 0 Td 48.206019 Tz (realized ) Tj 2.586111 0 Td 46.990741 Tz (that ) Tj 1.438889 0 Td 54.282407 Tz (such ) Tj 1.633333 0 Td 61.934156 Tz (compounds ) Tj 3.655556 0 Td 50.231481 Tz (as ) Tj 52.857143 0 0 52.857143 0 445.964512 Tm 6.186486 0 Td 42.567568 Tz (listed ) Tj 1.92973 0 Td 56.126126 Tz (above ) Tj 2.118919 0 Td 41.779279 Tz (\(di- ) Tj 1.4 0 Td 57.807808 Tz (and ) Tj 1.456757 0 Td 53.603604 Tz (mono-fluoromethylphenyl ) Tj 7.813514 0 Td 75.675676 Tz (Co-Cs ) Tj 51.428571 0 0 51.428571 0 401.977778 Tm 6.358333 0 Td 51.446759 Tz (phosphodiesters\) ) Tj 5.094444 0 Td 48.148148 Tz (exhibit ) Tj 2.158333 0 Td 48.971193 Tz (excellent ) Tj 2.8 0 Td 47.638889 Tz (capability ) Tj 3.013889 0 Td 59.953704 Tz (of ) Tj 0.797222 0 Td 53.06713 Tz (reducing ) Tj 2.722222 0 Td 49.691358 Tz (the ) Tj 51.428571 0 0 51.428571 0 353.285714 Tm 6.358333 0 Td 44.965278 Tz (activity ) Tj 2.294444 0 Td 51.851852 Tz (of ) Tj 0.7 0 Td 50.05144 Tz (autotaxin ) Tj 2.838889 0 Td 54.282407 Tz (such ) Tj 1.419444 0 Td 46.990741 Tz (that ) Tj 1.225 0 Td 49.691358 Tz (the ) Tj 0.991667 0 Td 47.170782 Tz (potential ) Tj 2.663889 0 Td 52.824074 Tz (conversion ) Tj 3.305556 0 Td 51.851852 Tz (of ) Tj 0.7 0 Td 73.45679 Tz (LPC ) Tj 51.428571 0 0 51.428571 0 309.945839 Tm 6.338889 0 Td 45.37037 Tz (to ) Tj 1.011111 0 Td 70.216049 Tz (LPA ) Tj 1.652778 0 Td 51.388889 Tz (thereby ) Tj 2.586111 0 Td 37.268519 Tz (is ) Tj 0.836111 0 Td 57.253086 Tz (compromised. ) Tj 4.491667 0 Td 64.814815 Tz (The ) Tj 1.536111 0 Td 52.211934 Tz (following ) Tj 3.188889 0 Td 61.033951 Tz (scheme ) Tj 51.428571 0 0 51.428571 0 262.104762 Tm 6.377778 0 Td 58.981481 Tz (shows ) Tj 1.925 0 Td 49.691358 Tz (the ) Tj 1.011111 0 Td 50.925926 Tz (general ) Tj 2.275 0 Td 48.611111 Tz (reaction ) Tj 2.469444 0 Td 51.388889 Tz (leading ) Tj 2.255556 0 Td 48.611111 Tz (to ) Tj 0.719444 0 Td 46.990741 Tz (inactivation ) Tj 3.558333 0 Td 53.472222 Tz (of ) Tj 0.7 0 Td 50.771605 Tz (the ) Tj 1.011111 0 Td 63.194444 Tz (auto ) Tj 51.428571 0 0 51.428571 0 216.332916 Tm 6.338889 0 Td 47.962963 Tz (taxin ) Tj 1.730556 0 Td 63.194444 Tz (enzyme ) Tj 2.508333 0 Td 53.703704 Tz (through ) Tj 2.508333 0 Td 50.771605 Tz (the ) Tj 1.166667 0 Td 44.191919 Tz (utilization ) Tj 3.208333 0 Td 56.712963 Tz (of ) Tj 0.816667 0 Td 50.771605 Tz (the ) Tj 1.166667 0 Td 48.971193 Tz (inventive ) Tj 2.877778 0 Td 83.179012 Tz (com ) Tj 51.428571 0 0 51.428571 0 171.010453 Tm 6.358333 0 Td 58.333333 Tz (pounds ) Tj 2.313889 0 Td 53.148148 Tz (noted ) Tj 1.75 0 Td 52.391975 Tz (above: ) Tj 30 0 0 30 0 2547 Tm 41.666667 0 Td 75 Tz (10 ) Tj 30 0 0 30 0 2339 Tm 41.666667 0 Td 72.222222 Tz (15 ) Tj 30 0 0 30 0 1923 Tm 41.6 0 Td 77.777778 Tz (25 ) Tj 30 0 0 30 0 1716 Tm 41.6 0 Td 80.555556 Tz (30 ) Tj 30 0 0 30 0 1507 Tm 41.6 0 Td 77.777778 Tz (35 ) Tj 30 0 0 30 0 1299 Tm 41.566667 0 Td 83.333333 Tz (40 ) Tj 30 0 0 30 0 1091 Tm 41.566667 0 Td 80.555556 Tz (45 ) Tj 30 0 0 30 0 883 Tm 41.6 0 Td 80.555556 Tz (50 ) Tj 30 0 0 30 0 675 Tm 41.6 0 Td 77.777778 Tz (55 ) Tj 30 0 0 30 0 467 Tm 41.633333 0 Td 77.777778 Tz (60 ) Tj 30 0 0 30 0 259 Tm 41.633333 0 Td 75 Tz (65 ) Tj 65.714286 0 0 65.714286 0 2847.333333 Tm 20.863043 0 Td 40.57971 Tz (F ) Tj 7.197826 0 Td 81.15942 Tz (Y ) Tj 31.428571 0 0 31.428571 0 2809.519608 Tm 41.427273 0 Td 164.393939 Tz (H-C-H ) Tj 14.604545 0 Td 160.151515 Tz (H-C-H ) Tj 40 0 0 40 0 2701 Tm 38.3 0 Td 53.333333 Tz (Hydrolysis ) Tj 18.571429 0 0 18.571429 0 2682.339921 Tm 82.007692 0 Td 749.358974 Tz (-> ) Tj 29.884615 0 Td 257.264957 Tz (--- ) Tj 58.571429 0 0 58.571429 0 2542.253731 Tm 23.356098 0 Td 59.756098 Tz (O ) Tj 7.887805 0 Td 130.894309 Tz (Y ) Tj 57.142857 0 0 57.142857 0 2508 Tm 32.3575 0 Td 80.208333 Tz (NH ) Tj 95 0 0 95 0 2438.150259 Tm 13.694737 0 Td 67.982456 Tz (o=-o ) Tj 6.368421 0 Td 66.666667 Tz (N ) Tj 40 0 0 40 0 2413 Tm 34.2 0 Td 87.5 Tz (O ) Tj 14.1 0 Td 58.333333 Tz (B ) Tj 31.428571 0 0 31.428571 0 2388 Tm 43.590909 0 Td 90.151515 Tz (R ) Tj 132.857143 0 0 132.857143 0 2253 Tm 11.591398 0 Td 45.16129 Tz (star ) Tj 38.571429 0 0 38.571429 0 2219 Tm 38.396296 0 Td 88.580247 Tz (CH ) Tj 40 0 0 40 0 2169.897959 Tm 43.65 0 Td 179.166667 Tz (-- ) Tj 3.225 0 Td 51.666667 Tz (Alkylation ) Tj 3.3 0 Td 58.333333 Tz (and ) Tj 1.225 0 Td 48.611111 Tz (Inactivation ) Tj 31.428571 0 0 31.428571 0 1958 Tm 47.090909 0 Td 111.363636 Tz (O ) Tj 40 0 0 40 0 1882 Tm 37.7 0 Td 59.52381 Tz (Quinone ) Tj 31.428571 0 0 31.428571 0 1858 Tm 48.013636 0 Td 74.242424 Tz (Methide ) Tj 51.428571 0 0 51.428571 0 1743.858926 Tm 26.016667 0 Td 63.734568 Tz (The ) Tj 1.322222 0 Td 46.450617 Tz (figure ) Tj 1.808333 0 Td 58.333333 Tz (above ) Tj 1.905556 0 Td 59.62963 Tz (shows ) Tj 1.944444 0 Td 66.975309 Tz (how ) Tj 1.4 0 Td 48.611111 Tz (the ) Tj 1.069444 0 Td 57.685185 Tz (mechanism-based ) Tj 5.347222 0 Td 54.012346 Tz (inhibi ) Tj 51.428571 0 0 51.428571 0 1700.320574 Tm 25.277778 0 Td 46.180556 Tz (tors ) Tj 1.263889 0 Td 46.843434 Tz (participate ) Tj 3.286111 0 Td 43.75 Tz (in ) Tj 0.719444 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 54.6875 Tz (enzyme-catalyzed ) Tj 5.425 0 Td 48.611111 Tz (reaction ) Tj 2.508333 0 Td 48.611111 Tz (to ) Tj 0.758333 0 Td 51.446759 Tz (generate ) Tj 52.857143 0 0 52.857143 0 1650.045169 Tm 24.613514 0 Td 50.45045 Tz (a ) Tj 0.586486 0 Td 46.114865 Tz (reactive ) Tj 2.478378 0 Td 48.648649 Tz (species ) Tj 2.289189 0 Td 45.720721 Tz (that ) Tj 1.362162 0 Td 44.66967 Tz (irreversibly ) Tj 3.518919 0 Td 45.004095 Tz (inactivates ) Tj 3.254054 0 Td 48.348348 Tz (the ) Tj 1.116216 0 Td 56.306306 Tz (enzyme. ) Tj 51.428571 0 0 51.428571 0 1601.142857 Tm 25.297222 0 Td 63.734568 Tz (The ) Tj 1.244444 0 Td 38.240741 Tz (first ) Tj 1.263889 0 Td 47.800926 Tz (step ) Tj 1.263889 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 49.691358 Tz (the ) Tj 0.991667 0 Td 54.890046 Tz (enzyme-catalyzed ) Tj 5.425 0 Td 47.800926 Tz (reaction ) Tj 2.430556 0 Td 38.888889 Tz (is ) Tj 0.602778 0 Td 48.611111 Tz (attack ) Tj 1.886111 0 Td 53.472222 Tz (of ) Tj 0.719444 0 Td 49.691358 Tz (the ) Tj 51.428571 0 0 51.428571 0 1555.150943 Tm 25.297222 0 Td 45.37037 Tz (catalytic ) Tj 2.566667 0 Td 51.49177 Tz (threonine ) Tj 2.897222 0 Td 59.953704 Tz (upon ) Tj 1.555556 0 Td 50.771605 Tz (the ) Tj 1.011111 0 Td 55.092593 Tz (phosphate ) Tj 3.091667 0 Td 56.388889 Tz (group ) Tj 1.847222 0 Td 53.472222 Tz (of ) Tj 0.719444 0 Td 48.611111 Tz (the ) Tj 1.030556 0 Td 45.37037 Tz (Substrate. ) Tj 51.428571 0 0 51.428571 0 1506.890084 Tm 25.297222 0 Td 55.632716 Tz (Within ) Tj 2.138889 0 Td 49.691358 Tz (the ) Tj 1.05 0 Td 46.990741 Tz (fluoro ) Tj 1.847222 0 Td 49.691358 Tz (\(or ) Tj 1.011111 0 Td 47.170782 Tz (difluoro\) ) Tj 2.722222 0 Td 54.552469 Tz (methylphenyl ) Tj 4.102778 0 Td 50.462963 Tz (leaving ) Tj 2.255556 0 Td 51.851852 Tz (group, ) Tj 2.022222 0 Td 55.092593 Tz (a ) Tj 51.428571 0 0 51.428571 0 1459.253028 Tm 25.297222 0 Td 47.395833 Tz (fluoride ) Tj 2.702778 0 Td 49.691358 Tz (ion ) Tj 1.361111 0 Td 37.268519 Tz (is ) Tj 0.875 0 Td 46.585648 Tz (ejected, ) Tj 2.663889 0 Td 51.527778 Tz (generating ) Tj 3.5 0 Td 49.691358 Tz (the ) Tj 1.341667 0 Td 46.990741 Tz (reactive ) Tj 2.683333 0 Td 56.018519 Tz (quinone ) Tj 51.428571 0 0 51.428571 0 1408.857494 Tm 25.297222 0 Td 52.256944 Tz (methide. ) Tj 2.722222 0 Td 46.990741 Tz (In ) Tj 0.738889 0 Td 49.691358 Tz (the ) Tj 1.088889 0 Td 55.632716 Tz (second ) Tj 2.158333 0 Td 44.722222 Tz (step, ) Tj 1.516667 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 55.555556 Tz (quinone ) Tj 2.547222 0 Td 55.092593 Tz (methide ) Tj 2.469444 0 Td 46.990741 Tz (reacts ) Tj 1.866667 0 Td 53.472222 Tz (with ) Tj 51.428571 0 0 51.428571 0 1360.91623 Tm 25.297222 0 Td 56.712963 Tz (an ) Tj 1.069444 0 Td 62.962963 Tz (unknown ) Tj 3.052778 0 Td 49.421296 Tz (nucleophilic ) Tj 3.908333 0 Td 60.277778 Tz (amino ) Tj 2.177778 0 Td 51.851852 Tz (acid ) Tj 1.594444 0 Td 50.771605 Tz (sidechain ) Tj 3.111111 0 Td 52.5 Tz (\(such ) Tj 1.944444 0 Td 50.231481 Tz (as ) Tj 51.428571 0 0 51.428571 0 1316.955504 Tm 25.297222 0 Td 45.37037 Tz (lysine, ) Tj 2.041667 0 Td 47.170782 Tz (arginine, ) Tj 2.702778 0 Td 44.722222 Tz (histidine, ) Tj 2.819444 0 Td 46.342593 Tz (aspartate, ) Tj 2.897222 0 Td 50.87963 Tz (glutamate, ) Tj 3.227778 0 Td 44.907407 Tz (serine, ) Tj 2.022222 0 Td 58.333333 Tz (threo ) Tj 51.428571 0 0 51.428571 0 1267.378313 Tm 25.297222 0 Td 52.662037 Tz (nine ) Tj 1.438889 0 Td 53.472222 Tz (or ) Tj 0.797222 0 Td 46.342593 Tz (cysteine\). ) Tj 2.955556 0 Td 64.814815 Tz (The ) Tj 1.361111 0 Td 45.37037 Tz (irreversible ) Tj 3.480556 0 Td 50.501543 Tz (modification ) Tj 3.830556 0 Td 59.953704 Tz (of ) Tj 0.797222 0 Td 50.771605 Tz (the ) Tj 1.069444 0 Td 48.611111 Tz (active ) Tj 51.428571 0 0 51.428571 0 1222.138018 Tm 25.316667 0 Td 41.319444 Tz (site ) Tj 1.205556 0 Td 50.636574 Tz (prevents ) Tj 2.683333 0 Td 50.555556 Tz (other ) Tj 1.730556 0 Td 47.530864 Tz (substrate ) Tj 2.838889 0 Td 53.652263 Tz (molecules ) Tj 3.15 0 Td 57.523148 Tz (from ) Tj 1.633333 0 Td 40.740741 Tz (fitting ) Tj 1.983333 0 Td 45.37037 Tz (into ) Tj 1.322222 0 Td 50.771605 Tz (the ) Tj 51.428571 0 0 51.428571 0 1177.742857 Tm 25.297222 0 Td 55.092593 Tz (reduced ) Tj 2.488889 0 Td 53.796296 Tz (space ) Tj 1.808333 0 Td 54.372428 Tz (remaining ) Tj 3.130556 0 Td 44.722222 Tz (after ) Tj 1.555556 0 Td 48.860399 Tz (modification, ) Tj 3.986111 0 Td 51.041667 Tz (thus ) Tj 1.4 0 Td 51.527778 Tz (preventing ) Tj 51.428571 0 0 51.428571 0 1130.809798 Tm 25.297222 0 Td 50.87963 Tz (generation ) Tj 3.247222 0 Td 58.333333 Tz (of ) Tj 0.816667 0 Td 71.296296 Tz (LPA ) Tj 1.458333 0 Td 58.333333 Tz (from ) Tj 1.613889 0 Td 49.691358 Tz (the ) Tj 1.108333 0 Td 46.296296 Tz (natural ) Tj 2.158333 0 Td 46.018519 Tz (substrate, ) Tj 2.975 0 Td 60.763889 Tz (LPC. ) Tj 51.428571 0 0 51.428571 0 1085.590377 Tm 26.036111 0 Td 48.611111 Tz (In ) Tj 0.738889 0 Td 44.560185 Tz (this ) Tj 1.263889 0 Td 54.62963 Tz (manner, ) Tj 2.488889 0 Td 48.611111 Tz (there ) Tj 1.652778 0 Td 37.268519 Tz (is ) Tj 0.602778 0 Td 58.333333 Tz (a ) Tj 0.525 0 Td 50.771605 Tz (strong ) Tj 1.983333 0 Td 45.664983 Tz (possibility ) Tj 3.188889 0 Td 46.990741 Tz (that ) Tj 1.302778 0 Td 54.282407 Tz (Such ) Tj 1.497222 0 Td 82.098765 Tz (com ) Tj 51.428571 0 0 51.428571 0 1041.595948 Tm 25.297222 0 Td 57.79321 Tz (pounds ) Tj 2.255556 0 Td 68.055556 Tz (may ) Tj 1.361111 0 Td 55.092593 Tz (prove ) Tj 1.769444 0 Td 51.851852 Tz (highly ) Tj 2.022222 0 Td 46.450617 Tz (effective ) Tj 2.625 0 Td 45.37037 Tz (at ) Tj 0.680556 0 Td 53.06713 Tz (reducing ) Tj 2.683333 0 Td 50.771605 Tz (the ) Tj 1.011111 0 Td 54.62963 Tz (chances ) Tj 2.469444 0 Td 56.712963 Tz (of ) Tj 51.428571 0 0 51.428571 0 996.603865 Tm 25.297222 0 Td 55.092593 Tz (a ) Tj 0.466667 0 Td 46.990741 Tz (target ) Tj 1.847222 0 Td 49.074074 Tz (Subject ) Tj 2.255556 0 Td 48.971193 Tz (incurring ) Tj 2.838889 0 Td 53.292181 Tz (cancerous ) Tj 3.033333 0 Td 55.555556 Tz (growths ) Tj 2.508333 0 Td 47.170782 Tz (typically ) Tj 2.722222 0 Td 59.41358 Tz (due ) Tj 1.225 0 Td 45.37037 Tz (to ) Tj 51.428571 0 0 51.428571 0 950.095238 Tm 25.277778 0 Td 50.771605 Tz (the ) Tj 1.069444 0 Td 53.472222 Tz (presence ) Tj 2.741667 0 Td 58.333333 Tz (of ) Tj 0.836111 0 Td 70.216049 Tz (LPA ) Tj 1.438889 0 Td 46.990741 Tz (in ) Tj 0.777778 0 Td 44.722222 Tz (their ) Tj 1.497222 0 Td 51.041667 Tz (systems. ) Tj 51.428571 0 0 51.428571 0 903.185659 Tm 26.016667 0 Td 63.734568 Tz (The ) Tj 1.380556 0 Td 49.691358 Tz (preferred ) Tj 2.955556 0 Td 62.294239 Tz (compounds ) Tj 3.636111 0 Td 47.530864 Tz (for ) Tj 1.108333 0 Td 42.12963 Tz (this ) Tj 1.283333 0 Td 50.411523 Tz (autotaxin ) Tj 2.994444 0 Td 47.260802 Tz (inactivation ) Tj 40 0 0 40 0 862 Tm 32.525 0 Td 64.583333 Tz (function ) Tj 3.375 0 Td 65.277778 Tz (are ) Tj 1.45 0 Td 66.666667 Tz (those ) Tj 2.275 0 Td 58.333333 Tz (that ) Tj 1.65 0 Td 75.595238 Tz (conform ) Tj 3.475 0 Td 60.416667 Tz (to ) Tj 1.05 0 Td 62.5 Tz (the ) Tj 1.4 0 Td 60.648148 Tz (structure ) Tj 3.575 0 Td 72.916667 Tz (of ) Tj 1.1 0 Td 74.404762 Tz (Formula ) Tj 51.428571 0 0 51.428571 0 812.474343 Tm 25.316667 0 Td 37.592593 Tz (\(II\), ) Tj 1.341667 0 Td 52.5 Tz (noted ) Tj 1.75 0 Td 51.851852 Tz (above. ) Tj 2.080556 0 Td 47.43266 Tz (Preferably, ) Tj 3.325 0 Td 51.851852 Tz (though, ) Tj 2.372222 0 Td 49.691358 Tz (the ) Tj 1.05 0 Td 47.962963 Tz (alkyl ) Tj 1.613889 0 Td 52.5 Tz (chain ) Tj 1.75 0 Td 38.888889 Tz (is ) Tj 0.738889 0 Td 53.472222 Tz (14 ) Tj 0.816667 0 Td 53.472222 Tz (or ) Tj 51.428571 0 0 51.428571 0 763.991495 Tm 25.375 0 Td 53.472222 Tz (16 ) Tj 0.797222 0 Td 53.703704 Tz (carbons ) Tj 2.430556 0 Td 43.75 Tz (in ) Tj 0.680556 0 Td 47.222222 Tz (length, ) Tj 2.158333 0 Td 54.282407 Tz (with ) Tj 1.438889 0 Td 46.990741 Tz (either ) Tj 1.827778 0 Td 47.530864 Tz (the ) Tj 1.011111 0 Td 44.290123 Tz (di- ) Tj 0.952778 0 Td 55.092593 Tz (or ) Tj 0.797222 0 Td 58.765432 Tz (mono-fluorometh ) Tj 51.428571 0 0 51.428571 0 721.414141 Tm 25.277778 0 Td 53.06713 Tz (ylphenyl ) Tj 2.741667 0 Td 56.388889 Tz (group ) Tj 1.886111 0 Td 47.395833 Tz (present. ) Tj 2.527778 0 Td 45.37037 Tz (If ) Tj 0.622222 0 Td 50.771605 Tz (the ) Tj 1.108333 0 Td 51.851852 Tz (chain ) Tj 1.769444 0 Td 40.509259 Tz (is ) Tj 0.758333 0 Td 53.472222 Tz (18 ) Tj 0.855556 0 Td 53.240741 Tz (carbons ) Tj 2.469444 0 Td 43.75 Tz (in ) Tj 0.738889 0 Td 47.222222 Tz (length, ) Tj 51.428571 0 0 51.428571 0 676.416993 Tm 25.277778 0 Td 52.662037 Tz (then ) Tj 1.555556 0 Td 34.027778 Tz (it ) Tj 0.7 0 Td 38.888889 Tz (is ) Tj 0.758333 0 Td 47.43266 Tz (preferable, ) Tj 3.422222 0 Td 56.17284 Tz (though ) Tj 2.352778 0 Td 50.771605 Tz (not ) Tj 1.205556 0 Td 47.890947 Tz (required, ) Tj 2.897222 0 Td 47.530864 Tz (for ) Tj 1.108333 0 Td 49.691358 Tz (the ) Tj 1.166667 0 Td 55.555556 Tz (pendant ) Tj 52.857143 0 0 52.857143 0 628.573653 Tm 24.613514 0 Td 54.864865 Tz (group ) Tj 1.778378 0 Td 44.144144 Tz (to ) Tj 0.662162 0 Td 56.756757 Tz (be ) Tj 0.813514 0 Td 74.887387 Tz (CFH. ) Tj 1.92973 0 Td 59.121622 Tz (Such ) Tj 1.57027 0 Td 44.932432 Tz (specific ) Tj 2.289189 0 Td 60.26026 Tz (compounds ) Tj 3.386486 0 Td 55.18018 Tz (have ) Tj 1.437838 0 Td 55.968468 Tz (been ) Tj 1.494595 0 Td 54.864865 Tz (found ) Tj 51.428571 0 0 51.428571 0 582.455726 Tm 25.277778 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 52.314815 Tz (provide ) Tj 2.352778 0 Td 48.611111 Tz (the ) Tj 1.011111 0 Td 59.143519 Tz (most ) Tj 1.536111 0 Td 46.450617 Tz (effective ) Tj 2.625 0 Td 50.05144 Tz (autotaxin ) Tj 2.858333 0 Td 46.720679 Tz (inactivation ) Tj 3.519444 0 Td 47.638889 Tz (capability ) Tj 51.428571 0 0 51.428571 0 536.467097 Tm 25.297222 0 Td 44.907407 Tz (results ) Tj 2.158333 0 Td 60.493827 Tz (and ) Tj 1.361111 0 Td 49.421296 Tz (thus ) Tj 1.477778 0 Td 49.691358 Tz (the ) Tj 1.147222 0 Td 47.800926 Tz (greatest ) Tj 2.566667 0 Td 56.018519 Tz (promise ) Tj 2.625 0 Td 45.37037 Tz (in ) Tj 0.875 0 Td 52.5 Tz (terms ) Tj 1.847222 0 Td 59.953704 Tz (of ) Tj 0.894444 0 Td 46.8107 Tz (effective ) Tj 51.428571 0 0 51.428571 0 491.014218 Tm 25.297222 0 Td 53.472222 Tz (cancer ) Tj 2.061111 0 Td 51.527778 Tz (prevention ) Tj 3.286111 0 Td 48.316498 Tz (treatments. ) Tj 51.428571 0 0 51.428571 0 447.694789 Tm 26.016667 0 Td 58.333333 Tz (These ) Tj 1.886111 0 Td 61.574074 Tz (compounds ) Tj 3.480556 0 Td 66.975309 Tz (may ) Tj 1.341667 0 Td 58.333333 Tz (be ) Tj 0.797222 0 Td 52.662037 Tz (included ) Tj 2.625 0 Td 46.990741 Tz (in ) Tj 0.7 0 Td 51.851852 Tz (a ) Tj 0.427778 0 Td 54.79798 Tz (composition ) Tj 3.733333 0 Td 51.851852 Tz (of ) Tj 0.7 0 Td 58.333333 Tz (any ) Tj 51.428571 0 0 51.428571 0 401.601685 Tm 25.277778 0 Td 53.472222 Tz (type ) Tj 1.438889 0 Td 46.180556 Tz (that ) Tj 1.263889 0 Td 38.888889 Tz (is ) Tj 0.641667 0 Td 51.851852 Tz (introduced ) Tj 3.286111 0 Td 50.771605 Tz (within ) Tj 1.983333 0 Td 58.333333 Tz (a ) Tj 0.486111 0 Td 46.8107 Tz (patients ) Tj 2.683333 0 Td 60.763889 Tz (body ) Tj 1.652778 0 Td 47.916667 Tz (intravenously, ) Tj 51.428571 0 0 51.428571 0 357.522822 Tm 25.297222 0 Td 51.041667 Tz (and, ) Tj 1.438889 0 Td 42.12963 Tz (if ) Tj 0.583333 0 Td 47.530864 Tz (possible, ) Tj 2.761111 0 Td 53.703704 Tz (through ) Tj 2.45 0 Td 46.990741 Tz (ingestion. ) Tj 51.428571 0 0 51.428571 0 308.515994 Tm 26.036111 0 Td 48.611111 Tz (In ) Tj 0.894444 0 Td 53.796296 Tz (terms ) Tj 1.925 0 Td 56.712963 Tz (of ) Tj 0.894444 0 Td 49.691358 Tz (the ) Tj 1.205556 0 Td 57.523148 Tz (form ) Tj 1.730556 0 Td 54.282407 Tz (Such ) Tj 1.613889 0 Td 53.742284 Tz (compositions ) Tj 4.2 0 Td 68.055556 Tz (may ) Tj 1.536111 0 Td 46.018519 Tz (take, ) Tj 1.672222 0 Td 58.333333 Tz (any ) Tj 51.428571 0 0 51.428571 0 263.568627 Tm 25.297222 0 Td 46.990741 Tz (orally ) Tj 1.886111 0 Td 47.314815 Tz (ingestible ) Tj 3.033333 0 Td 56.712963 Tz (form ) Tj 1.594444 0 Td 37.268519 Tz (is ) Tj 0.641667 0 Td 47.170782 Tz (possible. ) Tj 2.741667 0 Td 52.662037 Tz (This ) Tj 1.477778 0 Td 37.268519 Tz (list ) Tj 1.069444 0 Td 48.251029 Tz (includes, ) Tj 2.819444 0 Td 52.777778 Tz (without ) Tj 51.428571 0 0 51.428571 0 217.34 Tm 25.297222 0 Td 45.37037 Tz (limitation, ) Tj 3.325 0 Td 44.965278 Tz (liquids, ) Tj 2.488889 0 Td 46.990741 Tz (liquid ) Tj 2.002778 0 Td 48.971193 Tz (capsules, ) Tj 2.936111 0 Td 43.75 Tz (tablets, ) Tj 2.430556 0 Td 52.391975 Tz (coated ) Tj 2.177778 0 Td 43.344907 Tz (tablets, ) Tj 51.428571 0 0 51.428571 0 169.218863 Tm 25.297222 0 Td 46.990741 Tz (minitablets, ) Tj 3.558333 0 Td 51.041667 Tz (capsules ) Tj 2.625 0 Td 52.662037 Tz (with ) Tj 1.438889 0 Td 47.962963 Tz (individual ) Tj 3.052778 0 Td 50.771605 Tz (beads, ) Tj 1.944444 0 Td 60.493827 Tz (and ) Tj 1.225 0 Td 49.691358 Tz (the ) Tj 1.05 0 Td 40.185185 Tz (like. ) Tj 1.419444 0 Td 42.12963 Tz (If ) Tj 0.583333 0 Td 48.611111 Tz (in ) Tj ET Q endstream endobj 178 0 obj << /Length 1 >> stream q endstream endobj 179 0 obj << /Length 16201 >> stream Q q 0.24 0 0 0.24 0 0 cm BT /F1 1 Tf 3 Tr 62.857143 0 0 62.857143 0 3023 Tm 17.325 0 Td 83.522727 Tz (US ) Tj 1.240909 0 Td 58.333333 Tz (8,022,239 ) Tj 3.388636 0 Td 74.242424 Tz (B2 ) Tj 51.428571 0 0 51.428571 0 2968 Tm 14.875 0 Td 74.537037 Tz (5 ) Tj 51.428571 0 0 51.428571 0 2915.606742 Tm 6.358333 0 Td 52.932099 Tz (coated ) Tj 2.138889 0 Td 45.37037 Tz (tablet ) Tj 1.866667 0 Td 52.5 Tz (form, ) Tj 1.827778 0 Td 54.282407 Tz (such ) Tj 1.575 0 Td 53.472222 Tz (compositions ) Tj 4.122222 0 Td 68.055556 Tz (may ) Tj 1.458333 0 Td 58.333333 Tz (be ) Tj 0.952778 0 Td 55.092593 Tz (of ) Tj 0.836111 0 Td 50.411523 Tz (Sustained ) Tj 51.428571 0 0 51.428571 0 2872.764497 Tm 6.358333 0 Td 48.148148 Tz (release ) Tj 2.138889 0 Td 47.314815 Tz (type, ) Tj 1.536111 0 Td 59.41358 Tz (and ) Tj 1.186111 0 Td 68.055556 Tz (may ) Tj 1.361111 0 Td 50.925926 Tz (include ) Tj 2.255556 0 Td 55.092593 Tz (a ) Tj 0.447222 0 Td 53.796296 Tz (water ) Tj 1.711111 0 Td 49.331276 Tz (insoluble ) Tj 2.780556 0 Td 50.771605 Tz (but ) Tj 1.030556 0 Td 56.17284 Tz (permeable ) Tj 51.428571 0 0 51.428571 0 2830.831788 Tm 6.358333 0 Td 47.800926 Tz (film ) Tj 1.536111 0 Td 50.925926 Tz (coating ) Tj 2.508333 0 Td 53.030303 Tz (Surrounding ) Tj 3.85 0 Td 55.092593 Tz (a ) Tj 0.661111 0 Td 52.662037 Tz (core ) Tj 1.594444 0 Td 45.910494 Tz (tablet ) Tj 1.983333 0 Td 59.41358 Tz (and ) Tj 1.380556 0 Td 58.333333 Tz (a ) Tj 0.7 0 Td 44.830247 Tz (particulate, ) Tj 51.428571 0 0 51.428571 0 2785.352941 Tm 6.338889 0 Td 49.305556 Tz (water-soluble, ) Tj 4.433333 0 Td 54.282407 Tz (pore-forming ) Tj 4.258333 0 Td 48.611111 Tz (material ) Tj 2.683333 0 Td 50.771605 Tz (dispersed ) Tj 3.052778 0 Td 51.311728 Tz (within ) Tj 2.177778 0 Td 49.691358 Tz (the ) Tj 51.428571 0 0 51.428571 0 2743.523409 Tm 6.358333 0 Td 47.800926 Tz (film ) Tj 1.302778 0 Td 47.800926 Tz (coating. ) Tj 2.45 0 Td 59.143519 Tz (Such ) Tj 1.555556 0 Td 51.851852 Tz (a ) Tj 0.447222 0 Td 55.092593 Tz (system ) Tj 2.138889 0 Td 50.231481 Tz (thus ) Tj 1.341667 0 Td 51.851852 Tz (provides ) Tj 2.605556 0 Td 56.712963 Tz (an ) Tj 0.836111 0 Td 54.166667 Tz (osmotic ) Tj 2.411111 0 Td 49.826389 Tz (gradient ) Tj 51.428571 0 0 51.428571 0 2699.462455 Tm 6.358333 0 Td 58.333333 Tz (and ) Tj 1.225 0 Td 53.703704 Tz (channel ) Tj 2.430556 0 Td 56.018519 Tz (forming ) Tj 2.508333 0 Td 51.851852 Tz (system. ) Tj 2.352778 0 Td 51.388889 Tz (Typical ) Tj 2.352778 0 Td 50.231481 Tz (coatings ) Tj 2.566667 0 Td 56.712963 Tz (have ) Tj 1.516667 0 Td 53.06713 Tz (included ) Tj 51.428571 0 0 51.428571 0 2656.271028 Tm 6.358333 0 Td 55.092593 Tz (carnauba ) Tj 2.780556 0 Td 57.523148 Tz (wax, ) Tj 1.555556 0 Td 49.826389 Tz (cysteine ) Tj 2.527778 0 Td 50.694444 Tz (hydrochloride, ) Tj 4.413889 0 Td 55.34188 Tz (hydroxypropyl ) Tj 4.530556 0 Td 68.865741 Tz (meth ) Tj 51.428571 0 0 51.428571 0 2611.519527 Tm 6.338889 0 Td 46.450617 Tz (ylcellulose, ) Tj 3.597222 0 Td 61.213992 Tz (magnesium ) Tj 3.577778 0 Td 43.930041 Tz (Stearate, ) Tj 2.644444 0 Td 48.813657 Tz (microcrystalline ) Tj 4.919444 0 Td 45.37037 Tz (cellulose, ) Tj 51.428571 0 0 51.428571 0 2564.320191 Tm 6.358333 0 Td 52.391975 Tz (polyethylene ) Tj 3.927778 0 Td 50.231481 Tz (glycol ) Tj 2.022222 0 Td 59.41358 Tz (and ) Tj 1.263889 0 Td 49.826389 Tz (titanium ) Tj 2.625 0 Td 48.611111 Tz (dioxide. ) Tj 2.547222 0 Td 56.388889 Tz (Other ) Tj 1.866667 0 Td 48.611111 Tz (therapeutic ) Tj 52.857143 0 0 52.857143 0 2968 Tm 32.9 0 Td 69.369369 Tz (6 ) Tj 51.428571 0 0 51.428571 0 2918.419036 Tm 25.297222 0 Td 51.49177 Tz (precursor ) Tj 2.994444 0 Td 45.910494 Tz (reacts ) Tj 1.886111 0 Td 52.662037 Tz (with ) Tj 1.536111 0 Td 53.472222 Tz (cyanoethanol ) Tj 4.083333 0 Td 45.37037 Tz (in ) Tj 0.758333 0 Td 50.771605 Tz (the ) Tj 1.127778 0 Td 53.06713 Tz (presence ) Tj 2.761111 0 Td 58.333333 Tz (of ) Tj 0.836111 0 Td 61.574074 Tz (dicy ) Tj 51.428571 0 0 51.428571 0 2869.609844 Tm 25.297222 0 Td 51.851852 Tz (clohexyl ) Tj 2.741667 0 Td 53.472222 Tz (carbodiimide ) Tj 4.122222 0 Td 65.462963 Tz (\(DCC\) ) Tj 2.216667 0 Td 58.333333 Tz (and ) Tj 1.302778 0 Td 53.877315 Tz (dimethyl ) Tj 2.838889 0 Td 54.594017 Tz (aminopyridine ) Tj 51.428571 0 0 51.428571 0 2821.505402 Tm 25.316667 0 Td 71.83642 Tz (\(DMAP\) ) Tj 2.741667 0 Td 43.75 Tz (to ) Tj 0.680556 0 Td 51.851852 Tz (generate ) Tj 2.644444 0 Td 51.851852 Tz (a ) Tj 0.466667 0 Td 48.003472 Tz (phosphotriester, ) Tj 4.822222 0 Td 56.17284 Tz (needed ) Tj 2.177778 0 Td 49.691358 Tz (for ) Tj 1.011111 0 Td 50.771605 Tz (the ) Tj 1.05 0 Td 61.574074 Tz (subse ) Tj 51.428571 0 0 51.428571 0 2774.471483 Tm 25.297222 0 Td 54.444444 Tz (quent ) Tj 1.944444 0 Td 46.720679 Tz (fluorination ) Tj 3.694444 0 Td 58.333333 Tz (of ) Tj 0.913889 0 Td 50.771605 Tz (the ) Tj 1.205556 0 Td 51.58179 Tz (intermediary ) Tj 4.044444 0 Td 59.773663 Tz (compound. ) Tj 3.558333 0 Td 60.763889 Tz (Such ) Tj 1.769444 0 Td 55.092593 Tz (a ) Tj 51.428571 0 0 51.428571 0 2727.022556 Tm 25.277778 0 Td 51.851852 Tz (two-step ) Tj 2.741667 0 Td 51.851852 Tz (process ) Tj 2.391667 0 Td 55.092593 Tz (has ) Tj 1.225 0 Td 55.632716 Tz (proved ) Tj 2.216667 0 Td 46.990741 Tz (to ) Tj 0.777778 0 Td 59.953704 Tz (be ) Tj 0.952778 0 Td 48.611111 Tz (excellent ) Tj 2.838889 0 Td 45.37037 Tz (at ) Tj 0.738889 0 Td 51.203704 Tz (permitting ) Tj 3.286111 0 Td 55.092593 Tz (a ) Tj 51.428571 0 0 51.428571 0 2680.269468 Tm 25.316667 0 Td 48.287037 Tz (simplified ) Tj 3.15 0 Td 46.450617 Tz (purification ) Tj 3.616667 0 Td 54.372428 Tz (procedure ) Tj 3.227778 0 Td 48.611111 Tz (for ) Tj 1.108333 0 Td 49.691358 Tz (the ) Tj 1.147222 0 Td 52.5 Tz (production ) Tj 3.402778 0 Td 59.953704 Tz (of ) Tj 0.894444 0 Td 50.771605 Tz (the ) Tj 51.428571 0 0 51.428571 0 2632.988848 Tm 25.297222 0 Td 51.311728 Tz (intermediary ) Tj 4.316667 0 Td 51.557239 Tz (cyanoethanol-protected ) Tj 7.369444 0 Td 47.222222 Tz (diester ) Tj 2.547222 0 Td 59.41358 Tz (compound, ) Tj 51.428571 0 0 51.428571 0 2582.215311 Tm 25.277778 0 Td 51.851852 Tz (thereby ) Tj 2.352778 0 Td 50.87963 Tz (permitting ) Tj 3.266667 0 Td 60.763889 Tz (more ) Tj 1.613889 0 Td 46.8107 Tz (effective ) Tj 2.702778 0 Td 42.534722 Tz (triester ) Tj 2.197222 0 Td 52.211934 Tz (formation ) Tj 3.033333 0 Td 48.611111 Tz (for ) Tj 1.030556 0 Td 54.282407 Tz (easy ) Tj 52.063492 0 0 52.063492 0 2524.467879 Tm 6.280793 0 Td 50.685976 Tz (agents ) Tj 2.016768 0 Td 67.22561 Tz (may ) Tj 1.382927 0 Td 57.621951 Tz (be ) Tj 0.864329 0 Td 51.219512 Tz (included ) Tj 2.612195 0 Td 52.820122 Tz (with ) Tj 1.440549 0 Td 49.939024 Tz (these ) Tj 1.651829 0 Td 49.618902 Tz (anticancer ) Tj 3.111585 0 Td 50.685976 Tz (agents ) Tj 1.997561 0 Td 49.618902 Tz (as ) Tj 0.7875 0 Td 45.457317 Tz (well, ) Tj 1.86311 0 Td 43.216463 Tz (10 ) Tj 0.99878 0 Td 46.150915 Tz (fluorination ) Tj 3.610976 0 Td 45.617378 Tz (thereof. ) Tj 2.496951 0 Td 58.422256 Tz (Such ) Tj 1.709451 0 Td 45.884146 Tz (fluorination ) Tj 3.610976 0 Td 38.414634 Tz (is ) Tj 0.749085 0 Td 49.085366 Tz (generally ) Tj 2.919512 0 Td 71.067073 Tz (accom ) Tj 51.428571 0 0 51.428571 0 2478.389056 Tm 6.358333 0 Td 50.231481 Tz (as ) Tj 0.738889 0 Td 54.282407 Tz (long ) Tj 1.419444 0 Td 48.611111 Tz (as ) Tj 0.758333 0 Td 48.148148 Tz (neither ) Tj 2.119444 0 Td 45.694444 Tz (interferes ) Tj 2.897222 0 Td 52.662037 Tz (with ) Tj 1.380556 0 Td 49.691358 Tz (the ) Tj 1.030556 0 Td 47.863248 Tz (effectiveness ) Tj 3.869444 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 48.611111 Tz (the ) Tj 0.972222 0 Td 51.851852 Tz (other ) Tj 2.994444 0 Td 50 Tz (plished ) Tj 2.333333 0 Td 53.703704 Tz (through ) Tj 2.508333 0 Td 49.691358 Tz (the ) Tj 1.166667 0 Td 47.395833 Tz (reaction ) Tj 2.547222 0 Td 56.712963 Tz (of ) Tj 0.836111 0 Td 46.990741 Tz (either ) Tj 1.886111 0 Td 51.527778 Tz (bis\(2-methoxyethyl\)- ) Tj 51.428571 0 0 51.428571 0 2433.421949 Tm 6.358333 0 Td 45.37037 Tz (in ) Tj 0.758333 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 47.530864 Tz (user's ) Tj 1.905556 0 Td 52.5 Tz (body. ) Tj 15.225 0 Td 46.990741 Tz (sulfur ) Tj 1.944444 0 Td 43.897306 Tz (trifluoride ) Tj 3.169444 0 Td 40.509259 Tz (\(e.g., ) Tj 1.75 0 Td 75.035613 Tz (DEOXO-FLUORTM ) Tj 6.125 0 Td 56.712963 Tz (from ) Tj 1.633333 0 Td 52.932099 Tz (Air ) Tj 1.205556 0 Td 67.24537 Tz (Prod ) Tj 51.428571 0 0 51.428571 0 2384.48908 Tm 7.097222 0 Td 62.654321 Tz (The ) Tj 1.361111 0 Td 50.925926 Tz (general ) Tj 2.391667 0 Td 60.493827 Tz (method ) Tj 2.391667 0 Td 59.953704 Tz (of ) Tj 0.855556 0 Td 52.175926 Tz (production ) Tj 3.383333 0 Td 59.953704 Tz (of ) Tj 0.875 0 Td 48.611111 Tz (the ) Tj 1.108333 0 Td 48.971193 Tz (inventive ) Tj 2.858333 0 Td 62.384259 Tz (com- ) Tj 2.955556 0 Td 49.421296 Tz (ucts ) Tj 1.633333 0 Td 58.333333 Tz (and ) Tj 1.477778 0 Td 54.444444 Tz (Chemicals, ) Tj 3.752778 0 Td 44.722222 Tz (Inc.\) ) Tj 1.769444 0 Td 45.37037 Tz (to ) Tj 0.991667 0 Td 49.151235 Tz (create ) Tj 2.197222 0 Td 49.691358 Tz (the ) Tj 1.361111 0 Td 51.157407 Tz (difluoromethyl ) Tj 62.857143 0 0 62.857143 0 2335.607832 Tm 5.186364 0 Td 48.169192 Tz (pounds ) Tj 1.893182 0 Td 41.098485 Tz (involves ) Tj 2.1 0 Td 49.05303 Tz (an ) Tj 0.747727 0 Td 32.575758 Tz (initial ) Tj 1.511364 0 Td 42.159091 Tz (generation ) Tj 2.656818 0 Td 47.727273 Tz (of ) Tj 0.684091 0 Td 45.296717 Tz (benzaldehyde ) Tj 3.372727 0 Td 45.075758 Tz (phos- ) Tj 1.75 0 Td 35.795455 Tz (15 ) Tj 0.811364 0 Td 48.905724 Tz (compound, ) Tj 2.752273 0 Td 44.781145 Tz (Orthrough ) Tj 2.545455 0 Td 40.656566 Tz (the ) Tj 0.843182 0 Td 32.575758 Tz (initial ) Tj 1.479545 0 Td 40.951178 Tz (reduction ) Tj 2.354545 0 Td 43.087121 Tz (with ) Tj 1.161364 0 Td 47.727273 Tz (sodium ) Tj 1.845455 0 Td 53.693182 Tz (boro ) Tj 51.428571 0 0 51.428571 0 2293.352353 Tm 6.358333 0 Td 51.203704 Tz (phodiester ) Tj 3.227778 0 Td 53.240741 Tz (through ) Tj 2.430556 0 Td 50.771605 Tz (the ) Tj 1.088889 0 Td 48.611111 Tz (reaction ) Tj 2.547222 0 Td 56.712963 Tz (of ) Tj 0.797222 0 Td 55.976431 Tz (phosphorous ) Tj 3.927778 0 Td 52.441077 Tz (oxychloride ) Tj 4.9 0 Td 53.240741 Tz (hydride ) Tj 2.352778 0 Td 53.472222 Tz (with ) Tj 1.419444 0 Td 54.12037 Tz (subsequent ) Tj 3.383333 0 Td 46.720679 Tz (fluorination ) Tj 3.519444 0 Td 52.662037 Tz (with ) Tj 1.438889 0 Td 54.768519 Tz (Deoxofluor ) Tj 3.383333 0 Td 66.111111 Tz (togen ) Tj 52.232143 0 0 52.232143 0 2245.453237 Tm 6.241368 0 Td 53.447293 Tz (with ) Tj 1.474188 0 Td 57.435897 Tz (a ) Tj 0.574359 0 Td 53.447293 Tz (long ) Tj 1.455043 0 Td 51.692308 Tz (chain ) Tj 1.742222 0 Td 50.598291 Tz (alcohol ) Tj 2.335726 0 Td 61.823362 Tz (\(Co-Cs\), ) Tj 3.158974 0 Td 58.499525 Tz (and ) Tj 1.244444 0 Td 51.851852 Tz (subsequently ) Tj 3.982222 0 Td 53.447293 Tz (with ) Tj 2.699487 0 Td 46.586895 Tz (erate ) Tj 1.512479 0 Td 49.990503 Tz (the ) Tj 1.091282 0 Td 54.843305 Tz (monofluoromethyl ) Tj 5.45641 0 Td 58.499525 Tz (compound. ) Tj 3.292991 0 Td 63.817664 Tz (The ) Tj 1.26359 0 Td 50.598291 Tz (general ) Tj 2.278291 0 Td 48.262108 Tz (reaction ) Tj 48.888889 0 0 48.888889 0 2199.274633 Tm 6.688636 0 Td 57.179752 Tz (p-hydroxybenzaldehyde, ) Tj 7.854545 0 Td 62.5 Tz (and ) Tj 1.390909 0 Td 45.454545 Tz (lastly ) Tj 1.963636 0 Td 55.397727 Tz (with ) Tj 1.656818 0 Td 49.431818 Tz (water. ) Tj 2.065909 0 Td 57.102273 Tz (This ) Tj 1.656818 0 Td 42.37013 Tz (initial ) Tj 3.354545 0 Td 63.636364 Tz (scheme ) Tj 2.475 0 Td 36.363636 Tz (is: ) Tj 31.428571 0 0 31.428571 0 2035.5 Tm 52.5 0 Td 111.363636 Tz (O ) Tj 11.645455 0 Td 111.363636 Tz (O ) Tj 31.428571 0 0 31.428571 0 1984 Tm 40.759091 0 Td 111.363636 Tz (O ) Tj 31.428571 0 0 31.428571 0 1973.400763 Tm 19.409091 0 Td 111.363636 Tz (O ) Tj 9.640909 0 Td 111.363636 Tz (O ) Tj 32.995455 0 Td 166.666667 Tz (O-P-O-R ) Tj 69.52381 0 0 69.52381 0 1919.736979 Tm 8.831507 0 Td 31.164384 Tz (| ) Tj 2.114384 0 Td 69.520548 Tz (--- ) Tj 6.50137 0 Td 88.69863 Tz (o0-R ) Tj 4.099315 0 Td 69.520548 Tz (- ) Tj 0.949315 0 Td 52.739726 Tz (- ) Tj 1.294521 0 Td 26.369863 Tz (- ) Tj 59.52381 0 0 59.52381 0 1876.056338 Tm 9.072 0 Td 88.2 Tz (C1 ) Tj 1.5456 0 Td 81.2 Tz (Ne ) Tj 23.2512 0 Td 58.8 Tz (O ) Tj 31.428571 0 0 31.428571 0 1860 Tm 29.113636 0 Td 106.060606 Tz (H ) Tj 41.428571 0 0 41.428571 0 1839.5 Tm 14.748276 0 Td 84.482759 Tz (C ) Tj 16.172414 0 Td 84.482759 Tz (O ) Tj 21.428571 0 0 21.428571 0 1823 Tm 73.686667 0 Td 85.555556 Tz (e ) Tj 68.571429 0 0 68.571429 0 1773 Tm 23.041667 0 Td 102.083333 Tz (/ ) Tj 8.064583 0 Td 49.826389 Tz (CN ) Tj 31.428571 0 0 31.428571 0 1581 Tm 32.931818 0 Td 100.757576 Tz (H ) Tj 2.1 0 Td 108.712121 Tz (OH ) Tj 17.786364 0 Td 84.848485 Tz (F ) Tj 2.195455 0 Td 74.242424 Tz (F ) Tj 61.428571 0 0 61.428571 0 1503.764151 Tm 21.716279 0 Td 85.658915 Tz (O-P-O-R ) Tj 10.14186 0 Td 91.795866 Tz (o-i-o- ) Tj 46.785714 0 0 46.785714 0 1462.294872 Tm 22.122137 0 Td 71.246819 Tz (H ) Tj 7.844275 0 Td 60.559796 Tz (l ) Tj 5.49313 0 Td 71.246819 Tz (H ) Tj 7.801527 0 Td 74.80916 Tz (O ) Tj 56.190476 0 0 56.190476 0 1306.8125 Tm 24.559322 0 Td 130.508475 Tz (/ ) Tj 2.438136 0 Td 62.288136 Tz (CN ) Tj 11.087288 0 Td 62.288136 Tz (CN ) Tj 31.428571 0 0 31.428571 0 1106.841463 Tm 30.640909 0 Td 90.151515 Tz (H ) Tj 2.195455 0 Td 74.242424 Tz (F ) Tj 19.059091 0 Td 84.848485 Tz (F ) Tj 2.195455 0 Td 74.242424 Tz (F ) Tj 9.386364 0 Td 111.363636 Tz (O ) Tj 91.428571 0 0 91.428571 0 1026.926829 Tm 13.78125 0 Td 62.586806 Tz (o-i-o- ) Tj 7.30625 0 Td 74.375 Tz (o--o- ) Tj 68.571429 0 0 68.571429 0 829.406977 Tm 17.325 0 Td 109.375 Tz (7 ) Tj 3.747917 0 Td 49.826389 Tz (CN ) Tj 31.428571 0 0 31.428571 0 697 Tm 27.745455 0 Td 90.151515 Tz (H ) Tj 2.195455 0 Td 74.242424 Tz (F ) Tj 31.428571 0 0 31.428571 0 639 Tm 37.195455 0 Td 167.424242 Tz (O-P-O-R ) Tj 31.428571 0 0 31.428571 0 581 Tm 27.713636 0 Td 106.060606 Tz (H ) Tj 34.285714 0 0 34.285714 0 435.304038 Tm 15.75 0 Td 43.75 Tz (\(a\) ) Tj 0.9625 0 Td 54.79798 Tz (4-hydroxybenzaldehyde, ) Tj 7.379167 0 Td 117.881944 Tz (ROH, ) Tj 3.0625 0 Td 66.840278 Tz (THF, ) Tj 1.8375 0 Td 38.888889 Tz (1 ) Tj 0.495833 0 Td 51.041667 Tz (hr ) Tj 0.816667 0 Td 45.37037 Tz (\(b\) ) Tj 0.991667 0 Td 70.486111 Tz (DCC, ) Tj 1.895833 0 Td 75.833333 Tz (DMAP, ) Tj 2.45 0 Td 52.350427 Tz (cyanoethanol, ) Tj 4.316667 0 Td 56.944444 Tz (CH2Cl2, ) Tj 34.285714 0 0 34.285714 0 400.771218 Tm 15.779167 0 Td 60.763889 Tz (H2O, ) Tj 1.6625 0 Td 58.333333 Tz (3 ) Tj 0.525 0 Td 55.902778 Tz (days ) Tj 1.516667 0 Td 45.37037 Tz (\(c\) ) Tj 1.020833 0 Td 53.472222 Tz (Deoxofluor, ) Tj 3.704167 0 Td 48.611111 Tz (ethanol, ) Tj 2.479167 0 Td 58.333333 Tz (CH2Cl2, ) Tj 2.683333 0 Td 55.902778 Tz (16 ) Tj 0.845833 0 Td 51.851852 Tz (hrs ) Tj 1.108333 0 Td 46.990741 Tz (\(d\) ) Tj 1.05 0 Td 52.777778 Tz (n-propylamine, ) Tj 4.6375 0 Td 48.611111 Tz (pyridine, ) Tj 2.858333 0 Td 55.902778 Tz (10 ) Tj 0.904167 0 Td 52.256944 Tz (min, ) Tj 34.285714 0 0 34.285714 0 370.622754 Tm 15.75 0 Td 43.75 Tz (\(e\) ) Tj 0.9625 0 Td 64.814815 Tz (NaBH4, ) Tj 2.566667 0 Td 60.763889 Tz (H2O, ) Tj 1.633333 0 Td 64.409722 Tz (THF, ) Tj 1.779167 0 Td 55.902778 Tz (20 ) Tj 0.904167 0 Td 52.256944 Tz (min, ) Tj 1.4875 0 Td 38.888889 Tz (\(f\) ) Tj 0.904167 0 Td 53.472222 Tz (Deoxofluor, ) Tj 3.733333 0 Td 57.638889 Tz (CH2Cl2, ) Tj 2.654167 0 Td 58.333333 Tz (12hrs ) Tj 1.954167 0 Td 45.37037 Tz (\(g\) ) Tj 1.05 0 Td 53.125 Tz (n-propylamine, ) Tj 4.6375 0 Td 48.611111 Tz (pyridine, ) Tj 27.142857 0 0 27.142857 0 344 Tm 19.968421 0 Td 67.54386 Tz (10 ) Tj 1.068421 0 Td 67.54386 Tz (min. ) Tj 34.285714 0 0 34.285714 0 311.886016 Tm 15.75 0 Td 50.555556 Tz (\(with ) Tj 1.720833 0 Td 47.222222 Tz (further ) Tj 2.158333 0 Td 51.851852 Tz (confirmation ) Tj 3.9375 0 Td 58.333333 Tz (of ) Tj 0.7875 0 Td 64.409722 Tz (compound ) Tj 3.2375 0 Td 48.125 Tz (structures ) Tj 3.033333 0 Td 54.166667 Tz (through ) Tj 2.508333 0 Td 59.548611 Tz (mass ) Tj 1.604167 0 Td 51.228632 Tz (spectrometric ) Tj 4.170833 0 Td 59.953704 Tz (and ) Tj 1.283333 0 Td 50.694444 Tz (nuclear ) Tj 34.285714 0 0 34.285714 0 283.815166 Tm 15.720833 0 Td 55.902778 Tz (magnetic ) Tj 2.858333 0 Td 54.012346 Tz (resonance ) Tj 3.120833 0 Td 50.854701 Tz (spectroscopic ) Tj 4.141667 0 Td 45.694444 Tz (analysis\), ) Tj ET Q endstream endobj 180 0 obj << /Length 1 >> stream q endstream endobj 181 0 obj << /Length 40115 >> stream Q q 0.24 0 0 0.24 0 0 cm BT /F1 1 Tf 3 Tr 62.857143 0 0 62.857143 0 3023 Tm 17.325 0 Td 83.522727 Tz (US ) Tj 1.240909 0 Td 58.333333 Tz (8,022,239 ) Tj 3.388636 0 Td 74.242424 Tz (B2 ) Tj 51.428571 0 0 51.428571 0 2968 Tm 14.875 0 Td 77.777778 Tz (7 ) Tj 51.428571 0 0 51.428571 0 2915.866995 Tm 7.116667 0 Td 54.62963 Tz (Interms ) Tj 2.45 0 Td 53.472222 Tz (of ) Tj 0.719444 0 Td 48.611111 Tz (reacting ) Tj 2.45 0 Td 49.907407 Tz (these ) Tj 1.633333 0 Td 51.851852 Tz (novel ) Tj 1.711111 0 Td 61.574074 Tz (compounds ) Tj 3.461111 0 Td 52.662037 Tz (with ) Tj 1.380556 0 Td 47.962963 Tz (autotaxin, ) Tj 51.428571 0 0 51.428571 0 2873.61834 Tm 6.338889 0 Td 51.851852 Tz (they ) Tj 1.477778 0 Td 47.314815 Tz (react ) Tj 1.633333 0 Td 59.953704 Tz (upon ) Tj 1.711111 0 Td 56.17284 Tz (mixing ) Tj 2.236111 0 Td 52.662037 Tz (with ) Tj 1.477778 0 Td 50.411523 Tz (autotaxin ) Tj 2.936111 0 Td 46.990741 Tz (in ) Tj 0.777778 0 Td 56.944444 Tz (aqueous ) Tj 2.605556 0 Td 48.611111 Tz (solutions ) Tj 51.428571 0 0 51.428571 0 2826.782816 Tm 6.377778 0 Td 54.282407 Tz (such ) Tj 1.438889 0 Td 48.611111 Tz (as ) Tj 0.719444 0 Td 53.148148 Tz (assay ) Tj 1.711111 0 Td 48.611111 Tz (buffer ) Tj 1.866667 0 Td 51.851852 Tz (or ) Tj 0.719444 0 Td 50.231481 Tz (blood. ) Tj 1.925 0 Td 63.734568 Tz (The ) Tj 1.302778 0 Td 57.118056 Tz (measured ) Tj 2.897222 0 Td 46.666667 Tz (inhibition ) Tj 2.955556 0 Td 54.012346 Tz (should ) Tj 51.428571 0 0 51.428571 0 2786.640605 Tm 6.358333 0 Td 49.826389 Tz (increase ) Tj 2.761111 0 Td 59.143519 Tz (upon ) Tj 1.788889 0 Td 51.353276 Tz (preincubation ) Tj 4.316667 0 Td 55.092593 Tz (time ) Tj 1.691667 0 Td 46.018519 Tz (\(inhibitor ) Tj 3.072222 0 Td 51.041667 Tz (plus ) Tj 1.555556 0 Td 63.734568 Tz (enzyme ) Tj 51.428571 0 0 51.428571 0 2742.347447 Tm 6.358333 0 Td 50.231481 Tz (alone\) ) Tj 2.041667 0 Td 48.611111 Tz (prior ) Tj 1.672222 0 Td 46.990741 Tz (to ) Tj 0.797222 0 Td 49.421296 Tz (addition ) Tj 2.644444 0 Td 56.712963 Tz (of ) Tj 0.836111 0 Td 46.018519 Tz (substrate, ) Tj 3.013889 0 Td 51.388889 Tz (thereby ) Tj 2.430556 0 Td 48.611111 Tz (indicating ) Tj 3.15 0 Td 49.691358 Tz (the ) Tj 51.428571 0 0 51.428571 0 2696.997516 Tm 6.358333 0 Td 50.771605 Tz (reduction ) Tj 2.936111 0 Td 59.953704 Tz (of ) Tj 0.816667 0 Td 43.981481 Tz (ability ) Tj 2.1 0 Td 59.953704 Tz (of ) Tj 0.836111 0 Td 48.611111 Tz (the ) Tj 1.088889 0 Td 49.691358 Tz (autotaxin ) Tj 2.916667 0 Td 45.37037 Tz (to ) Tj 0.797222 0 Td 57.253086 Tz (modify ) Tj 2.313889 0 Td 48.611111 Tz (the ) Tj 1.088889 0 Td 47.890947 Tz (substrate ) Tj 51.428571 0 0 51.428571 0 2652.656619 Tm 6.377778 0 Td 51.203704 Tz (\(such ) Tj 1.711111 0 Td 51.851852 Tz (as ) Tj 0.855556 0 Td 64.814815 Tz (LPC\) ) Tj 1.730556 0 Td 43.75 Tz (to ) Tj 0.738889 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 52.572016 Tz (undesired ) Tj 3.013889 0 Td 64.00463 Tz (compound ) Tj 3.266667 0 Td 51.203704 Tz (\(such ) Tj 1.75 0 Td 48.611111 Tz (as ) Tj 0.816667 0 Td 55.740741 Tz (LPA\). ) Tj 51.428571 0 0 51.428571 0 2612.538259 Tm 7.097222 0 Td 62.654321 Tz (The ) Tj 1.361111 0 Td 45.775463 Tz (specific ) Tj 2.469444 0 Td 61.934156 Tz (compounds ) Tj 3.577778 0 Td 53.472222 Tz (below, ) Tj 2.177778 0 Td 48.611111 Tz (as ) Tj 0.836111 0 Td 51.851852 Tz (well ) Tj 1.497222 0 Td 50.231481 Tz (as ) Tj 0.855556 0 Td 49.691358 Tz (the ) Tj 1.147222 0 Td 52.211934 Tz (following ) Tj 51.428571 0 0 51.428571 0 2567.863369 Tm 6.358333 0 Td 51.851852 Tz (exemplified ) Tj 3.558333 0 Td 57.87037 Tz (methods ) Tj 2.586111 0 Td 53.472222 Tz (of ) Tj 0.719444 0 Td 54.73251 Tz (producing ) Tj 3.072222 0 Td 55.092593 Tz (Such ) Tj 1.458333 0 Td 58.333333 Tz (and ) Tj 1.186111 0 Td 58.333333 Tz (methods ) Tj 2.586111 0 Td 53.472222 Tz (of ) Tj 0.719444 0 Td 53.148148 Tz (using ) Tj 51.428571 0 0 51.428571 0 2523.782781 Tm 6.377778 0 Td 54.282407 Tz (Such ) Tj 1.672222 0 Td 61.574074 Tz (compounds ) Tj 3.675 0 Td 49.691358 Tz (are ) Tj 1.263889 0 Td 50.231481 Tz (non-limiting ) Tj 3.966667 0 Td 43.75 Tz (in ) Tj 0.894444 0 Td 50.231481 Tz (nature ) Tj 2.119444 0 Td 60.493827 Tz (and ) Tj 1.419444 0 Td 49.691358 Tz (are ) Tj 1.205556 0 Td 51.041667 Tz (thus ) Tj 51.428571 0 0 51.428571 0 2478.379653 Tm 6.358333 0 Td 47.638889 Tz (indicative ) Tj 3.033333 0 Td 56.712963 Tz (of ) Tj 0.777778 0 Td 49.691358 Tz (the ) Tj 1.05 0 Td 50.05144 Tz (preferred ) Tj 2.858333 0 Td 59.217172 Tz (embodiments ) Tj 4.102778 0 Td 58.333333 Tz (of ) Tj 0.777778 0 Td 44.560185 Tz (this ) Tj 1.263889 0 Td 47.638889 Tz (invention. ) Tj 38.571429 0 0 38.571429 0 2404 Tm 11.9 0 Td 101.783265 Tz (PREFERRED ) Tj 5.755556 0 Td 107.239057 Tz (EMBODIMENTS ) Tj 7.337037 0 Td 101.54321 Tz (OF ) Tj 1.477778 0 Td 105.144033 Tz (THE ) Tj 38.571429 0 0 38.571429 0 2360 Tm 17.474074 0 Td 98.902606 Tz (INVENTION ) Tj 51.428571 0 0 51.428571 0 2269.048193 Tm 6.358333 0 Td 68.055556 Tz (Compound ) Tj 3.441667 0 Td 53.148148 Tz (Production ) Tj 51.428571 0 0 51.428571 0 2225.267339 Tm 7.097222 0 Td 62.654321 Tz (The ) Tj 1.283333 0 Td 45.775463 Tz (specific ) Tj 2.372222 0 Td 61.934156 Tz (compounds ) Tj 3.519444 0 Td 58.333333 Tz (were ) Tj 1.555556 0 Td 55.902778 Tz (produced ) Tj 2.858333 0 Td 48.611111 Tz (as ) Tj 0.797222 0 Td 52.5 Tz (noted ) Tj 1.711111 0 Td 52.932099 Tz (below, ) Tj 2.061111 0 Td 50.231481 Tz (in ) Tj 51.428571 0 0 51.428571 0 2184.285171 Tm 6.338889 0 Td 50.771605 Tz (the ) Tj 1.108333 0 Td 51.851852 Tz (following ) Tj 2.994444 0 Td 50.501543 Tz (non-limiting ) Tj 3.811111 0 Td 53.292181 Tz (examples: ) Tj 51.428571 0 0 51.428571 0 2103.333333 Tm 13.552778 0 Td 61.111111 Tz (Example ) Tj 2.8 0 Td 38.888889 Tz (1 ) Tj 51.428571 0 0 51.428571 0 2017 Tm 10.441667 0 Td 50.283751 Tz (\(18:0\)-p-difluorophosphodiester ) Tj 31.428571 0 0 31.428571 0 1858 Tm 26.186364 0 Td 111.363636 Tz (O ) Tj 57.142857 0 0 57.142857 0 1815 Tm 14.4725 0 Td 37.916667 Tz (| ) Tj 172.857143 0 0 172.857143 0 1749.711409 Tm 2.56281 0 Td 30.853994 Tz (gic-\( ) Tj 1.261157 0 Td 38.21688 Tz (\)---o-clich ) Tj 31.428571 0 0 31.428571 0 1725 Tm 26.186364 0 Td 111.363636 Tz (OH ) Tj 51.428571 0 0 51.428571 0 1617.671214 Tm 7.116667 0 Td 55.976431 Tz (Phosphorous ) Tj 4.025 0 Td 53.030303 Tz (oxychloride ) Tj 3.791667 0 Td 42.12963 Tz (\(1 ) Tj 0.855556 0 Td 46.990741 Tz (eq.\) ) Tj 1.419444 0 Td 61.574074 Tz (was ) Tj 1.4 0 Td 58.333333 Tz (added ) Tj 2.041667 0 Td 46.990741 Tz (to ) Tj 0.836111 0 Td 55.092593 Tz (a ) Tj 0.680556 0 Td 55.740741 Tz (round ) Tj 51.428571 0 0 51.428571 0 1571.324528 Tm 6.338889 0 Td 57.253086 Tz (bottom ) Tj 2.391667 0 Td 46.018519 Tz (flask ) Tj 1.633333 0 Td 58.333333 Tz (and ) Tj 1.341667 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 46.990741 Tz (in ) Tj 0.875 0 Td 49.907407 Tz (tetrahydrofuran ) Tj 4.783333 0 Td 56.17284 Tz (\(THF\). ) Tj 2.313889 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 1526.95449 Tm 6.358333 0 Td 57.037037 Tz (round ) Tj 1.847222 0 Td 56.712963 Tz (bottom ) Tj 2.197222 0 Td 46.666667 Tz (flask ) Tj 1.536111 0 Td 60.493827 Tz (was ) Tj 1.263889 0 Td 51.041667 Tz (then ) Tj 1.4 0 Td 52.391975 Tz (placed ) Tj 2.061111 0 Td 43.75 Tz (in ) Tj 0.661111 0 Td 59.953704 Tz (an ) Tj 0.875 0 Td 46.450617 Tz (ice ) Tj 0.952778 0 Td 52.662037 Tz (bath ) Tj 1.419444 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 53.472222 Tz (maintain ) Tj 51.428571 0 0 51.428571 0 1484.516046 Tm 6.358333 0 Td 51.851852 Tz (a ) Tj 0.563889 0 Td 51.851852 Tz (0 ) Tj 0.894444 0 Td 53.472222 Tz (C. ) Tj 0.894444 0 Td 50.501543 Tz (temperature. ) Tj 3.908333 0 Td 54.79798 Tz (Octadecanol ) Tj 3.888889 0 Td 43.75 Tz (\(1 ) Tj 0.816667 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 50.771605 Tz (dissolved ) Tj 2.975 0 Td 45.37037 Tz (in ) Tj 0.777778 0 Td 76.697531 Tz (THF ) Tj 51.428571 0 0 51.428571 0 1441.895911 Tm 6.338889 0 Td 54.282407 Tz (with ) Tj 1.497222 0 Td 49.85755 Tz (triethylamine ) Tj 4.083333 0 Td 63.518519 Tz (\(TEA\) ) Tj 2.1 0 Td 42.12963 Tz (\(1 ) Tj 0.777778 0 Td 46.180556 Tz (eq.\) ) Tj 1.283333 0 Td 62.654321 Tz (was ) Tj 1.302778 0 Td 58.981481 Tz (added ) Tj 1.963889 0 Td 55.092593 Tz (dropwise ) Tj 2.858333 0 Td 45.37037 Tz (to ) Tj 0.738889 0 Td 49.691358 Tz (the ) Tj 51.428571 0 0 51.428571 0 1399.230317 Tm 6.358333 0 Td 55.976431 Tz (phosphorous ) Tj 3.85 0 Td 56.17284 Tz (oxychloride/THF ) Tj 5.211111 0 Td 46.090535 Tz (solution. ) Tj 2.625 0 Td 64.814815 Tz (Once ) Tj 1.672222 0 Td 41.049383 Tz (all ) Tj 0.894444 0 Td 55.092593 Tz (of ) Tj 0.738889 0 Td 49.691358 Tz (the ) Tj 1.011111 0 Td 60.763889 Tz (octa ) Tj 51.428571 0 0 51.428571 0 1351 Tm 6.358333 0 Td 60.925926 Tz (decanol/THF/TEA ) Tj 5.658333 0 Td 48.611111 Tz (solution ) Tj 2.527778 0 Td 61.574074 Tz (was ) Tj 1.302778 0 Td 58.981481 Tz (added ) Tj 1.963889 0 Td 57.523148 Tz (\(-20 ) Tj 1.594444 0 Td 46.990741 Tz (min.\), ) Tj 1.905556 0 Td 48.611111 Tz (the ) Tj 1.108333 0 Td 58.333333 Tz (reac ) Tj 40 0 0 40 0 1315 Tm 8.15 0 Td 61.458333 Tz (tion ) Tj 1.75 0 Td 67.857143 Tz (mixture ) Tj 3.05 0 Td 79.166667 Tz (was ) Tj 1.675 0 Td 56.547619 Tz (stirred ) Tj 2.6 0 Td 61.111111 Tz (for ) Tj 1.275 0 Td 72.916667 Tz (an ) Tj 1.075 0 Td 62.5 Tz (additional ) Tj 3.95 0 Td 81.25 Tz (40 ) Tj 1.175 0 Td 69.642857 Tz (minutes ) Tj 3.15 0 Td 56.25 Tz (at ) Tj 0.9 0 Td 77.083333 Tz (0C. ) Tj 51.428571 0 0 51.428571 0 1268.225847 Tm 6.358333 0 Td 87.5 Tz (A ) Tj 0.797222 0 Td 48.206019 Tz (solution ) Tj 2.586111 0 Td 58.333333 Tz (of ) Tj 0.836111 0 Td 56.018519 Tz (p-hydroxybenzaldehyde ) Tj 7.291667 0 Td 45.37037 Tz (\(1 ) Tj 0.855556 0 Td 46.990741 Tz (eq.\) ) Tj 1.4 0 Td 43.75 Tz (in ) Tj 0.758333 0 Td 77.777778 Tz (THF ) Tj 1.672222 0 Td 54.282407 Tz (with ) Tj 51.428571 0 0 51.428571 0 1221.896806 Tm 6.358333 0 Td 78.858025 Tz (TEA ) Tj 1.555556 0 Td 43.75 Tz (\(1 ) Tj 0.738889 0 Td 45.37037 Tz (eq.\) ) Tj 1.263889 0 Td 60.493827 Tz (was ) Tj 1.225 0 Td 58.333333 Tz (added ) Tj 1.886111 0 Td 55.497685 Tz (dropwise ) Tj 2.780556 0 Td 46.990741 Tz (to ) Tj 0.719444 0 Td 48.611111 Tz (the ) Tj 1.030556 0 Td 48.206019 Tz (reaction ) Tj 2.469444 0 Td 46.018519 Tz (flask ) Tj 1.477778 0 Td 59.41358 Tz (and ) Tj 1.225 0 Td 60.493827 Tz (was ) Tj 51.428571 0 0 51.428571 0 1176.570726 Tm 6.377778 0 Td 43.981481 Tz (stirred ) Tj 1.983333 0 Td 49.691358 Tz (for ) Tj 0.991667 0 Td 58.333333 Tz (an ) Tj 0.855556 0 Td 47.962963 Tz (additional ) Tj 3.052778 0 Td 63.194444 Tz (40 ) Tj 0.933333 0 Td 53.240741 Tz (minutes ) Tj 2.391667 0 Td 46.990741 Tz (at ) Tj 0.7 0 Td 59.953704 Tz (0C. ) Tj 1.613889 0 Td 57.685185 Tz (Water ) Tj 1.847222 0 Td 45.37037 Tz (\(1 ) Tj 0.758333 0 Td 46.990741 Tz (eq.\) ) Tj 1.263889 0 Td 60.493827 Tz (and ) Tj 51.428571 0 0 51.428571 0 1133.578811 Tm 6.358333 0 Td 78.858025 Tz (TEA ) Tj 1.652778 0 Td 43.75 Tz (\(1 ) Tj 0.816667 0 Td 45.37037 Tz (eq.\) ) Tj 1.341667 0 Td 58.333333 Tz (were ) Tj 1.613889 0 Td 58.333333 Tz (added ) Tj 1.963889 0 Td 46.990741 Tz (to ) Tj 0.797222 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 48.206019 Tz (reaction ) Tj 2.586111 0 Td 53.240741 Tz (mixture ) Tj 2.45 0 Td 58.333333 Tz (which ) Tj 2.002778 0 Td 61.574074 Tz (was ) Tj 40 0 0 40 0 1097 Tm 8.175 0 Td 70.238095 Tz (allowed ) Tj 3.25 0 Td 60.416667 Tz (to ) Tj 1.075 0 Td 50 Tz (stir ) Tj 1.475 0 Td 62.5 Tz (for ) Tj 1.4 0 Td 81.25 Tz (60 ) Tj 1.275 0 Td 69.642857 Tz (minutes ) Tj 3.25 0 Td 58.333333 Tz (at ) Tj 1 0 Td 82.291667 Tz (0C. ) Tj 2.275 0 Td 83.333333 Tz (The ) Tj 1.8 0 Td 64.583333 Tz (contents ) Tj 3.425 0 Td 75 Tz (of ) Tj 1.1 0 Td 63.888889 Tz (the ) Tj 40 0 0 40 0 1053 Tm 8.175 0 Td 62.5 Tz (reaction ) Tj 3.25 0 Td 60 Tz (flask ) Tj 2.05 0 Td 75 Tz (were ) Tj 2.05 0 Td 65.625 Tz (then ) Tj 1.875 0 Td 79.166667 Tz (vacuum ) Tj 3.15 0 Td 55.208333 Tz (filtered ) Tj 2.875 0 Td 76.388889 Tz (and ) Tj 1.65 0 Td 63.333333 Tz (dried ) Tj 2.15 0 Td 56.25 Tz (in ) Tj 0.975 0 Td 66.666667 Tz (vacuo. ) Tj 40 0 0 40 0 1010 Tm 8.175 0 Td 67.5 Tz (After ) Tj 2.2 0 Td 75 Tz (an ) Tj 1.15 0 Td 62.5 Tz (extraction ) Tj 4.025 0 Td 68.75 Tz (with ) Tj 1.925 0 Td 68.666667 Tz (chloroform/methanol/water ) Tj 10.6 0 Td 58.928571 Tz (1:1.5:1 ) Tj 51.428571 0 0 51.428571 0 961.576355 Tm 6.377778 0 Td 44.155093 Tz (\(v/v/v\), ) Tj 2.430556 0 Td 48.611111 Tz (the ) Tj 1.147222 0 Td 51.147343 Tz (\(18:0\)-p-phosphodiester ) Tj 7.291667 0 Td 62.654321 Tz (was ) Tj 1.4 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 45.37037 Tz (in ) Tj 0.836111 0 Td 73.45679 Tz (40% ) Tj 51.428571 0 0 51.428571 0 919.565841 Tm 6.358333 0 Td 47.962963 Tz (ethyl ) Tj 1.827778 0 Td 50.694444 Tz (acetate/hexane ) Tj 4.608333 0 Td 59.41358 Tz (and ) Tj 1.419444 0 Td 50.673401 Tz (centrifuged ) Tj 3.713889 0 Td 47.530864 Tz (for ) Tj 1.205556 0 Td 61.574074 Tz (7 ) Tj 0.758333 0 Td 50.636574 Tz (minutes. ) Tj 2.8 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 876.713574 Tm 6.377778 0 Td 50.673401 Tz (Supernatant ) Tj 3.597222 0 Td 61.574074 Tz (was ) Tj 1.380556 0 Td 54.282407 Tz (decanted ) Tj 2.838889 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 50.771605 Tz (the ) Tj 1.205556 0 Td 48.971193 Tz (insoluble ) Tj 2.916667 0 Td 46.8107 Tz (fractions ) Tj 2.819444 0 Td 58.333333 Tz (were ) Tj 40 0 0 40 0 841 Tm 8.175 0 Td 72.222222 Tz (combined. ) Tj 51.428571 0 0 51.428571 0 798.387909 Tm 7.097222 0 Td 62.654321 Tz (The ) Tj 1.341667 0 Td 44.722222 Tz (relatively ) Tj 2.877778 0 Td 54.282407 Tz (pure ) Tj 1.516667 0 Td 51.006441 Tz (\(18:0\)-p-phosphodiester ) Tj 7.213889 0 Td 43.75 Tz (\(1 ) Tj 0.777778 0 Td 43.425926 Tz (eq.\), ) Tj 1.536111 0 Td 81.018519 Tz (DCC ) Tj 51.428571 0 0 51.428571 0 753.081556 Tm 6.377778 0 Td 46.990741 Tz (\(2.2 ) Tj 1.341667 0 Td 61.574074 Tz (eq\) ) Tj 1.302778 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 87.5 Tz (DMAP ) Tj 2.313889 0 Td 43.75 Tz (\(0.1 ) Tj 1.322222 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 58.333333 Tz (were ) Tj 1.594444 0 Td 49.907407 Tz (dried ) Tj 1.711111 0 Td 53.472222 Tz (over ) Tj 1.458333 0 Td 56.565657 Tz (phosphorous ) Tj 51.428571 0 0 51.428571 0 712.961905 Tm 6.358333 0 Td 53.292181 Tz (pentoxide ) Tj 2.994444 0 Td 49.691358 Tz (for ) Tj 1.05 0 Td 56.712963 Tz (12 ) Tj 0.797222 0 Td 49.151235 Tz (hours. ) Tj 1.905556 0 Td 56.442901 Tz (Cyanoethanol ) Tj 4.2 0 Td 43.75 Tz (\(1.1 ) Tj 1.263889 0 Td 47.800926 Tz (eq.\) ) Tj 1.283333 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 51.131687 Tz (dissolved ) Tj 51.428571 0 0 51.428571 0 668.654501 Tm 6.358333 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 54.228395 Tz (dichloromethane ) Tj 5.036111 0 Td 59.41358 Tz (and ) Tj 1.244444 0 Td 49.259259 Tz (dried ) Tj 1.633333 0 Td 53.472222 Tz (with ) Tj 1.497222 0 Td 61.213992 Tz (magnesium ) Tj 3.5 0 Td 45.833333 Tz (sulfate ) Tj 2.1 0 Td 47.530864 Tz (for ) Tj 1.069444 0 Td 53.472222 Tz (12 ) Tj 51.428571 0 0 51.428571 0 629.44484 Tm 6.338889 0 Td 49.691358 Tz (hours. ) Tj 1.983333 0 Td 62.654321 Tz (The ) Tj 1.302778 0 Td 51.147343 Tz (\(18:0\)-p-phosphodiester ) Tj 7.213889 0 Td 60.493827 Tz (was ) Tj 1.302778 0 Td 50.411523 Tz (dissolved ) Tj 2.877778 0 Td 46.990741 Tz (in ) Tj 0.758333 0 Td 56.712963 Tz (dichlo ) Tj 40 0 0 40 0 592 Tm 8.175 0 Td 73.148148 Tz (romethane ) Tj 4.2 0 Td 75 Tz (and ) Tj 1.625 0 Td 105.555556 Tz (DCC ) Tj 2.15 0 Td 75 Tz (and ) Tj 1.625 0 Td 111.458333 Tz (DMAP ) Tj 2.925 0 Td 76.041667 Tz (were ) Tj 2.075 0 Td 74.166667 Tz (added ) Tj 2.5 0 Td 56.25 Tz (to ) Tj 0.975 0 Td 62.5 Tz (the ) Tj 1.4 0 Td 63.020833 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 544.180879 Tm 6.358333 0 Td 42.669753 Tz (flask. ) Tj 1.788889 0 Td 62.654321 Tz (The ) Tj 1.361111 0 Td 46.666667 Tz (flask ) Tj 1.633333 0 Td 61.574074 Tz (was ) Tj 1.361111 0 Td 50.231481 Tz (sealed ) Tj 2.041667 0 Td 53.472222 Tz (with ) Tj 1.536111 0 Td 51.851852 Tz (a ) Tj 0.583333 0 Td 57.253086 Tz (septum ) Tj 2.313889 0 Td 59.41358 Tz (and ) Tj 1.283333 0 Td 56.712963 Tz (purged ) Tj 2.294444 0 Td 54.282407 Tz (with ) Tj 51.428571 0 0 51.428571 0 504.976553 Tm 6.358333 0 Td 50.231481 Tz (nitrogen ) Tj 2.547222 0 Td 46.018519 Tz (after ) Tj 1.497222 0 Td 55.092593 Tz (adding ) Tj 2.1 0 Td 50.771605 Tz (the ) Tj 1.05 0 Td 53.472222 Tz (cyanoethanol ) Tj 4.005556 0 Td 46.450617 Tz (Solution. ) Tj 2.625 0 Td 64.814815 Tz (The ) Tj 1.302778 0 Td 49.421296 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 461.476433 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.361111 0 Td 44.444444 Tz (stirred ) Tj 2.080556 0 Td 48.611111 Tz (for ) Tj 1.05 0 Td 59.953704 Tz (48 ) Tj 0.952778 0 Td 53.148148 Tz (hours ) Tj 1.808333 0 Td 46.990741 Tz (at ) Tj 0.777778 0 Td 62.384259 Tz (room ) Tj 1.730556 0 Td 50.231481 Tz (temperature. ) Tj 3.869444 0 Td 57.685185 Tz (Water ) Tj 1.944444 0 Td 46.990741 Tz (\(5 ) Tj 0.797222 0 Td 46.180556 Tz (eq.\) ) Tj 40 0 0 40 0 426 Tm 8.15 0 Td 80.555556 Tz (was ) Tj 1.725 0 Td 75 Tz (added ) Tj 2.5 0 Td 76.388889 Tz (and ) Tj 1.625 0 Td 63.888889 Tz (the ) Tj 1.4 0 Td 62.5 Tz (reaction ) Tj 3.325 0 Td 68.452381 Tz (mixture ) Tj 3.125 0 Td 79.166667 Tz (was ) Tj 1.7 0 Td 57.142857 Tz (stirred ) Tj 2.65 0 Td 63.888889 Tz (for ) Tj 1.35 0 Td 72.916667 Tz (an ) Tj 1.125 0 Td 81.25 Tz (addi ) Tj 40 0 0 40 0 384 Tm 8.15 0 Td 59.722222 Tz (tional ) Tj 2.6 0 Td 79.166667 Tz (24 ) Tj 1.375 0 Td 63.194444 Tz (hours. ) Tj 2.75 0 Td 80.555556 Tz (The ) Tj 1.875 0 Td 65.104167 Tz (contents ) Tj 3.575 0 Td 75 Tz (of ) Tj 1.225 0 Td 63.888889 Tz (the ) Tj 1.6 0 Td 62.5 Tz (reaction ) Tj 3.475 0 Td 59.166667 Tz (flask ) Tj 2.225 0 Td 75 Tz (were ) Tj 40 0 0 40 0 343 Tm 8.175 0 Td 81.25 Tz (vacuum ) Tj 3.2 0 Td 55.208333 Tz (filtered ) Tj 2.85 0 Td 77.777778 Tz (and ) Tj 1.65 0 Td 64.166667 Tz (dried ) Tj 2.15 0 Td 60.416667 Tz (in ) Tj 0.975 0 Td 67.361111 Tz (vacuo. ) Tj 2.65 0 Td 66.666667 Tz (After ) Tj 2.225 0 Td 70.833333 Tz (an ) Tj 1.125 0 Td 61.666667 Tz (extraction ) Tj 4 0 Td 68.75 Tz (with ) Tj 51.428571 0 0 51.428571 0 296.390156 Tm 6.358333 0 Td 51.851852 Tz (chloroform/brine ) Tj 5.191667 0 Td 44.290123 Tz (1:1 ) Tj 1.069444 0 Td 43.209877 Tz (\(v/v\), ) Tj 1.730556 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 54.62963 Tz (coupled ) Tj 2.45 0 Td 53.703704 Tz (product ) Tj 2.411111 0 Td 61.574074 Tz (was ) Tj 1.263889 0 Td 48.206019 Tz (purified ) Tj 51.428571 0 0 51.428571 0 255.369077 Tm 6.338889 0 Td 61.574074 Tz (by ) Tj 1.011111 0 Td 45.37037 Tz (flash ) Tj 1.652778 0 Td 59.953704 Tz (column ) Tj 2.45 0 Td 56.25 Tz (chromatography ) Tj 4.997222 0 Td 53.148148 Tz (using ) Tj 1.847222 0 Td 73.45679 Tz (40% ) Tj 1.575 0 Td 48.611111 Tz (ethyl ) Tj 1.730556 0 Td 46.585648 Tz (acetate/ ) Tj 51.428571 0 0 51.428571 0 212.686061 Tm 6.338889 0 Td 57.79321 Tz (hexane ) Tj 2.236111 0 Td 51.041667 Tz (then ) Tj 1.419444 0 Td 51.851852 Tz (switching ) Tj 2.955556 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 73.45679 Tz (80% ) Tj 1.477778 0 Td 47.962963 Tz (ethyl ) Tj 1.594444 0 Td 51.157407 Tz (acetate/hexane ) Tj 4.433333 0 Td 48.611111 Tz (for ) Tj 1.011111 0 Td 51.851852 Tz (a ) Tj 0.486111 0 Td 47.800926 Tz (step ) Tj 51.428571 0 0 51.428571 0 172.169492 Tm 6.358333 0 Td 49.826389 Tz (gradient ) Tj 2.547222 0 Td 45.775463 Tz (elution. ) Tj 30 0 0 30 0 2547 Tm 41.666667 0 Td 75 Tz (10 ) Tj 30 0 0 30 0 2339 Tm 41.666667 0 Td 72.222222 Tz (15 ) Tj 30 0 0 30 0 1923 Tm 41.6 0 Td 77.777778 Tz (25 ) Tj 30 0 0 30 0 1716 Tm 41.6 0 Td 80.555556 Tz (30 ) Tj 30 0 0 30 0 1507 Tm 41.6 0 Td 77.777778 Tz (35 ) Tj 30 0 0 30 0 1299 Tm 41.566667 0 Td 83.333333 Tz (40 ) Tj 30 0 0 30 0 1091 Tm 41.566667 0 Td 80.555556 Tz (45 ) Tj 30 0 0 30 0 883 Tm 41.6 0 Td 80.555556 Tz (50 ) Tj 30 0 0 30 0 675 Tm 41.6 0 Td 77.777778 Tz (55 ) Tj 30 0 0 30 0 467 Tm 41.633333 0 Td 77.777778 Tz (60 ) Tj 30 0 0 30 0 259 Tm 41.633333 0 Td 75 Tz (65 ) Tj 52.857143 0 0 52.857143 0 2968 Tm 32.881081 0 Td 72.522523 Tz (8 ) Tj 51.428571 0 0 51.428571 0 2919.747226 Tm 26.016667 0 Td 52.5 Tz (After ) Tj 1.808333 0 Td 45.121083 Tz (purification, ) Tj 3.791667 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 50.771605 Tz (protected ) Tj 3.013889 0 Td 51.006441 Tz (\(18:0\)-p-phosphodiester ) Tj 51.428571 0 0 51.428571 0 2875.080808 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.4 0 Td 41.481481 Tz (split ) Tj 1.458333 0 Td 46.990741 Tz (into ) Tj 1.380556 0 Td 59.41358 Tz (two ) Tj 1.322222 0 Td 53.240741 Tz (roughly ) Tj 2.469444 0 Td 53.148148 Tz (equal ) Tj 1.808333 0 Td 47.530864 Tz (portions. ) Tj 2.8 0 Td 64.814815 Tz (The ) Tj 1.4 0 Td 37.592593 Tz (first ) Tj 1.322222 0 Td 50.925926 Tz (portion ) Tj 51.428571 0 0 51.428571 0 2827.08 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.380556 0 Td 55.092593 Tz (used ) Tj 1.536111 0 Td 47.530864 Tz (for ) Tj 1.069444 0 Td 45.910494 Tz (direct ) Tj 1.866667 0 Td 46.720679 Tz (fluorination ) Tj 3.577778 0 Td 59.41358 Tz (and ) Tj 1.263889 0 Td 50.771605 Tz (the ) Tj 1.108333 0 Td 56.712963 Tz (second ) Tj 2.236111 0 Td 50 Tz (portion ) Tj 2.333333 0 Td 61.574074 Tz (was ) Tj 51.428571 0 0 51.428571 0 2783.884763 Tm 25.277778 0 Td 55.902778 Tz (used ) Tj 1.672222 0 Td 48.611111 Tz (for ) Tj 1.205556 0 Td 49.691358 Tz (reduction ) Tj 3.052778 0 Td 53.472222 Tz (followed ) Tj 2.858333 0 Td 59.953704 Tz (by ) Tj 1.069444 0 Td 46.990741 Tz (fluorination ) Tj 3.694444 0 Td 59.548611 Tz (\(Example ) Tj 3.15 0 Td 42.12963 Tz (2\). ) Tj 51.428571 0 0 51.428571 0 2743.264631 Tm 25.316667 0 Td 50.771605 Tz (Protected ) Tj 3.091667 0 Td 51.006441 Tz (\(18:0\)-p-phosphodiester ) Tj 7.388889 0 Td 40.509259 Tz (\(1 ) Tj 0.933333 0 Td 46.180556 Tz (eq.\) ) Tj 1.458333 0 Td 61.574074 Tz (was ) Tj 1.458333 0 Td 49.907407 Tz (dried ) Tj 1.847222 0 Td 54.282407 Tz (over ) Tj 51.428571 0 0 51.428571 0 2698.26747 Tm 25.297222 0 Td 55.976431 Tz (phosphorous ) Tj 3.85 0 Td 53.652263 Tz (pentoxide ) Tj 3.052778 0 Td 48.611111 Tz (for ) Tj 1.069444 0 Td 55.092593 Tz (12 ) Tj 0.797222 0 Td 54.444444 Tz (hours ) Tj 1.788889 0 Td 58.333333 Tz (and ) Tj 1.225 0 Td 50.771605 Tz (dissolved ) Tj 2.897222 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 56.712963 Tz (dichlo ) Tj 51.428571 0 0 51.428571 0 2651.956522 Tm 25.297222 0 Td 53.796296 Tz (romethane. ) Tj 3.363889 0 Td 63.734568 Tz (The ) Tj 1.283333 0 Td 48.611111 Tz (reaction ) Tj 2.508333 0 Td 46.018519 Tz (flask ) Tj 1.477778 0 Td 62.654321 Tz (was ) Tj 1.263889 0 Td 50.771605 Tz (sealed ) Tj 1.963889 0 Td 58.333333 Tz (and ) Tj 1.166667 0 Td 53.472222 Tz (placed ) Tj 2.061111 0 Td 45.37037 Tz (in ) Tj 0.7 0 Td 56.712963 Tz (an ) Tj 0.836111 0 Td 47.530864 Tz (ice ) Tj 51.428571 0 0 51.428571 0 2610.565046 Tm 25.277778 0 Td 52.662037 Tz (bath ) Tj 1.555556 0 Td 45.37037 Tz (to ) Tj 0.875 0 Td 52.256944 Tz (maintain ) Tj 2.819444 0 Td 50.231481 Tz (0 ) Tj 0.894444 0 Td 55.092593 Tz (C. ) Tj 0.991667 0 Td 49.96142 Tz (temperature. ) Tj 3.927778 0 Td 55.416667 Tz (Deoxofluor ) Tj 3.597222 0 Td 46.990741 Tz (\(2 ) Tj 0.836111 0 Td 47.800926 Tz (eq.\) ) Tj 1.419444 0 Td 48.611111 Tz (in ) Tj 51.428571 0 0 51.428571 0 2564.92891 Tm 25.297222 0 Td 54.444444 Tz (dichloromethane ) Tj 5.036111 0 Td 61.574074 Tz (was ) Tj 1.283333 0 Td 52.932099 Tz (slowly ) Tj 2.041667 0 Td 58.981481 Tz (added ) Tj 1.905556 0 Td 55.092593 Tz (\(-2 ) Tj 1.205556 0 Td 52.256944 Tz (minutes\) ) Tj 2.644444 0 Td 59.41358 Tz (and ) Tj 1.186111 0 Td 51.388889 Tz (ethanol ) Tj 51.428571 0 0 51.428571 0 2523.183463 Tm 25.316667 0 Td 46.180556 Tz (\(0.2 ) Tj 1.341667 0 Td 46.180556 Tz (eq.\) ) Tj 1.322222 0 Td 61.574074 Tz (was ) Tj 1.341667 0 Td 57.685185 Tz (added ) Tj 1.944444 0 Td 45.37037 Tz (to ) Tj 0.777778 0 Td 51.446759 Tz (generate ) Tj 2.663889 0 Td 51.851852 Tz (a ) Tj 0.525 0 Td 44.650206 Tz (catalyst, ) Tj 2.663889 0 Td 55.092593 Tz (HF. ) Tj 1.205556 0 Td 63.734568 Tz (The ) Tj 1.341667 0 Td 47.530864 Tz (ice ) Tj 1.069444 0 Td 52.662037 Tz (bath ) Tj 40 0 0 40 0 2485 Tm 32.5 0 Td 80.555556 Tz (was ) Tj 1.875 0 Td 76.785714 Tz (removed ) Tj 3.625 0 Td 75 Tz (and ) Tj 1.725 0 Td 63.888889 Tz (the ) Tj 1.525 0 Td 62.5 Tz (reaction ) Tj 3.425 0 Td 69.047619 Tz (mixture ) Tj 3.3 0 Td 77.777778 Tz (was ) Tj 1.825 0 Td 56.547619 Tz (stirred ) Tj 2.775 0 Td 62.5 Tz (for ) Tj 1.55 0 Td 68.75 Tz (16 ) Tj 40 0 0 40 0 2441 Tm 32.5 0 Td 63.888889 Tz (hours. ) Tj 2.5 0 Td 91.666667 Tz (An ) Tj 1.325 0 Td 61.666667 Tz (extraction ) Tj 3.925 0 Td 68.75 Tz (with ) Tj 1.875 0 Td 66 Tz (dichloromethane/saturated ) Tj 10.125 0 Td 75.694444 Tz (sodium ) Tj 51.428571 0 0 51.428571 0 2391.583433 Tm 25.277778 0 Td 51.557239 Tz (bicarbonate ) Tj 3.558333 0 Td 48.611111 Tz (solution ) Tj 2.547222 0 Td 43.209877 Tz (1:1 ) Tj 1.030556 0 Td 46.666667 Tz (\(v/v\) ) Tj 1.536111 0 Td 61.574074 Tz (was ) Tj 1.244444 0 Td 56.532922 Tz (performed ) Tj 3.169444 0 Td 59.41358 Tz (and ) Tj 1.225 0 Td 48.611111 Tz (the ) Tj 0.991667 0 Td 51.851852 Tz (organic ) Tj 51.428571 0 0 51.428571 0 2348.210909 Tm 25.297222 0 Td 49.259259 Tz (layer ) Tj 1.652778 0 Td 60.493827 Tz (was ) Tj 1.283333 0 Td 46.342593 Tz (collected. ) Tj 51.428571 0 0 51.428571 0 2307.343958 Tm 26.016667 0 Td 52.5 Tz (After ) Tj 1.905556 0 Td 52.391975 Tz (drying ) Tj 2.236111 0 Td 45.37037 Tz (in ) Tj 0.933333 0 Td 51.851852 Tz (vacuo, ) Tj 2.236111 0 Td 48.611111 Tz (the ) Tj 1.186111 0 Td 50.771605 Tz (protected ) Tj 3.091667 0 Td 50.517429 Tz (\(18:0\)-p-difluoro ) Tj 51.428571 0 0 51.428571 0 2265.697561 Tm 25.297222 0 Td 52.777778 Tz (phosphodiester ) Tj 4.647222 0 Td 61.574074 Tz (was ) Tj 1.341667 0 Td 47.800926 Tz (purified ) Tj 2.527778 0 Td 59.953704 Tz (by ) Tj 0.991667 0 Td 44.722222 Tz (flash ) Tj 1.633333 0 Td 59.41358 Tz (column ) Tj 2.411111 0 Td 59.217172 Tz (chromatogra ) Tj 51.428571 0 0 51.428571 0 2222.551122 Tm 25.297222 0 Td 59.41358 Tz (phy ) Tj 1.322222 0 Td 52.5 Tz (using ) Tj 1.788889 0 Td 72.376543 Tz (40% ) Tj 1.555556 0 Td 47.962963 Tz (ethyl ) Tj 1.672222 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.491667 0 Td 51.041667 Tz (then ) Tj 1.458333 0 Td 52.572016 Tz (switching ) Tj 3.072222 0 Td 43.75 Tz (to ) Tj 0.758333 0 Td 74.537037 Tz (80% ) Tj 51.428571 0 0 51.428571 0 2180.743468 Tm 25.297222 0 Td 47.314815 Tz (ethyl ) Tj 1.555556 0 Td 51.388889 Tz (acetate/hexane ) Tj 4.433333 0 Td 48.611111 Tz (for ) Tj 0.972222 0 Td 55.092593 Tz (a ) Tj 0.486111 0 Td 46.990741 Tz (step ) Tj 1.283333 0 Td 49.826389 Tz (gradient ) Tj 2.508333 0 Td 45.37037 Tz (elution. ) Tj 2.372222 0 Td 56.17284 Tz (For ) Tj 1.127778 0 Td 56.712963 Tz (deprotec ) Tj 51.428571 0 0 51.428571 0 2142.653846 Tm 25.277778 0 Td 44.074074 Tz (tion, ) Tj 1.594444 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 50.411523 Tz (protected ) Tj 2.955556 0 Td 50.130208 Tz (\(18:0\)-p-difluoro-phosphodiester ) Tj 9.858333 0 Td 42.12963 Tz (\(1 ) Tj 0.836111 0 Td 46.180556 Tz (eq.\) ) Tj 51.428571 0 0 51.428571 0 2098.813725 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 50.771605 Tz (dissolved ) Tj 2.955556 0 Td 43.75 Tz (in ) Tj 0.719444 0 Td 47.890947 Tz (pyridine. ) Tj 2.819444 0 Td 56.837607 Tz (N-propylamine ) Tj 4.627778 0 Td 56.712963 Tz (\(100 ) Tj 1.536111 0 Td 46.180556 Tz (eq.\) ) Tj 1.302778 0 Td 46.990741 Tz (in ) Tj 0.758333 0 Td 59.143519 Tz (pyri ) Tj 40 0 0 40 0 2061 Tm 32.525 0 Td 67.708333 Tz (dine ) Tj 1.8 0 Td 76.388889 Tz (was ) Tj 1.55 0 Td 75.833333 Tz (added ) Tj 2.4 0 Td 60.416667 Tz (to ) Tj 0.925 0 Td 62.5 Tz (the ) Tj 1.3 0 Td 61.979167 Tz (reaction ) Tj 3.15 0 Td 68.229167 Tz (flaskand ) Tj 3.425 0 Td 63.888889 Tz (the ) Tj 1.3 0 Td 62.5 Tz (clear ) Tj 1.975 0 Td 63.020833 Tz (solution ) Tj 3.2 0 Td 79.166667 Tz (was ) Tj 51.428571 0 0 51.428571 0 2012.80268 Tm 25.316667 0 Td 43.981481 Tz (stirred ) Tj 1.983333 0 Td 48.611111 Tz (for ) Tj 1.069444 0 Td 55.092593 Tz (10 ) Tj 0.816667 0 Td 54.166667 Tz (minutes ) Tj 2.430556 0 Td 45.37037 Tz (at ) Tj 0.719444 0 Td 61.574074 Tz (room ) Tj 1.652778 0 Td 49.96142 Tz (temperature. ) Tj 3.752778 0 Td 51.851852 Tz (All ) Tj 1.108333 0 Td 48.611111 Tz (solvents ) Tj 2.508333 0 Td 59.143519 Tz (were ) Tj 51.428571 0 0 51.428571 0 1972.621359 Tm 25.297222 0 Td 60.185185 Tz (removed ) Tj 2.702778 0 Td 43.75 Tz (in ) Tj 0.738889 0 Td 55.092593 Tz (vacuo ) Tj 1.847222 0 Td 45.37037 Tz (to ) Tj 0.7 0 Td 49.907407 Tz (yield ) Tj 1.633333 0 Td 50.771605 Tz (the ) Tj 1.088889 0 Td 59.953704 Tz (n-propylammonium ) Tj 5.930556 0 Td 42.939815 Tz (salt ) Tj 1.186111 0 Td 55.092593 Tz (of ) Tj 0.738889 0 Td 50.771605 Tz (the ) Tj 51.428571 0 0 51.428571 0 1932.596532 Tm 25.316667 0 Td 48.80752 Tz (\(18:0\)-p-difluoro-phosphodiester. ) Tj 9.838889 0 Td 72.916667 Tz (An ) Tj 1.011111 0 Td 47.962963 Tz (extraction ) Tj 3.052778 0 Td 53.472222 Tz (with ) Tj 1.419444 0 Td 58.873457 Tz (chloro ) Tj 51.428571 0 0 51.428571 0 1888.753939 Tm 25.297222 0 Td 52.875244 Tz (form/methanol/brine ) Tj 6.3 0 Td 45.37037 Tz (1:1.5:1 ) Tj 2.197222 0 Td 62.654321 Tz (was ) Tj 1.361111 0 Td 56.17284 Tz (performed ) Tj 3.247222 0 Td 45.37037 Tz (to ) Tj 0.758333 0 Td 51.851852 Tz (generate ) Tj 2.702778 0 Td 50.771605 Tz (the ) Tj 51.428571 0 0 51.428571 0 1850.336986 Tm 25.316667 0 Td 58.333333 Tz (sodium ) Tj 2.294444 0 Td 42.939815 Tz (salt ) Tj 1.205556 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 50.771605 Tz (the ) Tj 1.088889 0 Td 49.320023 Tz (\(18:0\)-p-difluorophosphodiester. ) Tj 51.428571 0 0 51.428571 0 1773.046358 Tm 32.472222 0 Td 61.574074 Tz (Example ) Tj 2.761111 0 Td 58.333333 Tz (2 ) Tj 51.428571 0 0 51.428571 0 1691 Tm 28.836111 0 Td 52.73569 Tz (\(18:0\)-p-monofluorophosphodiester ) Tj 31.428571 0 0 31.428571 0 1533 Tm 57.209091 0 Td 111.363636 Tz (O ) Tj 57.142857 0 0 57.142857 0 1490 Tm 31.535 0 Td 37.916667 Tz (| ) Tj 171.428571 0 0 171.428571 0 1418 Tm 8.26 0 Td 35.864198 Tz (cis-\(\)--i-o-clich, ) Tj 31.428571 0 0 31.428571 0 1399 Tm 57.209091 0 Td 111.363636 Tz (OH ) Tj 51.428571 0 0 51.428571 0 1295.683995 Tm 26.036111 0 Td 56.565657 Tz (Phosphorous ) Tj 4.044444 0 Td 52.73569 Tz (oxychloride ) Tj 3.772222 0 Td 43.75 Tz (\(1 ) Tj 0.894444 0 Td 46.180556 Tz (eq.\) ) Tj 1.419444 0 Td 60.493827 Tz (was ) Tj 1.380556 0 Td 58.333333 Tz (added ) Tj 2.041667 0 Td 45.37037 Tz (to ) Tj 0.855556 0 Td 51.851852 Tz (a ) Tj 0.661111 0 Td 55.740741 Tz (round ) Tj 51.428571 0 0 51.428571 0 1251.327456 Tm 25.277778 0 Td 57.253086 Tz (bottom ) Tj 2.391667 0 Td 46.018519 Tz (flask ) Tj 1.633333 0 Td 58.333333 Tz (and ) Tj 1.341667 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 45.37037 Tz (in ) Tj 0.875 0 Td 49.907407 Tz (tetrahydrofuran ) Tj 4.783333 0 Td 56.17284 Tz (\(THF\). ) Tj 2.313889 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 1208.961963 Tm 25.297222 0 Td 57.037037 Tz (round ) Tj 1.847222 0 Td 56.712963 Tz (bottom ) Tj 2.197222 0 Td 46.666667 Tz (flask ) Tj 1.536111 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 51.851852 Tz (then ) Tj 1.4 0 Td 52.932099 Tz (placed ) Tj 2.061111 0 Td 45.37037 Tz (in ) Tj 0.680556 0 Td 59.953704 Tz (an ) Tj 0.875 0 Td 46.450617 Tz (ice ) Tj 0.952778 0 Td 52.662037 Tz (bath ) Tj 1.419444 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 53.06713 Tz (maintain ) Tj 51.428571 0 0 51.428571 0 1168.522523 Tm 25.297222 0 Td 51.851852 Tz (a ) Tj 0.563889 0 Td 51.851852 Tz (0 ) Tj 0.894444 0 Td 53.472222 Tz (C. ) Tj 0.894444 0 Td 50.501543 Tz (temperature. ) Tj 3.908333 0 Td 54.79798 Tz (Octadecanol ) Tj 3.888889 0 Td 42.12963 Tz (\(1 ) Tj 0.816667 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 50.771605 Tz (dissolved ) Tj 2.975 0 Td 45.37037 Tz (in ) Tj 0.777778 0 Td 75.617284 Tz (THF ) Tj 51.428571 0 0 51.428571 0 1127.905824 Tm 25.277778 0 Td 54.282407 Tz (with ) Tj 1.497222 0 Td 49.85755 Tz (triethylamine ) Tj 4.083333 0 Td 62.87037 Tz (\(TEA\) ) Tj 2.1 0 Td 42.12963 Tz (\(1 ) Tj 0.758333 0 Td 46.990741 Tz (eq.\) ) Tj 1.302778 0 Td 62.654321 Tz (was ) Tj 1.302778 0 Td 58.333333 Tz (added ) Tj 1.963889 0 Td 55.092593 Tz (dropwise ) Tj 2.858333 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 50.771605 Tz (the ) Tj 51.428571 0 0 51.428571 0 1087.220399 Tm 25.297222 0 Td 55.976431 Tz (phosphorous ) Tj 3.85 0 Td 56.17284 Tz (oxychloride/THF ) Tj 5.211111 0 Td 46.090535 Tz (solution. ) Tj 2.625 0 Td 64.814815 Tz (Once ) Tj 1.672222 0 Td 41.049383 Tz (all ) Tj 0.855556 0 Td 58.333333 Tz (of ) Tj 0.777778 0 Td 49.691358 Tz (the ) Tj 1.011111 0 Td 60.763889 Tz (octa ) Tj 51.428571 0 0 51.428571 0 1041 Tm 25.297222 0 Td 60.925926 Tz (decanol/THF/TEA ) Tj 5.638889 0 Td 48.611111 Tz (solution ) Tj 2.547222 0 Td 61.574074 Tz (was ) Tj 1.302778 0 Td 58.333333 Tz (added ) Tj 1.963889 0 Td 57.523148 Tz (\(-20 ) Tj 1.575 0 Td 46.990741 Tz (min.\), ) Tj 1.925 0 Td 48.611111 Tz (the ) Tj 1.088889 0 Td 59.143519 Tz (reac ) Tj 40 0 0 40 0 1008 Tm 32.5 0 Td 60.416667 Tz (tion ) Tj 1.725 0 Td 68.452381 Tz (mixture ) Tj 3.075 0 Td 79.166667 Tz (was ) Tj 1.675 0 Td 56.547619 Tz (stirred ) Tj 2.6 0 Td 61.111111 Tz (for ) Tj 1.275 0 Td 70.833333 Tz (an ) Tj 1.05 0 Td 62.916667 Tz (additional ) Tj 3.975 0 Td 81.25 Tz (40 ) Tj 1.175 0 Td 69.642857 Tz (minutes ) Tj 3.15 0 Td 56.25 Tz (at ) Tj 0.9 0 Td 77.083333 Tz (0C. ) Tj 51.428571 0 0 51.428571 0 962.215809 Tm 25.297222 0 Td 87.5 Tz (A ) Tj 0.797222 0 Td 48.206019 Tz (solution ) Tj 2.586111 0 Td 58.333333 Tz (of ) Tj 0.836111 0 Td 55.864198 Tz (p-hydroxybenzaldehyde ) Tj 7.291667 0 Td 45.37037 Tz (\(1 ) Tj 0.855556 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 46.990741 Tz (in ) Tj 0.797222 0 Td 77.777778 Tz (THF ) Tj 1.672222 0 Td 53.472222 Tz (with ) Tj 51.428571 0 0 51.428571 0 918.899633 Tm 25.297222 0 Td 78.858025 Tz (TEA ) Tj 1.536111 0 Td 45.37037 Tz (\(1 ) Tj 0.738889 0 Td 46.180556 Tz (eq.\) ) Tj 1.263889 0 Td 61.574074 Tz (was ) Tj 1.244444 0 Td 58.333333 Tz (added ) Tj 1.886111 0 Td 55.497685 Tz (dropwise ) Tj 2.780556 0 Td 46.990741 Tz (to ) Tj 0.719444 0 Td 48.611111 Tz (the ) Tj 1.030556 0 Td 47.800926 Tz (reaction ) Tj 2.469444 0 Td 46.018519 Tz (flask ) Tj 1.477778 0 Td 59.41358 Tz (and ) Tj 1.205556 0 Td 61.574074 Tz (was ) Tj 51.428571 0 0 51.428571 0 875.573548 Tm 25.316667 0 Td 43.981481 Tz (stirred ) Tj 1.983333 0 Td 48.611111 Tz (for ) Tj 0.991667 0 Td 56.712963 Tz (an ) Tj 0.855556 0 Td 47.962963 Tz (additional ) Tj 3.052778 0 Td 63.194444 Tz (40 ) Tj 0.933333 0 Td 53.240741 Tz (minutes ) Tj 2.391667 0 Td 45.37037 Tz (at ) Tj 0.7 0 Td 59.953704 Tz (0C. ) Tj 1.613889 0 Td 57.685185 Tz (Water ) Tj 1.847222 0 Td 45.37037 Tz (\(1 ) Tj 0.758333 0 Td 46.990741 Tz (eq.\) ) Tj 1.263889 0 Td 59.41358 Tz (and ) Tj 51.428571 0 0 51.428571 0 833.57956 Tm 25.297222 0 Td 78.858025 Tz (TEA ) Tj 1.652778 0 Td 43.75 Tz (\(1 ) Tj 0.816667 0 Td 45.37037 Tz (eq.\) ) Tj 1.341667 0 Td 58.333333 Tz (were ) Tj 1.613889 0 Td 58.333333 Tz (added ) Tj 1.963889 0 Td 45.37037 Tz (to ) Tj 0.797222 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 48.206019 Tz (reaction ) Tj 2.586111 0 Td 52.777778 Tz (mixture ) Tj 2.430556 0 Td 58.981481 Tz (which ) Tj 2.022222 0 Td 61.574074 Tz (was ) Tj 40 0 0 40 0 800 Tm 32.525 0 Td 70.238095 Tz (allowed ) Tj 3.25 0 Td 58.333333 Tz (to ) Tj 1.075 0 Td 50 Tz (stir ) Tj 1.475 0 Td 62.5 Tz (for ) Tj 1.4 0 Td 81.25 Tz (60 ) Tj 1.275 0 Td 69.642857 Tz (minutes ) Tj 3.25 0 Td 58.333333 Tz (at ) Tj 1 0 Td 82.291667 Tz (0C. ) Tj 2.275 0 Td 81.944444 Tz (The ) Tj 1.8 0 Td 64.583333 Tz (contents ) Tj 3.425 0 Td 72.916667 Tz (of ) Tj 1.075 0 Td 65.277778 Tz (the ) Tj 40 0 0 40 0 758 Tm 32.525 0 Td 62.5 Tz (reaction ) Tj 3.25 0 Td 60 Tz (flask ) Tj 2.05 0 Td 75 Tz (were ) Tj 2.025 0 Td 66.666667 Tz (then ) Tj 1.9 0 Td 79.166667 Tz (vacuum ) Tj 3.15 0 Td 55.208333 Tz (filtered ) Tj 2.875 0 Td 76.388889 Tz (and ) Tj 1.65 0 Td 63.333333 Tz (dried ) Tj 2.125 0 Td 58.333333 Tz (in ) Tj 0.975 0 Td 67.361111 Tz (vacuo. ) Tj 40 0 0 40 0 717 Tm 32.525 0 Td 66.666667 Tz (After ) Tj 2.2 0 Td 75 Tz (an ) Tj 1.15 0 Td 62.083333 Tz (extraction ) Tj 4.025 0 Td 67.708333 Tz (with ) Tj 1.925 0 Td 68.666667 Tz (chloroform/methanol/water ) Tj 10.6 0 Td 58.928571 Tz (1:1.5:1 ) Tj 51.428571 0 0 51.428571 0 670.580764 Tm 25.316667 0 Td 44.155093 Tz (\(v/v/v\), ) Tj 2.430556 0 Td 48.611111 Tz (the ) Tj 1.147222 0 Td 51.147343 Tz (\(18:0\)-p-phosphodiester ) Tj 7.291667 0 Td 61.574074 Tz (was ) Tj 1.4 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 45.37037 Tz (in ) Tj 0.836111 0 Td 73.45679 Tz (40% ) Tj 51.428571 0 0 51.428571 0 628.548303 Tm 25.297222 0 Td 47.962963 Tz (ethyl ) Tj 1.808333 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.627778 0 Td 59.41358 Tz (and ) Tj 1.419444 0 Td 50.084175 Tz (centrifuged ) Tj 3.713889 0 Td 47.530864 Tz (for ) Tj 1.186111 0 Td 61.574074 Tz (7 ) Tj 0.777778 0 Td 50.636574 Tz (minutes. ) Tj 2.8 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 585.713574 Tm 25.316667 0 Td 50.673401 Tz (Supernatant ) Tj 3.597222 0 Td 61.574074 Tz (was ) Tj 1.380556 0 Td 53.877315 Tz (decanted ) Tj 2.838889 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 50.771605 Tz (the ) Tj 1.186111 0 Td 49.331276 Tz (insoluble ) Tj 2.936111 0 Td 46.450617 Tz (fractions ) Tj 2.8 0 Td 59.143519 Tz (were ) Tj 40 0 0 40 0 550 Tm 32.525 0 Td 72.222222 Tz (combined. ) Tj 51.428571 0 0 51.428571 0 507.38394 Tm 26.016667 0 Td 63.734568 Tz (The ) Tj 1.361111 0 Td 45.046296 Tz (relatively ) Tj 2.858333 0 Td 55.092593 Tz (pure ) Tj 1.536111 0 Td 51.006441 Tz (\(18:0\)-p-phosphodiester ) Tj 7.213889 0 Td 43.75 Tz (\(1 ) Tj 0.777778 0 Td 43.425926 Tz (eq.\), ) Tj 1.536111 0 Td 81.018519 Tz (DCC ) Tj 51.428571 0 0 51.428571 0 462.085427 Tm 25.316667 0 Td 46.180556 Tz (\(2.2 ) Tj 1.341667 0 Td 61.574074 Tz (eq\) ) Tj 1.302778 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 87.5 Tz (DMAP ) Tj 2.313889 0 Td 43.75 Tz (\(0.1 ) Tj 1.322222 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 58.333333 Tz (were ) Tj 1.594444 0 Td 49.907407 Tz (dried ) Tj 1.711111 0 Td 53.472222 Tz (over ) Tj 1.458333 0 Td 56.565657 Tz (phosphorous ) Tj 51.428571 0 0 51.428571 0 421.971223 Tm 25.297222 0 Td 53.292181 Tz (pentoxide ) Tj 2.994444 0 Td 48.611111 Tz (for ) Tj 1.05 0 Td 53.472222 Tz (12 ) Tj 0.797222 0 Td 49.151235 Tz (hours. ) Tj 1.905556 0 Td 56.442901 Tz (Cyanoethanol ) Tj 4.2 0 Td 43.75 Tz (\(1.1 ) Tj 1.263889 0 Td 46.180556 Tz (eq.\) ) Tj 1.283333 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 50.771605 Tz (dissolved ) Tj 51.428571 0 0 51.428571 0 377.646772 Tm 25.297222 0 Td 45.37037 Tz (in ) Tj 0.719444 0 Td 54.444444 Tz (dichloromethane ) Tj 5.055556 0 Td 59.41358 Tz (and ) Tj 1.244444 0 Td 49.259259 Tz (dried ) Tj 1.633333 0 Td 53.472222 Tz (with ) Tj 1.497222 0 Td 60.853909 Tz (magnesium ) Tj 3.5 0 Td 45.833333 Tz (sulfate ) Tj 2.1 0 Td 47.530864 Tz (for ) Tj 1.069444 0 Td 51.851852 Tz (12 ) Tj 51.428571 0 0 51.428571 0 338.44484 Tm 25.277778 0 Td 49.691358 Tz (hours. ) Tj 1.983333 0 Td 62.654321 Tz (The ) Tj 1.302778 0 Td 51.147343 Tz (\(18:0\)-p-phosphodiester ) Tj 7.213889 0 Td 60.493827 Tz (was ) Tj 1.302778 0 Td 50.411523 Tz (dissolved ) Tj 2.877778 0 Td 46.990741 Tz (in ) Tj 0.758333 0 Td 56.712963 Tz (dichlo ) Tj 40 0 0 40 0 301 Tm 32.525 0 Td 73.148148 Tz (romethane ) Tj 4.2 0 Td 75 Tz (and ) Tj 1.625 0 Td 105.555556 Tz (DCC ) Tj 2.15 0 Td 75 Tz (and ) Tj 1.625 0 Td 111.458333 Tz (DMAP ) Tj 2.925 0 Td 76.041667 Tz (were ) Tj 2.05 0 Td 75 Tz (added ) Tj 2.525 0 Td 56.25 Tz (to ) Tj 0.975 0 Td 62.5 Tz (the ) Tj 1.4 0 Td 62.5 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 253.168612 Tm 25.297222 0 Td 42.669753 Tz (flask. ) Tj 1.788889 0 Td 62.654321 Tz (The ) Tj 1.361111 0 Td 46.666667 Tz (flask ) Tj 1.633333 0 Td 60.493827 Tz (was ) Tj 1.341667 0 Td 50.771605 Tz (sealed ) Tj 2.061111 0 Td 53.472222 Tz (with ) Tj 1.536111 0 Td 51.851852 Tz (a ) Tj 0.583333 0 Td 57.253086 Tz (septum ) Tj 2.313889 0 Td 59.41358 Tz (and ) Tj 1.283333 0 Td 55.632716 Tz (purged ) Tj 2.294444 0 Td 53.472222 Tz (with ) Tj 51.428571 0 0 51.428571 0 213.985899 Tm 25.297222 0 Td 50.231481 Tz (nitrogen ) Tj 2.547222 0 Td 46.018519 Tz (after ) Tj 1.497222 0 Td 55.092593 Tz (adding ) Tj 2.1 0 Td 50.771605 Tz (the ) Tj 1.05 0 Td 53.472222 Tz (cyanoethanol ) Tj 4.005556 0 Td 46.090535 Tz (Solution. ) Tj 2.625 0 Td 64.814815 Tz (The ) Tj 1.302778 0 Td 49.016204 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 170.476433 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.361111 0 Td 44.444444 Tz (stirred ) Tj 2.080556 0 Td 48.611111 Tz (for ) Tj 1.05 0 Td 59.953704 Tz (48 ) Tj 0.952778 0 Td 53.148148 Tz (hours ) Tj 1.808333 0 Td 46.990741 Tz (at ) Tj 0.777778 0 Td 62.384259 Tz (room ) Tj 1.730556 0 Td 50.231481 Tz (temperature. ) Tj 3.869444 0 Td 57.685185 Tz (Water ) Tj 1.944444 0 Td 46.990741 Tz (\(5 ) Tj 0.797222 0 Td 46.180556 Tz (eq.\) ) Tj ET Q endstream endobj 182 0 obj << /Length 1 >> stream q endstream endobj 183 0 obj << /Length 41013 >> stream Q q 0.24 0 0 0.24 0 0 cm BT /F1 1 Tf 3 Tr 62.857143 0 0 62.857143 0 3023 Tm 17.325 0 Td 83.522727 Tz (US ) Tj 1.240909 0 Td 58.333333 Tz (8,022,239 ) Tj 3.388636 0 Td 74.242424 Tz (B2 ) Tj 40 0 0 40 0 2921 Tm 8.15 0 Td 80.555556 Tz (was ) Tj 1.725 0 Td 75 Tz (added ) Tj 2.5 0 Td 76.388889 Tz (and ) Tj 1.625 0 Td 63.888889 Tz (the ) Tj 1.4 0 Td 62.5 Tz (reaction ) Tj 3.325 0 Td 68.452381 Tz (mixture ) Tj 3.125 0 Td 79.166667 Tz (was ) Tj 1.7 0 Td 57.142857 Tz (stirred ) Tj 2.65 0 Td 63.888889 Tz (for ) Tj 1.35 0 Td 72.916667 Tz (an ) Tj 1.125 0 Td 81.25 Tz (addi ) Tj 40 0 0 40 0 2878 Tm 8.15 0 Td 59.722222 Tz (tional ) Tj 2.6 0 Td 79.166667 Tz (24 ) Tj 1.375 0 Td 63.194444 Tz (hours. ) Tj 2.75 0 Td 80.555556 Tz (The ) Tj 1.875 0 Td 65.104167 Tz (contents ) Tj 3.575 0 Td 75 Tz (of ) Tj 1.225 0 Td 63.888889 Tz (the ) Tj 1.6 0 Td 62.5 Tz (reaction ) Tj 3.475 0 Td 59.166667 Tz (flask ) Tj 2.225 0 Td 75 Tz (were ) Tj 40 0 0 40 0 2834 Tm 8.175 0 Td 81.25 Tz (vacuum ) Tj 3.2 0 Td 55.208333 Tz (filtered ) Tj 2.85 0 Td 77.777778 Tz (and ) Tj 1.65 0 Td 64.166667 Tz (dried ) Tj 2.15 0 Td 60.416667 Tz (in ) Tj 0.975 0 Td 67.361111 Tz (vacuo. ) Tj 2.65 0 Td 66.666667 Tz (After ) Tj 2.225 0 Td 70.833333 Tz (an ) Tj 1.125 0 Td 61.666667 Tz (extraction ) Tj 4 0 Td 68.75 Tz (with ) Tj 51.428571 0 0 51.428571 0 2785.390156 Tm 6.358333 0 Td 51.851852 Tz (chloroform/brine ) Tj 5.191667 0 Td 44.290123 Tz (1:1 ) Tj 1.069444 0 Td 43.209877 Tz (\(v/v\), ) Tj 1.730556 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 54.62963 Tz (coupled ) Tj 2.45 0 Td 53.703704 Tz (product ) Tj 2.411111 0 Td 61.574074 Tz (was ) Tj 1.263889 0 Td 48.206019 Tz (purified ) Tj 51.428571 0 0 51.428571 0 2743.369077 Tm 6.338889 0 Td 61.574074 Tz (by ) Tj 1.011111 0 Td 45.37037 Tz (flash ) Tj 1.652778 0 Td 59.953704 Tz (column ) Tj 2.45 0 Td 56.25 Tz (chromatography ) Tj 4.997222 0 Td 53.148148 Tz (using ) Tj 1.847222 0 Td 73.45679 Tz (40% ) Tj 1.575 0 Td 48.611111 Tz (ethyl ) Tj 1.730556 0 Td 46.585648 Tz (acetate/ ) Tj 51.428571 0 0 51.428571 0 2697.686061 Tm 6.338889 0 Td 57.79321 Tz (hexane ) Tj 2.236111 0 Td 51.041667 Tz (then ) Tj 1.419444 0 Td 51.851852 Tz (switching ) Tj 2.955556 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 73.45679 Tz (80% ) Tj 1.477778 0 Td 47.962963 Tz (ethyl ) Tj 1.594444 0 Td 51.157407 Tz (acetate/hexane ) Tj 4.433333 0 Td 48.611111 Tz (for ) Tj 1.011111 0 Td 51.851852 Tz (a ) Tj 0.486111 0 Td 47.800926 Tz (step ) Tj 51.428571 0 0 51.428571 0 2655.169492 Tm 6.358333 0 Td 49.826389 Tz (gradient ) Tj 2.547222 0 Td 45.775463 Tz (elution. ) Tj 51.428571 0 0 51.428571 0 2614.763906 Tm 7.097222 0 Td 51.851852 Tz (After ) Tj 1.788889 0 Td 45.121083 Tz (purification, ) Tj 3.811111 0 Td 48.611111 Tz (the ) Tj 1.108333 0 Td 50.771605 Tz (protected ) Tj 3.013889 0 Td 51.006441 Tz (\(18:0\)-p-phosphodiester ) Tj 51.428571 0 0 51.428571 0 2569.093671 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.4 0 Td 41.481481 Tz (split ) Tj 1.477778 0 Td 46.180556 Tz (into ) Tj 1.361111 0 Td 59.41358 Tz (two ) Tj 1.341667 0 Td 52.777778 Tz (roughly ) Tj 2.45 0 Td 53.148148 Tz (equal ) Tj 1.808333 0 Td 47.530864 Tz (portions. ) Tj 2.819444 0 Td 63.734568 Tz (The ) Tj 1.380556 0 Td 37.592593 Tz (first ) Tj 1.322222 0 Td 51.388889 Tz (portion ) Tj 51.428571 0 0 51.428571 0 2521.433869 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 55.902778 Tz (used ) Tj 1.536111 0 Td 46.450617 Tz (for ) Tj 1.011111 0 Td 46.450617 Tz (direct ) Tj 1.866667 0 Td 46.450617 Tz (fluorination ) Tj 3.597222 0 Td 58.738426 Tz (\(Example ) Tj 3.072222 0 Td 45.37037 Tz (1\) ) Tj 0.7 0 Td 59.41358 Tz (and ) Tj 1.263889 0 Td 50.771605 Tz (the ) Tj 1.069444 0 Td 57.253086 Tz (second ) Tj 51.428571 0 0 51.428571 0 2478.410037 Tm 6.358333 0 Td 49.537037 Tz (portion ) Tj 2.275 0 Td 61.574074 Tz (was ) Tj 1.302778 0 Td 55.902778 Tz (used ) Tj 1.536111 0 Td 47.530864 Tz (for ) Tj 1.030556 0 Td 50.411523 Tz (reduction ) Tj 2.936111 0 Td 52.662037 Tz (followed ) Tj 2.722222 0 Td 59.953704 Tz (by ) Tj 0.913889 0 Td 45.37037 Tz (fluorination. ) Tj 3.791667 0 Td 55.092593 Tz (For ) Tj 51.428571 0 0 51.428571 0 2438.355689 Tm 6.358333 0 Td 48.287037 Tz (reduction, ) Tj 3.111111 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 49.691358 Tz (protected ) Tj 2.877778 0 Td 51.147343 Tz (\(18:0\)-p-phosphodiester ) Tj 7.233333 0 Td 40.509259 Tz (\(1 ) Tj 0.758333 0 Td 46.990741 Tz (eq.\) ) Tj 1.322222 0 Td 60.493827 Tz (was ) Tj 51.428571 0 0 51.428571 0 2392.415842 Tm 6.358333 0 Td 50.771605 Tz (dissolved ) Tj 3.033333 0 Td 43.75 Tz (in ) Tj 0.816667 0 Td 59.773663 Tz (THF/water ) Tj 3.480556 0 Td 46.666667 Tz (3:0.1 ) Tj 1.75 0 Td 49.494949 Tz (equivalents ) Tj 3.597222 0 Td 47.800926 Tz (respectively ) Tj 3.713889 0 Td 61.574074 Tz (and ) Tj 51.428571 0 0 51.428571 0 2348.427307 Tm 6.377778 0 Td 58.333333 Tz (sodium ) Tj 2.313889 0 Td 54.208754 Tz (borohydride ) Tj 3.791667 0 Td 42.12963 Tz (\(1 ) Tj 0.797222 0 Td 45.37037 Tz (eq.\) ) Tj 1.302778 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 57.685185 Tz (added ) Tj 1.925 0 Td 46.990741 Tz (to ) Tj 0.797222 0 Td 48.611111 Tz (the ) Tj 1.108333 0 Td 47.800926 Tz (reaction ) Tj 2.527778 0 Td 42.12963 Tz (flask. ) Tj 51.428571 0 0 51.428571 0 2303.748219 Tm 6.358333 0 Td 63.734568 Tz (The ) Tj 1.302778 0 Td 47.800926 Tz (reaction ) Tj 2.430556 0 Td 53.703704 Tz (mixture ) Tj 2.372222 0 Td 60.493827 Tz (was ) Tj 1.263889 0 Td 43.981481 Tz (stirred ) Tj 1.983333 0 Td 44.074074 Tz (until ) Tj 1.438889 0 Td 39.969136 Tz (all ) Tj 0.855556 0 Td 58.873457 Tz (sodium ) Tj 2.255556 0 Td 54.208754 Tz (borohydride ) Tj 51.428571 0 0 51.428571 0 2261.106599 Tm 6.358333 0 Td 50.771605 Tz (dissolved ) Tj 3.033333 0 Td 54.012346 Tz (\(~2 ) Tj 1.283333 0 Td 51.851852 Tz (minutes\) ) Tj 2.761111 0 Td 59.41358 Tz (and ) Tj 1.341667 0 Td 52.932099 Tz (continued ) Tj 3.111111 0 Td 44.155093 Tz (stirring ) Tj 2.372222 0 Td 48.611111 Tz (for ) Tj 1.108333 0 Td 56.712963 Tz (an ) Tj 0.933333 0 Td 63.194444 Tz (addi ) Tj 51.428571 0 0 51.428571 0 2219.598226 Tm 6.338889 0 Td 45.910494 Tz (tional ) Tj 1.963889 0 Td 56.712963 Tz (10 ) Tj 0.875 0 Td 50.636574 Tz (minutes. ) Tj 2.663889 0 Td 57.685185 Tz (Water ) Tj 1.905556 0 Td 46.990741 Tz (\(3 ) Tj 0.777778 0 Td 47.800926 Tz (eq.\) ) Tj 1.361111 0 Td 60.493827 Tz (was ) Tj 1.302778 0 Td 57.685185 Tz (added ) Tj 1.925 0 Td 59.41358 Tz (and ) Tj 1.283333 0 Td 49.691358 Tz (the ) Tj 1.108333 0 Td 49.016204 Tz (reaction ) Tj 40 0 0 40 0 2185 Tm 8.225 0 Td 68.452381 Tz (mixture ) Tj 3.2 0 Td 80.555556 Tz (was ) Tj 1.8 0 Td 57.142857 Tz (stirred ) Tj 2.725 0 Td 72.916667 Tz (an ) Tj 1.225 0 Td 62.5 Tz (additional ) Tj 4.2 0 Td 72.916667 Tz (10 ) Tj 1.225 0 Td 65.104167 Tz (minutes. ) Tj 3.475 0 Td 63.888889 Tz (All ) Tj 1.525 0 Td 63.020833 Tz (solvents ) Tj 51.428571 0 0 51.428571 0 2138.696078 Tm 6.338889 0 Td 59.953704 Tz (were ) Tj 1.652778 0 Td 59.259259 Tz (removed ) Tj 2.702778 0 Td 43.75 Tz (in ) Tj 0.758333 0 Td 55.740741 Tz (vacuo ) Tj 1.866667 0 Td 59.41358 Tz (and ) Tj 1.263889 0 Td 47.530864 Tz (the ) Tj 1.069444 0 Td 51.446759 Tz (reduced, ) Tj 2.644444 0 Td 50.411523 Tz (protected ) Tj 2.897222 0 Td 48.611111 Tz (\(18:0\)-p- ) Tj 51.428571 0 0 51.428571 0 2099.69475 Tm 6.358333 0 Td 52.777778 Tz (phosphodiester ) Tj 4.647222 0 Td 61.574074 Tz (was ) Tj 1.361111 0 Td 47.395833 Tz (purified ) Tj 2.508333 0 Td 59.953704 Tz (by ) Tj 1.011111 0 Td 44.722222 Tz (flash ) Tj 1.613889 0 Td 59.41358 Tz (column ) Tj 2.411111 0 Td 59.217172 Tz (chromatogra ) Tj 51.428571 0 0 51.428571 0 2056.551122 Tm 6.358333 0 Td 59.41358 Tz (phy ) Tj 1.322222 0 Td 52.5 Tz (using ) Tj 1.788889 0 Td 72.376543 Tz (40% ) Tj 1.555556 0 Td 47.962963 Tz (ethyl ) Tj 1.672222 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.491667 0 Td 51.041667 Tz (then ) Tj 1.458333 0 Td 52.572016 Tz (switching ) Tj 3.072222 0 Td 43.75 Tz (to ) Tj 0.758333 0 Td 74.537037 Tz (80% ) Tj 51.428571 0 0 51.428571 0 2013.455635 Tm 6.358333 0 Td 47.314815 Tz (ethyl ) Tj 1.613889 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.413889 0 Td 48.611111 Tz (for ) Tj 0.972222 0 Td 58.333333 Tz (a ) Tj 0.505556 0 Td 47.800926 Tz (step ) Tj 1.302778 0 Td 50.231481 Tz (gradient ) Tj 2.547222 0 Td 44.965278 Tz (elution. ) Tj 2.352778 0 Td 63.734568 Tz (The ) Tj 1.302778 0 Td 50.636574 Tz (reduced, ) Tj 51.428571 0 0 51.428571 0 1974.699746 Tm 6.358333 0 Td 50.411523 Tz (protected ) Tj 3.072222 0 Td 51.147343 Tz (\(18:0\)-p-phosphodiester ) Tj 7.388889 0 Td 42.12963 Tz (\(1 ) Tj 0.952778 0 Td 46.180556 Tz (eq.\) ) Tj 1.477778 0 Td 60.493827 Tz (was ) Tj 1.458333 0 Td 49.907407 Tz (dried ) Tj 1.847222 0 Td 54.282407 Tz (over ) Tj 51.428571 0 0 51.428571 0 1931.271411 Tm 6.358333 0 Td 55.976431 Tz (phosphorous ) Tj 3.85 0 Td 53.652263 Tz (pentoxide ) Tj 3.052778 0 Td 48.611111 Tz (for ) Tj 1.069444 0 Td 55.092593 Tz (12 ) Tj 0.816667 0 Td 53.796296 Tz (hours ) Tj 1.769444 0 Td 58.333333 Tz (and ) Tj 1.225 0 Td 50.771605 Tz (dissolved ) Tj 2.897222 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 56.712963 Tz (dichlo ) Tj 51.428571 0 0 51.428571 0 1886.96 Tm 6.358333 0 Td 53.796296 Tz (romethane. ) Tj 3.363889 0 Td 63.734568 Tz (The ) Tj 1.283333 0 Td 48.611111 Tz (reaction ) Tj 2.508333 0 Td 46.018519 Tz (flask ) Tj 1.516667 0 Td 60.493827 Tz (was ) Tj 1.225 0 Td 50.771605 Tz (sealed ) Tj 1.963889 0 Td 58.333333 Tz (and ) Tj 1.166667 0 Td 53.472222 Tz (placed ) Tj 2.061111 0 Td 45.37037 Tz (in ) Tj 0.7 0 Td 56.712963 Tz (an ) Tj 0.855556 0 Td 46.450617 Tz (ice ) Tj 51.428571 0 0 51.428571 0 1847.544021 Tm 6.338889 0 Td 52.662037 Tz (bath ) Tj 1.555556 0 Td 45.37037 Tz (to ) Tj 0.875 0 Td 52.256944 Tz (maintain ) Tj 2.819444 0 Td 51.851852 Tz (0 ) Tj 0.894444 0 Td 55.092593 Tz (C. ) Tj 0.991667 0 Td 49.96142 Tz (temperature. ) Tj 3.927778 0 Td 55.416667 Tz (Deoxofluor ) Tj 3.597222 0 Td 46.990741 Tz (\(2 ) Tj 0.875 0 Td 46.180556 Tz (eq.\) ) Tj 1.380556 0 Td 50.231481 Tz (in ) Tj 51.428571 0 0 51.428571 0 1803.993663 Tm 6.358333 0 Td 54.444444 Tz (dichloromethane ) Tj 5.191667 0 Td 61.574074 Tz (was ) Tj 1.419444 0 Td 52.932099 Tz (slowly ) Tj 2.197222 0 Td 58.981481 Tz (added ) Tj 2.061111 0 Td 55.092593 Tz (\(-2 ) Tj 1.341667 0 Td 49.331276 Tz (minutes\). ) Tj 2.955556 0 Td 64.814815 Tz (The ) Tj 1.477778 0 Td 46.450617 Tz (ice ) Tj 40 0 0 40 0 1770 Tm 8.15 0 Td 67.708333 Tz (bath ) Tj 1.85 0 Td 77.777778 Tz (was ) Tj 1.6 0 Td 77.380952 Tz (removed ) Tj 3.45 0 Td 75 Tz (and ) Tj 1.525 0 Td 62.5 Tz (the ) Tj 1.325 0 Td 62.5 Tz (reaction ) Tj 3.25 0 Td 68.452381 Tz (mixture ) Tj 3.05 0 Td 80.555556 Tz (was ) Tj 1.65 0 Td 57.142857 Tz (stirred ) Tj 2.575 0 Td 62.5 Tz (for ) Tj 1.35 0 Td 70.833333 Tz (12 ) Tj 40 0 0 40 0 1728 Tm 8.15 0 Td 63.888889 Tz (hours. ) Tj 2.5 0 Td 91.666667 Tz (An ) Tj 1.325 0 Td 61.666667 Tz (extraction ) Tj 3.925 0 Td 68.75 Tz (with ) Tj 1.875 0 Td 66.166667 Tz (dichloromethane/saturated ) Tj 10.125 0 Td 75.694444 Tz (sodium ) Tj 51.428571 0 0 51.428571 0 1680.583433 Tm 6.338889 0 Td 51.557239 Tz (bicarbonate ) Tj 3.558333 0 Td 48.611111 Tz (solution ) Tj 2.547222 0 Td 43.209877 Tz (1:1 ) Tj 1.030556 0 Td 46.666667 Tz (\(v/v\) ) Tj 1.536111 0 Td 61.574074 Tz (was ) Tj 1.244444 0 Td 56.532922 Tz (performed ) Tj 3.169444 0 Td 59.41358 Tz (and ) Tj 1.225 0 Td 48.611111 Tz (the ) Tj 0.991667 0 Td 51.851852 Tz (organic ) Tj 52.857143 0 0 52.857143 0 1638.202899 Tm 6.186486 0 Td 47.927928 Tz (layer ) Tj 1.608108 0 Td 59.90991 Tz (was ) Tj 1.248649 0 Td 45.09009 Tz (collected. ) Tj 51.428571 0 0 51.428571 0 1599.517923 Tm 7.097222 0 Td 51.851852 Tz (After ) Tj 1.691667 0 Td 52.932099 Tz (drying ) Tj 2.061111 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 52.391975 Tz (vacuo, ) Tj 2.061111 0 Td 49.691358 Tz (the ) Tj 1.05 0 Td 50.05144 Tz (protected ) Tj 2.877778 0 Td 54.751462 Tz (\(18:0\)-p-monofluoro ) Tj 51.428571 0 0 51.428571 0 1558.69475 Tm 6.358333 0 Td 52.777778 Tz (phosphodiester ) Tj 4.647222 0 Td 61.574074 Tz (was ) Tj 1.361111 0 Td 47.395833 Tz (purified ) Tj 2.508333 0 Td 59.953704 Tz (by ) Tj 1.011111 0 Td 44.722222 Tz (flash ) Tj 1.613889 0 Td 59.41358 Tz (column ) Tj 2.411111 0 Td 59.217172 Tz (chromatogra ) Tj 51.428571 0 0 51.428571 0 1514.551122 Tm 6.358333 0 Td 59.41358 Tz (phy ) Tj 1.322222 0 Td 52.5 Tz (using ) Tj 1.788889 0 Td 72.376543 Tz (40% ) Tj 1.555556 0 Td 47.962963 Tz (ethyl ) Tj 1.672222 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.491667 0 Td 51.041667 Tz (then ) Tj 1.458333 0 Td 52.572016 Tz (switching ) Tj 3.072222 0 Td 43.75 Tz (to ) Tj 0.758333 0 Td 74.537037 Tz (80% ) Tj 51.428571 0 0 51.428571 0 1473.748517 Tm 6.358333 0 Td 47.314815 Tz (ethyl ) Tj 1.594444 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.394444 0 Td 48.611111 Tz (for ) Tj 0.972222 0 Td 58.333333 Tz (a ) Tj 0.486111 0 Td 47.800926 Tz (step ) Tj 1.283333 0 Td 49.826389 Tz (gradient ) Tj 2.508333 0 Td 45.775463 Tz (elution. ) Tj 2.372222 0 Td 56.17284 Tz (For ) Tj 1.127778 0 Td 56.712963 Tz (deprotec ) Tj 51.428571 0 0 51.428571 0 1434.634615 Tm 6.338889 0 Td 44.074074 Tz (tion, ) Tj 1.652778 0 Td 49.691358 Tz (the ) Tj 1.186111 0 Td 50.771605 Tz (protected ) Tj 3.072222 0 Td 52.328431 Tz (\(18:0\)-p-monofluoro-phosphodiester ) Tj 10.966667 0 Td 45.37037 Tz (\(1 ) Tj 51.428571 0 0 51.428571 0 1390.774032 Tm 6.358333 0 Td 46.180556 Tz (eq.\) ) Tj 1.361111 0 Td 61.574074 Tz (was ) Tj 1.361111 0 Td 50.411523 Tz (dissolved ) Tj 2.955556 0 Td 45.37037 Tz (in ) Tj 0.777778 0 Td 48.611111 Tz (pyridine. ) Tj 2.858333 0 Td 57.086895 Tz (N-propylamine ) Tj 4.686111 0 Td 55.092593 Tz (\(100 ) Tj 1.555556 0 Td 46.180556 Tz (eq.\) ) Tj 1.361111 0 Td 48.611111 Tz (in ) Tj 51.428571 0 0 51.428571 0 1346.204819 Tm 6.358333 0 Td 50.636574 Tz (pyridine ) Tj 2.566667 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 57.685185 Tz (added ) Tj 1.886111 0 Td 43.75 Tz (to ) Tj 0.7 0 Td 48.611111 Tz (the ) Tj 1.011111 0 Td 48.611111 Tz (reaction ) Tj 2.469444 0 Td 46.018519 Tz (flask ) Tj 1.477778 0 Td 58.333333 Tz (and ) Tj 1.205556 0 Td 49.691358 Tz (the ) Tj 0.991667 0 Td 48.611111 Tz (clear ) Tj 1.575 0 Td 49.421296 Tz (solution ) Tj 51.428571 0 0 51.428571 0 1304.853779 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 43.981481 Tz (stirred ) Tj 2.041667 0 Td 47.530864 Tz (for ) Tj 1.088889 0 Td 55.092593 Tz (10 ) Tj 0.855556 0 Td 54.166667 Tz (minutes ) Tj 2.45 0 Td 43.75 Tz (at ) Tj 0.738889 0 Td 62.384259 Tz (room ) Tj 1.691667 0 Td 50.501543 Tz (temperature. ) Tj 3.811111 0 Td 50.771605 Tz (All ) Tj 1.108333 0 Td 49.016204 Tz (solvents ) Tj 51.428571 0 0 51.428571 0 1265.629268 Tm 6.338889 0 Td 59.953704 Tz (were ) Tj 1.633333 0 Td 60.185185 Tz (removed ) Tj 2.702778 0 Td 45.37037 Tz (in ) Tj 0.777778 0 Td 56.388889 Tz (vacuo ) Tj 1.866667 0 Td 46.990741 Tz (to ) Tj 0.758333 0 Td 49.259259 Tz (yield ) Tj 1.633333 0 Td 50.771605 Tz (the ) Tj 1.147222 0 Td 59.953704 Tz (n-propylammonium ) Tj 5.95 0 Td 42.939815 Tz (salt ) Tj 51.428571 0 0 51.428571 0 1225.330132 Tm 6.358333 0 Td 58.333333 Tz (of ) Tj 0.972222 0 Td 49.691358 Tz (the ) Tj 1.225 0 Td 51.388889 Tz (\(18:0\)-p-monofluoro-phosphodiester. ) Tj 11.141667 0 Td 71.296296 Tz (An ) Tj 1.205556 0 Td 49.259259 Tz (extraction ) Tj 51.428571 0 0 51.428571 0 1179.598985 Tm 6.338889 0 Td 54.282407 Tz (with ) Tj 1.691667 0 Td 52.759259 Tz (chloroform/methanol/brine ) Tj 8.361111 0 Td 44.907407 Tz (1:1.5:1 ) Tj 2.391667 0 Td 47.222222 Tz (\(v/v/v\) ) Tj 2.372222 0 Td 60.493827 Tz (was ) Tj 1.516667 0 Td 63.734568 Tz (per ) Tj 51.428571 0 0 51.428571 0 1140.976162 Tm 6.358333 0 Td 58.333333 Tz (formed ) Tj 2.255556 0 Td 45.37037 Tz (to ) Tj 0.7 0 Td 51.446759 Tz (generate ) Tj 2.625 0 Td 48.611111 Tz (the ) Tj 1.011111 0 Td 58.873457 Tz (sodium ) Tj 2.313889 0 Td 42.12963 Tz (salt ) Tj 1.127778 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 48.611111 Tz (the ) Tj 1.030556 0 Td 55.283224 Tz (\(18:0\)-p-monofluo ) Tj 51.428571 0 0 51.428571 0 1103 Tm 6.358333 0 Td 50.326797 Tz (rophosphodiester. ) Tj 51.428571 0 0 51.428571 0 1023.087248 Tm 13.552778 0 Td 61.111111 Tz (Example ) Tj 2.741667 0 Td 55.092593 Tz (3 ) Tj 51.428571 0 0 51.428571 0 941 Tm 10.441667 0 Td 50.283751 Tz (\(16:0\)-p-difluorophosphodiester ) Tj 31.428571 0 0 31.428571 0 784 Tm 26.186364 0 Td 111.363636 Tz (O ) Tj 171.428571 0 0 171.428571 0 694 Tm 2.584167 0 Td 37.401961 Tz (gic-\(\)--i-o-clich ) Tj 31.428571 0 0 31.428571 0 651 Tm 26.186364 0 Td 111.363636 Tz (OH ) Tj 51.428571 0 0 51.428571 0 546.671214 Tm 7.116667 0 Td 55.976431 Tz (Phosphorous ) Tj 4.025 0 Td 53.030303 Tz (oxychloride ) Tj 3.791667 0 Td 42.12963 Tz (\(1 ) Tj 0.855556 0 Td 46.990741 Tz (eq.\) ) Tj 1.419444 0 Td 61.574074 Tz (was ) Tj 1.4 0 Td 58.333333 Tz (added ) Tj 2.041667 0 Td 46.990741 Tz (to ) Tj 0.836111 0 Td 55.092593 Tz (a ) Tj 0.680556 0 Td 55.740741 Tz (round ) Tj 51.428571 0 0 51.428571 0 503.324528 Tm 6.338889 0 Td 57.253086 Tz (bottom ) Tj 2.391667 0 Td 46.018519 Tz (flask ) Tj 1.633333 0 Td 58.333333 Tz (and ) Tj 1.341667 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 46.990741 Tz (in ) Tj 0.875 0 Td 49.907407 Tz (tetrahydrofuran ) Tj 4.783333 0 Td 56.17284 Tz (\(THF\). ) Tj 2.313889 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 459.95449 Tm 6.358333 0 Td 57.037037 Tz (round ) Tj 1.847222 0 Td 56.712963 Tz (bottom ) Tj 2.197222 0 Td 46.666667 Tz (flask ) Tj 1.536111 0 Td 60.493827 Tz (was ) Tj 1.263889 0 Td 51.041667 Tz (then ) Tj 1.4 0 Td 52.391975 Tz (placed ) Tj 2.061111 0 Td 43.75 Tz (in ) Tj 0.661111 0 Td 59.953704 Tz (an ) Tj 0.875 0 Td 46.450617 Tz (ice ) Tj 0.952778 0 Td 52.662037 Tz (bath ) Tj 1.419444 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 53.472222 Tz (maintain ) Tj 51.428571 0 0 51.428571 0 420.452261 Tm 6.358333 0 Td 51.851852 Tz (a ) Tj 0.544444 0 Td 63.194444 Tz (0C. ) Tj 1.769444 0 Td 50.231481 Tz (temperature. ) Tj 3.908333 0 Td 56.860269 Tz (Hexadecanol ) Tj 4.005556 0 Td 42.12963 Tz (\(1 ) Tj 0.797222 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 50.411523 Tz (dissolved ) Tj 2.936111 0 Td 45.37037 Tz (in ) Tj 0.758333 0 Td 76.697531 Tz (THF ) Tj 51.428571 0 0 51.428571 0 379.895911 Tm 6.338889 0 Td 54.282407 Tz (with ) Tj 1.497222 0 Td 49.85755 Tz (triethylamine ) Tj 4.083333 0 Td 63.518519 Tz (\(TEA\) ) Tj 2.1 0 Td 42.12963 Tz (\(1 ) Tj 0.777778 0 Td 46.180556 Tz (eq.\) ) Tj 1.283333 0 Td 62.654321 Tz (was ) Tj 1.302778 0 Td 58.981481 Tz (added ) Tj 1.963889 0 Td 55.092593 Tz (dropwise ) Tj 2.858333 0 Td 45.37037 Tz (to ) Tj 0.738889 0 Td 49.691358 Tz (the ) Tj 51.428571 0 0 51.428571 0 339.215457 Tm 6.358333 0 Td 55.976431 Tz (phosphorous ) Tj 3.830556 0 Td 56.17284 Tz (oxychloride/THF ) Tj 5.191667 0 Td 46.090535 Tz (solution. ) Tj 2.605556 0 Td 64.814815 Tz (Once ) Tj 1.672222 0 Td 39.969136 Tz (all ) Tj 0.836111 0 Td 53.472222 Tz (of ) Tj 0.738889 0 Td 47.530864 Tz (the ) Tj 0.991667 0 Td 66.435185 Tz (hexa ) Tj 51.428571 0 0 51.428571 0 293 Tm 6.358333 0 Td 60.925926 Tz (decanol/THF/TEA ) Tj 5.775 0 Td 48.206019 Tz (solution ) Tj 2.644444 0 Td 61.574074 Tz (was ) Tj 1.419444 0 Td 57.685185 Tz (added ) Tj 2.061111 0 Td 56.712963 Tz (\(-20 ) Tj 1.672222 0 Td 50.05144 Tz (minutes\), ) Tj 3.013889 0 Td 49.691358 Tz (the ) Tj 40 0 0 40 0 259 Tm 8.175 0 Td 63.020833 Tz (reaction ) Tj 3.2 0 Td 69.047619 Tz (mixture ) Tj 3.05 0 Td 79.166667 Tz (was ) Tj 1.625 0 Td 56.547619 Tz (stirred ) Tj 2.55 0 Td 61.111111 Tz (for ) Tj 1.2 0 Td 72.916667 Tz (an ) Tj 1.025 0 Td 62.5 Tz (additional ) Tj 3.925 0 Td 79.166667 Tz (40 ) Tj 1.125 0 Td 70.238095 Tz (minutes ) Tj 3.075 0 Td 58.333333 Tz (at ) Tj 0.85 0 Td 66.666667 Tz (0 ) Tj 51.428571 0 0 51.428571 0 214.072727 Tm 6.358333 0 Td 53.472222 Tz (C. ) Tj 0.777778 0 Td 87.5 Tz (A ) Tj 0.7 0 Td 48.206019 Tz (solution ) Tj 2.469444 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 56.018519 Tz (p-hydroxybenzaldehyde ) Tj 7.213889 0 Td 42.12963 Tz (\(1 ) Tj 0.758333 0 Td 46.180556 Tz (eq.\) ) Tj 1.283333 0 Td 43.75 Tz (in ) Tj 0.680556 0 Td 76.697531 Tz (THF ) Tj 1.555556 0 Td 54.282407 Tz (with ) Tj 51.428571 0 0 51.428571 0 169.896806 Tm 6.358333 0 Td 78.858025 Tz (TEA ) Tj 1.555556 0 Td 43.75 Tz (\(1 ) Tj 0.738889 0 Td 45.37037 Tz (eq.\) ) Tj 1.263889 0 Td 60.493827 Tz (was ) Tj 1.225 0 Td 58.333333 Tz (added ) Tj 1.886111 0 Td 55.497685 Tz (dropwise ) Tj 2.780556 0 Td 46.990741 Tz (to ) Tj 0.719444 0 Td 48.611111 Tz (the ) Tj 1.030556 0 Td 48.206019 Tz (reaction ) Tj 2.469444 0 Td 46.018519 Tz (flask ) Tj 1.477778 0 Td 59.41358 Tz (and ) Tj 1.225 0 Td 60.493827 Tz (was ) Tj 30 0 0 30 0 2755 Tm 41.833333 0 Td 72.222222 Tz (5 ) Tj 30 0 0 30 0 2547 Tm 41.666667 0 Td 75 Tz (10 ) Tj 30 0 0 30 0 2339 Tm 41.666667 0 Td 72.222222 Tz (15 ) Tj 30 0 0 30 0 1923 Tm 41.6 0 Td 77.777778 Tz (25 ) Tj 30 0 0 30 0 1716 Tm 41.6 0 Td 80.555556 Tz (30 ) Tj 30 0 0 30 0 1507 Tm 41.6 0 Td 77.777778 Tz (35 ) Tj 30 0 0 30 0 1299 Tm 41.566667 0 Td 83.333333 Tz (40 ) Tj 30 0 0 30 0 1091 Tm 41.566667 0 Td 80.555556 Tz (45 ) Tj 30 0 0 30 0 883 Tm 41.6 0 Td 80.555556 Tz (50 ) Tj 30 0 0 30 0 675 Tm 41.6 0 Td 77.777778 Tz (55 ) Tj 30 0 0 30 0 467 Tm 41.633333 0 Td 77.777778 Tz (60 ) Tj 30 0 0 30 0 259 Tm 41.633333 0 Td 75 Tz (65 ) Tj 52.857143 0 0 52.857143 0 2968 Tm 32.672973 0 Td 74.099099 Tz (10 ) Tj 51.428571 0 0 51.428571 0 2913.573548 Tm 25.316667 0 Td 43.981481 Tz (stirred ) Tj 1.983333 0 Td 48.611111 Tz (for ) Tj 0.991667 0 Td 56.712963 Tz (an ) Tj 0.855556 0 Td 47.962963 Tz (additional ) Tj 3.052778 0 Td 63.194444 Tz (40 ) Tj 0.933333 0 Td 53.240741 Tz (minutes ) Tj 2.391667 0 Td 45.37037 Tz (at ) Tj 0.7 0 Td 59.953704 Tz (0C. ) Tj 1.613889 0 Td 57.685185 Tz (Water ) Tj 1.847222 0 Td 45.37037 Tz (\(1 ) Tj 0.758333 0 Td 46.990741 Tz (eq.\) ) Tj 1.263889 0 Td 59.41358 Tz (and ) Tj 51.428571 0 0 51.428571 0 2870.57956 Tm 25.297222 0 Td 78.858025 Tz (TEA ) Tj 1.652778 0 Td 43.75 Tz (\(1 ) Tj 0.816667 0 Td 45.37037 Tz (eq.\) ) Tj 1.341667 0 Td 58.333333 Tz (were ) Tj 1.613889 0 Td 58.333333 Tz (added ) Tj 1.963889 0 Td 45.37037 Tz (to ) Tj 0.797222 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 48.206019 Tz (reaction ) Tj 2.586111 0 Td 52.777778 Tz (mixture ) Tj 2.430556 0 Td 58.981481 Tz (which ) Tj 2.022222 0 Td 61.574074 Tz (was ) Tj 40 0 0 40 0 2834 Tm 32.525 0 Td 70.238095 Tz (allowed ) Tj 3.25 0 Td 58.333333 Tz (to ) Tj 1.075 0 Td 50 Tz (stir ) Tj 1.475 0 Td 62.5 Tz (for ) Tj 1.4 0 Td 81.25 Tz (60 ) Tj 1.275 0 Td 69.642857 Tz (minutes ) Tj 3.25 0 Td 58.333333 Tz (at ) Tj 1 0 Td 82.291667 Tz (0C. ) Tj 2.275 0 Td 81.944444 Tz (The ) Tj 1.8 0 Td 64.583333 Tz (contents ) Tj 3.425 0 Td 72.916667 Tz (of ) Tj 1.075 0 Td 65.277778 Tz (the ) Tj 40 0 0 40 0 2790 Tm 32.525 0 Td 62.5 Tz (reaction ) Tj 3.25 0 Td 60 Tz (flask ) Tj 2.05 0 Td 75 Tz (were ) Tj 2.025 0 Td 66.666667 Tz (then ) Tj 1.9 0 Td 79.166667 Tz (vacuum ) Tj 3.15 0 Td 55.208333 Tz (filtered ) Tj 2.875 0 Td 76.388889 Tz (and ) Tj 1.65 0 Td 63.333333 Tz (dried ) Tj 2.125 0 Td 58.333333 Tz (in ) Tj 0.975 0 Td 67.361111 Tz (vacuo. ) Tj 40 0 0 40 0 2747 Tm 32.525 0 Td 66.666667 Tz (After ) Tj 2.2 0 Td 75 Tz (an ) Tj 1.15 0 Td 62.083333 Tz (extraction ) Tj 4.025 0 Td 67.708333 Tz (with ) Tj 1.925 0 Td 68.666667 Tz (chloroform/methanol/water ) Tj 10.6 0 Td 58.928571 Tz (1:1.5:1 ) Tj 51.428571 0 0 51.428571 0 2698.580764 Tm 25.316667 0 Td 44.155093 Tz (\(v/v/v\), ) Tj 2.430556 0 Td 48.611111 Tz (the ) Tj 1.147222 0 Td 51.147343 Tz (\(16:0\)-p-phosphodiester ) Tj 7.291667 0 Td 61.574074 Tz (was ) Tj 1.4 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 45.37037 Tz (in ) Tj 0.836111 0 Td 73.45679 Tz (40% ) Tj 51.428571 0 0 51.428571 0 2653.548303 Tm 25.297222 0 Td 47.962963 Tz (ethyl ) Tj 1.808333 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.627778 0 Td 59.41358 Tz (and ) Tj 1.419444 0 Td 50.084175 Tz (centrifuged ) Tj 3.713889 0 Td 47.530864 Tz (for ) Tj 1.186111 0 Td 61.574074 Tz (7 ) Tj 0.777778 0 Td 50.636574 Tz (minutes. ) Tj 2.8 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 2609.713574 Tm 25.316667 0 Td 50.673401 Tz (Supernatant ) Tj 3.597222 0 Td 61.574074 Tz (was ) Tj 1.380556 0 Td 53.877315 Tz (decanted ) Tj 2.838889 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 50.771605 Tz (the ) Tj 1.186111 0 Td 49.331276 Tz (insoluble ) Tj 2.936111 0 Td 46.450617 Tz (fractions ) Tj 2.8 0 Td 59.143519 Tz (were ) Tj 40 0 0 40 0 2572 Tm 32.525 0 Td 72.222222 Tz (combined. ) Tj 51.428571 0 0 51.428571 0 2526.38394 Tm 26.016667 0 Td 63.734568 Tz (The ) Tj 1.361111 0 Td 45.046296 Tz (relatively ) Tj 2.858333 0 Td 55.092593 Tz (pure ) Tj 1.536111 0 Td 51.006441 Tz (\(16:0\)-p-phosphodiester ) Tj 7.213889 0 Td 43.75 Tz (\(1 ) Tj 0.777778 0 Td 43.425926 Tz (eq.\), ) Tj 1.536111 0 Td 81.018519 Tz (DCC ) Tj 51.428571 0 0 51.428571 0 2480.085427 Tm 25.316667 0 Td 46.180556 Tz (\(2.2 ) Tj 1.341667 0 Td 61.574074 Tz (eq\) ) Tj 1.302778 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 87.5 Tz (DMAP ) Tj 2.313889 0 Td 43.75 Tz (\(0.1 ) Tj 1.322222 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 58.333333 Tz (were ) Tj 1.594444 0 Td 49.907407 Tz (dried ) Tj 1.711111 0 Td 53.472222 Tz (over ) Tj 1.458333 0 Td 56.565657 Tz (phosphorous ) Tj 51.428571 0 0 51.428571 0 2436.971223 Tm 25.297222 0 Td 53.292181 Tz (pentoxide ) Tj 2.994444 0 Td 48.611111 Tz (for ) Tj 1.05 0 Td 53.472222 Tz (12 ) Tj 0.797222 0 Td 49.151235 Tz (hours. ) Tj 1.905556 0 Td 56.442901 Tz (Cyanoethanol ) Tj 4.2 0 Td 43.75 Tz (\(1.1 ) Tj 1.263889 0 Td 46.180556 Tz (eq.\) ) Tj 1.283333 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 50.771605 Tz (dissolved ) Tj 51.428571 0 0 51.428571 0 2390.646772 Tm 25.297222 0 Td 45.37037 Tz (in ) Tj 0.719444 0 Td 54.444444 Tz (dichloromethane ) Tj 5.055556 0 Td 59.41358 Tz (and ) Tj 1.244444 0 Td 49.259259 Tz (dried ) Tj 1.633333 0 Td 53.472222 Tz (with ) Tj 1.497222 0 Td 60.853909 Tz (magnesium ) Tj 3.5 0 Td 45.833333 Tz (sulfate ) Tj 2.1 0 Td 47.530864 Tz (for ) Tj 1.069444 0 Td 51.851852 Tz (12 ) Tj 51.428571 0 0 51.428571 0 2349.44484 Tm 25.277778 0 Td 49.691358 Tz (hours. ) Tj 1.983333 0 Td 62.654321 Tz (The ) Tj 1.302778 0 Td 51.147343 Tz (\(16:0\)-p-phosphodiester ) Tj 7.213889 0 Td 60.493827 Tz (was ) Tj 1.302778 0 Td 50.411523 Tz (dissolved ) Tj 2.877778 0 Td 46.990741 Tz (in ) Tj 0.758333 0 Td 56.712963 Tz (dichlo ) Tj 40 0 0 40 0 2310 Tm 32.525 0 Td 73.148148 Tz (romethane ) Tj 4.2 0 Td 75 Tz (and ) Tj 1.625 0 Td 105.555556 Tz (DCC ) Tj 2.15 0 Td 75 Tz (and ) Tj 1.625 0 Td 111.458333 Tz (DMAP ) Tj 2.925 0 Td 76.041667 Tz (were ) Tj 2.05 0 Td 75 Tz (added ) Tj 2.525 0 Td 56.25 Tz (to ) Tj 0.975 0 Td 62.5 Tz (the ) Tj 1.4 0 Td 62.5 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 2262.168612 Tm 25.297222 0 Td 42.669753 Tz (flask. ) Tj 1.788889 0 Td 62.654321 Tz (The ) Tj 1.361111 0 Td 46.666667 Tz (flask ) Tj 1.633333 0 Td 60.493827 Tz (was ) Tj 1.341667 0 Td 50.771605 Tz (sealed ) Tj 2.061111 0 Td 53.472222 Tz (with ) Tj 1.536111 0 Td 51.851852 Tz (a ) Tj 0.583333 0 Td 57.253086 Tz (septum ) Tj 2.313889 0 Td 59.41358 Tz (and ) Tj 1.283333 0 Td 55.632716 Tz (purged ) Tj 2.294444 0 Td 53.472222 Tz (with ) Tj 51.428571 0 0 51.428571 0 2222.985899 Tm 25.297222 0 Td 50.231481 Tz (nitrogen ) Tj 2.547222 0 Td 46.018519 Tz (after ) Tj 1.497222 0 Td 55.092593 Tz (adding ) Tj 2.1 0 Td 50.771605 Tz (the ) Tj 1.05 0 Td 53.472222 Tz (cyanoethanol ) Tj 4.005556 0 Td 46.090535 Tz (Solution. ) Tj 2.625 0 Td 64.814815 Tz (The ) Tj 1.302778 0 Td 49.016204 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 2179.476433 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.361111 0 Td 44.444444 Tz (stirred ) Tj 2.080556 0 Td 48.611111 Tz (for ) Tj 1.05 0 Td 59.953704 Tz (48 ) Tj 0.952778 0 Td 53.148148 Tz (hours ) Tj 1.808333 0 Td 46.990741 Tz (at ) Tj 0.777778 0 Td 62.384259 Tz (room ) Tj 1.730556 0 Td 50.231481 Tz (temperature. ) Tj 3.869444 0 Td 57.685185 Tz (Water ) Tj 1.944444 0 Td 46.990741 Tz (\(5 ) Tj 0.797222 0 Td 46.180556 Tz (eq.\) ) Tj 40 0 0 40 0 2144 Tm 32.5 0 Td 80.555556 Tz (was ) Tj 1.725 0 Td 75 Tz (added ) Tj 2.5 0 Td 76.388889 Tz (and ) Tj 1.625 0 Td 63.888889 Tz (the ) Tj 1.4 0 Td 62.5 Tz (reaction ) Tj 3.325 0 Td 68.452381 Tz (mixture ) Tj 3.125 0 Td 79.166667 Tz (was ) Tj 1.7 0 Td 57.142857 Tz (stirred ) Tj 2.65 0 Td 62.5 Tz (for ) Tj 1.35 0 Td 72.916667 Tz (an ) Tj 1.125 0 Td 81.25 Tz (addi ) Tj 40 0 0 40 0 2102 Tm 32.5 0 Td 59.722222 Tz (tional ) Tj 2.6 0 Td 79.166667 Tz (24 ) Tj 1.375 0 Td 63.194444 Tz (hours. ) Tj 2.75 0 Td 80.555556 Tz (The ) Tj 1.875 0 Td 65.104167 Tz (contents ) Tj 3.575 0 Td 75 Tz (of ) Tj 1.225 0 Td 63.888889 Tz (the ) Tj 1.6 0 Td 61.979167 Tz (reaction ) Tj 3.475 0 Td 59.166667 Tz (flask ) Tj 2.2 0 Td 75 Tz (were ) Tj 40 0 0 40 0 2061 Tm 32.525 0 Td 80.555556 Tz (vacuum ) Tj 3.175 0 Td 55.729167 Tz (filtered ) Tj 2.875 0 Td 77.777778 Tz (and ) Tj 1.65 0 Td 63.333333 Tz (dried ) Tj 2.15 0 Td 58.333333 Tz (in ) Tj 0.975 0 Td 66.666667 Tz (vacuo. ) Tj 2.65 0 Td 66.666667 Tz (After ) Tj 2.2 0 Td 72.916667 Tz (an ) Tj 1.15 0 Td 61.666667 Tz (extraction ) Tj 4 0 Td 67.708333 Tz (with ) Tj 51.428571 0 0 51.428571 0 2014.386091 Tm 25.297222 0 Td 51.851852 Tz (chloroform/brine ) Tj 5.191667 0 Td 44.290123 Tz (1:1 ) Tj 1.069444 0 Td 43.209877 Tz (\(v/v\), ) Tj 1.730556 0 Td 49.691358 Tz (the ) Tj 1.05 0 Td 55.092593 Tz (coupled ) Tj 2.45 0 Td 53.703704 Tz (product ) Tj 2.411111 0 Td 62.654321 Tz (was ) Tj 1.283333 0 Td 47.800926 Tz (purified ) Tj 51.428571 0 0 51.428571 0 1973.374532 Tm 25.277778 0 Td 61.574074 Tz (by ) Tj 1.011111 0 Td 45.37037 Tz (flash ) Tj 1.652778 0 Td 59.41358 Tz (column ) Tj 2.45 0 Td 56.25 Tz (chromatography ) Tj 4.997222 0 Td 53.148148 Tz (using ) Tj 1.847222 0 Td 73.45679 Tz (40% ) Tj 1.575 0 Td 48.611111 Tz (ethyl ) Tj 1.730556 0 Td 46.585648 Tz (acetate/ ) Tj 51.428571 0 0 51.428571 0 1930.689238 Tm 25.277778 0 Td 57.79321 Tz (hexane ) Tj 2.236111 0 Td 51.041667 Tz (then ) Tj 1.380556 0 Td 52.572016 Tz (switching ) Tj 2.994444 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 73.45679 Tz (80% ) Tj 1.477778 0 Td 47.962963 Tz (ethyl ) Tj 1.594444 0 Td 51.157407 Tz (acetate/hexane ) Tj 4.433333 0 Td 48.611111 Tz (for ) Tj 0.972222 0 Td 55.092593 Tz (a ) Tj 0.525 0 Td 46.990741 Tz (step ) Tj 51.428571 0 0 51.428571 0 1890.169492 Tm 25.297222 0 Td 49.826389 Tz (gradient ) Tj 2.547222 0 Td 45.775463 Tz (elution. ) Tj 51.428571 0 0 51.428571 0 1851.747226 Tm 26.016667 0 Td 52.5 Tz (After ) Tj 1.808333 0 Td 45.121083 Tz (purification, ) Tj 3.791667 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 50.771605 Tz (protected ) Tj 3.013889 0 Td 51.006441 Tz (\(16:0\)-p-phosphodiester ) Tj 51.428571 0 0 51.428571 0 1808.080808 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.4 0 Td 41.481481 Tz (split ) Tj 1.458333 0 Td 46.990741 Tz (into ) Tj 1.380556 0 Td 59.41358 Tz (two ) Tj 1.322222 0 Td 53.240741 Tz (roughly ) Tj 2.469444 0 Td 53.148148 Tz (equal ) Tj 1.808333 0 Td 47.530864 Tz (portions. ) Tj 2.8 0 Td 64.814815 Tz (The ) Tj 1.4 0 Td 37.592593 Tz (first ) Tj 1.322222 0 Td 50.925926 Tz (portion ) Tj 51.428571 0 0 51.428571 0 1763.08 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.380556 0 Td 55.092593 Tz (used ) Tj 1.536111 0 Td 47.530864 Tz (for ) Tj 1.069444 0 Td 45.910494 Tz (direct ) Tj 1.866667 0 Td 46.720679 Tz (fluorination ) Tj 3.577778 0 Td 59.41358 Tz (and ) Tj 1.263889 0 Td 50.771605 Tz (the ) Tj 1.108333 0 Td 56.712963 Tz (second ) Tj 2.236111 0 Td 50 Tz (portion ) Tj 2.333333 0 Td 61.574074 Tz (was ) Tj 51.428571 0 0 51.428571 0 1721.872123 Tm 25.277778 0 Td 55.902778 Tz (used ) Tj 1.672222 0 Td 48.611111 Tz (for ) Tj 1.166667 0 Td 59.143519 Tz (\(Example ) Tj 3.15 0 Td 50.231481 Tz (4\) ) Tj 0.933333 0 Td 50.411523 Tz (reduction ) Tj 3.072222 0 Td 53.06713 Tz (followed ) Tj 2.858333 0 Td 59.953704 Tz (by ) Tj 1.05 0 Td 45.619658 Tz (fluorination. ) Tj 51.428571 0 0 51.428571 0 1682.264631 Tm 25.316667 0 Td 50.771605 Tz (Protected ) Tj 3.091667 0 Td 51.006441 Tz (\(16:0\)-p-phosphodiester ) Tj 7.388889 0 Td 40.509259 Tz (\(1 ) Tj 0.933333 0 Td 46.180556 Tz (eq.\) ) Tj 1.458333 0 Td 61.574074 Tz (was ) Tj 1.458333 0 Td 49.907407 Tz (dried ) Tj 1.847222 0 Td 54.282407 Tz (over ) Tj 52.857143 0 0 52.857143 0 1639.269231 Tm 24.594595 0 Td 54.750205 Tz (phosphorous ) Tj 3.764865 0 Td 52.202202 Tz (pentoxide ) Tj 2.97027 0 Td 47.297297 Tz (for ) Tj 1.040541 0 Td 55.18018 Tz (12 ) Tj 0.775676 0 Td 52.972973 Tz (hours ) Tj 1.740541 0 Td 56.756757 Tz (and ) Tj 1.191892 0 Td 49.399399 Tz (dissolved ) Tj 2.818919 0 Td 44.144144 Tz (in ) Tj 0.718919 0 Td 55.18018 Tz (dichlo ) Tj 51.428571 0 0 51.428571 0 1594.956522 Tm 25.297222 0 Td 53.796296 Tz (romethane. ) Tj 3.363889 0 Td 63.734568 Tz (The ) Tj 1.283333 0 Td 48.611111 Tz (reaction ) Tj 2.508333 0 Td 46.018519 Tz (flask ) Tj 1.477778 0 Td 62.654321 Tz (was ) Tj 1.263889 0 Td 50.771605 Tz (sealed ) Tj 1.963889 0 Td 58.333333 Tz (and ) Tj 1.166667 0 Td 53.472222 Tz (placed ) Tj 2.061111 0 Td 45.37037 Tz (in ) Tj 0.7 0 Td 56.712963 Tz (an ) Tj 0.836111 0 Td 47.530864 Tz (ice ) Tj 51.428571 0 0 51.428571 0 1555.565046 Tm 25.277778 0 Td 52.662037 Tz (bath ) Tj 1.555556 0 Td 45.37037 Tz (to ) Tj 0.875 0 Td 52.256944 Tz (maintain ) Tj 2.819444 0 Td 50.231481 Tz (0 ) Tj 0.894444 0 Td 55.092593 Tz (C. ) Tj 0.991667 0 Td 49.96142 Tz (temperature. ) Tj 3.927778 0 Td 55.416667 Tz (Deoxofluor ) Tj 3.597222 0 Td 46.990741 Tz (\(2 ) Tj 0.836111 0 Td 47.800926 Tz (eq.\) ) Tj 1.419444 0 Td 48.611111 Tz (in ) Tj 51.428571 0 0 51.428571 0 1511.92891 Tm 25.297222 0 Td 54.444444 Tz (dichloromethane ) Tj 5.036111 0 Td 61.574074 Tz (was ) Tj 1.283333 0 Td 52.932099 Tz (slowly ) Tj 2.041667 0 Td 58.981481 Tz (added ) Tj 1.905556 0 Td 55.092593 Tz (\(-2 ) Tj 1.205556 0 Td 52.256944 Tz (minutes\) ) Tj 2.644444 0 Td 59.41358 Tz (and ) Tj 1.186111 0 Td 51.388889 Tz (ethanol ) Tj 51.428571 0 0 51.428571 0 1473.183463 Tm 25.316667 0 Td 46.180556 Tz (\(0.2 ) Tj 1.341667 0 Td 46.180556 Tz (eq.\) ) Tj 1.322222 0 Td 61.574074 Tz (was ) Tj 1.341667 0 Td 57.685185 Tz (added ) Tj 1.944444 0 Td 45.37037 Tz (to ) Tj 0.777778 0 Td 51.446759 Tz (generate ) Tj 2.663889 0 Td 51.851852 Tz (a ) Tj 0.525 0 Td 44.650206 Tz (catalyst, ) Tj 2.663889 0 Td 55.092593 Tz (HF. ) Tj 1.205556 0 Td 63.734568 Tz (The ) Tj 1.341667 0 Td 47.530864 Tz (ice ) Tj 1.069444 0 Td 52.662037 Tz (bath ) Tj 40 0 0 40 0 1436 Tm 32.5 0 Td 80.555556 Tz (was ) Tj 1.875 0 Td 76.785714 Tz (removed ) Tj 3.625 0 Td 75 Tz (and ) Tj 1.725 0 Td 63.888889 Tz (the ) Tj 1.525 0 Td 62.5 Tz (reaction ) Tj 3.425 0 Td 69.047619 Tz (mixture ) Tj 3.3 0 Td 77.777778 Tz (was ) Tj 1.825 0 Td 56.547619 Tz (stirred ) Tj 2.775 0 Td 62.5 Tz (for ) Tj 1.55 0 Td 68.75 Tz (16 ) Tj 40 0 0 40 0 1394 Tm 32.5 0 Td 63.888889 Tz (hours. ) Tj 2.5 0 Td 91.666667 Tz (An ) Tj 1.325 0 Td 61.666667 Tz (extraction ) Tj 3.925 0 Td 68.75 Tz (with ) Tj 1.875 0 Td 66 Tz (dichloromethane/saturated ) Tj 10.125 0 Td 75.694444 Tz (sodium ) Tj 51.428571 0 0 51.428571 0 1347.583433 Tm 25.277778 0 Td 51.557239 Tz (bicarbonate ) Tj 3.558333 0 Td 48.611111 Tz (solution ) Tj 2.547222 0 Td 43.209877 Tz (1:1 ) Tj 1.030556 0 Td 46.666667 Tz (\(v/v\) ) Tj 1.536111 0 Td 61.574074 Tz (was ) Tj 1.244444 0 Td 56.532922 Tz (performed ) Tj 3.169444 0 Td 59.41358 Tz (and ) Tj 1.225 0 Td 48.611111 Tz (the ) Tj 0.991667 0 Td 51.851852 Tz (organic ) Tj 51.428571 0 0 51.428571 0 1305.210909 Tm 25.297222 0 Td 49.259259 Tz (layer ) Tj 1.652778 0 Td 60.493827 Tz (was ) Tj 1.283333 0 Td 46.342593 Tz (collected. ) Tj 51.428571 0 0 51.428571 0 1267.343958 Tm 26.016667 0 Td 52.5 Tz (After ) Tj 1.905556 0 Td 52.391975 Tz (drying ) Tj 2.236111 0 Td 45.37037 Tz (in ) Tj 0.933333 0 Td 51.851852 Tz (vacuo, ) Tj 2.236111 0 Td 48.611111 Tz (the ) Tj 1.186111 0 Td 50.771605 Tz (protected ) Tj 3.091667 0 Td 50.517429 Tz (\(16:0\)-p-difluoro ) Tj 51.428571 0 0 51.428571 0 1225.697561 Tm 25.297222 0 Td 52.777778 Tz (phosphodiester ) Tj 4.647222 0 Td 61.574074 Tz (was ) Tj 1.341667 0 Td 47.800926 Tz (purified ) Tj 2.527778 0 Td 59.953704 Tz (by ) Tj 0.991667 0 Td 44.722222 Tz (flash ) Tj 1.633333 0 Td 59.41358 Tz (column ) Tj 2.411111 0 Td 59.217172 Tz (chromatogra ) Tj 51.428571 0 0 51.428571 0 1182.551122 Tm 25.297222 0 Td 59.41358 Tz (phy ) Tj 1.322222 0 Td 52.5 Tz (using ) Tj 1.788889 0 Td 72.376543 Tz (40% ) Tj 1.555556 0 Td 47.962963 Tz (ethyl ) Tj 1.672222 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.491667 0 Td 51.041667 Tz (then ) Tj 1.458333 0 Td 52.572016 Tz (switching ) Tj 3.072222 0 Td 43.75 Tz (to ) Tj 0.758333 0 Td 74.537037 Tz (80% ) Tj 51.428571 0 0 51.428571 0 1140.743468 Tm 25.297222 0 Td 47.314815 Tz (ethyl ) Tj 1.555556 0 Td 51.388889 Tz (acetate/hexane ) Tj 4.433333 0 Td 48.611111 Tz (for ) Tj 0.972222 0 Td 55.092593 Tz (a ) Tj 0.486111 0 Td 46.990741 Tz (step ) Tj 1.283333 0 Td 49.826389 Tz (gradient ) Tj 2.508333 0 Td 45.37037 Tz (elution. ) Tj 2.372222 0 Td 56.17284 Tz (For ) Tj 1.127778 0 Td 56.712963 Tz (deprotec ) Tj 51.428571 0 0 51.428571 0 1101.653846 Tm 25.277778 0 Td 44.074074 Tz (tion, ) Tj 1.594444 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 50.411523 Tz (protected ) Tj 2.955556 0 Td 50.130208 Tz (\(16:0\)-p-difluoro-phosphodiester ) Tj 9.858333 0 Td 42.12963 Tz (\(1 ) Tj 0.836111 0 Td 46.180556 Tz (eq.\) ) Tj 51.428571 0 0 51.428571 0 1058.813725 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 50.771605 Tz (dissolved ) Tj 2.955556 0 Td 43.75 Tz (in ) Tj 0.719444 0 Td 47.890947 Tz (pyridine. ) Tj 2.819444 0 Td 56.837607 Tz (N-propylamine ) Tj 4.627778 0 Td 56.712963 Tz (\(100 ) Tj 1.536111 0 Td 46.180556 Tz (eq.\) ) Tj 1.302778 0 Td 46.990741 Tz (in ) Tj 0.758333 0 Td 59.143519 Tz (pyri ) Tj 40 0 0 40 0 1020 Tm 32.525 0 Td 67.708333 Tz (dine ) Tj 1.8 0 Td 76.388889 Tz (was ) Tj 1.55 0 Td 75.833333 Tz (added ) Tj 2.4 0 Td 60.416667 Tz (to ) Tj 0.925 0 Td 62.5 Tz (the ) Tj 1.3 0 Td 61.979167 Tz (reaction ) Tj 3.15 0 Td 68.229167 Tz (flaskand ) Tj 3.425 0 Td 63.888889 Tz (the ) Tj 1.3 0 Td 62.5 Tz (clear ) Tj 1.975 0 Td 63.020833 Tz (solution ) Tj 3.2 0 Td 79.166667 Tz (was ) Tj 51.428571 0 0 51.428571 0 972.80268 Tm 25.316667 0 Td 43.981481 Tz (stirred ) Tj 1.983333 0 Td 48.611111 Tz (for ) Tj 1.069444 0 Td 55.092593 Tz (10 ) Tj 0.816667 0 Td 54.166667 Tz (minutes ) Tj 2.430556 0 Td 45.37037 Tz (at ) Tj 0.719444 0 Td 61.574074 Tz (room ) Tj 1.652778 0 Td 49.96142 Tz (temperature. ) Tj 3.752778 0 Td 51.851852 Tz (All ) Tj 1.108333 0 Td 48.611111 Tz (solvents ) Tj 2.508333 0 Td 59.143519 Tz (were ) Tj 51.428571 0 0 51.428571 0 932.621359 Tm 25.297222 0 Td 60.185185 Tz (removed ) Tj 2.702778 0 Td 43.75 Tz (in ) Tj 0.738889 0 Td 55.092593 Tz (vacuo ) Tj 1.847222 0 Td 45.37037 Tz (to ) Tj 0.7 0 Td 49.907407 Tz (yield ) Tj 1.633333 0 Td 50.771605 Tz (the ) Tj 1.088889 0 Td 59.953704 Tz (n-propylammonium ) Tj 5.930556 0 Td 42.939815 Tz (salt ) Tj 1.186111 0 Td 55.092593 Tz (of ) Tj 0.738889 0 Td 50.771605 Tz (the ) Tj 51.428571 0 0 51.428571 0 891.533958 Tm 25.316667 0 Td 49.016204 Tz (\(16:0\)-p-difluorophosphodiester. ) Tj 9.625 0 Td 72.916667 Tz (An ) Tj 1.088889 0 Td 48.287037 Tz (extraction ) Tj 3.130556 0 Td 54.282407 Tz (with ) Tj 1.477778 0 Td 58.873457 Tz (chloro ) Tj 51.428571 0 0 51.428571 0 848.379147 Tm 25.297222 0 Td 52.875244 Tz (form/methanol/brine ) Tj 6.241667 0 Td 44.907407 Tz (1:1.5:1 ) Tj 2.1 0 Td 47.685185 Tz (\(v/v/v\) ) Tj 2.158333 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 56.17284 Tz (performed ) Tj 3.188889 0 Td 43.75 Tz (to ) Tj 0.680556 0 Td 61.574074 Tz (gener ) Tj 51.428571 0 0 51.428571 0 808.753056 Tm 25.297222 0 Td 47.530864 Tz (ate ) Tj 1.030556 0 Td 49.691358 Tz (the ) Tj 1.088889 0 Td 58.333333 Tz (sodium ) Tj 2.333333 0 Td 41.319444 Tz (salt ) Tj 1.166667 0 Td 58.333333 Tz (of ) Tj 0.777778 0 Td 50.771605 Tz (the ) Tj 1.088889 0 Td 49.21875 Tz (\(16:0\)-p-difluorophosphodiester. ) Tj 51.428571 0 0 51.428571 0 732.046358 Tm 32.472222 0 Td 61.574074 Tz (Example ) Tj 2.761111 0 Td 58.333333 Tz (4 ) Tj 51.428571 0 0 51.428571 0 650 Tm 28.836111 0 Td 52.73569 Tz (\(16:0\)-p-monofluorophosphodiester ) Tj 31.428571 0 0 31.428571 0 493 Tm 57.209091 0 Td 111.363636 Tz (O ) Tj 171.428571 0 0 171.428571 0 379 Tm 8.26 0 Td 31.305556 Tz (cis-\( ) Tj 1.289167 0 Td 35.891204 Tz (\)---o-clich, ) Tj 31.428571 0 0 31.428571 0 360 Tm 57.209091 0 Td 111.363636 Tz (OH ) Tj 51.428571 0 0 51.428571 0 255.683995 Tm 26.036111 0 Td 56.565657 Tz (Phosphorous ) Tj 4.044444 0 Td 52.73569 Tz (oxychloride ) Tj 3.772222 0 Td 43.75 Tz (\(1 ) Tj 0.894444 0 Td 46.180556 Tz (eq.\) ) Tj 1.419444 0 Td 60.493827 Tz (was ) Tj 1.380556 0 Td 58.333333 Tz (added ) Tj 2.041667 0 Td 45.37037 Tz (to ) Tj 0.855556 0 Td 51.851852 Tz (a ) Tj 0.661111 0 Td 55.740741 Tz (round ) Tj 51.428571 0 0 51.428571 0 212.327456 Tm 25.277778 0 Td 57.253086 Tz (bottom ) Tj 2.391667 0 Td 46.018519 Tz (flask ) Tj 1.633333 0 Td 58.333333 Tz (and ) Tj 1.341667 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 45.37037 Tz (in ) Tj 0.875 0 Td 49.907407 Tz (tetrahydrofuran ) Tj 4.783333 0 Td 56.17284 Tz (\(THF\). ) Tj 2.313889 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 168.961963 Tm 25.297222 0 Td 57.037037 Tz (round ) Tj 1.847222 0 Td 56.712963 Tz (bottom ) Tj 2.197222 0 Td 46.666667 Tz (flask ) Tj 1.536111 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 51.851852 Tz (then ) Tj 1.4 0 Td 52.932099 Tz (placed ) Tj 2.061111 0 Td 45.37037 Tz (in ) Tj 0.680556 0 Td 59.953704 Tz (an ) Tj 0.875 0 Td 46.450617 Tz (ice ) Tj 0.952778 0 Td 52.662037 Tz (bath ) Tj 1.419444 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 53.06713 Tz (maintain ) Tj ET Q endstream endobj 184 0 obj << /Length 1 >> stream q endstream endobj 185 0 obj << /Length 45111 >> stream Q q 0.24 0 0 0.24 0 0 cm BT /F1 1 Tf 3 Tr 62.857143 0 0 62.857143 0 3023 Tm 17.325 0 Td 83.522727 Tz (US ) Tj 1.240909 0 Td 58.333333 Tz (8,022,239 ) Tj 3.388636 0 Td 74.242424 Tz (B2 ) Tj 51.428571 0 0 51.428571 0 2969 Tm 14.661111 0 Td 71.296296 Tz (11 ) Tj 51.428571 0 0 51.428571 0 2915.452261 Tm 6.358333 0 Td 51.851852 Tz (a ) Tj 0.544444 0 Td 63.194444 Tz (0C. ) Tj 1.769444 0 Td 50.231481 Tz (temperature. ) Tj 3.908333 0 Td 56.860269 Tz (Hexadecanol ) Tj 4.005556 0 Td 42.12963 Tz (\(1 ) Tj 0.797222 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 50.411523 Tz (dissolved ) Tj 2.936111 0 Td 45.37037 Tz (in ) Tj 0.758333 0 Td 76.697531 Tz (THF ) Tj 51.428571 0 0 51.428571 0 2873.895911 Tm 6.338889 0 Td 54.282407 Tz (with ) Tj 1.497222 0 Td 49.85755 Tz (triethylamine ) Tj 4.083333 0 Td 63.518519 Tz (\(TEA\) ) Tj 2.1 0 Td 42.12963 Tz (\(1 ) Tj 0.777778 0 Td 46.180556 Tz (eq.\) ) Tj 1.283333 0 Td 62.654321 Tz (was ) Tj 1.302778 0 Td 58.981481 Tz (added ) Tj 1.963889 0 Td 55.092593 Tz (dropwise ) Tj 2.858333 0 Td 45.37037 Tz (to ) Tj 0.738889 0 Td 49.691358 Tz (the ) Tj 51.428571 0 0 51.428571 0 2830.215457 Tm 6.358333 0 Td 55.976431 Tz (phosphorous ) Tj 3.830556 0 Td 56.17284 Tz (oxychloride/THF ) Tj 5.191667 0 Td 46.090535 Tz (solution. ) Tj 2.605556 0 Td 64.814815 Tz (Once ) Tj 1.672222 0 Td 39.969136 Tz (all ) Tj 0.836111 0 Td 53.472222 Tz (of ) Tj 0.738889 0 Td 47.530864 Tz (the ) Tj 0.991667 0 Td 66.435185 Tz (hexa ) Tj 51.428571 0 0 51.428571 0 2782 Tm 6.358333 0 Td 60.925926 Tz (decanol/THF/TEA ) Tj 5.775 0 Td 48.206019 Tz (solution ) Tj 2.644444 0 Td 61.574074 Tz (was ) Tj 1.419444 0 Td 57.685185 Tz (added ) Tj 2.061111 0 Td 56.712963 Tz (\(-20 ) Tj 1.672222 0 Td 50.05144 Tz (minutes\), ) Tj 3.013889 0 Td 49.691358 Tz (the ) Tj 40 0 0 40 0 2747 Tm 8.175 0 Td 63.020833 Tz (reaction ) Tj 3.2 0 Td 69.047619 Tz (mixture ) Tj 3.05 0 Td 79.166667 Tz (was ) Tj 1.625 0 Td 56.547619 Tz (stirred ) Tj 2.55 0 Td 61.111111 Tz (for ) Tj 1.2 0 Td 72.916667 Tz (an ) Tj 1.025 0 Td 62.5 Tz (additional ) Tj 3.925 0 Td 79.166667 Tz (40 ) Tj 1.125 0 Td 70.238095 Tz (minutes ) Tj 3.075 0 Td 58.333333 Tz (at ) Tj 0.85 0 Td 66.666667 Tz (0 ) Tj 51.428571 0 0 51.428571 0 2699.072727 Tm 6.358333 0 Td 53.472222 Tz (C. ) Tj 0.777778 0 Td 87.5 Tz (A ) Tj 0.7 0 Td 48.206019 Tz (solution ) Tj 2.469444 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 56.018519 Tz (p-hydroxybenzaldehyde ) Tj 7.213889 0 Td 42.12963 Tz (\(1 ) Tj 0.758333 0 Td 46.180556 Tz (eq.\) ) Tj 1.283333 0 Td 43.75 Tz (in ) Tj 0.680556 0 Td 76.697531 Tz (THF ) Tj 1.555556 0 Td 54.282407 Tz (with ) Tj 51.428571 0 0 51.428571 0 2653.031579 Tm 6.358333 0 Td 78.858025 Tz (TEA ) Tj 1.672222 0 Td 45.37037 Tz (\(1 ) Tj 0.875 0 Td 46.180556 Tz (eq.\) ) Tj 1.361111 0 Td 61.574074 Tz (was ) Tj 1.380556 0 Td 58.333333 Tz (added ) Tj 2.022222 0 Td 55.092593 Tz (dropwise ) Tj 2.897222 0 Td 46.990741 Tz (to ) Tj 0.836111 0 Td 49.691358 Tz (the ) Tj 1.186111 0 Td 46.990741 Tz (reaction ) Tj 2.566667 0 Td 46.018519 Tz (flask ) Tj 1.594444 0 Td 61.574074 Tz (and ) Tj 51.428571 0 0 51.428571 0 2608.570726 Tm 6.377778 0 Td 43.981481 Tz (stirred ) Tj 1.983333 0 Td 49.691358 Tz (for ) Tj 0.991667 0 Td 58.333333 Tz (an ) Tj 0.855556 0 Td 47.962963 Tz (additional ) Tj 3.052778 0 Td 63.194444 Tz (40 ) Tj 0.933333 0 Td 53.240741 Tz (minutes ) Tj 2.391667 0 Td 46.990741 Tz (at ) Tj 0.7 0 Td 59.953704 Tz (0C. ) Tj 1.613889 0 Td 57.685185 Tz (Water ) Tj 1.847222 0 Td 45.37037 Tz (\(1 ) Tj 0.758333 0 Td 46.990741 Tz (eq.\) ) Tj 1.263889 0 Td 60.493827 Tz (and ) Tj 51.428571 0 0 51.428571 0 2564.578811 Tm 6.358333 0 Td 78.858025 Tz (TEA ) Tj 1.652778 0 Td 43.75 Tz (\(1 ) Tj 0.816667 0 Td 45.37037 Tz (eq.\) ) Tj 1.341667 0 Td 58.333333 Tz (were ) Tj 1.613889 0 Td 58.333333 Tz (added ) Tj 1.963889 0 Td 46.990741 Tz (to ) Tj 0.797222 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 48.206019 Tz (reaction ) Tj 2.586111 0 Td 53.240741 Tz (mixture ) Tj 2.45 0 Td 58.333333 Tz (which ) Tj 2.002778 0 Td 61.574074 Tz (was ) Tj 40 0 0 40 0 2528 Tm 8.175 0 Td 70.238095 Tz (allowed ) Tj 3.25 0 Td 60.416667 Tz (to ) Tj 1.075 0 Td 50 Tz (stir ) Tj 1.475 0 Td 62.5 Tz (for ) Tj 1.4 0 Td 81.25 Tz (60 ) Tj 1.275 0 Td 69.642857 Tz (minutes ) Tj 3.25 0 Td 58.333333 Tz (at ) Tj 1 0 Td 82.291667 Tz (0C. ) Tj 2.275 0 Td 83.333333 Tz (The ) Tj 1.8 0 Td 64.583333 Tz (contents ) Tj 3.425 0 Td 75 Tz (of ) Tj 1.1 0 Td 63.888889 Tz (the ) Tj 40 0 0 40 0 2485 Tm 8.175 0 Td 62.5 Tz (reaction ) Tj 3.25 0 Td 60 Tz (flask ) Tj 2.05 0 Td 75 Tz (were ) Tj 2.05 0 Td 65.625 Tz (then ) Tj 1.875 0 Td 79.166667 Tz (vacuum ) Tj 3.15 0 Td 55.208333 Tz (filtered ) Tj 2.875 0 Td 76.388889 Tz (and ) Tj 1.65 0 Td 63.333333 Tz (dried ) Tj 2.15 0 Td 56.25 Tz (in ) Tj 0.975 0 Td 66.666667 Tz (vacuo. ) Tj 40 0 0 40 0 2441 Tm 8.175 0 Td 67.5 Tz (After ) Tj 2.2 0 Td 75 Tz (an ) Tj 1.15 0 Td 62.5 Tz (extraction ) Tj 4.025 0 Td 68.75 Tz (with ) Tj 1.925 0 Td 68.666667 Tz (chloroform/methanol/water ) Tj 10.6 0 Td 58.928571 Tz (1:1.5:1 ) Tj 51.428571 0 0 51.428571 0 2392.576355 Tm 6.377778 0 Td 44.155093 Tz (\(v/v/v\), ) Tj 2.430556 0 Td 48.611111 Tz (the ) Tj 1.147222 0 Td 51.147343 Tz (\(16:0\)-p-phosphodiester ) Tj 7.291667 0 Td 62.654321 Tz (was ) Tj 1.4 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 45.37037 Tz (in ) Tj 0.836111 0 Td 73.45679 Tz (40% ) Tj 51.428571 0 0 51.428571 0 2348.565841 Tm 6.358333 0 Td 47.962963 Tz (ethyl ) Tj 1.827778 0 Td 50.694444 Tz (acetate/hexane ) Tj 4.608333 0 Td 59.41358 Tz (and ) Tj 1.419444 0 Td 50.673401 Tz (centrifuged ) Tj 3.713889 0 Td 47.530864 Tz (for ) Tj 1.205556 0 Td 61.574074 Tz (7 ) Tj 0.758333 0 Td 50.636574 Tz (minutes. ) Tj 2.8 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 2303.713574 Tm 6.377778 0 Td 50.673401 Tz (Supernatant ) Tj 3.597222 0 Td 61.574074 Tz (was ) Tj 1.380556 0 Td 54.282407 Tz (decanted ) Tj 2.838889 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 50.771605 Tz (the ) Tj 1.205556 0 Td 48.971193 Tz (insoluble ) Tj 2.916667 0 Td 46.8107 Tz (fractions ) Tj 2.819444 0 Td 58.333333 Tz (were ) Tj 40 0 0 40 0 2266 Tm 8.175 0 Td 72.222222 Tz (combined. ) Tj 51.428571 0 0 51.428571 0 2221.387909 Tm 7.097222 0 Td 62.654321 Tz (The ) Tj 1.341667 0 Td 44.722222 Tz (relatively ) Tj 2.877778 0 Td 54.282407 Tz (pure ) Tj 1.516667 0 Td 51.006441 Tz (\(16:0\)-p-phosphodiester ) Tj 7.213889 0 Td 43.75 Tz (\(1 ) Tj 0.777778 0 Td 43.425926 Tz (eq.\), ) Tj 1.536111 0 Td 81.018519 Tz (DCC ) Tj 51.428571 0 0 51.428571 0 2174.081556 Tm 6.377778 0 Td 46.990741 Tz (\(2.2 ) Tj 1.341667 0 Td 61.574074 Tz (eq\) ) Tj 1.302778 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 87.5 Tz (DMAP ) Tj 2.313889 0 Td 43.75 Tz (\(0.1 ) Tj 1.322222 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 58.333333 Tz (were ) Tj 1.594444 0 Td 49.907407 Tz (dried ) Tj 1.711111 0 Td 53.472222 Tz (over ) Tj 1.458333 0 Td 56.565657 Tz (phosphorous ) Tj 51.428571 0 0 51.428571 0 2130.961905 Tm 6.358333 0 Td 53.292181 Tz (pentoxide ) Tj 2.994444 0 Td 49.691358 Tz (for ) Tj 1.05 0 Td 56.712963 Tz (12 ) Tj 0.797222 0 Td 49.151235 Tz (hours. ) Tj 1.905556 0 Td 56.442901 Tz (Cyanoethanol ) Tj 4.2 0 Td 43.75 Tz (\(1.1 ) Tj 1.263889 0 Td 47.800926 Tz (eq.\) ) Tj 1.283333 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 51.131687 Tz (dissolved ) Tj 51.428571 0 0 51.428571 0 2085.654501 Tm 6.358333 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 54.228395 Tz (dichloromethane ) Tj 5.036111 0 Td 59.41358 Tz (and ) Tj 1.244444 0 Td 49.259259 Tz (dried ) Tj 1.633333 0 Td 53.472222 Tz (with ) Tj 1.497222 0 Td 61.213992 Tz (magnesium ) Tj 3.5 0 Td 45.833333 Tz (sulfate ) Tj 2.1 0 Td 47.530864 Tz (for ) Tj 1.069444 0 Td 53.472222 Tz (12 ) Tj 51.428571 0 0 51.428571 0 2043.44484 Tm 6.338889 0 Td 49.691358 Tz (hours. ) Tj 1.983333 0 Td 62.654321 Tz (The ) Tj 1.302778 0 Td 51.147343 Tz (\(16:0\)-p-phosphodiester ) Tj 7.213889 0 Td 60.493827 Tz (was ) Tj 1.302778 0 Td 50.411523 Tz (dissolved ) Tj 2.877778 0 Td 46.990741 Tz (in ) Tj 0.758333 0 Td 56.712963 Tz (dichlo ) Tj 40 0 0 40 0 2007 Tm 8.175 0 Td 73.148148 Tz (romethane ) Tj 4.2 0 Td 75 Tz (and ) Tj 1.625 0 Td 105.555556 Tz (DCC ) Tj 2.15 0 Td 75 Tz (and ) Tj 1.625 0 Td 111.458333 Tz (DMAP ) Tj 2.925 0 Td 76.041667 Tz (were ) Tj 2.075 0 Td 74.166667 Tz (added ) Tj 2.5 0 Td 56.25 Tz (to ) Tj 0.975 0 Td 62.5 Tz (the ) Tj 1.4 0 Td 63.020833 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 1959.180879 Tm 6.358333 0 Td 42.669753 Tz (flask. ) Tj 1.788889 0 Td 62.654321 Tz (The ) Tj 1.361111 0 Td 46.666667 Tz (flask ) Tj 1.633333 0 Td 61.574074 Tz (was ) Tj 1.361111 0 Td 50.231481 Tz (sealed ) Tj 2.041667 0 Td 53.472222 Tz (with ) Tj 1.536111 0 Td 51.851852 Tz (a ) Tj 0.583333 0 Td 57.253086 Tz (septum ) Tj 2.313889 0 Td 59.41358 Tz (and ) Tj 1.283333 0 Td 56.712963 Tz (purged ) Tj 2.294444 0 Td 54.282407 Tz (with ) Tj 51.428571 0 0 51.428571 0 1918.976553 Tm 6.358333 0 Td 50.231481 Tz (nitrogen ) Tj 2.547222 0 Td 46.018519 Tz (after ) Tj 1.497222 0 Td 55.092593 Tz (adding ) Tj 2.1 0 Td 50.771605 Tz (the ) Tj 1.05 0 Td 53.472222 Tz (cyanoethanol ) Tj 4.005556 0 Td 46.450617 Tz (Solution. ) Tj 2.625 0 Td 64.814815 Tz (The ) Tj 1.302778 0 Td 49.421296 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 1876.476433 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.361111 0 Td 44.444444 Tz (stirred ) Tj 2.080556 0 Td 48.611111 Tz (for ) Tj 1.05 0 Td 59.953704 Tz (48 ) Tj 0.952778 0 Td 53.148148 Tz (hours ) Tj 1.808333 0 Td 46.990741 Tz (at ) Tj 0.777778 0 Td 62.384259 Tz (room ) Tj 1.730556 0 Td 50.231481 Tz (temperature. ) Tj 3.869444 0 Td 57.685185 Tz (Water ) Tj 1.944444 0 Td 46.990741 Tz (\(5 ) Tj 0.797222 0 Td 46.180556 Tz (eq.\) ) Tj 40 0 0 40 0 1840 Tm 8.15 0 Td 80.555556 Tz (was ) Tj 1.725 0 Td 75 Tz (added ) Tj 2.5 0 Td 76.388889 Tz (and ) Tj 1.625 0 Td 63.888889 Tz (the ) Tj 1.4 0 Td 62.5 Tz (reaction ) Tj 3.325 0 Td 68.452381 Tz (mixture ) Tj 3.125 0 Td 79.166667 Tz (was ) Tj 1.7 0 Td 57.142857 Tz (stirred ) Tj 2.65 0 Td 63.888889 Tz (for ) Tj 1.35 0 Td 72.916667 Tz (an ) Tj 1.125 0 Td 81.25 Tz (addi ) Tj 40 0 0 40 0 1799 Tm 8.15 0 Td 59.722222 Tz (tional ) Tj 2.6 0 Td 79.166667 Tz (24 ) Tj 1.375 0 Td 63.194444 Tz (hours. ) Tj 2.75 0 Td 80.555556 Tz (The ) Tj 1.875 0 Td 65.104167 Tz (contents ) Tj 3.575 0 Td 75 Tz (of ) Tj 1.225 0 Td 63.888889 Tz (the ) Tj 1.6 0 Td 62.5 Tz (reaction ) Tj 3.475 0 Td 59.166667 Tz (flask ) Tj 2.225 0 Td 75 Tz (were ) Tj 40 0 0 40 0 1757 Tm 8.175 0 Td 81.25 Tz (vacuum ) Tj 3.2 0 Td 55.208333 Tz (filtered ) Tj 2.85 0 Td 77.777778 Tz (and ) Tj 1.65 0 Td 64.166667 Tz (dried ) Tj 2.15 0 Td 60.416667 Tz (in ) Tj 0.975 0 Td 67.361111 Tz (vacuo. ) Tj 2.65 0 Td 66.666667 Tz (After ) Tj 2.225 0 Td 70.833333 Tz (an ) Tj 1.125 0 Td 61.666667 Tz (extraction ) Tj 4 0 Td 68.75 Tz (with ) Tj 51.428571 0 0 51.428571 0 1711.390156 Tm 6.358333 0 Td 51.851852 Tz (chloroform/brine ) Tj 5.191667 0 Td 44.290123 Tz (1:1 ) Tj 1.069444 0 Td 43.209877 Tz (\(v/v\), ) Tj 1.730556 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 54.62963 Tz (coupled ) Tj 2.45 0 Td 53.703704 Tz (product ) Tj 2.411111 0 Td 61.574074 Tz (was ) Tj 1.263889 0 Td 48.206019 Tz (purified ) Tj 51.428571 0 0 51.428571 0 1670.369077 Tm 6.338889 0 Td 61.574074 Tz (by ) Tj 1.011111 0 Td 45.37037 Tz (flash ) Tj 1.652778 0 Td 59.953704 Tz (column ) Tj 2.45 0 Td 56.25 Tz (chromatography ) Tj 4.997222 0 Td 53.148148 Tz (using ) Tj 1.847222 0 Td 73.45679 Tz (40% ) Tj 1.575 0 Td 48.611111 Tz (ethyl ) Tj 1.730556 0 Td 46.585648 Tz (acetate/ ) Tj 52.857143 0 0 52.857143 0 1625.676294 Tm 6.167568 0 Td 56.756757 Tz (hexane ) Tj 2.137838 0 Td 52.027027 Tz (then ) Tj 1.418919 0 Td 50.45045 Tz (switching ) Tj 2.856757 0 Td 45.720721 Tz (to ) Tj 0.7 0 Td 72.522523 Tz (80% ) Tj 1.456757 0 Td 46.666667 Tz (ethyl ) Tj 1.57027 0 Td 49.774775 Tz (acetate/hexane ) Tj 4.313514 0 Td 45.195195 Tz (for ) Tj 0.945946 0 Td 53.603604 Tz (a ) Tj 0.472973 0 Td 47.297297 Tz (step ) Tj 51.428571 0 0 51.428571 0 1586.169492 Tm 6.358333 0 Td 49.826389 Tz (gradient ) Tj 2.547222 0 Td 45.775463 Tz (elution. ) Tj 51.428571 0 0 51.428571 0 1546.763906 Tm 7.097222 0 Td 51.851852 Tz (After ) Tj 1.788889 0 Td 45.121083 Tz (purification, ) Tj 3.811111 0 Td 48.611111 Tz (the ) Tj 1.108333 0 Td 50.771605 Tz (protected ) Tj 3.013889 0 Td 51.006441 Tz (\(16:0\)-p-phosphodiester ) Tj 51.428571 0 0 51.428571 0 1504.093671 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.4 0 Td 41.481481 Tz (split ) Tj 1.477778 0 Td 46.180556 Tz (into ) Tj 1.361111 0 Td 59.41358 Tz (two ) Tj 1.341667 0 Td 52.777778 Tz (roughly ) Tj 2.45 0 Td 53.148148 Tz (equal ) Tj 1.808333 0 Td 47.530864 Tz (portions. ) Tj 2.819444 0 Td 63.734568 Tz (The ) Tj 1.380556 0 Td 37.592593 Tz (first ) Tj 1.322222 0 Td 51.388889 Tz (portion ) Tj 51.428571 0 0 51.428571 0 1458.425061 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 55.902778 Tz (used ) Tj 1.536111 0 Td 46.450617 Tz (for ) Tj 1.011111 0 Td 46.450617 Tz (direct ) Tj 1.866667 0 Td 46.450617 Tz (fluorination ) Tj 3.597222 0 Td 58.738426 Tz (\(Example ) Tj 2.975 0 Td 53.472222 Tz (3\) ) Tj 0.797222 0 Td 59.41358 Tz (and ) Tj 1.263889 0 Td 50.771605 Tz (the ) Tj 1.069444 0 Td 57.253086 Tz (second ) Tj 51.428571 0 0 51.428571 0 1416.410037 Tm 6.358333 0 Td 49.537037 Tz (portion ) Tj 2.275 0 Td 61.574074 Tz (was ) Tj 1.302778 0 Td 55.902778 Tz (used ) Tj 1.536111 0 Td 47.530864 Tz (for ) Tj 1.030556 0 Td 50.411523 Tz (reduction ) Tj 2.936111 0 Td 52.662037 Tz (followed ) Tj 2.722222 0 Td 59.953704 Tz (by ) Tj 0.913889 0 Td 45.37037 Tz (fluorination. ) Tj 3.791667 0 Td 55.092593 Tz (For ) Tj 51.428571 0 0 51.428571 0 1379.346062 Tm 6.358333 0 Td 48.611111 Tz (reduction, ) Tj 3.091667 0 Td 50.771605 Tz (the ) Tj 1.069444 0 Td 50.411523 Tz (protected ) Tj 2.897222 0 Td 51.147343 Tz (\(16:0\)-p-phosphodiester ) Tj 7.233333 0 Td 40.509259 Tz (\(1 ) Tj 0.758333 0 Td 46.180556 Tz (eq.\) ) Tj 1.322222 0 Td 60.493827 Tz (was ) Tj 51.428571 0 0 51.428571 0 1335.415842 Tm 6.358333 0 Td 50.771605 Tz (dissolved ) Tj 3.033333 0 Td 43.75 Tz (in ) Tj 0.816667 0 Td 59.773663 Tz (THF/water ) Tj 3.480556 0 Td 46.666667 Tz (3:0.1 ) Tj 1.75 0 Td 49.494949 Tz (equivalents ) Tj 3.597222 0 Td 47.800926 Tz (respectively ) Tj 3.713889 0 Td 61.574074 Tz (and ) Tj 51.428571 0 0 51.428571 0 1293.427307 Tm 6.377778 0 Td 58.333333 Tz (sodium ) Tj 2.313889 0 Td 54.208754 Tz (borohydride ) Tj 3.791667 0 Td 42.12963 Tz (\(1 ) Tj 0.797222 0 Td 45.37037 Tz (eq.\) ) Tj 1.302778 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 57.685185 Tz (added ) Tj 1.925 0 Td 46.990741 Tz (to ) Tj 0.797222 0 Td 48.611111 Tz (the ) Tj 1.108333 0 Td 47.800926 Tz (reaction ) Tj 2.527778 0 Td 42.12963 Tz (flask. ) Tj 51.428571 0 0 51.428571 0 1250.748219 Tm 6.358333 0 Td 63.734568 Tz (The ) Tj 1.302778 0 Td 47.800926 Tz (reaction ) Tj 2.430556 0 Td 53.703704 Tz (mixture ) Tj 2.372222 0 Td 60.493827 Tz (was ) Tj 1.263889 0 Td 43.981481 Tz (stirred ) Tj 1.983333 0 Td 44.074074 Tz (until ) Tj 1.438889 0 Td 39.969136 Tz (all ) Tj 0.855556 0 Td 58.873457 Tz (sodium ) Tj 2.255556 0 Td 54.208754 Tz (borohydride ) Tj 51.428571 0 0 51.428571 0 1209.106599 Tm 6.358333 0 Td 50.771605 Tz (dissolved ) Tj 3.033333 0 Td 54.012346 Tz (\(~2 ) Tj 1.283333 0 Td 51.851852 Tz (minutes\) ) Tj 2.761111 0 Td 59.41358 Tz (and ) Tj 1.341667 0 Td 52.932099 Tz (continued ) Tj 3.111111 0 Td 44.155093 Tz (stirring ) Tj 2.372222 0 Td 48.611111 Tz (for ) Tj 1.108333 0 Td 56.712963 Tz (an ) Tj 0.933333 0 Td 63.194444 Tz (addi ) Tj 51.428571 0 0 51.428571 0 1166.598226 Tm 6.338889 0 Td 45.910494 Tz (tional ) Tj 1.963889 0 Td 56.712963 Tz (10 ) Tj 0.875 0 Td 50.636574 Tz (minutes. ) Tj 2.663889 0 Td 57.685185 Tz (Water ) Tj 1.905556 0 Td 46.990741 Tz (\(3 ) Tj 0.777778 0 Td 47.800926 Tz (eq.\) ) Tj 1.361111 0 Td 60.493827 Tz (was ) Tj 1.302778 0 Td 57.685185 Tz (added ) Tj 1.925 0 Td 59.41358 Tz (and ) Tj 1.283333 0 Td 49.691358 Tz (the ) Tj 1.108333 0 Td 49.016204 Tz (reaction ) Tj 40 0 0 40 0 1132 Tm 8.225 0 Td 68.452381 Tz (mixture ) Tj 3.2 0 Td 80.555556 Tz (was ) Tj 1.8 0 Td 57.142857 Tz (stirred ) Tj 2.725 0 Td 72.916667 Tz (an ) Tj 1.225 0 Td 62.5 Tz (additional ) Tj 4.2 0 Td 72.916667 Tz (10 ) Tj 1.225 0 Td 65.104167 Tz (minutes. ) Tj 3.475 0 Td 63.888889 Tz (All ) Tj 1.525 0 Td 63.020833 Tz (solvents ) Tj 51.428571 0 0 51.428571 0 1085.696078 Tm 6.338889 0 Td 59.953704 Tz (were ) Tj 1.652778 0 Td 59.259259 Tz (removed ) Tj 2.702778 0 Td 43.75 Tz (in ) Tj 0.758333 0 Td 55.740741 Tz (vacuo ) Tj 1.866667 0 Td 59.41358 Tz (and ) Tj 1.263889 0 Td 47.530864 Tz (the ) Tj 1.069444 0 Td 51.446759 Tz (reduced, ) Tj 2.644444 0 Td 50.411523 Tz (protected ) Tj 2.897222 0 Td 48.611111 Tz (\(16:0\)-p- ) Tj 51.428571 0 0 51.428571 0 1046.69475 Tm 6.358333 0 Td 52.777778 Tz (phosphodiester ) Tj 4.647222 0 Td 61.574074 Tz (was ) Tj 1.361111 0 Td 47.395833 Tz (purified ) Tj 2.508333 0 Td 59.953704 Tz (by ) Tj 1.011111 0 Td 44.722222 Tz (flash ) Tj 1.613889 0 Td 59.41358 Tz (column ) Tj 2.411111 0 Td 59.217172 Tz (chromatogra ) Tj 51.428571 0 0 51.428571 0 1003.551122 Tm 6.358333 0 Td 59.41358 Tz (phy ) Tj 1.322222 0 Td 52.5 Tz (using ) Tj 1.788889 0 Td 72.376543 Tz (40% ) Tj 1.555556 0 Td 47.962963 Tz (ethyl ) Tj 1.672222 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.491667 0 Td 51.041667 Tz (then ) Tj 1.458333 0 Td 52.572016 Tz (switching ) Tj 3.072222 0 Td 43.75 Tz (to ) Tj 0.758333 0 Td 74.537037 Tz (80% ) Tj 51.428571 0 0 51.428571 0 961.133641 Tm 6.358333 0 Td 47.314815 Tz (ethyl ) Tj 1.633333 0 Td 51.157407 Tz (acetate/hexane ) Tj 4.472222 0 Td 48.611111 Tz (for ) Tj 1.011111 0 Td 55.092593 Tz (a ) Tj 0.525 0 Td 47.800926 Tz (step ) Tj 1.341667 0 Td 49.826389 Tz (gradient ) Tj 2.547222 0 Td 45.775463 Tz (elution. ) Tj 51.428571 0 0 51.428571 0 922.815345 Tm 7.097222 0 Td 62.654321 Tz (The ) Tj 1.497222 0 Td 50.636574 Tz (reduced, ) Tj 2.761111 0 Td 50.411523 Tz (protected ) Tj 3.072222 0 Td 51.006441 Tz (\(16:0\)-p-phosphodiester ) Tj 7.35 0 Td 43.75 Tz (\(1 ) Tj 0.933333 0 Td 46.180556 Tz (eq.\) ) Tj 51.428571 0 0 51.428571 0 878.395466 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.380556 0 Td 49.907407 Tz (dried ) Tj 1.711111 0 Td 54.282407 Tz (over ) Tj 1.497222 0 Td 55.681818 Tz (phosphorous ) Tj 3.927778 0 Td 53.292181 Tz (pentoxide ) Tj 3.130556 0 Td 47.530864 Tz (for ) Tj 1.069444 0 Td 55.092593 Tz (2 ) Tj 0.544444 0 Td 54.444444 Tz (hours ) Tj 1.847222 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 59.41358 Tz (dis ) Tj 40 0 0 40 0 841 Tm 8.2 0 Td 67.361111 Tz (solved ) Tj 2.6 0 Td 58.333333 Tz (in ) Tj 0.9 0 Td 67.447917 Tz (dichloromethane. ) Tj 6.65 0 Td 81.944444 Tz (The ) Tj 1.675 0 Td 61.979167 Tz (reaction ) Tj 3.175 0 Td 59.166667 Tz (flask ) Tj 1.975 0 Td 77.777778 Tz (was ) Tj 1.6 0 Td 64.583333 Tz (sealed ) Tj 2.475 0 Td 79.166667 Tz (and ) Tj 51.428571 0 0 51.428571 0 794.811881 Tm 6.358333 0 Td 52.932099 Tz (placed ) Tj 2.080556 0 Td 45.37037 Tz (in ) Tj 0.7 0 Td 58.333333 Tz (an ) Tj 0.894444 0 Td 45.37037 Tz (ice ) Tj 0.991667 0 Td 51.851852 Tz (bath ) Tj 1.438889 0 Td 45.37037 Tz (to ) Tj 0.758333 0 Td 52.256944 Tz (maintain ) Tj 2.702778 0 Td 60.763889 Tz (0C. ) Tj 1.672222 0 Td 50.231481 Tz (temperature. ) Tj 3.85 0 Td 65.895062 Tz (Deoxof ) Tj 51.428571 0 0 51.428571 0 751.559494 Tm 6.358333 0 Td 50.231481 Tz (luor ) Tj 1.419444 0 Td 45.37037 Tz (\(2 ) Tj 0.797222 0 Td 46.180556 Tz (eq.\) ) Tj 1.322222 0 Td 46.990741 Tz (in ) Tj 0.797222 0 Td 54.228395 Tz (dichloromethane ) Tj 5.094444 0 Td 61.574074 Tz (was ) Tj 1.361111 0 Td 52.391975 Tz (slowly ) Tj 2.119444 0 Td 58.333333 Tz (added ) Tj 1.963889 0 Td 55.092593 Tz (\(~2 ) Tj 1.263889 0 Td 73.45679 Tz (min ) Tj 51.428571 0 0 51.428571 0 709 Tm 6.338889 0 Td 44.290123 Tz (utes\). ) Tj 1.711111 0 Td 64.814815 Tz (The ) Tj 1.283333 0 Td 47.530864 Tz (ice ) Tj 0.991667 0 Td 51.851852 Tz (bath ) Tj 1.380556 0 Td 61.574074 Tz (was ) Tj 1.302778 0 Td 59.259259 Tz (removed ) Tj 2.605556 0 Td 59.41358 Tz (and ) Tj 1.186111 0 Td 49.691358 Tz (the ) Tj 1.05 0 Td 48.611111 Tz (reaction ) Tj 2.488889 0 Td 53.703704 Tz (mixture ) Tj 2.372222 0 Td 61.574074 Tz (was ) Tj 40 0 0 40 0 675 Tm 8.2 0 Td 56.547619 Tz (stirred ) Tj 2.775 0 Td 61.111111 Tz (for ) Tj 1.55 0 Td 68.75 Tz (12 ) Tj 1.225 0 Td 63.194444 Tz (hours. ) Tj 2.675 0 Td 91.666667 Tz (An ) Tj 1.475 0 Td 62.083333 Tz (extraction ) Tj 4.125 0 Td 68.75 Tz (with ) Tj 2.075 0 Td 68.229167 Tz (dichloromethane/ ) Tj 51.428571 0 0 51.428571 0 626.625815 Tm 6.377778 0 Td 48.251029 Tz (saturated ) Tj 2.936111 0 Td 58.873457 Tz (sodium ) Tj 2.488889 0 Td 51.557239 Tz (bicarbonate ) Tj 3.713889 0 Td 48.611111 Tz (solution ) Tj 2.761111 0 Td 43.209877 Tz (1:1 ) Tj 1.186111 0 Td 46.666667 Tz (\(v/v\) ) Tj 1.75 0 Td 61.574074 Tz (was ) Tj 1.438889 0 Td 64.814815 Tz (per ) Tj 51.428571 0 0 51.428571 0 586.50084 Tm 6.358333 0 Td 58.333333 Tz (formed ) Tj 2.275 0 Td 59.41358 Tz (and ) Tj 1.244444 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 51.388889 Tz (organic ) Tj 2.372222 0 Td 48.611111 Tz (layer ) Tj 1.613889 0 Td 61.574074 Tz (was ) Tj 1.302778 0 Td 46.342593 Tz (collected. ) Tj 51.428571 0 0 51.428571 0 547.517923 Tm 7.097222 0 Td 51.851852 Tz (After ) Tj 1.691667 0 Td 52.932099 Tz (drying ) Tj 2.061111 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 52.391975 Tz (vacuo, ) Tj 2.061111 0 Td 49.691358 Tz (the ) Tj 1.05 0 Td 50.05144 Tz (protected ) Tj 2.877778 0 Td 54.751462 Tz (\(16:0\)-p-monofluoro ) Tj 51.428571 0 0 51.428571 0 506.69475 Tm 6.358333 0 Td 52.777778 Tz (phosphodiester ) Tj 4.647222 0 Td 61.574074 Tz (was ) Tj 1.361111 0 Td 47.395833 Tz (purified ) Tj 2.508333 0 Td 59.953704 Tz (by ) Tj 1.011111 0 Td 44.722222 Tz (flash ) Tj 1.613889 0 Td 59.41358 Tz (column ) Tj 2.411111 0 Td 59.217172 Tz (chromatogra ) Tj 51.428571 0 0 51.428571 0 462.551122 Tm 6.358333 0 Td 59.41358 Tz (phy ) Tj 1.322222 0 Td 52.5 Tz (using ) Tj 1.788889 0 Td 72.376543 Tz (40% ) Tj 1.555556 0 Td 47.962963 Tz (ethyl ) Tj 1.672222 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.491667 0 Td 51.041667 Tz (then ) Tj 1.458333 0 Td 52.572016 Tz (switching ) Tj 3.072222 0 Td 43.75 Tz (to ) Tj 0.758333 0 Td 74.537037 Tz (80% ) Tj 51.428571 0 0 51.428571 0 421.748517 Tm 6.358333 0 Td 47.314815 Tz (ethyl ) Tj 1.594444 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.394444 0 Td 48.611111 Tz (for ) Tj 0.972222 0 Td 58.333333 Tz (a ) Tj 0.486111 0 Td 47.800926 Tz (step ) Tj 1.283333 0 Td 49.826389 Tz (gradient ) Tj 2.508333 0 Td 45.775463 Tz (elution. ) Tj 2.372222 0 Td 56.17284 Tz (For ) Tj 1.127778 0 Td 56.712963 Tz (deprotec ) Tj 51.428571 0 0 51.428571 0 382.634615 Tm 6.338889 0 Td 44.074074 Tz (tion, ) Tj 1.652778 0 Td 49.691358 Tz (the ) Tj 1.186111 0 Td 50.771605 Tz (protected ) Tj 3.072222 0 Td 52.328431 Tz (\(16:0\)-p-monofluoro-phosphodiester ) Tj 10.966667 0 Td 45.37037 Tz (\(1 ) Tj 51.428571 0 0 51.428571 0 339.774032 Tm 6.358333 0 Td 46.180556 Tz (eq.\) ) Tj 1.361111 0 Td 61.574074 Tz (was ) Tj 1.361111 0 Td 50.411523 Tz (dissolved ) Tj 2.955556 0 Td 45.37037 Tz (in ) Tj 0.777778 0 Td 48.611111 Tz (pyridine. ) Tj 2.858333 0 Td 57.086895 Tz (N-propylamine ) Tj 4.686111 0 Td 55.092593 Tz (\(100 ) Tj 1.555556 0 Td 46.180556 Tz (eq.\) ) Tj 1.361111 0 Td 48.611111 Tz (in ) Tj 51.428571 0 0 51.428571 0 294.204819 Tm 6.358333 0 Td 50.636574 Tz (pyridine ) Tj 2.566667 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 57.685185 Tz (added ) Tj 1.886111 0 Td 43.75 Tz (to ) Tj 0.7 0 Td 48.611111 Tz (the ) Tj 1.011111 0 Td 48.611111 Tz (reaction ) Tj 2.469444 0 Td 46.018519 Tz (flask ) Tj 1.477778 0 Td 58.333333 Tz (and ) Tj 1.205556 0 Td 49.691358 Tz (the ) Tj 0.991667 0 Td 48.611111 Tz (clear ) Tj 1.575 0 Td 49.421296 Tz (solution ) Tj 51.428571 0 0 51.428571 0 252.853779 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 43.981481 Tz (stirred ) Tj 2.041667 0 Td 47.530864 Tz (for ) Tj 1.088889 0 Td 55.092593 Tz (10 ) Tj 0.855556 0 Td 54.166667 Tz (minutes ) Tj 2.45 0 Td 43.75 Tz (at ) Tj 0.738889 0 Td 62.384259 Tz (room ) Tj 1.691667 0 Td 50.501543 Tz (temperature. ) Tj 3.811111 0 Td 50.771605 Tz (All ) Tj 1.108333 0 Td 49.016204 Tz (solvents ) Tj 51.428571 0 0 51.428571 0 213.629268 Tm 6.338889 0 Td 59.953704 Tz (were ) Tj 1.633333 0 Td 60.185185 Tz (removed ) Tj 2.702778 0 Td 45.37037 Tz (in ) Tj 0.777778 0 Td 56.388889 Tz (vacuo ) Tj 1.866667 0 Td 46.990741 Tz (to ) Tj 0.758333 0 Td 49.259259 Tz (yield ) Tj 1.633333 0 Td 50.771605 Tz (the ) Tj 1.147222 0 Td 59.953704 Tz (n-propylammonium ) Tj 5.95 0 Td 42.939815 Tz (salt ) Tj 51.428571 0 0 51.428571 0 173.330132 Tm 6.358333 0 Td 58.333333 Tz (of ) Tj 0.972222 0 Td 49.691358 Tz (the ) Tj 1.225 0 Td 51.388889 Tz (\(16:0\)-p-monofluoro-phosphodiester. ) Tj 11.141667 0 Td 71.296296 Tz (An ) Tj 1.205556 0 Td 49.259259 Tz (extraction ) Tj 30 0 0 30 0 2547 Tm 41.666667 0 Td 75 Tz (10 ) Tj 30 0 0 30 0 2339 Tm 41.666667 0 Td 72.222222 Tz (15 ) Tj 30 0 0 30 0 1923 Tm 41.6 0 Td 77.777778 Tz (25 ) Tj 30 0 0 30 0 1716 Tm 41.6 0 Td 80.555556 Tz (30 ) Tj 30 0 0 30 0 1507 Tm 41.6 0 Td 77.777778 Tz (35 ) Tj 30 0 0 30 0 1299 Tm 41.566667 0 Td 83.333333 Tz (40 ) Tj 30 0 0 30 0 1091 Tm 41.566667 0 Td 80.555556 Tz (45 ) Tj 30 0 0 30 0 883 Tm 41.6 0 Td 80.555556 Tz (50 ) Tj 30 0 0 30 0 675 Tm 41.6 0 Td 77.777778 Tz (55 ) Tj 30 0 0 30 0 467 Tm 41.633333 0 Td 77.777778 Tz (60 ) Tj 30 0 0 30 0 259 Tm 41.633333 0 Td 75 Tz (65 ) Tj 51.428571 0 0 51.428571 0 2969 Tm 33.6 0 Td 72.916667 Tz (12 ) Tj 51.428571 0 0 51.428571 0 2913.598226 Tm 25.277778 0 Td 54.282407 Tz (with ) Tj 1.691667 0 Td 52.759259 Tz (chloroform/methanol/brine ) Tj 8.361111 0 Td 44.907407 Tz (1:1.5:1 ) Tj 2.391667 0 Td 47.222222 Tz (\(v/v/v\) ) Tj 2.352778 0 Td 61.574074 Tz (was ) Tj 1.536111 0 Td 63.734568 Tz (per ) Tj 51.428571 0 0 51.428571 0 2873.971429 Tm 25.297222 0 Td 58.333333 Tz (formed ) Tj 2.255556 0 Td 45.37037 Tz (to ) Tj 0.7 0 Td 51.446759 Tz (generate ) Tj 2.625 0 Td 48.611111 Tz (the ) Tj 1.011111 0 Td 58.873457 Tz (sodium ) Tj 2.294444 0 Td 42.939815 Tz (salt ) Tj 1.147222 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 48.611111 Tz (the ) Tj 1.030556 0 Td 55.283224 Tz (\(16:0\)-p-monofluo ) Tj 51.428571 0 0 51.428571 0 2834 Tm 25.297222 0 Td 50.326797 Tz (rophosphodiester. ) Tj 51.428571 0 0 51.428571 0 2752.093333 Tm 32.472222 0 Td 61.574074 Tz (Example ) Tj 2.761111 0 Td 55.092593 Tz (5 ) Tj 51.428571 0 0 51.428571 0 2666 Tm 29.380556 0 Td 50.283751 Tz (\(14:0\)-p-difluorophosphodiester ) Tj 31.428571 0 0 31.428571 0 2507 Tm 57.177273 0 Td 111.363636 Tz (O ) Tj 171.428571 0 0 171.428571 0 2398.4 Tm 8.265833 0 Td 31.111111 Tz (gic-\( ) Tj 1.248333 0 Td 42.777778 Tz (\)----cloch ) Tj 31.428571 0 0 31.428571 0 2373 Tm 57.177273 0 Td 111.363636 Tz (OH ) Tj 51.428571 0 0 51.428571 0 2267.683995 Tm 26.036111 0 Td 56.565657 Tz (Phosphorous ) Tj 4.044444 0 Td 52.73569 Tz (oxychloride ) Tj 3.772222 0 Td 43.75 Tz (\(1 ) Tj 0.894444 0 Td 46.180556 Tz (eq.\) ) Tj 1.419444 0 Td 60.493827 Tz (was ) Tj 1.380556 0 Td 58.333333 Tz (added ) Tj 2.041667 0 Td 45.37037 Tz (to ) Tj 0.855556 0 Td 51.851852 Tz (a ) Tj 0.661111 0 Td 55.740741 Tz (round ) Tj 51.428571 0 0 51.428571 0 2221.327456 Tm 25.277778 0 Td 57.253086 Tz (bottom ) Tj 2.391667 0 Td 46.018519 Tz (flask ) Tj 1.633333 0 Td 58.333333 Tz (and ) Tj 1.341667 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 45.37037 Tz (in ) Tj 0.875 0 Td 49.907407 Tz (tetrahydrofuran ) Tj 4.783333 0 Td 56.17284 Tz (\(THF\). ) Tj 2.313889 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 2175.961963 Tm 25.297222 0 Td 57.037037 Tz (round ) Tj 1.847222 0 Td 56.712963 Tz (bottom ) Tj 2.197222 0 Td 46.666667 Tz (flask ) Tj 1.536111 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 51.851852 Tz (then ) Tj 1.4 0 Td 52.932099 Tz (placed ) Tj 2.061111 0 Td 45.37037 Tz (in ) Tj 0.680556 0 Td 59.953704 Tz (an ) Tj 0.875 0 Td 46.450617 Tz (ice ) Tj 0.952778 0 Td 52.662037 Tz (bath ) Tj 1.419444 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 53.06713 Tz (maintain ) Tj 51.428571 0 0 51.428571 0 2134.442211 Tm 25.297222 0 Td 51.851852 Tz (a ) Tj 0.544444 0 Td 64.00463 Tz (0C. ) Tj 1.788889 0 Td 49.96142 Tz (temperature. ) Tj 3.869444 0 Td 51.851852 Tz (Tetradecanol ) Tj 3.986111 0 Td 43.75 Tz (\(1 ) Tj 0.816667 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 50.411523 Tz (dissolved ) Tj 2.936111 0 Td 46.990741 Tz (in ) Tj 0.777778 0 Td 75.617284 Tz (THF ) Tj 51.428571 0 0 51.428571 0 2091.905824 Tm 25.277778 0 Td 54.282407 Tz (with ) Tj 1.497222 0 Td 49.85755 Tz (triethylamine ) Tj 4.083333 0 Td 62.87037 Tz (\(TEA\) ) Tj 2.1 0 Td 42.12963 Tz (\(1 ) Tj 0.758333 0 Td 46.990741 Tz (eq.\) ) Tj 1.302778 0 Td 62.654321 Tz (was ) Tj 1.302778 0 Td 58.333333 Tz (added ) Tj 1.963889 0 Td 55.092593 Tz (dropwise ) Tj 2.858333 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 50.771605 Tz (the ) Tj 51.428571 0 0 51.428571 0 2048.368039 Tm 25.297222 0 Td 55.976431 Tz (phosphorous ) Tj 3.908333 0 Td 56.388889 Tz (oxychloride/THF ) Tj 5.288889 0 Td 46.090535 Tz (solution. ) Tj 2.722222 0 Td 64.00463 Tz (Once ) Tj 1.730556 0 Td 39.969136 Tz (all ) Tj 0.933333 0 Td 59.953704 Tz (of ) Tj 0.836111 0 Td 48.611111 Tz (the ) Tj 1.088889 0 Td 52.932099 Tz (tet ) Tj 51.428571 0 0 51.428571 0 2001 Tm 25.297222 0 Td 59.095861 Tz (radecanol/THF/TEA ) Tj 6.241667 0 Td 48.206019 Tz (solution ) Tj 2.547222 0 Td 61.574074 Tz (was ) Tj 1.302778 0 Td 58.981481 Tz (added ) Tj 1.983333 0 Td 57.523148 Tz (\(-20 ) Tj 1.594444 0 Td 49.691358 Tz (minutes\), ) Tj 2.897222 0 Td 50.771605 Tz (the ) Tj 40 0 0 40 0 1965 Tm 32.525 0 Td 63.020833 Tz (reaction ) Tj 3.2 0 Td 69.047619 Tz (mixture ) Tj 3.025 0 Td 80.555556 Tz (was ) Tj 1.65 0 Td 55.952381 Tz (stirred ) Tj 2.525 0 Td 62.5 Tz (for ) Tj 1.225 0 Td 72.916667 Tz (an ) Tj 1.025 0 Td 62.5 Tz (additional ) Tj 3.925 0 Td 79.166667 Tz (40 ) Tj 1.125 0 Td 69.047619 Tz (minutes ) Tj 3.075 0 Td 58.333333 Tz (at ) Tj 0.85 0 Td 66.666667 Tz (0 ) Tj 51.428571 0 0 51.428571 0 1919.087167 Tm 25.297222 0 Td 53.472222 Tz (C. ) Tj 0.777778 0 Td 87.5 Tz (A ) Tj 0.7 0 Td 48.206019 Tz (solution ) Tj 2.469444 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 56.018519 Tz (p-hydroxybenzaldehyde ) Tj 7.213889 0 Td 42.12963 Tz (\(1 ) Tj 0.719444 0 Td 47.800926 Tz (eq.\) ) Tj 1.322222 0 Td 43.75 Tz (in ) Tj 0.680556 0 Td 76.697531 Tz (THF ) Tj 1.555556 0 Td 53.472222 Tz (with ) Tj 51.428571 0 0 51.428571 0 1875.899633 Tm 25.297222 0 Td 78.858025 Tz (TEA ) Tj 1.536111 0 Td 45.37037 Tz (\(1 ) Tj 0.738889 0 Td 46.180556 Tz (eq.\) ) Tj 1.263889 0 Td 61.574074 Tz (was ) Tj 1.244444 0 Td 58.333333 Tz (added ) Tj 1.886111 0 Td 55.497685 Tz (dropwise ) Tj 2.780556 0 Td 46.990741 Tz (to ) Tj 0.719444 0 Td 48.611111 Tz (the ) Tj 1.030556 0 Td 47.800926 Tz (reaction ) Tj 2.469444 0 Td 46.018519 Tz (flask ) Tj 1.477778 0 Td 59.41358 Tz (and ) Tj 1.205556 0 Td 61.574074 Tz (was ) Tj 51.428571 0 0 51.428571 0 1832.573548 Tm 25.316667 0 Td 43.981481 Tz (stirred ) Tj 1.983333 0 Td 48.611111 Tz (for ) Tj 0.991667 0 Td 56.712963 Tz (an ) Tj 0.855556 0 Td 47.962963 Tz (additional ) Tj 3.052778 0 Td 63.194444 Tz (40 ) Tj 0.933333 0 Td 53.240741 Tz (minutes ) Tj 2.391667 0 Td 45.37037 Tz (at ) Tj 0.7 0 Td 59.953704 Tz (0C. ) Tj 1.613889 0 Td 57.685185 Tz (Water ) Tj 1.847222 0 Td 45.37037 Tz (\(1 ) Tj 0.758333 0 Td 46.990741 Tz (eq.\) ) Tj 1.263889 0 Td 59.41358 Tz (and ) Tj 51.428571 0 0 51.428571 0 1791.57956 Tm 25.297222 0 Td 78.858025 Tz (TEA ) Tj 1.652778 0 Td 43.75 Tz (\(1 ) Tj 0.816667 0 Td 45.37037 Tz (eq.\) ) Tj 1.341667 0 Td 58.333333 Tz (were ) Tj 1.613889 0 Td 58.333333 Tz (added ) Tj 1.963889 0 Td 45.37037 Tz (to ) Tj 0.797222 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 48.206019 Tz (reaction ) Tj 2.586111 0 Td 52.777778 Tz (mixture ) Tj 2.430556 0 Td 58.981481 Tz (which ) Tj 2.022222 0 Td 61.574074 Tz (was ) Tj 40 0 0 40 0 1757 Tm 32.525 0 Td 70.238095 Tz (allowed ) Tj 3.25 0 Td 58.333333 Tz (to ) Tj 1.075 0 Td 50 Tz (stir ) Tj 1.475 0 Td 62.5 Tz (for ) Tj 1.4 0 Td 81.25 Tz (60 ) Tj 1.275 0 Td 69.642857 Tz (minutes ) Tj 3.25 0 Td 58.333333 Tz (at ) Tj 1 0 Td 82.291667 Tz (0C. ) Tj 2.275 0 Td 81.944444 Tz (The ) Tj 1.8 0 Td 64.583333 Tz (contents ) Tj 3.425 0 Td 72.916667 Tz (of ) Tj 1.075 0 Td 65.277778 Tz (the ) Tj 40 0 0 40 0 1716 Tm 32.525 0 Td 62.5 Tz (reaction ) Tj 3.25 0 Td 60 Tz (flask ) Tj 2.05 0 Td 75 Tz (were ) Tj 2.025 0 Td 66.666667 Tz (then ) Tj 1.9 0 Td 79.166667 Tz (vacuum ) Tj 3.15 0 Td 55.208333 Tz (filtered ) Tj 2.875 0 Td 76.388889 Tz (and ) Tj 1.65 0 Td 63.333333 Tz (dried ) Tj 2.125 0 Td 58.333333 Tz (in ) Tj 0.975 0 Td 67.361111 Tz (vacuo. ) Tj 40 0 0 40 0 1674 Tm 32.525 0 Td 66.666667 Tz (After ) Tj 2.2 0 Td 75 Tz (an ) Tj 1.15 0 Td 62.083333 Tz (extraction ) Tj 4.025 0 Td 67.708333 Tz (with ) Tj 1.925 0 Td 68.666667 Tz (chloroform/methanol/water ) Tj 10.6 0 Td 58.928571 Tz (1:1.5:1 ) Tj 52.857143 0 0 52.857143 0 1626.580764 Tm 24.632432 0 Td 43.355856 Tz (\(v/v/v\), ) Tj 2.327027 0 Td 49.399399 Tz (the ) Tj 1.154054 0 Td 49.764982 Tz (\(14:0\)-p-phosphodiester ) Tj 7.094595 0 Td 58.858859 Tz (was ) Tj 1.381081 0 Td 48.698699 Tz (dissolved ) Tj 2.932432 0 Td 44.144144 Tz (in ) Tj 0.794595 0 Td 71.471471 Tz (40% ) Tj 51.428571 0 0 51.428571 0 1584.548303 Tm 25.297222 0 Td 47.962963 Tz (ethyl ) Tj 1.808333 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.627778 0 Td 59.41358 Tz (and ) Tj 1.419444 0 Td 50.084175 Tz (centrifuged ) Tj 3.713889 0 Td 47.530864 Tz (for ) Tj 1.186111 0 Td 61.574074 Tz (7 ) Tj 0.777778 0 Td 50.636574 Tz (minutes. ) Tj 2.8 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 1541.713574 Tm 25.316667 0 Td 50.673401 Tz (Supernatant ) Tj 3.597222 0 Td 61.574074 Tz (was ) Tj 1.380556 0 Td 53.877315 Tz (decanted ) Tj 2.838889 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 50.771605 Tz (the ) Tj 1.186111 0 Td 49.331276 Tz (insoluble ) Tj 2.936111 0 Td 46.450617 Tz (fractions ) Tj 2.8 0 Td 59.143519 Tz (were ) Tj 40 0 0 40 0 1507 Tm 32.525 0 Td 72.222222 Tz (combined. ) Tj 51.428571 0 0 51.428571 0 1463.38394 Tm 26.016667 0 Td 63.734568 Tz (The ) Tj 1.361111 0 Td 45.046296 Tz (relatively ) Tj 2.858333 0 Td 55.092593 Tz (pure ) Tj 1.536111 0 Td 51.006441 Tz (\(14:0\)-p-phosphodiester ) Tj 7.213889 0 Td 43.75 Tz (\(1 ) Tj 0.777778 0 Td 43.425926 Tz (eq.\), ) Tj 1.536111 0 Td 81.018519 Tz (DCC ) Tj 51.428571 0 0 51.428571 0 1418.085427 Tm 25.316667 0 Td 46.180556 Tz (\(2.2 ) Tj 1.341667 0 Td 61.574074 Tz (eq\) ) Tj 1.302778 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 87.5 Tz (DMAP ) Tj 2.313889 0 Td 43.75 Tz (\(0.1 ) Tj 1.322222 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 58.333333 Tz (were ) Tj 1.594444 0 Td 49.907407 Tz (dried ) Tj 1.711111 0 Td 53.472222 Tz (over ) Tj 1.458333 0 Td 56.565657 Tz (phosphorous ) Tj 51.428571 0 0 51.428571 0 1377.971223 Tm 25.297222 0 Td 53.292181 Tz (pentoxide ) Tj 2.994444 0 Td 48.611111 Tz (for ) Tj 1.05 0 Td 53.472222 Tz (12 ) Tj 0.797222 0 Td 49.151235 Tz (hours. ) Tj 1.905556 0 Td 56.442901 Tz (Cyanoethanol ) Tj 4.2 0 Td 43.75 Tz (\(1.1 ) Tj 1.263889 0 Td 46.180556 Tz (eq.\) ) Tj 1.283333 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 50.771605 Tz (dissolved ) Tj 51.428571 0 0 51.428571 0 1333.646772 Tm 25.297222 0 Td 45.37037 Tz (in ) Tj 0.719444 0 Td 54.444444 Tz (dichloromethane ) Tj 5.055556 0 Td 59.41358 Tz (and ) Tj 1.244444 0 Td 49.259259 Tz (dried ) Tj 1.633333 0 Td 53.472222 Tz (with ) Tj 1.497222 0 Td 60.853909 Tz (magnesium ) Tj 3.5 0 Td 45.833333 Tz (sulfate ) Tj 2.1 0 Td 47.530864 Tz (for ) Tj 1.069444 0 Td 51.851852 Tz (12 ) Tj 51.428571 0 0 51.428571 0 1294.44484 Tm 25.277778 0 Td 49.691358 Tz (hours. ) Tj 1.983333 0 Td 62.654321 Tz (The ) Tj 1.302778 0 Td 51.147343 Tz (\(14:0\)-p-phosphodiester ) Tj 7.213889 0 Td 60.493827 Tz (was ) Tj 1.302778 0 Td 50.411523 Tz (dissolved ) Tj 2.877778 0 Td 46.990741 Tz (in ) Tj 0.758333 0 Td 56.712963 Tz (dichlo ) Tj 40 0 0 40 0 1257 Tm 32.525 0 Td 73.148148 Tz (romethane ) Tj 4.2 0 Td 75 Tz (and ) Tj 1.625 0 Td 105.555556 Tz (DCC ) Tj 2.15 0 Td 75 Tz (and ) Tj 1.625 0 Td 111.458333 Tz (DMAP ) Tj 2.925 0 Td 76.041667 Tz (were ) Tj 2.05 0 Td 75 Tz (added ) Tj 2.525 0 Td 56.25 Tz (to ) Tj 0.975 0 Td 62.5 Tz (the ) Tj 1.4 0 Td 62.5 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 1210.168612 Tm 25.297222 0 Td 42.669753 Tz (flask. ) Tj 1.788889 0 Td 62.654321 Tz (The ) Tj 1.361111 0 Td 46.666667 Tz (flask ) Tj 1.633333 0 Td 60.493827 Tz (was ) Tj 1.341667 0 Td 50.771605 Tz (sealed ) Tj 2.061111 0 Td 53.472222 Tz (with ) Tj 1.536111 0 Td 51.851852 Tz (a ) Tj 0.583333 0 Td 57.253086 Tz (septum ) Tj 2.313889 0 Td 59.41358 Tz (and ) Tj 1.283333 0 Td 55.632716 Tz (purged ) Tj 2.294444 0 Td 53.472222 Tz (with ) Tj 51.428571 0 0 51.428571 0 1169.985899 Tm 25.297222 0 Td 50.231481 Tz (nitrogen ) Tj 2.547222 0 Td 46.018519 Tz (after ) Tj 1.497222 0 Td 55.092593 Tz (adding ) Tj 2.1 0 Td 50.771605 Tz (the ) Tj 1.05 0 Td 53.472222 Tz (cyanoethanol ) Tj 4.005556 0 Td 46.090535 Tz (Solution. ) Tj 2.625 0 Td 64.814815 Tz (The ) Tj 1.302778 0 Td 49.016204 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 1126.476433 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.361111 0 Td 44.444444 Tz (stirred ) Tj 2.080556 0 Td 48.611111 Tz (for ) Tj 1.05 0 Td 59.953704 Tz (48 ) Tj 0.952778 0 Td 53.148148 Tz (hours ) Tj 1.808333 0 Td 46.990741 Tz (at ) Tj 0.777778 0 Td 62.384259 Tz (room ) Tj 1.730556 0 Td 50.231481 Tz (temperature. ) Tj 3.869444 0 Td 57.685185 Tz (Water ) Tj 1.944444 0 Td 46.990741 Tz (\(5 ) Tj 0.797222 0 Td 46.180556 Tz (eq.\) ) Tj 40 0 0 40 0 1091 Tm 32.5 0 Td 80.555556 Tz (was ) Tj 1.725 0 Td 75 Tz (added ) Tj 2.5 0 Td 76.388889 Tz (and ) Tj 1.625 0 Td 63.888889 Tz (the ) Tj 1.4 0 Td 62.5 Tz (reaction ) Tj 3.325 0 Td 68.452381 Tz (mixture ) Tj 3.125 0 Td 79.166667 Tz (was ) Tj 1.7 0 Td 57.142857 Tz (stirred ) Tj 2.65 0 Td 62.5 Tz (for ) Tj 1.35 0 Td 72.916667 Tz (an ) Tj 1.125 0 Td 81.25 Tz (addi ) Tj 40 0 0 40 0 1049 Tm 32.5 0 Td 59.722222 Tz (tional ) Tj 2.6 0 Td 79.166667 Tz (24 ) Tj 1.375 0 Td 63.194444 Tz (hours. ) Tj 2.75 0 Td 80.555556 Tz (The ) Tj 1.875 0 Td 65.104167 Tz (contents ) Tj 3.575 0 Td 75 Tz (of ) Tj 1.225 0 Td 63.888889 Tz (the ) Tj 1.6 0 Td 61.979167 Tz (reaction ) Tj 3.475 0 Td 59.166667 Tz (flask ) Tj 2.2 0 Td 75 Tz (were ) Tj 40 0 0 40 0 1008 Tm 32.525 0 Td 80.555556 Tz (vacuum ) Tj 3.175 0 Td 55.729167 Tz (filtered ) Tj 2.875 0 Td 77.777778 Tz (and ) Tj 1.65 0 Td 63.333333 Tz (dried ) Tj 2.15 0 Td 58.333333 Tz (in ) Tj 0.975 0 Td 66.666667 Tz (vacuo. ) Tj 2.65 0 Td 66.666667 Tz (After ) Tj 2.2 0 Td 72.916667 Tz (an ) Tj 1.15 0 Td 61.666667 Tz (extraction ) Tj 4 0 Td 67.708333 Tz (with ) Tj 51.428571 0 0 51.428571 0 961.386091 Tm 25.297222 0 Td 51.851852 Tz (chloroform/brine ) Tj 5.191667 0 Td 44.290123 Tz (1:1 ) Tj 1.069444 0 Td 43.209877 Tz (\(v/v\), ) Tj 1.730556 0 Td 49.691358 Tz (the ) Tj 1.05 0 Td 55.092593 Tz (coupled ) Tj 2.45 0 Td 53.703704 Tz (product ) Tj 2.411111 0 Td 62.654321 Tz (was ) Tj 1.283333 0 Td 47.800926 Tz (purified ) Tj 51.428571 0 0 51.428571 0 921.374532 Tm 25.277778 0 Td 61.574074 Tz (by ) Tj 1.011111 0 Td 45.37037 Tz (flash ) Tj 1.652778 0 Td 59.41358 Tz (column ) Tj 2.45 0 Td 56.25 Tz (chromatography ) Tj 4.997222 0 Td 53.148148 Tz (using ) Tj 1.847222 0 Td 73.45679 Tz (40% ) Tj 1.575 0 Td 48.611111 Tz (ethyl ) Tj 1.730556 0 Td 46.585648 Tz (acetate/ ) Tj 51.428571 0 0 51.428571 0 877.689238 Tm 25.277778 0 Td 57.79321 Tz (hexane ) Tj 2.236111 0 Td 51.041667 Tz (then ) Tj 1.380556 0 Td 52.572016 Tz (switching ) Tj 2.994444 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 73.45679 Tz (80% ) Tj 1.477778 0 Td 47.962963 Tz (ethyl ) Tj 1.594444 0 Td 51.157407 Tz (acetate/hexane ) Tj 4.433333 0 Td 48.611111 Tz (for ) Tj 0.972222 0 Td 55.092593 Tz (a ) Tj 0.525 0 Td 46.990741 Tz (step ) Tj 51.428571 0 0 51.428571 0 837.169492 Tm 25.297222 0 Td 49.826389 Tz (gradient ) Tj 2.547222 0 Td 45.775463 Tz (elution. ) Tj 51.428571 0 0 51.428571 0 798.747226 Tm 26.016667 0 Td 52.5 Tz (After ) Tj 1.808333 0 Td 45.121083 Tz (purification, ) Tj 3.791667 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 50.771605 Tz (protected ) Tj 3.013889 0 Td 51.006441 Tz (\(14:0\)-p-phosphodiester ) Tj 51.428571 0 0 51.428571 0 755.080808 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.4 0 Td 41.481481 Tz (split ) Tj 1.458333 0 Td 46.990741 Tz (into ) Tj 1.380556 0 Td 59.41358 Tz (two ) Tj 1.322222 0 Td 53.240741 Tz (roughly ) Tj 2.469444 0 Td 53.148148 Tz (equal ) Tj 1.808333 0 Td 47.530864 Tz (portions. ) Tj 2.8 0 Td 64.814815 Tz (The ) Tj 1.4 0 Td 37.592593 Tz (first ) Tj 1.322222 0 Td 50.925926 Tz (portion ) Tj 51.428571 0 0 51.428571 0 710.08 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.380556 0 Td 55.092593 Tz (used ) Tj 1.536111 0 Td 47.530864 Tz (for ) Tj 1.069444 0 Td 45.910494 Tz (direct ) Tj 1.866667 0 Td 46.720679 Tz (fluorination ) Tj 3.577778 0 Td 59.41358 Tz (and ) Tj 1.263889 0 Td 50.771605 Tz (the ) Tj 1.108333 0 Td 56.712963 Tz (second ) Tj 2.236111 0 Td 50 Tz (portion ) Tj 2.333333 0 Td 61.574074 Tz (was ) Tj 51.428571 0 0 51.428571 0 668.887179 Tm 25.277778 0 Td 55.902778 Tz (used ) Tj 1.672222 0 Td 48.611111 Tz (for ) Tj 1.205556 0 Td 49.691358 Tz (reduction ) Tj 3.052778 0 Td 53.472222 Tz (followed ) Tj 2.858333 0 Td 59.953704 Tz (by ) Tj 1.069444 0 Td 46.990741 Tz (fluorination ) Tj 3.694444 0 Td 59.548611 Tz (\(Example ) Tj 3.169444 0 Td 41.049383 Tz (6\). ) Tj 51.428571 0 0 51.428571 0 630.264631 Tm 25.316667 0 Td 50.771605 Tz (Protected ) Tj 3.091667 0 Td 51.006441 Tz (\(14:0\)-p-phosphodiester ) Tj 7.388889 0 Td 40.509259 Tz (\(1 ) Tj 0.933333 0 Td 46.180556 Tz (eq.\) ) Tj 1.458333 0 Td 61.574074 Tz (was ) Tj 1.458333 0 Td 49.907407 Tz (dried ) Tj 1.847222 0 Td 54.282407 Tz (over ) Tj 51.428571 0 0 51.428571 0 587.26747 Tm 25.297222 0 Td 55.976431 Tz (phosphorous ) Tj 3.85 0 Td 53.652263 Tz (pentoxide ) Tj 3.052778 0 Td 48.611111 Tz (for ) Tj 1.069444 0 Td 55.092593 Tz (12 ) Tj 0.797222 0 Td 54.444444 Tz (hours ) Tj 1.788889 0 Td 58.333333 Tz (and ) Tj 1.225 0 Td 50.771605 Tz (dissolved ) Tj 2.897222 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 56.712963 Tz (dichlo ) Tj 51.428571 0 0 51.428571 0 542.956522 Tm 25.297222 0 Td 53.796296 Tz (romethane. ) Tj 3.363889 0 Td 63.734568 Tz (The ) Tj 1.283333 0 Td 48.611111 Tz (reaction ) Tj 2.508333 0 Td 46.018519 Tz (flask ) Tj 1.477778 0 Td 62.654321 Tz (was ) Tj 1.263889 0 Td 50.771605 Tz (sealed ) Tj 1.963889 0 Td 58.333333 Tz (and ) Tj 1.166667 0 Td 53.472222 Tz (placed ) Tj 2.061111 0 Td 45.37037 Tz (in ) Tj 0.7 0 Td 56.712963 Tz (an ) Tj 0.836111 0 Td 47.530864 Tz (ice ) Tj 51.428571 0 0 51.428571 0 503.565046 Tm 25.277778 0 Td 52.662037 Tz (bath ) Tj 1.555556 0 Td 45.37037 Tz (to ) Tj 0.875 0 Td 52.256944 Tz (maintain ) Tj 2.819444 0 Td 50.231481 Tz (0 ) Tj 0.894444 0 Td 55.092593 Tz (C. ) Tj 0.991667 0 Td 49.96142 Tz (temperature. ) Tj 3.927778 0 Td 55.416667 Tz (Deoxofluor ) Tj 3.597222 0 Td 46.990741 Tz (\(2 ) Tj 0.836111 0 Td 47.800926 Tz (eq.\) ) Tj 1.419444 0 Td 48.611111 Tz (in ) Tj 51.428571 0 0 51.428571 0 459.92891 Tm 25.297222 0 Td 54.444444 Tz (dichloromethane ) Tj 5.036111 0 Td 61.574074 Tz (was ) Tj 1.283333 0 Td 52.932099 Tz (slowly ) Tj 2.041667 0 Td 58.981481 Tz (added ) Tj 1.905556 0 Td 55.092593 Tz (\(-2 ) Tj 1.205556 0 Td 52.256944 Tz (minutes\) ) Tj 2.644444 0 Td 59.41358 Tz (and ) Tj 1.186111 0 Td 51.388889 Tz (ethanol ) Tj 51.428571 0 0 51.428571 0 421.183463 Tm 25.316667 0 Td 46.180556 Tz (\(0.2 ) Tj 1.341667 0 Td 46.180556 Tz (eq.\) ) Tj 1.322222 0 Td 61.574074 Tz (was ) Tj 1.341667 0 Td 57.685185 Tz (added ) Tj 1.944444 0 Td 45.37037 Tz (to ) Tj 0.777778 0 Td 51.446759 Tz (generate ) Tj 2.663889 0 Td 51.851852 Tz (a ) Tj 0.525 0 Td 44.650206 Tz (catalyst, ) Tj 2.663889 0 Td 55.092593 Tz (HF. ) Tj 1.205556 0 Td 63.734568 Tz (The ) Tj 1.341667 0 Td 47.530864 Tz (ice ) Tj 1.069444 0 Td 52.662037 Tz (bath ) Tj 40 0 0 40 0 384 Tm 32.5 0 Td 80.555556 Tz (was ) Tj 1.875 0 Td 76.785714 Tz (removed ) Tj 3.625 0 Td 75 Tz (and ) Tj 1.725 0 Td 63.888889 Tz (the ) Tj 1.525 0 Td 62.5 Tz (reaction ) Tj 3.425 0 Td 69.047619 Tz (mixture ) Tj 3.3 0 Td 77.777778 Tz (was ) Tj 1.825 0 Td 56.547619 Tz (stirred ) Tj 2.775 0 Td 62.5 Tz (for ) Tj 1.55 0 Td 68.75 Tz (16 ) Tj 40 0 0 40 0 343 Tm 32.5 0 Td 63.888889 Tz (hours. ) Tj 2.5 0 Td 91.666667 Tz (An ) Tj 1.325 0 Td 61.666667 Tz (extraction ) Tj 3.925 0 Td 68.75 Tz (with ) Tj 1.875 0 Td 66 Tz (dichloromethane/saturated ) Tj 10.125 0 Td 75.694444 Tz (sodium ) Tj 51.428571 0 0 51.428571 0 295.583433 Tm 25.277778 0 Td 51.557239 Tz (bicarbonate ) Tj 3.558333 0 Td 48.611111 Tz (solution ) Tj 2.547222 0 Td 43.209877 Tz (1:1 ) Tj 1.030556 0 Td 46.666667 Tz (\(v/v\) ) Tj 1.536111 0 Td 61.574074 Tz (was ) Tj 1.244444 0 Td 56.532922 Tz (performed ) Tj 3.169444 0 Td 59.41358 Tz (and ) Tj 1.225 0 Td 48.611111 Tz (the ) Tj 0.991667 0 Td 51.851852 Tz (organic ) Tj 51.428571 0 0 51.428571 0 253.210909 Tm 25.297222 0 Td 49.259259 Tz (layer ) Tj 1.652778 0 Td 60.493827 Tz (was ) Tj 1.283333 0 Td 46.342593 Tz (collected. ) Tj 51.428571 0 0 51.428571 0 215.343958 Tm 26.016667 0 Td 52.5 Tz (After ) Tj 1.905556 0 Td 52.391975 Tz (drying ) Tj 2.236111 0 Td 45.37037 Tz (in ) Tj 0.933333 0 Td 51.851852 Tz (vacuo, ) Tj 2.236111 0 Td 48.611111 Tz (the ) Tj 1.186111 0 Td 50.771605 Tz (protected ) Tj 3.091667 0 Td 50.517429 Tz (\(14:0\)-p-difluoro ) Tj 51.428571 0 0 51.428571 0 173.697561 Tm 25.297222 0 Td 52.777778 Tz (phosphodiester ) Tj 4.647222 0 Td 61.574074 Tz (was ) Tj 1.341667 0 Td 47.800926 Tz (purified ) Tj 2.527778 0 Td 59.953704 Tz (by ) Tj 0.991667 0 Td 44.722222 Tz (flash ) Tj 1.633333 0 Td 59.41358 Tz (column ) Tj 2.411111 0 Td 59.217172 Tz (chromatogra ) Tj ET Q endstream endobj 186 0 obj << /Length 1 >> stream q endstream endobj 187 0 obj << /Length 41602 >> stream Q q 0.24 0 0 0.24 0 0 cm BT /F1 1 Tf 3 Tr 62.857143 0 0 62.857143 0 3023 Tm 17.325 0 Td 83.522727 Tz (US ) Tj 1.240909 0 Td 58.333333 Tz (8,022,239 ) Tj 3.388636 0 Td 74.242424 Tz (B2 ) Tj 52.857143 0 0 52.857143 0 2968 Tm 14.245946 0 Td 72.522523 Tz (13 ) Tj 51.428571 0 0 51.428571 0 2916.551122 Tm 6.358333 0 Td 59.41358 Tz (phy ) Tj 1.322222 0 Td 52.5 Tz (using ) Tj 1.788889 0 Td 72.376543 Tz (40% ) Tj 1.555556 0 Td 47.962963 Tz (ethyl ) Tj 1.672222 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.491667 0 Td 51.041667 Tz (then ) Tj 1.458333 0 Td 52.572016 Tz (switching ) Tj 3.072222 0 Td 43.75 Tz (to ) Tj 0.758333 0 Td 74.537037 Tz (80% ) Tj 51.428571 0 0 51.428571 0 2873.748517 Tm 6.358333 0 Td 47.314815 Tz (ethyl ) Tj 1.594444 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.394444 0 Td 48.611111 Tz (for ) Tj 0.972222 0 Td 58.333333 Tz (a ) Tj 0.486111 0 Td 47.800926 Tz (step ) Tj 1.283333 0 Td 49.826389 Tz (gradient ) Tj 2.508333 0 Td 45.775463 Tz (elution. ) Tj 2.372222 0 Td 56.17284 Tz (For ) Tj 1.127778 0 Td 56.712963 Tz (deprotec ) Tj 51.428571 0 0 51.428571 0 2832.661853 Tm 6.338889 0 Td 44.074074 Tz (tion, ) Tj 1.613889 0 Td 48.611111 Tz (the ) Tj 1.108333 0 Td 50.411523 Tz (protected ) Tj 2.955556 0 Td 50.130208 Tz (\(14:0\)-p-difluoro-phosphodiester ) Tj 9.858333 0 Td 42.12963 Tz (\(1 ) Tj 0.836111 0 Td 46.180556 Tz (eq.\) ) Tj 51.428571 0 0 51.428571 0 2786.829448 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 50.771605 Tz (dissolved ) Tj 2.955556 0 Td 43.75 Tz (in ) Tj 0.719444 0 Td 48.251029 Tz (pyridine. ) Tj 2.819444 0 Td 56.837607 Tz (N-propylamine ) Tj 4.647222 0 Td 55.902778 Tz (\(100 ) Tj 1.516667 0 Td 46.180556 Tz (eq.\) ) Tj 1.322222 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 59.143519 Tz (pyri ) Tj 40 0 0 40 0 2747 Tm 8.175 0 Td 67.708333 Tz (dine ) Tj 1.8 0 Td 76.388889 Tz (was ) Tj 1.55 0 Td 75.833333 Tz (added ) Tj 2.4 0 Td 60.416667 Tz (to ) Tj 0.925 0 Td 62.5 Tz (the ) Tj 1.3 0 Td 61.979167 Tz (reaction ) Tj 3.15 0 Td 68.229167 Tz (flaskand ) Tj 3.425 0 Td 65.277778 Tz (the ) Tj 1.325 0 Td 61.666667 Tz (clear ) Tj 1.95 0 Td 63.020833 Tz (solution ) Tj 3.2 0 Td 79.166667 Tz (was ) Tj 51.428571 0 0 51.428571 0 2696.82439 Tm 6.377778 0 Td 43.981481 Tz (stirred ) Tj 1.983333 0 Td 48.611111 Tz (for ) Tj 1.088889 0 Td 53.472222 Tz (10 ) Tj 0.816667 0 Td 54.166667 Tz (minutes ) Tj 2.411111 0 Td 45.37037 Tz (at ) Tj 0.719444 0 Td 61.574074 Tz (room ) Tj 1.652778 0 Td 50.501543 Tz (temperature. ) Tj 3.772222 0 Td 50.771605 Tz (All ) Tj 1.088889 0 Td 48.611111 Tz (solvents ) Tj 2.527778 0 Td 58.333333 Tz (were ) Tj 51.428571 0 0 51.428571 0 2654.621359 Tm 6.358333 0 Td 60.185185 Tz (removed ) Tj 2.702778 0 Td 43.75 Tz (in ) Tj 0.738889 0 Td 55.092593 Tz (vacuo ) Tj 1.847222 0 Td 45.37037 Tz (to ) Tj 0.7 0 Td 49.907407 Tz (yield ) Tj 1.633333 0 Td 50.771605 Tz (the ) Tj 1.088889 0 Td 59.953704 Tz (n-propylammonium ) Tj 5.930556 0 Td 42.939815 Tz (salt ) Tj 1.186111 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 49.691358 Tz (the ) Tj 51.428571 0 0 51.428571 0 2612.533958 Tm 6.377778 0 Td 49.016204 Tz (\(14:0\)-p-difluorophosphodiester. ) Tj 9.625 0 Td 72.916667 Tz (An ) Tj 1.088889 0 Td 48.287037 Tz (extraction ) Tj 3.130556 0 Td 54.282407 Tz (with ) Tj 1.477778 0 Td 58.873457 Tz (chloro ) Tj 51.428571 0 0 51.428571 0 2566.777101 Tm 6.358333 0 Td 52.875244 Tz (form/methanol/brine ) Tj 6.377778 0 Td 44.907407 Tz (1:1.5:1 ) Tj 2.255556 0 Td 46.759259 Tz (\(v/v/v\) ) Tj 2.216667 0 Td 56.532922 Tz (performed ) Tj 3.325 0 Td 45.37037 Tz (to ) Tj 0.816667 0 Td 51.851852 Tz (generate ) Tj 51.428571 0 0 51.428571 0 2525.003861 Tm 6.338889 0 Td 50.771605 Tz (the ) Tj 1.088889 0 Td 58.873457 Tz (sodium ) Tj 2.333333 0 Td 42.12963 Tz (salt ) Tj 1.186111 0 Td 59.953704 Tz (of ) Tj 0.797222 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 49.21875 Tz (\(14:0\)-p-difluorophosphodiester. ) Tj 51.428571 0 0 51.428571 0 2446.087248 Tm 13.552778 0 Td 61.111111 Tz (Example ) Tj 2.761111 0 Td 55.092593 Tz (6 ) Tj 51.428571 0 0 51.428571 0 2360 Tm 9.897222 0 Td 52.73569 Tz (\(14:0\)-p-monofluorophosphodiester ) Tj 31.428571 0 0 31.428571 0 2201 Tm 26.218182 0 Td 111.363636 Tz (O ) Tj 57.142857 0 0 57.142857 0 2158 Tm 14.49 0 Td 37.916667 Tz (| ) Tj 172.857143 0 0 172.857143 0 2086 Tm 2.557025 0 Td 30.853994 Tz (cis-\( ) Tj 1.261157 0 Td 38.47984 Tz (\)-o-o-clich ) Tj 31.428571 0 0 31.428571 0 2068 Tm 26.218182 0 Td 111.363636 Tz (OH ) Tj 51.428571 0 0 51.428571 0 1961.671214 Tm 7.116667 0 Td 55.976431 Tz (Phosphorous ) Tj 4.025 0 Td 53.030303 Tz (oxychloride ) Tj 3.791667 0 Td 42.12963 Tz (\(1 ) Tj 0.855556 0 Td 46.990741 Tz (eq.\) ) Tj 1.419444 0 Td 61.574074 Tz (was ) Tj 1.4 0 Td 58.333333 Tz (added ) Tj 2.041667 0 Td 46.990741 Tz (to ) Tj 0.836111 0 Td 55.092593 Tz (a ) Tj 0.680556 0 Td 55.740741 Tz (round ) Tj 51.428571 0 0 51.428571 0 1917.324528 Tm 6.338889 0 Td 57.253086 Tz (bottom ) Tj 2.391667 0 Td 46.018519 Tz (flask ) Tj 1.633333 0 Td 58.333333 Tz (and ) Tj 1.341667 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 46.990741 Tz (in ) Tj 0.875 0 Td 49.907407 Tz (tetrahydrofuran ) Tj 4.783333 0 Td 56.17284 Tz (\(THF\). ) Tj 2.313889 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 1874.95449 Tm 6.358333 0 Td 57.037037 Tz (round ) Tj 1.847222 0 Td 56.712963 Tz (bottom ) Tj 2.197222 0 Td 46.666667 Tz (flask ) Tj 1.536111 0 Td 60.493827 Tz (was ) Tj 1.263889 0 Td 51.041667 Tz (then ) Tj 1.4 0 Td 52.391975 Tz (placed ) Tj 2.061111 0 Td 43.75 Tz (in ) Tj 0.661111 0 Td 59.953704 Tz (an ) Tj 0.875 0 Td 46.450617 Tz (ice ) Tj 0.952778 0 Td 52.662037 Tz (bath ) Tj 1.419444 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 53.472222 Tz (maintain ) Tj 51.428571 0 0 51.428571 0 1834.45614 Tm 6.358333 0 Td 51.851852 Tz (a ) Tj 0.544444 0 Td 64.00463 Tz (0C. ) Tj 1.788889 0 Td 50.501543 Tz (temperature. ) Tj 3.869444 0 Td 51.851852 Tz (Tetradecanol ) Tj 3.986111 0 Td 43.75 Tz (\(1 ) Tj 0.816667 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 50.411523 Tz (dissolved ) Tj 2.955556 0 Td 45.37037 Tz (in ) Tj 0.758333 0 Td 76.697531 Tz (THF ) Tj 51.428571 0 0 51.428571 0 1794.895911 Tm 6.338889 0 Td 54.282407 Tz (with ) Tj 1.497222 0 Td 49.85755 Tz (triethylamine ) Tj 4.083333 0 Td 63.518519 Tz (\(TEA\) ) Tj 2.1 0 Td 42.12963 Tz (\(1 ) Tj 0.777778 0 Td 46.180556 Tz (eq.\) ) Tj 1.283333 0 Td 62.654321 Tz (was ) Tj 1.302778 0 Td 58.981481 Tz (added ) Tj 1.963889 0 Td 55.092593 Tz (dropwise ) Tj 2.858333 0 Td 45.37037 Tz (to ) Tj 0.738889 0 Td 49.691358 Tz (the ) Tj 51.428571 0 0 51.428571 0 1753.368039 Tm 6.358333 0 Td 55.976431 Tz (phosphorous ) Tj 3.908333 0 Td 56.388889 Tz (oxychloride/THF ) Tj 5.288889 0 Td 46.090535 Tz (solution. ) Tj 2.722222 0 Td 64.00463 Tz (Once ) Tj 1.730556 0 Td 39.969136 Tz (all ) Tj 0.933333 0 Td 59.953704 Tz (of ) Tj 0.836111 0 Td 48.611111 Tz (the ) Tj 1.088889 0 Td 52.932099 Tz (tet ) Tj 51.428571 0 0 51.428571 0 1708 Tm 6.358333 0 Td 59.095861 Tz (radecanol/THF/TEA ) Tj 6.241667 0 Td 48.206019 Tz (solution ) Tj 2.547222 0 Td 61.574074 Tz (was ) Tj 1.302778 0 Td 58.981481 Tz (added ) Tj 1.983333 0 Td 57.523148 Tz (\(-20 ) Tj 1.594444 0 Td 49.691358 Tz (minutes\), ) Tj 2.916667 0 Td 49.691358 Tz (the ) Tj 40 0 0 40 0 1674 Tm 8.175 0 Td 63.020833 Tz (reaction ) Tj 3.2 0 Td 69.047619 Tz (mixture ) Tj 3.05 0 Td 79.166667 Tz (was ) Tj 1.625 0 Td 56.547619 Tz (stirred ) Tj 2.55 0 Td 61.111111 Tz (for ) Tj 1.2 0 Td 72.916667 Tz (an ) Tj 1.025 0 Td 62.5 Tz (additional ) Tj 3.925 0 Td 79.166667 Tz (40 ) Tj 1.125 0 Td 70.238095 Tz (minutes ) Tj 3.075 0 Td 58.333333 Tz (at ) Tj 0.85 0 Td 66.666667 Tz (0 ) Tj 52.857143 0 0 52.857143 0 1627.028846 Tm 6.186486 0 Td 52.027027 Tz (C. ) Tj 0.756757 0 Td 88.288288 Tz (A ) Tj 0.662162 0 Td 47.297297 Tz (solution ) Tj 2.421622 0 Td 56.756757 Tz (of ) Tj 0.756757 0 Td 54.354354 Tz (p-hydroxybenzaldehyde ) Tj 7 0 Td 40.990991 Tz (\(1 ) Tj 0.737838 0 Td 44.932432 Tz (eq.\) ) Tj 1.22973 0 Td 45.720721 Tz (in ) Tj 0.662162 0 Td 75.675676 Tz (THF ) Tj 1.494595 0 Td 54.391892 Tz (with ) Tj 51.428571 0 0 51.428571 0 1583.896806 Tm 6.358333 0 Td 78.858025 Tz (TEA ) Tj 1.555556 0 Td 43.75 Tz (\(1 ) Tj 0.738889 0 Td 45.37037 Tz (eq.\) ) Tj 1.263889 0 Td 60.493827 Tz (was ) Tj 1.225 0 Td 58.333333 Tz (added ) Tj 1.886111 0 Td 55.497685 Tz (dropwise ) Tj 2.780556 0 Td 46.990741 Tz (to ) Tj 0.719444 0 Td 48.611111 Tz (the ) Tj 1.030556 0 Td 48.206019 Tz (reaction ) Tj 2.469444 0 Td 46.018519 Tz (flask ) Tj 1.477778 0 Td 59.41358 Tz (and ) Tj 1.225 0 Td 60.493827 Tz (was ) Tj 51.428571 0 0 51.428571 0 1540.570726 Tm 6.377778 0 Td 43.981481 Tz (stirred ) Tj 1.983333 0 Td 49.691358 Tz (for ) Tj 0.991667 0 Td 58.333333 Tz (an ) Tj 0.855556 0 Td 47.962963 Tz (additional ) Tj 3.052778 0 Td 63.194444 Tz (40 ) Tj 0.933333 0 Td 53.240741 Tz (minutes ) Tj 2.391667 0 Td 46.990741 Tz (at ) Tj 0.7 0 Td 59.953704 Tz (0C. ) Tj 1.613889 0 Td 57.685185 Tz (Water ) Tj 1.847222 0 Td 45.37037 Tz (\(1 ) Tj 0.758333 0 Td 46.990741 Tz (eq.\) ) Tj 1.263889 0 Td 60.493827 Tz (and ) Tj 51.428571 0 0 51.428571 0 1499.578811 Tm 6.358333 0 Td 78.858025 Tz (TEA ) Tj 1.652778 0 Td 43.75 Tz (\(1 ) Tj 0.816667 0 Td 45.37037 Tz (eq.\) ) Tj 1.341667 0 Td 58.333333 Tz (were ) Tj 1.613889 0 Td 58.333333 Tz (added ) Tj 1.963889 0 Td 46.990741 Tz (to ) Tj 0.797222 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 48.206019 Tz (reaction ) Tj 2.586111 0 Td 53.240741 Tz (mixture ) Tj 2.45 0 Td 58.333333 Tz (which ) Tj 2.002778 0 Td 61.574074 Tz (was ) Tj 40 0 0 40 0 1465 Tm 8.175 0 Td 70.238095 Tz (allowed ) Tj 3.25 0 Td 60.416667 Tz (to ) Tj 1.075 0 Td 50 Tz (stir ) Tj 1.475 0 Td 62.5 Tz (for ) Tj 1.4 0 Td 81.25 Tz (60 ) Tj 1.275 0 Td 69.642857 Tz (minutes ) Tj 3.25 0 Td 58.333333 Tz (at ) Tj 1 0 Td 82.291667 Tz (0C. ) Tj 2.275 0 Td 83.333333 Tz (The ) Tj 1.8 0 Td 64.583333 Tz (contents ) Tj 3.425 0 Td 75 Tz (of ) Tj 1.1 0 Td 63.888889 Tz (the ) Tj 40 0 0 40 0 1423 Tm 8.175 0 Td 62.5 Tz (reaction ) Tj 3.25 0 Td 60 Tz (flask ) Tj 2.05 0 Td 75 Tz (were ) Tj 2.05 0 Td 65.625 Tz (then ) Tj 1.875 0 Td 79.166667 Tz (vacuum ) Tj 3.15 0 Td 55.208333 Tz (filtered ) Tj 2.875 0 Td 76.388889 Tz (and ) Tj 1.65 0 Td 63.333333 Tz (dried ) Tj 2.15 0 Td 56.25 Tz (in ) Tj 0.975 0 Td 66.666667 Tz (vacuo. ) Tj 40 0 0 40 0 1382 Tm 8.175 0 Td 67.5 Tz (After ) Tj 2.2 0 Td 75 Tz (an ) Tj 1.15 0 Td 62.5 Tz (extraction ) Tj 4.025 0 Td 68.75 Tz (with ) Tj 1.925 0 Td 68.666667 Tz (chloroform/methanol/water ) Tj 10.6 0 Td 58.928571 Tz (1:1.5:1 ) Tj 51.428571 0 0 51.428571 0 1335.576355 Tm 6.377778 0 Td 44.155093 Tz (\(v/v/v\), ) Tj 2.430556 0 Td 48.611111 Tz (the ) Tj 1.147222 0 Td 51.147343 Tz (\(14:0\)-p-phosphodiester ) Tj 7.291667 0 Td 62.654321 Tz (was ) Tj 1.4 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 45.37037 Tz (in ) Tj 0.836111 0 Td 73.45679 Tz (40% ) Tj 51.428571 0 0 51.428571 0 1293.565841 Tm 6.358333 0 Td 47.962963 Tz (ethyl ) Tj 1.827778 0 Td 50.694444 Tz (acetate/hexane ) Tj 4.608333 0 Td 59.41358 Tz (and ) Tj 1.419444 0 Td 50.673401 Tz (centrifuged ) Tj 3.713889 0 Td 47.530864 Tz (for ) Tj 1.205556 0 Td 61.574074 Tz (7 ) Tj 0.758333 0 Td 50.636574 Tz (minutes. ) Tj 2.8 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 1250.713574 Tm 6.377778 0 Td 50.673401 Tz (Supernatant ) Tj 3.597222 0 Td 61.574074 Tz (was ) Tj 1.380556 0 Td 54.282407 Tz (decanted ) Tj 2.838889 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 50.771605 Tz (the ) Tj 1.205556 0 Td 48.971193 Tz (insoluble ) Tj 2.916667 0 Td 46.8107 Tz (fractions ) Tj 2.819444 0 Td 58.333333 Tz (were ) Tj 40 0 0 40 0 1216 Tm 8.175 0 Td 72.222222 Tz (combined. ) Tj 51.428571 0 0 51.428571 0 1172.387909 Tm 7.097222 0 Td 62.654321 Tz (The ) Tj 1.341667 0 Td 44.722222 Tz (relatively ) Tj 2.877778 0 Td 54.282407 Tz (pure ) Tj 1.516667 0 Td 51.006441 Tz (\(14:0\)-p-phosphodiester ) Tj 7.213889 0 Td 43.75 Tz (\(1 ) Tj 0.777778 0 Td 43.425926 Tz (eq.\), ) Tj 1.536111 0 Td 81.018519 Tz (DCC ) Tj 51.428571 0 0 51.428571 0 1127.081556 Tm 6.377778 0 Td 46.990741 Tz (\(2.2 ) Tj 1.341667 0 Td 61.574074 Tz (eq\) ) Tj 1.302778 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 87.5 Tz (DMAP ) Tj 2.313889 0 Td 43.75 Tz (\(0.1 ) Tj 1.322222 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 58.333333 Tz (were ) Tj 1.594444 0 Td 49.907407 Tz (dried ) Tj 1.711111 0 Td 53.472222 Tz (over ) Tj 1.458333 0 Td 56.565657 Tz (phosphorous ) Tj 51.428571 0 0 51.428571 0 1086.961905 Tm 6.358333 0 Td 53.292181 Tz (pentoxide ) Tj 2.994444 0 Td 49.691358 Tz (for ) Tj 1.05 0 Td 56.712963 Tz (12 ) Tj 0.797222 0 Td 49.151235 Tz (hours. ) Tj 1.905556 0 Td 56.442901 Tz (Cyanoethanol ) Tj 4.2 0 Td 43.75 Tz (\(1.1 ) Tj 1.263889 0 Td 47.800926 Tz (eq.\) ) Tj 1.283333 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 51.131687 Tz (dissolved ) Tj 51.428571 0 0 51.428571 0 1042.654501 Tm 6.358333 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 54.228395 Tz (dichloromethane ) Tj 5.036111 0 Td 59.41358 Tz (and ) Tj 1.244444 0 Td 49.259259 Tz (dried ) Tj 1.633333 0 Td 53.472222 Tz (with ) Tj 1.497222 0 Td 61.213992 Tz (magnesium ) Tj 3.5 0 Td 45.833333 Tz (sulfate ) Tj 2.1 0 Td 47.530864 Tz (for ) Tj 1.069444 0 Td 53.472222 Tz (12 ) Tj 51.428571 0 0 51.428571 0 1003.44484 Tm 6.338889 0 Td 49.691358 Tz (hours. ) Tj 1.983333 0 Td 62.654321 Tz (The ) Tj 1.302778 0 Td 51.147343 Tz (\(14:0\)-p-phosphodiester ) Tj 7.213889 0 Td 60.493827 Tz (was ) Tj 1.302778 0 Td 50.411523 Tz (dissolved ) Tj 2.877778 0 Td 46.990741 Tz (in ) Tj 0.758333 0 Td 56.712963 Tz (dichlo ) Tj 40 0 0 40 0 966 Tm 8.175 0 Td 73.148148 Tz (romethane ) Tj 4.2 0 Td 75 Tz (and ) Tj 1.625 0 Td 105.555556 Tz (DCC ) Tj 2.15 0 Td 75 Tz (and ) Tj 1.625 0 Td 111.458333 Tz (DMAP ) Tj 2.925 0 Td 76.041667 Tz (were ) Tj 2.075 0 Td 74.166667 Tz (added ) Tj 2.5 0 Td 56.25 Tz (to ) Tj 0.975 0 Td 62.5 Tz (the ) Tj 1.4 0 Td 63.020833 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 919.180879 Tm 6.358333 0 Td 42.669753 Tz (flask. ) Tj 1.788889 0 Td 62.654321 Tz (The ) Tj 1.361111 0 Td 46.666667 Tz (flask ) Tj 1.633333 0 Td 61.574074 Tz (was ) Tj 1.361111 0 Td 50.231481 Tz (sealed ) Tj 2.041667 0 Td 53.472222 Tz (with ) Tj 1.536111 0 Td 51.851852 Tz (a ) Tj 0.583333 0 Td 57.253086 Tz (septum ) Tj 2.313889 0 Td 59.41358 Tz (and ) Tj 1.283333 0 Td 56.712963 Tz (purged ) Tj 2.294444 0 Td 54.282407 Tz (with ) Tj 51.428571 0 0 51.428571 0 878.976553 Tm 6.358333 0 Td 50.231481 Tz (nitrogen ) Tj 2.547222 0 Td 46.018519 Tz (after ) Tj 1.497222 0 Td 55.092593 Tz (adding ) Tj 2.1 0 Td 50.771605 Tz (the ) Tj 1.05 0 Td 53.472222 Tz (cyanoethanol ) Tj 4.005556 0 Td 46.450617 Tz (Solution. ) Tj 2.625 0 Td 64.814815 Tz (The ) Tj 1.302778 0 Td 49.421296 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 835.476433 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.361111 0 Td 44.444444 Tz (stirred ) Tj 2.080556 0 Td 48.611111 Tz (for ) Tj 1.05 0 Td 59.953704 Tz (48 ) Tj 0.952778 0 Td 53.148148 Tz (hours ) Tj 1.808333 0 Td 46.990741 Tz (at ) Tj 0.777778 0 Td 62.384259 Tz (room ) Tj 1.730556 0 Td 50.231481 Tz (temperature. ) Tj 3.869444 0 Td 57.685185 Tz (Water ) Tj 1.944444 0 Td 46.990741 Tz (\(5 ) Tj 0.797222 0 Td 46.180556 Tz (eq.\) ) Tj 40 0 0 40 0 800 Tm 8.15 0 Td 80.555556 Tz (was ) Tj 1.725 0 Td 75 Tz (added ) Tj 2.5 0 Td 76.388889 Tz (and ) Tj 1.625 0 Td 63.888889 Tz (the ) Tj 1.4 0 Td 62.5 Tz (reaction ) Tj 3.325 0 Td 68.452381 Tz (mixture ) Tj 3.125 0 Td 79.166667 Tz (was ) Tj 1.7 0 Td 57.142857 Tz (stirred ) Tj 2.65 0 Td 63.888889 Tz (for ) Tj 1.35 0 Td 72.916667 Tz (an ) Tj 1.125 0 Td 81.25 Tz (addi ) Tj 40 0 0 40 0 758 Tm 8.15 0 Td 59.722222 Tz (tional ) Tj 2.6 0 Td 79.166667 Tz (24 ) Tj 1.375 0 Td 63.194444 Tz (hours. ) Tj 2.75 0 Td 80.555556 Tz (The ) Tj 1.875 0 Td 65.104167 Tz (contents ) Tj 3.575 0 Td 75 Tz (of ) Tj 1.225 0 Td 63.888889 Tz (the ) Tj 1.6 0 Td 62.5 Tz (reaction ) Tj 3.475 0 Td 59.166667 Tz (flask ) Tj 2.225 0 Td 75 Tz (were ) Tj 40 0 0 40 0 717 Tm 8.175 0 Td 81.25 Tz (vacuum ) Tj 3.2 0 Td 55.208333 Tz (filtered ) Tj 2.85 0 Td 77.777778 Tz (and ) Tj 1.65 0 Td 64.166667 Tz (dried ) Tj 2.15 0 Td 60.416667 Tz (in ) Tj 0.975 0 Td 67.361111 Tz (vacuo. ) Tj 2.65 0 Td 66.666667 Tz (After ) Tj 2.225 0 Td 70.833333 Tz (an ) Tj 1.125 0 Td 61.666667 Tz (extraction ) Tj 4 0 Td 68.75 Tz (with ) Tj 51.428571 0 0 51.428571 0 670.390156 Tm 6.358333 0 Td 51.851852 Tz (chloroform/brine ) Tj 5.191667 0 Td 44.290123 Tz (1:1 ) Tj 1.069444 0 Td 43.209877 Tz (\(v/v\), ) Tj 1.730556 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 54.62963 Tz (coupled ) Tj 2.45 0 Td 53.703704 Tz (product ) Tj 2.411111 0 Td 61.574074 Tz (was ) Tj 1.263889 0 Td 48.206019 Tz (purified ) Tj 51.428571 0 0 51.428571 0 630.369077 Tm 6.338889 0 Td 61.574074 Tz (by ) Tj 1.011111 0 Td 45.37037 Tz (flash ) Tj 1.652778 0 Td 59.953704 Tz (column ) Tj 2.45 0 Td 56.25 Tz (chromatography ) Tj 4.997222 0 Td 53.148148 Tz (using ) Tj 1.847222 0 Td 73.45679 Tz (40% ) Tj 1.575 0 Td 48.611111 Tz (ethyl ) Tj 1.730556 0 Td 46.585648 Tz (acetate/ ) Tj 51.428571 0 0 51.428571 0 586.686061 Tm 6.338889 0 Td 57.79321 Tz (hexane ) Tj 2.236111 0 Td 51.041667 Tz (then ) Tj 1.419444 0 Td 51.851852 Tz (switching ) Tj 2.955556 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 73.45679 Tz (80% ) Tj 1.477778 0 Td 47.962963 Tz (ethyl ) Tj 1.594444 0 Td 51.157407 Tz (acetate/hexane ) Tj 4.433333 0 Td 48.611111 Tz (for ) Tj 1.011111 0 Td 51.851852 Tz (a ) Tj 0.486111 0 Td 47.800926 Tz (step ) Tj 51.428571 0 0 51.428571 0 546.169492 Tm 6.358333 0 Td 49.826389 Tz (gradient ) Tj 2.547222 0 Td 45.775463 Tz (elution. ) Tj 51.428571 0 0 51.428571 0 507.763906 Tm 7.097222 0 Td 51.851852 Tz (After ) Tj 1.788889 0 Td 45.121083 Tz (purification, ) Tj 3.811111 0 Td 48.611111 Tz (the ) Tj 1.108333 0 Td 50.771605 Tz (protected ) Tj 3.013889 0 Td 51.006441 Tz (\(14:0\)-p-phosphodiester ) Tj 51.428571 0 0 51.428571 0 464.093671 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.4 0 Td 41.481481 Tz (split ) Tj 1.477778 0 Td 46.180556 Tz (into ) Tj 1.361111 0 Td 59.41358 Tz (two ) Tj 1.341667 0 Td 52.777778 Tz (roughly ) Tj 2.45 0 Td 53.148148 Tz (equal ) Tj 1.808333 0 Td 47.530864 Tz (portions. ) Tj 2.819444 0 Td 63.734568 Tz (The ) Tj 1.380556 0 Td 37.592593 Tz (first ) Tj 1.322222 0 Td 51.388889 Tz (portion ) Tj 51.428571 0 0 51.428571 0 419.428571 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 55.902778 Tz (used ) Tj 1.536111 0 Td 46.450617 Tz (for ) Tj 1.011111 0 Td 46.450617 Tz (direct ) Tj 1.866667 0 Td 46.450617 Tz (fluorination ) Tj 3.597222 0 Td 58.738426 Tz (\(Example ) Tj 3.013889 0 Td 50.231481 Tz (5\) ) Tj 0.758333 0 Td 59.41358 Tz (and ) Tj 1.263889 0 Td 50.771605 Tz (the ) Tj 1.069444 0 Td 57.253086 Tz (second ) Tj 51.428571 0 0 51.428571 0 377.410037 Tm 6.358333 0 Td 49.537037 Tz (portion ) Tj 2.275 0 Td 61.574074 Tz (was ) Tj 1.302778 0 Td 55.902778 Tz (used ) Tj 1.536111 0 Td 47.530864 Tz (for ) Tj 1.030556 0 Td 50.411523 Tz (reduction ) Tj 2.936111 0 Td 52.662037 Tz (followed ) Tj 2.722222 0 Td 59.953704 Tz (by ) Tj 0.913889 0 Td 45.37037 Tz (fluorination. ) Tj 3.791667 0 Td 55.092593 Tz (For ) Tj 51.428571 0 0 51.428571 0 340.346062 Tm 6.358333 0 Td 48.611111 Tz (reduction, ) Tj 3.091667 0 Td 50.771605 Tz (the ) Tj 1.069444 0 Td 50.411523 Tz (protected ) Tj 2.897222 0 Td 51.147343 Tz (\(14:0\)-p-phosphodiester ) Tj 7.233333 0 Td 40.509259 Tz (\(1 ) Tj 0.758333 0 Td 46.180556 Tz (eq.\) ) Tj 1.322222 0 Td 60.493827 Tz (was ) Tj 51.428571 0 0 51.428571 0 294.714286 Tm 6.358333 0 Td 50.771605 Tz (dissolved ) Tj 2.936111 0 Td 46.990741 Tz (in ) Tj 0.758333 0 Td 59.773663 Tz (THF/water ) Tj 3.363889 0 Td 47.962963 Tz (3:0.1 ) Tj 1.730556 0 Td 46.666667 Tz (\(v/v\) ) Tj 1.613889 0 Td 47.800926 Tz (respectively ) Tj 3.655556 0 Td 60.493827 Tz (and ) Tj 1.263889 0 Td 59.953704 Tz (sodium ) Tj 51.428571 0 0 51.428571 0 253.576819 Tm 6.338889 0 Td 53.914141 Tz (borohydride ) Tj 3.888889 0 Td 45.37037 Tz (\(1 ) Tj 0.933333 0 Td 45.37037 Tz (eq.\) ) Tj 1.438889 0 Td 60.493827 Tz (was ) Tj 1.419444 0 Td 57.685185 Tz (added ) Tj 2.061111 0 Td 45.37037 Tz (to ) Tj 0.894444 0 Td 49.691358 Tz (the ) Tj 1.225 0 Td 47.800926 Tz (reaction ) Tj 2.625 0 Td 42.669753 Tz (flask. ) Tj 1.866667 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 211.882353 Tm 6.358333 0 Td 48.611111 Tz (reaction ) Tj 2.683333 0 Td 53.240741 Tz (mixture ) Tj 2.547222 0 Td 60.493827 Tz (was ) Tj 1.438889 0 Td 43.518519 Tz (stirred ) Tj 2.138889 0 Td 44.074074 Tz (until ) Tj 1.633333 0 Td 38.888889 Tz (all ) Tj 1.030556 0 Td 58.873457 Tz (sodium ) Tj 2.430556 0 Td 54.208754 Tz (borohydride ) Tj 51.428571 0 0 51.428571 0 169.106599 Tm 6.358333 0 Td 50.771605 Tz (dissolved ) Tj 3.033333 0 Td 54.012346 Tz (\(~2 ) Tj 1.283333 0 Td 51.851852 Tz (minutes\) ) Tj 2.761111 0 Td 59.41358 Tz (and ) Tj 1.341667 0 Td 52.932099 Tz (continued ) Tj 3.111111 0 Td 44.155093 Tz (stirring ) Tj 2.372222 0 Td 48.611111 Tz (for ) Tj 1.108333 0 Td 56.712963 Tz (an ) Tj 0.933333 0 Td 63.194444 Tz (addi ) Tj 30 0 0 30 0 2547 Tm 41.666667 0 Td 75 Tz (10 ) Tj 30 0 0 30 0 2339 Tm 41.666667 0 Td 72.222222 Tz (15 ) Tj 30 0 0 30 0 1923 Tm 41.6 0 Td 77.777778 Tz (25 ) Tj 30 0 0 30 0 1716 Tm 41.6 0 Td 80.555556 Tz (30 ) Tj 30 0 0 30 0 1507 Tm 41.6 0 Td 77.777778 Tz (35 ) Tj 30 0 0 30 0 1299 Tm 41.566667 0 Td 83.333333 Tz (40 ) Tj 30 0 0 30 0 1091 Tm 41.566667 0 Td 80.555556 Tz (45 ) Tj 30 0 0 30 0 883 Tm 41.6 0 Td 80.555556 Tz (50 ) Tj 30 0 0 30 0 675 Tm 41.6 0 Td 77.777778 Tz (55 ) Tj 30 0 0 30 0 467 Tm 41.633333 0 Td 77.777778 Tz (60 ) Tj 30 0 0 30 0 259 Tm 41.633333 0 Td 75 Tz (65 ) Tj 51.428571 0 0 51.428571 0 2969 Tm 33.6 0 Td 74.537037 Tz (14 ) Tj 51.428571 0 0 51.428571 0 2913.599746 Tm 25.277778 0 Td 45.910494 Tz (tional ) Tj 1.963889 0 Td 53.472222 Tz (10 ) Tj 0.875 0 Td 50.636574 Tz (minutes. ) Tj 2.663889 0 Td 57.685185 Tz (Water ) Tj 1.905556 0 Td 46.990741 Tz (\(3 ) Tj 0.777778 0 Td 47.800926 Tz (eq.\) ) Tj 1.361111 0 Td 60.493827 Tz (was ) Tj 1.302778 0 Td 57.685185 Tz (added ) Tj 1.925 0 Td 59.41358 Tz (and ) Tj 1.263889 0 Td 50.771605 Tz (the ) Tj 1.127778 0 Td 48.611111 Tz (reaction ) Tj 40 0 0 40 0 2878 Tm 32.575 0 Td 68.452381 Tz (mixture ) Tj 3.2 0 Td 79.166667 Tz (was ) Tj 1.8 0 Td 57.142857 Tz (stirred ) Tj 2.725 0 Td 72.916667 Tz (an ) Tj 1.225 0 Td 62.083333 Tz (additional ) Tj 4.2 0 Td 70.833333 Tz (10 ) Tj 1.225 0 Td 64.583333 Tz (minutes. ) Tj 3.45 0 Td 65.277778 Tz (All ) Tj 1.55 0 Td 63.020833 Tz (solvents ) Tj 51.428571 0 0 51.428571 0 2828.702703 Tm 25.277778 0 Td 59.953704 Tz (were ) Tj 1.652778 0 Td 59.259259 Tz (removed ) Tj 2.702778 0 Td 43.75 Tz (in ) Tj 0.758333 0 Td 55.740741 Tz (vacuo ) Tj 1.866667 0 Td 58.333333 Tz (and ) Tj 1.263889 0 Td 47.530864 Tz (the ) Tj 1.069444 0 Td 51.041667 Tz (reduced, ) Tj 2.644444 0 Td 50.411523 Tz (protected ) Tj 2.897222 0 Td 48.611111 Tz (\(14:0\)-p- ) Tj 51.428571 0 0 51.428571 0 2787.697561 Tm 25.297222 0 Td 52.777778 Tz (phosphodiester ) Tj 4.647222 0 Td 61.574074 Tz (was ) Tj 1.341667 0 Td 47.800926 Tz (purified ) Tj 2.527778 0 Td 59.953704 Tz (by ) Tj 0.991667 0 Td 44.722222 Tz (flash ) Tj 1.633333 0 Td 59.41358 Tz (column ) Tj 2.411111 0 Td 59.217172 Tz (chromatogra ) Tj 51.428571 0 0 51.428571 0 2742.551122 Tm 25.297222 0 Td 59.41358 Tz (phy ) Tj 1.322222 0 Td 52.5 Tz (using ) Tj 1.788889 0 Td 72.376543 Tz (40% ) Tj 1.555556 0 Td 47.962963 Tz (ethyl ) Tj 1.672222 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.491667 0 Td 51.041667 Tz (then ) Tj 1.458333 0 Td 52.572016 Tz (switching ) Tj 3.072222 0 Td 43.75 Tz (to ) Tj 0.758333 0 Td 74.537037 Tz (80% ) Tj 51.428571 0 0 51.428571 0 2698.138462 Tm 25.297222 0 Td 47.314815 Tz (ethyl ) Tj 1.633333 0 Td 51.157407 Tz (acetate/hexane ) Tj 4.472222 0 Td 48.611111 Tz (for ) Tj 1.011111 0 Td 55.092593 Tz (a ) Tj 0.525 0 Td 47.800926 Tz (step ) Tj 1.341667 0 Td 49.826389 Tz (gradient ) Tj 2.547222 0 Td 45.37037 Tz (elution. ) Tj 51.428571 0 0 51.428571 0 2656.800259 Tm 26.016667 0 Td 63.734568 Tz (The ) Tj 1.497222 0 Td 51.041667 Tz (reduced, ) Tj 2.8 0 Td 50.05144 Tz (protected ) Tj 3.052778 0 Td 51.006441 Tz (\(14:0\)-p-phosphodiester ) Tj 7.35 0 Td 43.75 Tz (\(1 ) Tj 0.913889 0 Td 46.990741 Tz (eq.\) ) Tj 51.428571 0 0 51.428571 0 2611.352287 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 49.259259 Tz (dried ) Tj 1.652778 0 Td 54.282407 Tz (over ) Tj 1.458333 0 Td 55.976431 Tz (phosphorous ) Tj 3.888889 0 Td 53.652263 Tz (pentoxide ) Tj 3.091667 0 Td 46.450617 Tz (for ) Tj 1.088889 0 Td 53.472222 Tz (12 ) Tj 0.836111 0 Td 53.148148 Tz (hours ) Tj 1.788889 0 Td 59.41358 Tz (and ) Tj 1.244444 0 Td 60.493827 Tz (dis ) Tj 40 0 0 40 0 2572 Tm 32.55 0 Td 66.666667 Tz (solved ) Tj 2.6 0 Td 68.287037 Tz (indichloromethane. ) Tj 7.55 0 Td 81.944444 Tz (The ) Tj 1.675 0 Td 61.979167 Tz (reaction ) Tj 3.175 0 Td 59.166667 Tz (flask ) Tj 1.975 0 Td 77.777778 Tz (was ) Tj 1.6 0 Td 64.583333 Tz (sealed ) Tj 2.475 0 Td 77.777778 Tz (and ) Tj 51.428571 0 0 51.428571 0 2522.80198 Tm 25.297222 0 Td 52.932099 Tz (placed ) Tj 2.080556 0 Td 45.37037 Tz (in ) Tj 0.7 0 Td 58.333333 Tz (an ) Tj 0.894444 0 Td 45.37037 Tz (ice ) Tj 0.991667 0 Td 51.851852 Tz (bath ) Tj 1.438889 0 Td 45.37037 Tz (to ) Tj 0.758333 0 Td 52.256944 Tz (maintain ) Tj 2.702778 0 Td 60.763889 Tz (0C. ) Tj 1.672222 0 Td 49.96142 Tz (temperature. ) Tj 3.830556 0 Td 66.435185 Tz (Deoxof ) Tj 51.428571 0 0 51.428571 0 2478.551331 Tm 25.297222 0 Td 50.231481 Tz (luor ) Tj 1.4 0 Td 46.990741 Tz (\(2 ) Tj 0.816667 0 Td 45.37037 Tz (eq.\) ) Tj 1.322222 0 Td 43.75 Tz (in ) Tj 0.797222 0 Td 54.228395 Tz (dichloromethane ) Tj 5.094444 0 Td 61.574074 Tz (was ) Tj 1.361111 0 Td 52.391975 Tz (slowly ) Tj 2.119444 0 Td 58.333333 Tz (added ) Tj 1.963889 0 Td 55.092593 Tz (\(~2 ) Tj 1.244444 0 Td 74.537037 Tz (min ) Tj 51.428571 0 0 51.428571 0 2433 Tm 25.277778 0 Td 44.290123 Tz (utes\). ) Tj 1.711111 0 Td 64.814815 Tz (The ) Tj 1.283333 0 Td 47.530864 Tz (ice ) Tj 0.991667 0 Td 51.041667 Tz (bath ) Tj 1.380556 0 Td 61.574074 Tz (was ) Tj 1.302778 0 Td 59.259259 Tz (removed ) Tj 2.605556 0 Td 59.41358 Tz (and ) Tj 1.186111 0 Td 49.691358 Tz (the ) Tj 1.05 0 Td 48.611111 Tz (reaction ) Tj 2.488889 0 Td 53.703704 Tz (mixture ) Tj 2.372222 0 Td 61.574074 Tz (was ) Tj 40 0 0 40 0 2397 Tm 32.55 0 Td 56.547619 Tz (stirred ) Tj 2.775 0 Td 61.111111 Tz (for ) Tj 1.55 0 Td 68.75 Tz (12 ) Tj 1.225 0 Td 63.194444 Tz (hours. ) Tj 2.675 0 Td 91.666667 Tz (An ) Tj 1.475 0 Td 62.083333 Tz (extraction ) Tj 4.125 0 Td 68.75 Tz (with ) Tj 2.075 0 Td 68.229167 Tz (dichloromethane/ ) Tj 51.428571 0 0 51.428571 0 2346.625815 Tm 25.316667 0 Td 48.251029 Tz (saturated ) Tj 2.936111 0 Td 58.873457 Tz (sodium ) Tj 2.469444 0 Td 51.557239 Tz (bicarbonate ) Tj 3.733333 0 Td 48.611111 Tz (solution ) Tj 2.761111 0 Td 43.209877 Tz (1:1 ) Tj 1.186111 0 Td 46.666667 Tz (\(v/v\) ) Tj 1.75 0 Td 61.574074 Tz (was ) Tj 1.438889 0 Td 64.814815 Tz (per ) Tj 51.428571 0 0 51.428571 0 2304.496644 Tm 25.297222 0 Td 58.333333 Tz (formed ) Tj 2.255556 0 Td 60.493827 Tz (and ) Tj 1.263889 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 51.388889 Tz (organic ) Tj 2.372222 0 Td 48.611111 Tz (layer ) Tj 1.613889 0 Td 61.574074 Tz (was ) Tj 1.302778 0 Td 46.342593 Tz (collected. ) Tj 51.428571 0 0 51.428571 0 2265.517241 Tm 26.016667 0 Td 52.5 Tz (After ) Tj 1.711111 0 Td 52.932099 Tz (drying ) Tj 2.080556 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 51.851852 Tz (vacuo, ) Tj 2.002778 0 Td 50.771605 Tz (the ) Tj 1.05 0 Td 50.771605 Tz (protected ) Tj 2.916667 0 Td 54.751462 Tz (\(14:0\)-p-monofluoro ) Tj 51.428571 0 0 51.428571 0 2224.697561 Tm 25.297222 0 Td 52.777778 Tz (phosphodiester ) Tj 4.647222 0 Td 61.574074 Tz (was ) Tj 1.341667 0 Td 47.800926 Tz (purified ) Tj 2.527778 0 Td 59.953704 Tz (by ) Tj 0.991667 0 Td 44.722222 Tz (flash ) Tj 1.633333 0 Td 59.41358 Tz (column ) Tj 2.411111 0 Td 59.217172 Tz (chromatogra ) Tj 51.428571 0 0 51.428571 0 2180.551122 Tm 25.297222 0 Td 59.41358 Tz (phy ) Tj 1.322222 0 Td 52.5 Tz (using ) Tj 1.788889 0 Td 72.376543 Tz (40% ) Tj 1.555556 0 Td 47.962963 Tz (ethyl ) Tj 1.672222 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.491667 0 Td 51.041667 Tz (then ) Tj 1.458333 0 Td 52.572016 Tz (switching ) Tj 3.072222 0 Td 43.75 Tz (to ) Tj 0.758333 0 Td 74.537037 Tz (80% ) Tj 51.428571 0 0 51.428571 0 2139.743468 Tm 25.297222 0 Td 47.314815 Tz (ethyl ) Tj 1.555556 0 Td 51.388889 Tz (acetate/hexane ) Tj 4.433333 0 Td 48.611111 Tz (for ) Tj 0.972222 0 Td 55.092593 Tz (a ) Tj 0.486111 0 Td 46.990741 Tz (step ) Tj 1.283333 0 Td 49.826389 Tz (gradient ) Tj 2.508333 0 Td 45.37037 Tz (elution. ) Tj 2.372222 0 Td 56.17284 Tz (For ) Tj 1.127778 0 Td 56.712963 Tz (deprotec ) Tj 51.428571 0 0 51.428571 0 2100.642599 Tm 25.277778 0 Td 44.074074 Tz (tion, ) Tj 1.652778 0 Td 49.691358 Tz (the ) Tj 1.186111 0 Td 50.771605 Tz (protected ) Tj 3.072222 0 Td 52.328431 Tz (\(14:0\)-p-monofluoro-phosphodiester ) Tj 10.966667 0 Td 43.75 Tz (\(1 ) Tj 51.428571 0 0 51.428571 0 2057.777917 Tm 25.297222 0 Td 46.180556 Tz (eq.\) ) Tj 1.361111 0 Td 60.493827 Tz (was ) Tj 1.361111 0 Td 50.411523 Tz (dissolved ) Tj 2.955556 0 Td 45.37037 Tz (in ) Tj 0.777778 0 Td 47.890947 Tz (pyridine. ) Tj 2.858333 0 Td 57.086895 Tz (N-propylamine ) Tj 4.686111 0 Td 55.092593 Tz (\(100 ) Tj 1.555556 0 Td 46.180556 Tz (eq.\) ) Tj 1.361111 0 Td 46.990741 Tz (in ) Tj 51.428571 0 0 51.428571 0 2012.206273 Tm 25.297222 0 Td 50.636574 Tz (pyridine ) Tj 2.566667 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 57.685185 Tz (added ) Tj 1.886111 0 Td 43.75 Tz (to ) Tj 0.7 0 Td 48.611111 Tz (the ) Tj 1.011111 0 Td 48.611111 Tz (reaction ) Tj 2.469444 0 Td 46.018519 Tz (flask ) Tj 1.477778 0 Td 58.333333 Tz (and ) Tj 1.205556 0 Td 49.691358 Tz (the ) Tj 0.991667 0 Td 48.611111 Tz (clear ) Tj 1.575 0 Td 49.016204 Tz (solution ) Tj 51.428571 0 0 51.428571 0 1970.848447 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 43.981481 Tz (stirred ) Tj 2.041667 0 Td 47.530864 Tz (for ) Tj 1.088889 0 Td 55.092593 Tz (10 ) Tj 0.836111 0 Td 54.166667 Tz (minutes ) Tj 2.469444 0 Td 43.75 Tz (at ) Tj 0.719444 0 Td 62.384259 Tz (room ) Tj 1.711111 0 Td 50.231481 Tz (temperature. ) Tj 3.811111 0 Td 49.691358 Tz (All ) Tj 1.108333 0 Td 49.016204 Tz (solvents ) Tj 51.428571 0 0 51.428571 0 1931.632803 Tm 25.277778 0 Td 59.953704 Tz (were ) Tj 1.633333 0 Td 59.722222 Tz (removed ) Tj 2.702778 0 Td 45.37037 Tz (in ) Tj 0.777778 0 Td 55.740741 Tz (vacuo ) Tj 1.866667 0 Td 46.990741 Tz (to ) Tj 0.758333 0 Td 49.259259 Tz (yield ) Tj 1.633333 0 Td 50.771605 Tz (the ) Tj 1.147222 0 Td 59.751157 Tz (n-propylammonium ) Tj 5.95 0 Td 42.939815 Tz (salt ) Tj 51.428571 0 0 51.428571 0 1891.34296 Tm 25.297222 0 Td 58.333333 Tz (of ) Tj 0.972222 0 Td 48.611111 Tz (the ) Tj 1.225 0 Td 51.388889 Tz (\(14:0\)-p-monofluoro-phosphodiester. ) Tj 11.141667 0 Td 71.296296 Tz (An ) Tj 1.205556 0 Td 48.935185 Tz (extraction ) Tj 51.428571 0 0 51.428571 0 1845.598226 Tm 25.277778 0 Td 54.282407 Tz (with ) Tj 1.691667 0 Td 52.759259 Tz (chloroform/methanol/brine ) Tj 8.361111 0 Td 44.907407 Tz (1:1.5:1 ) Tj 2.391667 0 Td 47.222222 Tz (\(v/v/v\) ) Tj 2.352778 0 Td 61.574074 Tz (was ) Tj 1.536111 0 Td 63.734568 Tz (per ) Tj 51.428571 0 0 51.428571 0 1806.971429 Tm 25.297222 0 Td 58.333333 Tz (formed ) Tj 2.255556 0 Td 45.37037 Tz (to ) Tj 0.7 0 Td 51.446759 Tz (generate ) Tj 2.625 0 Td 48.611111 Tz (the ) Tj 1.011111 0 Td 58.873457 Tz (sodium ) Tj 2.294444 0 Td 42.939815 Tz (salt ) Tj 1.147222 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 48.611111 Tz (the ) Tj 1.030556 0 Td 55.283224 Tz (\(14:0\)-p-monofluo ) Tj 51.428571 0 0 51.428571 0 1770 Tm 25.297222 0 Td 50.326797 Tz (rophosphodiester. ) Tj 51.428571 0 0 51.428571 0 1690.046358 Tm 32.472222 0 Td 61.574074 Tz (Example ) Tj 2.761111 0 Td 58.333333 Tz (7 ) Tj 51.428571 0 0 51.428571 0 1606 Tm 29.380556 0 Td 50.283751 Tz (\(12:0\)-p-difluorophosphodiester ) Tj 31.428571 0 0 31.428571 0 1450 Tm 57.177273 0 Td 111.363636 Tz (O ) Tj 171.428571 0 0 171.428571 0 1341.4 Tm 8.265833 0 Td 31.111111 Tz (gic-\( ) Tj 1.248333 0 Td 42.777778 Tz (\)----cloch ) Tj 31.428571 0 0 31.428571 0 1316 Tm 57.177273 0 Td 111.363636 Tz (OH ) Tj 51.428571 0 0 51.428571 0 1212.683995 Tm 26.036111 0 Td 56.565657 Tz (Phosphorous ) Tj 4.044444 0 Td 52.73569 Tz (oxychloride ) Tj 3.772222 0 Td 43.75 Tz (\(1 ) Tj 0.894444 0 Td 46.180556 Tz (eq.\) ) Tj 1.419444 0 Td 60.493827 Tz (was ) Tj 1.380556 0 Td 58.333333 Tz (added ) Tj 2.041667 0 Td 45.37037 Tz (to ) Tj 0.855556 0 Td 51.851852 Tz (a ) Tj 0.661111 0 Td 55.740741 Tz (round ) Tj 51.428571 0 0 51.428571 0 1168.327456 Tm 25.277778 0 Td 57.253086 Tz (bottom ) Tj 2.391667 0 Td 46.018519 Tz (flask ) Tj 1.633333 0 Td 58.333333 Tz (and ) Tj 1.341667 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 45.37037 Tz (in ) Tj 0.875 0 Td 49.907407 Tz (tetrahydrofuran ) Tj 4.783333 0 Td 56.17284 Tz (\(THF\). ) Tj 2.313889 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 1124.961963 Tm 25.297222 0 Td 57.037037 Tz (round ) Tj 1.847222 0 Td 56.712963 Tz (bottom ) Tj 2.197222 0 Td 46.666667 Tz (flask ) Tj 1.536111 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 51.851852 Tz (then ) Tj 1.4 0 Td 52.932099 Tz (placed ) Tj 2.061111 0 Td 45.37037 Tz (in ) Tj 0.680556 0 Td 59.953704 Tz (an ) Tj 0.875 0 Td 46.450617 Tz (ice ) Tj 0.952778 0 Td 52.662037 Tz (bath ) Tj 1.419444 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 53.06713 Tz (maintain ) Tj 51.428571 0 0 51.428571 0 1085.363196 Tm 25.297222 0 Td 51.851852 Tz (a ) Tj 0.447222 0 Td 59.953704 Tz (0C. ) Tj 1.594444 0 Td 50.501543 Tz (temperature. ) Tj 3.830556 0 Td 57.613169 Tz (Dodecanol ) Tj 3.247222 0 Td 45.37037 Tz (\(1 ) Tj 0.738889 0 Td 46.180556 Tz (eq.\) ) Tj 1.263889 0 Td 50.411523 Tz (dissolved ) Tj 2.877778 0 Td 43.75 Tz (in ) Tj 0.661111 0 Td 76.697531 Tz (THF ) Tj 1.536111 0 Td 53.472222 Tz (with ) Tj 51.428571 0 0 51.428571 0 1045.659341 Tm 25.277778 0 Td 50.106838 Tz (triethylamine ) Tj 4.063889 0 Td 62.222222 Tz (\(TEA\) ) Tj 2.041667 0 Td 43.75 Tz (\(1 ) Tj 0.758333 0 Td 46.180556 Tz (eq.\) ) Tj 1.283333 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 58.333333 Tz (added ) Tj 1.925 0 Td 55.092593 Tz (dropwise ) Tj 2.819444 0 Td 42.12963 Tz (to ) Tj 0.680556 0 Td 50.771605 Tz (the ) Tj 1.05 0 Td 67.24537 Tz (phos ) Tj 51.428571 0 0 51.428571 0 1003.848485 Tm 25.297222 0 Td 55.555556 Tz (phorous ) Tj 2.625 0 Td 56.388889 Tz (oxychloride/THF ) Tj 5.386111 0 Td 46.090535 Tz (solution. ) Tj 2.819444 0 Td 64.00463 Tz (Once ) Tj 1.847222 0 Td 39.969136 Tz (all ) Tj 1.011111 0 Td 59.953704 Tz (of ) Tj 0.933333 0 Td 49.691358 Tz (the ) Tj 1.205556 0 Td 68.055556 Tz (dode ) Tj 51.428571 0 0 51.428571 0 958 Tm 25.297222 0 Td 61.075499 Tz (canol/THF/TEA ) Tj 4.938889 0 Td 48.206019 Tz (solution ) Tj 2.469444 0 Td 61.574074 Tz (was ) Tj 1.263889 0 Td 58.333333 Tz (added ) Tj 1.905556 0 Td 58.333333 Tz (\(-20 ) Tj 1.536111 0 Td 49.691358 Tz (minutes\), ) Tj 2.858333 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 59.143519 Tz (reac ) Tj 40 0 0 40 0 925 Tm 32.5 0 Td 60.416667 Tz (tion ) Tj 1.725 0 Td 68.452381 Tz (mixture ) Tj 3.075 0 Td 79.166667 Tz (was ) Tj 1.675 0 Td 56.547619 Tz (stirred ) Tj 2.6 0 Td 61.111111 Tz (for ) Tj 1.275 0 Td 70.833333 Tz (an ) Tj 1.05 0 Td 62.916667 Tz (additional ) Tj 3.975 0 Td 81.25 Tz (40 ) Tj 1.175 0 Td 69.642857 Tz (minutes ) Tj 3.15 0 Td 56.25 Tz (at ) Tj 0.9 0 Td 77.083333 Tz (0C. ) Tj 51.428571 0 0 51.428571 0 879.215809 Tm 25.297222 0 Td 87.5 Tz (A ) Tj 0.797222 0 Td 48.206019 Tz (solution ) Tj 2.586111 0 Td 58.333333 Tz (of ) Tj 0.836111 0 Td 55.864198 Tz (p-hydroxybenzaldehyde ) Tj 7.291667 0 Td 45.37037 Tz (\(1 ) Tj 0.855556 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 46.990741 Tz (in ) Tj 0.797222 0 Td 77.777778 Tz (THF ) Tj 1.672222 0 Td 53.472222 Tz (with ) Tj 51.428571 0 0 51.428571 0 834.899633 Tm 25.297222 0 Td 78.858025 Tz (TEA ) Tj 1.536111 0 Td 45.37037 Tz (\(1 ) Tj 0.738889 0 Td 46.180556 Tz (eq.\) ) Tj 1.263889 0 Td 61.574074 Tz (was ) Tj 1.244444 0 Td 58.333333 Tz (added ) Tj 1.886111 0 Td 55.497685 Tz (dropwise ) Tj 2.780556 0 Td 46.990741 Tz (to ) Tj 0.719444 0 Td 48.611111 Tz (the ) Tj 1.030556 0 Td 47.800926 Tz (reaction ) Tj 2.469444 0 Td 46.018519 Tz (flask ) Tj 1.477778 0 Td 59.41358 Tz (and ) Tj 1.205556 0 Td 61.574074 Tz (was ) Tj 51.428571 0 0 51.428571 0 792.573548 Tm 25.316667 0 Td 43.981481 Tz (stirred ) Tj 1.983333 0 Td 48.611111 Tz (for ) Tj 0.991667 0 Td 56.712963 Tz (an ) Tj 0.855556 0 Td 47.962963 Tz (additional ) Tj 3.052778 0 Td 63.194444 Tz (40 ) Tj 0.933333 0 Td 53.240741 Tz (minutes ) Tj 2.391667 0 Td 45.37037 Tz (at ) Tj 0.7 0 Td 59.953704 Tz (0C. ) Tj 1.613889 0 Td 57.685185 Tz (Water ) Tj 1.847222 0 Td 45.37037 Tz (\(1 ) Tj 0.758333 0 Td 46.990741 Tz (eq.\) ) Tj 1.263889 0 Td 59.41358 Tz (and ) Tj 51.428571 0 0 51.428571 0 750.57956 Tm 25.297222 0 Td 78.858025 Tz (TEA ) Tj 1.652778 0 Td 43.75 Tz (\(1 ) Tj 0.816667 0 Td 45.37037 Tz (eq.\) ) Tj 1.341667 0 Td 58.333333 Tz (were ) Tj 1.613889 0 Td 58.333333 Tz (added ) Tj 1.963889 0 Td 45.37037 Tz (to ) Tj 0.797222 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 48.206019 Tz (reaction ) Tj 2.586111 0 Td 52.777778 Tz (mixture ) Tj 2.430556 0 Td 58.981481 Tz (which ) Tj 2.022222 0 Td 61.574074 Tz (was ) Tj 40 0 0 40 0 717 Tm 32.525 0 Td 70.238095 Tz (allowed ) Tj 3.25 0 Td 58.333333 Tz (to ) Tj 1.075 0 Td 50 Tz (stir ) Tj 1.475 0 Td 62.5 Tz (for ) Tj 1.4 0 Td 81.25 Tz (60 ) Tj 1.275 0 Td 69.642857 Tz (minutes ) Tj 3.25 0 Td 58.333333 Tz (at ) Tj 1 0 Td 82.291667 Tz (0C. ) Tj 2.275 0 Td 81.944444 Tz (The ) Tj 1.8 0 Td 64.583333 Tz (contents ) Tj 3.425 0 Td 72.916667 Tz (of ) Tj 1.075 0 Td 65.277778 Tz (the ) Tj 40 0 0 40 0 675 Tm 32.525 0 Td 62.5 Tz (reaction ) Tj 3.25 0 Td 60 Tz (flask ) Tj 2.05 0 Td 75 Tz (were ) Tj 2.025 0 Td 66.666667 Tz (then ) Tj 1.9 0 Td 79.166667 Tz (vacuum ) Tj 3.15 0 Td 55.208333 Tz (filtered ) Tj 2.875 0 Td 76.388889 Tz (and ) Tj 1.65 0 Td 63.333333 Tz (dried ) Tj 2.125 0 Td 58.333333 Tz (in ) Tj 0.975 0 Td 67.361111 Tz (vacuo. ) Tj 40 0 0 40 0 634 Tm 32.525 0 Td 66.666667 Tz (After ) Tj 2.2 0 Td 75 Tz (an ) Tj 1.15 0 Td 62.083333 Tz (extraction ) Tj 4.025 0 Td 67.708333 Tz (with ) Tj 1.925 0 Td 68.666667 Tz (chloroform/methanol/water ) Tj 10.6 0 Td 58.928571 Tz (1:1.5:1 ) Tj 51.428571 0 0 51.428571 0 587.580764 Tm 25.316667 0 Td 44.155093 Tz (\(v/v/v\), ) Tj 2.430556 0 Td 48.611111 Tz (the ) Tj 1.147222 0 Td 51.147343 Tz (\(12:0\)-p-phosphodiester ) Tj 7.291667 0 Td 61.574074 Tz (was ) Tj 1.4 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 45.37037 Tz (in ) Tj 0.836111 0 Td 73.45679 Tz (40% ) Tj 51.428571 0 0 51.428571 0 544.548303 Tm 25.297222 0 Td 47.962963 Tz (ethyl ) Tj 1.808333 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.627778 0 Td 59.41358 Tz (and ) Tj 1.419444 0 Td 50.084175 Tz (centrifuged ) Tj 3.713889 0 Td 47.530864 Tz (for ) Tj 1.186111 0 Td 61.574074 Tz (7 ) Tj 0.777778 0 Td 50.636574 Tz (minutes. ) Tj 2.8 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 502.713574 Tm 25.316667 0 Td 50.673401 Tz (Supernatant ) Tj 3.597222 0 Td 61.574074 Tz (was ) Tj 1.380556 0 Td 53.877315 Tz (decanted ) Tj 2.838889 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 50.771605 Tz (the ) Tj 1.186111 0 Td 49.331276 Tz (insoluble ) Tj 2.936111 0 Td 46.450617 Tz (fractions ) Tj 2.8 0 Td 59.143519 Tz (were ) Tj 40 0 0 40 0 467 Tm 32.525 0 Td 72.222222 Tz (combined. ) Tj 51.428571 0 0 51.428571 0 424.38394 Tm 26.016667 0 Td 63.734568 Tz (The ) Tj 1.361111 0 Td 45.046296 Tz (relatively ) Tj 2.858333 0 Td 55.092593 Tz (pure ) Tj 1.536111 0 Td 51.006441 Tz (\(12:0\)-p-phosphodiester ) Tj 7.213889 0 Td 43.75 Tz (\(1 ) Tj 0.777778 0 Td 43.425926 Tz (eq.\), ) Tj 1.536111 0 Td 81.018519 Tz (DCC ) Tj 51.428571 0 0 51.428571 0 379.085427 Tm 25.316667 0 Td 46.180556 Tz (\(2.2 ) Tj 1.341667 0 Td 61.574074 Tz (eq\) ) Tj 1.302778 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 87.5 Tz (DMAP ) Tj 2.313889 0 Td 43.75 Tz (\(0.1 ) Tj 1.322222 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 58.333333 Tz (were ) Tj 1.594444 0 Td 49.907407 Tz (dried ) Tj 1.711111 0 Td 53.472222 Tz (over ) Tj 1.458333 0 Td 56.565657 Tz (phosphorous ) Tj 51.428571 0 0 51.428571 0 338.971223 Tm 25.297222 0 Td 53.292181 Tz (pentoxide ) Tj 2.994444 0 Td 48.611111 Tz (for ) Tj 1.05 0 Td 53.472222 Tz (12 ) Tj 0.797222 0 Td 49.151235 Tz (hours. ) Tj 1.905556 0 Td 56.442901 Tz (Cyanoethanol ) Tj 4.2 0 Td 43.75 Tz (\(1.1 ) Tj 1.263889 0 Td 46.180556 Tz (eq.\) ) Tj 1.283333 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 50.771605 Tz (dissolved ) Tj 51.428571 0 0 51.428571 0 294.646772 Tm 25.297222 0 Td 45.37037 Tz (in ) Tj 0.719444 0 Td 54.444444 Tz (dichloromethane ) Tj 5.055556 0 Td 59.41358 Tz (and ) Tj 1.244444 0 Td 49.259259 Tz (dried ) Tj 1.633333 0 Td 53.472222 Tz (with ) Tj 1.497222 0 Td 60.853909 Tz (magnesium ) Tj 3.5 0 Td 45.833333 Tz (sulfate ) Tj 2.1 0 Td 47.530864 Tz (for ) Tj 1.069444 0 Td 51.851852 Tz (12 ) Tj 51.428571 0 0 51.428571 0 254.44484 Tm 25.277778 0 Td 49.691358 Tz (hours. ) Tj 1.983333 0 Td 62.654321 Tz (The ) Tj 1.302778 0 Td 51.147343 Tz (\(12:0\)-p-phosphodiester ) Tj 7.213889 0 Td 60.493827 Tz (was ) Tj 1.302778 0 Td 50.411523 Tz (dissolved ) Tj 2.877778 0 Td 46.990741 Tz (in ) Tj 0.758333 0 Td 56.712963 Tz (dichlo ) Tj 40 0 0 40 0 218 Tm 32.525 0 Td 73.148148 Tz (romethane ) Tj 4.2 0 Td 75 Tz (and ) Tj 1.625 0 Td 105.555556 Tz (DCC ) Tj 2.15 0 Td 75 Tz (and ) Tj 1.625 0 Td 111.458333 Tz (DMAP ) Tj 2.925 0 Td 76.041667 Tz (were ) Tj 2.05 0 Td 75 Tz (added ) Tj 2.525 0 Td 56.25 Tz (to ) Tj 0.975 0 Td 62.5 Tz (the ) Tj 1.4 0 Td 62.5 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 170.168612 Tm 25.297222 0 Td 42.669753 Tz (flask. ) Tj 1.788889 0 Td 62.654321 Tz (The ) Tj 1.361111 0 Td 46.666667 Tz (flask ) Tj 1.633333 0 Td 60.493827 Tz (was ) Tj 1.341667 0 Td 50.771605 Tz (sealed ) Tj 2.061111 0 Td 53.472222 Tz (with ) Tj 1.536111 0 Td 51.851852 Tz (a ) Tj 0.583333 0 Td 57.253086 Tz (septum ) Tj 2.313889 0 Td 59.41358 Tz (and ) Tj 1.283333 0 Td 55.632716 Tz (purged ) Tj 2.294444 0 Td 53.472222 Tz (with ) Tj ET Q endstream endobj 188 0 obj << /Length 1 >> stream q endstream endobj 189 0 obj << /Length 40685 >> stream Q q 0.24 0 0 0.24 0 0 cm BT /F1 1 Tf 3 Tr 62.857143 0 0 62.857143 0 3023 Tm 17.325 0 Td 83.522727 Tz (US ) Tj 1.240909 0 Td 58.333333 Tz (8,022,239 ) Tj 3.388636 0 Td 74.242424 Tz (B2 ) Tj 52.857143 0 0 52.857143 0 2968 Tm 14.245946 0 Td 74.099099 Tz (15 ) Tj 51.428571 0 0 51.428571 0 2916.976553 Tm 6.358333 0 Td 50.231481 Tz (nitrogen ) Tj 2.547222 0 Td 46.018519 Tz (after ) Tj 1.497222 0 Td 55.092593 Tz (adding ) Tj 2.1 0 Td 50.771605 Tz (the ) Tj 1.05 0 Td 53.472222 Tz (cyanoethanol ) Tj 4.005556 0 Td 46.450617 Tz (Solution. ) Tj 2.625 0 Td 64.814815 Tz (The ) Tj 1.302778 0 Td 49.421296 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 2872.476433 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.361111 0 Td 44.444444 Tz (stirred ) Tj 2.080556 0 Td 48.611111 Tz (for ) Tj 1.05 0 Td 59.953704 Tz (48 ) Tj 0.952778 0 Td 53.148148 Tz (hours ) Tj 1.808333 0 Td 46.990741 Tz (at ) Tj 0.777778 0 Td 62.384259 Tz (room ) Tj 1.730556 0 Td 50.231481 Tz (temperature. ) Tj 3.869444 0 Td 57.685185 Tz (Water ) Tj 1.944444 0 Td 46.990741 Tz (\(5 ) Tj 0.797222 0 Td 46.180556 Tz (eq.\) ) Tj 40 0 0 40 0 2834 Tm 8.15 0 Td 80.555556 Tz (was ) Tj 1.725 0 Td 75 Tz (added ) Tj 2.5 0 Td 76.388889 Tz (and ) Tj 1.625 0 Td 63.888889 Tz (the ) Tj 1.4 0 Td 62.5 Tz (reaction ) Tj 3.325 0 Td 68.452381 Tz (mixture ) Tj 3.125 0 Td 79.166667 Tz (was ) Tj 1.7 0 Td 57.142857 Tz (stirred ) Tj 2.65 0 Td 63.888889 Tz (for ) Tj 1.35 0 Td 72.916667 Tz (an ) Tj 1.125 0 Td 81.25 Tz (addi ) Tj 40 0 0 40 0 2790 Tm 8.15 0 Td 59.722222 Tz (tional ) Tj 2.6 0 Td 79.166667 Tz (24 ) Tj 1.375 0 Td 63.194444 Tz (hours. ) Tj 2.75 0 Td 80.555556 Tz (The ) Tj 1.875 0 Td 65.104167 Tz (contents ) Tj 3.575 0 Td 75 Tz (of ) Tj 1.225 0 Td 63.888889 Tz (the ) Tj 1.6 0 Td 62.5 Tz (reaction ) Tj 3.475 0 Td 59.166667 Tz (flask ) Tj 2.225 0 Td 75 Tz (were ) Tj 40 0 0 40 0 2747 Tm 8.175 0 Td 81.25 Tz (vacuum ) Tj 3.2 0 Td 55.208333 Tz (filtered ) Tj 2.85 0 Td 77.777778 Tz (and ) Tj 1.65 0 Td 64.166667 Tz (dried ) Tj 2.15 0 Td 60.416667 Tz (in ) Tj 0.975 0 Td 67.361111 Tz (vacuo. ) Tj 2.65 0 Td 66.666667 Tz (After ) Tj 2.225 0 Td 70.833333 Tz (an ) Tj 1.125 0 Td 61.666667 Tz (extraction ) Tj 4 0 Td 68.75 Tz (with ) Tj 51.428571 0 0 51.428571 0 2698.390156 Tm 6.358333 0 Td 51.851852 Tz (chloroform/brine ) Tj 5.191667 0 Td 44.290123 Tz (1:1 ) Tj 1.069444 0 Td 43.209877 Tz (\(v/v\), ) Tj 1.730556 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 54.62963 Tz (coupled ) Tj 2.45 0 Td 53.703704 Tz (product ) Tj 2.411111 0 Td 61.574074 Tz (was ) Tj 1.263889 0 Td 48.206019 Tz (purified ) Tj 51.428571 0 0 51.428571 0 2655.369077 Tm 6.338889 0 Td 61.574074 Tz (by ) Tj 1.011111 0 Td 45.37037 Tz (flash ) Tj 1.652778 0 Td 59.953704 Tz (column ) Tj 2.45 0 Td 56.25 Tz (chromatography ) Tj 4.997222 0 Td 53.148148 Tz (using ) Tj 1.847222 0 Td 73.45679 Tz (40% ) Tj 1.575 0 Td 48.611111 Tz (ethyl ) Tj 1.730556 0 Td 46.585648 Tz (acetate/ ) Tj 51.428571 0 0 51.428571 0 2610.686061 Tm 6.338889 0 Td 57.79321 Tz (hexane ) Tj 2.236111 0 Td 51.041667 Tz (then ) Tj 1.419444 0 Td 51.851852 Tz (switching ) Tj 2.955556 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 73.45679 Tz (80% ) Tj 1.477778 0 Td 47.962963 Tz (ethyl ) Tj 1.594444 0 Td 51.157407 Tz (acetate/hexane ) Tj 4.433333 0 Td 48.611111 Tz (for ) Tj 1.011111 0 Td 51.851852 Tz (a ) Tj 0.486111 0 Td 47.800926 Tz (step ) Tj 51.428571 0 0 51.428571 0 2568.169492 Tm 6.358333 0 Td 49.826389 Tz (gradient ) Tj 2.547222 0 Td 45.775463 Tz (elution. ) Tj 51.428571 0 0 51.428571 0 2526.763906 Tm 7.097222 0 Td 51.851852 Tz (After ) Tj 1.788889 0 Td 45.121083 Tz (purification, ) Tj 3.811111 0 Td 48.611111 Tz (the ) Tj 1.108333 0 Td 50.771605 Tz (protected ) Tj 3.013889 0 Td 51.006441 Tz (\(12:0\)-p-phosphodiester ) Tj 51.428571 0 0 51.428571 0 2482.093671 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.4 0 Td 41.481481 Tz (split ) Tj 1.477778 0 Td 46.180556 Tz (into ) Tj 1.361111 0 Td 59.41358 Tz (two ) Tj 1.341667 0 Td 52.777778 Tz (roughly ) Tj 2.45 0 Td 53.148148 Tz (equal ) Tj 1.808333 0 Td 47.530864 Tz (portions. ) Tj 2.819444 0 Td 63.734568 Tz (The ) Tj 1.380556 0 Td 37.592593 Tz (first ) Tj 1.322222 0 Td 51.388889 Tz (portion ) Tj 51.428571 0 0 51.428571 0 2434.081352 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.380556 0 Td 55.092593 Tz (used ) Tj 1.536111 0 Td 48.611111 Tz (for ) Tj 1.069444 0 Td 45.910494 Tz (direct ) Tj 1.866667 0 Td 46.720679 Tz (fluorination ) Tj 3.577778 0 Td 59.41358 Tz (and ) Tj 1.263889 0 Td 50.771605 Tz (the ) Tj 1.147222 0 Td 55.632716 Tz (second ) Tj 2.197222 0 Td 50 Tz (portion ) Tj 2.333333 0 Td 61.574074 Tz (was ) Tj 51.428571 0 0 51.428571 0 2390.882353 Tm 6.338889 0 Td 55.902778 Tz (used ) Tj 1.672222 0 Td 48.611111 Tz (for ) Tj 1.205556 0 Td 50.05144 Tz (reduction ) Tj 3.052778 0 Td 53.472222 Tz (followed ) Tj 2.858333 0 Td 59.953704 Tz (by ) Tj 1.069444 0 Td 46.990741 Tz (fluorination ) Tj 3.694444 0 Td 59.548611 Tz (\(Example ) Tj 3.15 0 Td 42.12963 Tz (8\). ) Tj 51.428571 0 0 51.428571 0 2350.270064 Tm 6.377778 0 Td 50.771605 Tz (Protected ) Tj 3.091667 0 Td 51.006441 Tz (\(12:0\)-p-phosphodiester ) Tj 7.388889 0 Td 40.509259 Tz (\(1 ) Tj 0.933333 0 Td 46.180556 Tz (eq.\) ) Tj 1.477778 0 Td 60.493827 Tz (was ) Tj 1.438889 0 Td 49.907407 Tz (dried ) Tj 1.847222 0 Td 54.282407 Tz (over ) Tj 51.428571 0 0 51.428571 0 2305.271411 Tm 6.358333 0 Td 55.976431 Tz (phosphorous ) Tj 3.85 0 Td 53.652263 Tz (pentoxide ) Tj 3.052778 0 Td 48.611111 Tz (for ) Tj 1.069444 0 Td 55.092593 Tz (12 ) Tj 0.816667 0 Td 53.796296 Tz (hours ) Tj 1.769444 0 Td 58.333333 Tz (and ) Tj 1.225 0 Td 50.771605 Tz (dissolved ) Tj 2.897222 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 56.712963 Tz (dichlo ) Tj 51.428571 0 0 51.428571 0 2260.96 Tm 6.358333 0 Td 53.796296 Tz (romethane. ) Tj 3.363889 0 Td 63.734568 Tz (The ) Tj 1.283333 0 Td 48.611111 Tz (reaction ) Tj 2.508333 0 Td 46.018519 Tz (flask ) Tj 1.516667 0 Td 60.493827 Tz (was ) Tj 1.225 0 Td 50.771605 Tz (sealed ) Tj 1.963889 0 Td 58.333333 Tz (and ) Tj 1.166667 0 Td 53.472222 Tz (placed ) Tj 2.061111 0 Td 45.37037 Tz (in ) Tj 0.7 0 Td 56.712963 Tz (an ) Tj 0.855556 0 Td 46.450617 Tz (ice ) Tj 51.428571 0 0 51.428571 0 2221.544021 Tm 6.338889 0 Td 52.662037 Tz (bath ) Tj 1.555556 0 Td 45.37037 Tz (to ) Tj 0.875 0 Td 52.256944 Tz (maintain ) Tj 2.819444 0 Td 51.851852 Tz (0 ) Tj 0.894444 0 Td 55.092593 Tz (C. ) Tj 0.991667 0 Td 49.96142 Tz (temperature. ) Tj 3.927778 0 Td 55.416667 Tz (Deoxofluor ) Tj 3.597222 0 Td 46.990741 Tz (\(2 ) Tj 0.875 0 Td 46.180556 Tz (eq.\) ) Tj 1.380556 0 Td 50.231481 Tz (in ) Tj 51.428571 0 0 51.428571 0 2177.927811 Tm 6.358333 0 Td 54.444444 Tz (dichloromethane ) Tj 5.036111 0 Td 62.654321 Tz (was ) Tj 1.283333 0 Td 52.932099 Tz (slowly ) Tj 2.041667 0 Td 58.981481 Tz (added ) Tj 1.905556 0 Td 55.092593 Tz (\(-2 ) Tj 1.205556 0 Td 52.256944 Tz (minutes\) ) Tj 2.644444 0 Td 59.41358 Tz (and ) Tj 1.186111 0 Td 51.388889 Tz (ethanol ) Tj 51.428571 0 0 51.428571 0 2139.175258 Tm 6.377778 0 Td 46.990741 Tz (\(0.2 ) Tj 1.341667 0 Td 46.180556 Tz (eq.\) ) Tj 1.322222 0 Td 61.574074 Tz (was ) Tj 1.341667 0 Td 57.685185 Tz (added ) Tj 1.944444 0 Td 45.37037 Tz (to ) Tj 0.777778 0 Td 51.446759 Tz (generate ) Tj 2.663889 0 Td 51.851852 Tz (a ) Tj 0.525 0 Td 44.650206 Tz (catalyst, ) Tj 2.663889 0 Td 55.092593 Tz (HF. ) Tj 1.205556 0 Td 63.734568 Tz (The ) Tj 1.341667 0 Td 47.530864 Tz (ice ) Tj 1.069444 0 Td 53.472222 Tz (bath ) Tj 40 0 0 40 0 2102 Tm 8.15 0 Td 80.555556 Tz (was ) Tj 1.875 0 Td 77.380952 Tz (removed ) Tj 3.625 0 Td 75 Tz (and ) Tj 1.725 0 Td 63.888889 Tz (the ) Tj 1.525 0 Td 62.5 Tz (reaction ) Tj 3.425 0 Td 69.047619 Tz (mixture ) Tj 3.3 0 Td 79.166667 Tz (was ) Tj 1.825 0 Td 57.142857 Tz (stirred ) Tj 2.775 0 Td 62.5 Tz (for ) Tj 1.55 0 Td 70.833333 Tz (16 ) Tj 40 0 0 40 0 2061 Tm 8.15 0 Td 63.888889 Tz (hours. ) Tj 2.5 0 Td 91.666667 Tz (An ) Tj 1.325 0 Td 61.666667 Tz (extraction ) Tj 3.925 0 Td 68.75 Tz (with ) Tj 1.875 0 Td 66.166667 Tz (dichloromethane/saturated ) Tj 10.125 0 Td 75.694444 Tz (sodium ) Tj 51.428571 0 0 51.428571 0 2013.583433 Tm 6.338889 0 Td 51.557239 Tz (bicarbonate ) Tj 3.558333 0 Td 48.611111 Tz (solution ) Tj 2.547222 0 Td 43.209877 Tz (1:1 ) Tj 1.030556 0 Td 46.666667 Tz (\(v/v\) ) Tj 1.536111 0 Td 61.574074 Tz (was ) Tj 1.244444 0 Td 56.532922 Tz (performed ) Tj 3.169444 0 Td 59.41358 Tz (and ) Tj 1.225 0 Td 48.611111 Tz (the ) Tj 0.991667 0 Td 51.851852 Tz (organic ) Tj 51.428571 0 0 51.428571 0 1971.202899 Tm 6.358333 0 Td 49.259259 Tz (layer ) Tj 1.652778 0 Td 61.574074 Tz (was ) Tj 1.283333 0 Td 46.342593 Tz (collected. ) Tj 51.428571 0 0 51.428571 0 1933.361702 Tm 7.097222 0 Td 51.851852 Tz (After ) Tj 1.866667 0 Td 52.932099 Tz (drying ) Tj 2.275 0 Td 42.12963 Tz (in ) Tj 0.894444 0 Td 52.391975 Tz (vacuo, ) Tj 2.255556 0 Td 48.611111 Tz (the ) Tj 1.186111 0 Td 50.771605 Tz (protected ) Tj 3.091667 0 Td 50.517429 Tz (\(12:0\)-p-difluoro ) Tj 51.428571 0 0 51.428571 0 1891.69475 Tm 6.358333 0 Td 52.777778 Tz (phosphodiester ) Tj 4.647222 0 Td 61.574074 Tz (was ) Tj 1.361111 0 Td 47.395833 Tz (purified ) Tj 2.508333 0 Td 59.953704 Tz (by ) Tj 1.011111 0 Td 44.722222 Tz (flash ) Tj 1.613889 0 Td 59.41358 Tz (column ) Tj 2.411111 0 Td 59.217172 Tz (chromatogra ) Tj 51.428571 0 0 51.428571 0 1848.551122 Tm 6.358333 0 Td 59.41358 Tz (phy ) Tj 1.322222 0 Td 52.5 Tz (using ) Tj 1.788889 0 Td 72.376543 Tz (40% ) Tj 1.555556 0 Td 47.962963 Tz (ethyl ) Tj 1.672222 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.491667 0 Td 51.041667 Tz (then ) Tj 1.458333 0 Td 52.572016 Tz (switching ) Tj 3.072222 0 Td 43.75 Tz (to ) Tj 0.758333 0 Td 74.537037 Tz (80% ) Tj 51.428571 0 0 51.428571 0 1806.748517 Tm 6.358333 0 Td 47.314815 Tz (ethyl ) Tj 1.594444 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.394444 0 Td 48.611111 Tz (for ) Tj 0.972222 0 Td 58.333333 Tz (a ) Tj 0.486111 0 Td 47.800926 Tz (step ) Tj 1.283333 0 Td 49.826389 Tz (gradient ) Tj 2.508333 0 Td 45.775463 Tz (elution. ) Tj 2.372222 0 Td 56.17284 Tz (For ) Tj 1.127778 0 Td 56.712963 Tz (deprotec ) Tj 51.428571 0 0 51.428571 0 1768.661853 Tm 6.338889 0 Td 44.074074 Tz (tion, ) Tj 1.613889 0 Td 48.611111 Tz (the ) Tj 1.108333 0 Td 50.411523 Tz (protected ) Tj 2.955556 0 Td 50.130208 Tz (\(12:0\)-p-difluoro-phosphodiester ) Tj 9.858333 0 Td 42.12963 Tz (\(1 ) Tj 0.836111 0 Td 46.180556 Tz (eq.\) ) Tj 51.428571 0 0 51.428571 0 1724.829448 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 50.771605 Tz (dissolved ) Tj 2.955556 0 Td 43.75 Tz (in ) Tj 0.719444 0 Td 48.251029 Tz (pyridine. ) Tj 2.819444 0 Td 56.837607 Tz (N-propylamine ) Tj 4.647222 0 Td 55.902778 Tz (\(100 ) Tj 1.516667 0 Td 46.180556 Tz (eq.\) ) Tj 1.322222 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 59.143519 Tz (pyri ) Tj 40 0 0 40 0 1686 Tm 8.175 0 Td 67.708333 Tz (dine ) Tj 1.8 0 Td 76.388889 Tz (was ) Tj 1.55 0 Td 75.833333 Tz (added ) Tj 2.4 0 Td 60.416667 Tz (to ) Tj 0.925 0 Td 62.5 Tz (the ) Tj 1.3 0 Td 61.979167 Tz (reaction ) Tj 3.15 0 Td 68.229167 Tz (flaskand ) Tj 3.425 0 Td 65.277778 Tz (the ) Tj 1.325 0 Td 61.666667 Tz (clear ) Tj 1.95 0 Td 63.020833 Tz (solution ) Tj 3.2 0 Td 79.166667 Tz (was ) Tj 52.857143 0 0 52.857143 0 1637.829684 Tm 6.205405 0 Td 42.792793 Tz (stirred ) Tj 1.92973 0 Td 47.297297 Tz (for ) Tj 1.059459 0 Td 52.027027 Tz (10 ) Tj 0.794595 0 Td 52.702703 Tz (minutes ) Tj 2.345946 0 Td 44.144144 Tz (at ) Tj 0.681081 0 Td 60.698198 Tz (room ) Tj 1.608108 0 Td 49.399399 Tz (temperature. ) Tj 3.689189 0 Td 49.399399 Tz (All ) Tj 1.059459 0 Td 47.297297 Tz (solvents ) Tj 2.459459 0 Td 56.756757 Tz (were ) Tj 51.428571 0 0 51.428571 0 1597.621359 Tm 6.358333 0 Td 60.185185 Tz (removed ) Tj 2.702778 0 Td 43.75 Tz (in ) Tj 0.738889 0 Td 55.092593 Tz (vacuo ) Tj 1.847222 0 Td 45.37037 Tz (to ) Tj 0.7 0 Td 49.907407 Tz (yield ) Tj 1.633333 0 Td 50.771605 Tz (the ) Tj 1.088889 0 Td 59.953704 Tz (n-propylammonium ) Tj 5.930556 0 Td 42.939815 Tz (salt ) Tj 1.186111 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 49.691358 Tz (the ) Tj 51.428571 0 0 51.428571 0 1557.533958 Tm 6.377778 0 Td 49.016204 Tz (\(12:0\)-p-difluorophosphodiester. ) Tj 9.625 0 Td 72.916667 Tz (An ) Tj 1.088889 0 Td 48.287037 Tz (extraction ) Tj 3.130556 0 Td 54.282407 Tz (with ) Tj 1.477778 0 Td 58.873457 Tz (chloro ) Tj 51.428571 0 0 51.428571 0 1513.381969 Tm 6.358333 0 Td 52.875244 Tz (form/methanol/brine ) Tj 6.241667 0 Td 44.907407 Tz (1:1.5:1 ) Tj 2.119444 0 Td 47.222222 Tz (\(v/v/v\) ) Tj 2.138889 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 56.17284 Tz (performed ) Tj 3.188889 0 Td 43.75 Tz (to ) Tj 0.680556 0 Td 61.574074 Tz (gener ) Tj 51.428571 0 0 51.428571 0 1474.749082 Tm 6.358333 0 Td 47.530864 Tz (ate ) Tj 1.030556 0 Td 49.691358 Tz (the ) Tj 1.088889 0 Td 58.333333 Tz (sodium ) Tj 2.333333 0 Td 41.319444 Tz (salt ) Tj 1.166667 0 Td 59.953704 Tz (of ) Tj 0.797222 0 Td 49.691358 Tz (the ) Tj 1.088889 0 Td 49.117477 Tz (\(12:0\)-p-difluorophosphodiester. ) Tj 51.428571 0 0 51.428571 0 1398.04 Tm 13.552778 0 Td 61.111111 Tz (Example ) Tj 2.741667 0 Td 58.333333 Tz (8 ) Tj 51.428571 0 0 51.428571 0 1315 Tm 9.897222 0 Td 52.73569 Tz (\(12:0\)-p-monofluorophosphodiester ) Tj 31.428571 0 0 31.428571 0 1159 Tm 26.218182 0 Td 111.363636 Tz (O ) Tj 171.428571 0 0 171.428571 0 1044 Tm 2.578333 0 Td 31.305556 Tz (cis-\( ) Tj 1.289167 0 Td 41.416667 Tz (\)---o-clic ) Tj 31.428571 0 0 31.428571 0 1025 Tm 26.218182 0 Td 111.363636 Tz (OH ) Tj 51.428571 0 0 51.428571 0 921.671214 Tm 7.116667 0 Td 55.976431 Tz (Phosphorous ) Tj 4.025 0 Td 53.030303 Tz (oxychloride ) Tj 3.791667 0 Td 42.12963 Tz (\(1 ) Tj 0.855556 0 Td 46.990741 Tz (eq.\) ) Tj 1.419444 0 Td 61.574074 Tz (was ) Tj 1.4 0 Td 58.333333 Tz (added ) Tj 2.041667 0 Td 46.990741 Tz (to ) Tj 0.836111 0 Td 55.092593 Tz (a ) Tj 0.680556 0 Td 55.740741 Tz (round ) Tj 51.428571 0 0 51.428571 0 877.324528 Tm 6.338889 0 Td 57.253086 Tz (bottom ) Tj 2.391667 0 Td 46.018519 Tz (flask ) Tj 1.633333 0 Td 58.333333 Tz (and ) Tj 1.341667 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 46.990741 Tz (in ) Tj 0.875 0 Td 49.907407 Tz (tetrahydrofuran ) Tj 4.783333 0 Td 56.17284 Tz (\(THF\). ) Tj 2.313889 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 833.95449 Tm 6.358333 0 Td 57.037037 Tz (round ) Tj 1.847222 0 Td 56.712963 Tz (bottom ) Tj 2.197222 0 Td 46.666667 Tz (flask ) Tj 1.536111 0 Td 60.493827 Tz (was ) Tj 1.263889 0 Td 51.041667 Tz (then ) Tj 1.4 0 Td 52.391975 Tz (placed ) Tj 2.061111 0 Td 43.75 Tz (in ) Tj 0.661111 0 Td 59.953704 Tz (an ) Tj 0.875 0 Td 46.450617 Tz (ice ) Tj 0.952778 0 Td 52.662037 Tz (bath ) Tj 1.419444 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 53.472222 Tz (maintain ) Tj 51.428571 0 0 51.428571 0 794.366061 Tm 6.358333 0 Td 51.851852 Tz (a ) Tj 0.486111 0 Td 58.333333 Tz (0C. ) Tj 1.555556 0 Td 50.501543 Tz (temperature. ) Tj 3.830556 0 Td 57.613169 Tz (Dodecanol ) Tj 3.247222 0 Td 45.37037 Tz (\(1 ) Tj 0.738889 0 Td 46.180556 Tz (eq.\) ) Tj 1.263889 0 Td 50.411523 Tz (dissolved ) Tj 2.877778 0 Td 43.75 Tz (in ) Tj 0.661111 0 Td 76.697531 Tz (THF ) Tj 1.536111 0 Td 54.282407 Tz (with ) Tj 51.428571 0 0 51.428571 0 754.653659 Tm 6.338889 0 Td 50.106838 Tz (triethylamine ) Tj 4.063889 0 Td 63.518519 Tz (\(TEA\) ) Tj 2.041667 0 Td 43.75 Tz (\(1 ) Tj 0.758333 0 Td 46.180556 Tz (eq.\) ) Tj 1.283333 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 58.333333 Tz (added ) Tj 1.925 0 Td 55.092593 Tz (dropwise ) Tj 2.819444 0 Td 42.12963 Tz (to ) Tj 0.7 0 Td 49.691358 Tz (the ) Tj 1.030556 0 Td 67.24537 Tz (phos ) Tj 51.428571 0 0 51.428571 0 712.838791 Tm 6.358333 0 Td 55.555556 Tz (phorous ) Tj 2.625 0 Td 56.388889 Tz (oxychloride/THF ) Tj 5.386111 0 Td 46.090535 Tz (solution. ) Tj 2.819444 0 Td 64.814815 Tz (Once ) Tj 1.847222 0 Td 39.969136 Tz (all ) Tj 1.011111 0 Td 61.574074 Tz (of ) Tj 0.933333 0 Td 49.691358 Tz (the ) Tj 1.205556 0 Td 68.055556 Tz (dode ) Tj 51.428571 0 0 51.428571 0 667 Tm 6.358333 0 Td 61.075499 Tz (canol/THF/TEA ) Tj 4.938889 0 Td 48.206019 Tz (solution ) Tj 2.469444 0 Td 62.654321 Tz (was ) Tj 1.263889 0 Td 58.981481 Tz (added ) Tj 1.905556 0 Td 58.333333 Tz (\(-20 ) Tj 1.536111 0 Td 49.691358 Tz (minutes\), ) Tj 2.858333 0 Td 49.691358 Tz (the ) Tj 1.088889 0 Td 58.333333 Tz (reac ) Tj 40 0 0 40 0 634 Tm 8.15 0 Td 61.458333 Tz (tion ) Tj 1.75 0 Td 67.857143 Tz (mixture ) Tj 3.05 0 Td 79.166667 Tz (was ) Tj 1.675 0 Td 56.547619 Tz (stirred ) Tj 2.6 0 Td 61.111111 Tz (for ) Tj 1.275 0 Td 72.916667 Tz (an ) Tj 1.075 0 Td 62.5 Tz (additional ) Tj 3.95 0 Td 81.25 Tz (40 ) Tj 1.175 0 Td 69.642857 Tz (minutes ) Tj 3.15 0 Td 56.25 Tz (at ) Tj 0.9 0 Td 77.083333 Tz (0C. ) Tj 51.428571 0 0 51.428571 0 588.225847 Tm 6.358333 0 Td 87.5 Tz (A ) Tj 0.797222 0 Td 48.206019 Tz (solution ) Tj 2.586111 0 Td 58.333333 Tz (of ) Tj 0.836111 0 Td 56.018519 Tz (p-hydroxybenzaldehyde ) Tj 7.291667 0 Td 45.37037 Tz (\(1 ) Tj 0.855556 0 Td 46.990741 Tz (eq.\) ) Tj 1.4 0 Td 43.75 Tz (in ) Tj 0.758333 0 Td 77.777778 Tz (THF ) Tj 1.672222 0 Td 54.282407 Tz (with ) Tj 51.428571 0 0 51.428571 0 543.896806 Tm 6.358333 0 Td 78.858025 Tz (TEA ) Tj 1.555556 0 Td 43.75 Tz (\(1 ) Tj 0.738889 0 Td 45.37037 Tz (eq.\) ) Tj 1.263889 0 Td 60.493827 Tz (was ) Tj 1.225 0 Td 58.333333 Tz (added ) Tj 1.886111 0 Td 55.497685 Tz (dropwise ) Tj 2.780556 0 Td 46.990741 Tz (to ) Tj 0.719444 0 Td 48.611111 Tz (the ) Tj 1.030556 0 Td 48.206019 Tz (reaction ) Tj 2.469444 0 Td 46.018519 Tz (flask ) Tj 1.477778 0 Td 59.41358 Tz (and ) Tj 1.225 0 Td 60.493827 Tz (was ) Tj 51.428571 0 0 51.428571 0 501.570726 Tm 6.377778 0 Td 43.981481 Tz (stirred ) Tj 1.983333 0 Td 49.691358 Tz (for ) Tj 0.991667 0 Td 58.333333 Tz (an ) Tj 0.855556 0 Td 47.962963 Tz (additional ) Tj 3.052778 0 Td 63.194444 Tz (40 ) Tj 0.933333 0 Td 53.240741 Tz (minutes ) Tj 2.391667 0 Td 46.990741 Tz (at ) Tj 0.7 0 Td 59.953704 Tz (0C. ) Tj 1.613889 0 Td 57.685185 Tz (Water ) Tj 1.847222 0 Td 45.37037 Tz (\(1 ) Tj 0.758333 0 Td 46.990741 Tz (eq.\) ) Tj 1.263889 0 Td 60.493827 Tz (and ) Tj 51.428571 0 0 51.428571 0 459.578811 Tm 6.358333 0 Td 78.858025 Tz (TEA ) Tj 1.652778 0 Td 43.75 Tz (\(1 ) Tj 0.816667 0 Td 45.37037 Tz (eq.\) ) Tj 1.341667 0 Td 58.333333 Tz (were ) Tj 1.613889 0 Td 58.333333 Tz (added ) Tj 1.963889 0 Td 46.990741 Tz (to ) Tj 0.797222 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 48.206019 Tz (reaction ) Tj 2.586111 0 Td 53.240741 Tz (mixture ) Tj 2.45 0 Td 58.333333 Tz (which ) Tj 2.002778 0 Td 61.574074 Tz (was ) Tj 40 0 0 40 0 426 Tm 8.175 0 Td 70.238095 Tz (allowed ) Tj 3.25 0 Td 60.416667 Tz (to ) Tj 1.075 0 Td 50 Tz (stir ) Tj 1.475 0 Td 62.5 Tz (for ) Tj 1.4 0 Td 81.25 Tz (60 ) Tj 1.275 0 Td 69.642857 Tz (minutes ) Tj 3.25 0 Td 58.333333 Tz (at ) Tj 1 0 Td 82.291667 Tz (0C. ) Tj 2.275 0 Td 83.333333 Tz (The ) Tj 1.8 0 Td 64.583333 Tz (contents ) Tj 3.425 0 Td 75 Tz (of ) Tj 1.1 0 Td 63.888889 Tz (the ) Tj 40 0 0 40 0 384 Tm 8.175 0 Td 62.5 Tz (reaction ) Tj 3.25 0 Td 60 Tz (flask ) Tj 2.05 0 Td 75 Tz (were ) Tj 2.05 0 Td 65.625 Tz (then ) Tj 1.875 0 Td 79.166667 Tz (vacuum ) Tj 3.15 0 Td 55.208333 Tz (filtered ) Tj 2.875 0 Td 76.388889 Tz (and ) Tj 1.65 0 Td 63.333333 Tz (dried ) Tj 2.15 0 Td 56.25 Tz (in ) Tj 0.975 0 Td 66.666667 Tz (vacuo. ) Tj 40 0 0 40 0 343 Tm 8.175 0 Td 67.5 Tz (After ) Tj 2.2 0 Td 75 Tz (an ) Tj 1.15 0 Td 62.5 Tz (extraction ) Tj 4.025 0 Td 68.75 Tz (with ) Tj 1.925 0 Td 68.666667 Tz (chloroform/methanol/water ) Tj 10.6 0 Td 58.928571 Tz (1:1.5:1 ) Tj 51.428571 0 0 51.428571 0 296.576355 Tm 6.377778 0 Td 44.155093 Tz (\(v/v/v\), ) Tj 2.430556 0 Td 48.611111 Tz (the ) Tj 1.147222 0 Td 51.147343 Tz (\(14:0\)-p-phosphodiester ) Tj 7.291667 0 Td 62.654321 Tz (was ) Tj 1.4 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 45.37037 Tz (in ) Tj 0.836111 0 Td 73.45679 Tz (40% ) Tj 51.428571 0 0 51.428571 0 253.565841 Tm 6.358333 0 Td 47.962963 Tz (ethyl ) Tj 1.827778 0 Td 50.694444 Tz (acetate/hexane ) Tj 4.608333 0 Td 59.41358 Tz (and ) Tj 1.419444 0 Td 50.673401 Tz (centrifuged ) Tj 3.713889 0 Td 47.530864 Tz (for ) Tj 1.205556 0 Td 61.574074 Tz (7 ) Tj 0.758333 0 Td 50.636574 Tz (minutes. ) Tj 2.8 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 211.713574 Tm 6.377778 0 Td 50.673401 Tz (Supernatant ) Tj 3.597222 0 Td 61.574074 Tz (was ) Tj 1.380556 0 Td 54.282407 Tz (decanted ) Tj 2.838889 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 50.771605 Tz (the ) Tj 1.205556 0 Td 48.971193 Tz (insoluble ) Tj 2.916667 0 Td 46.8107 Tz (fractions ) Tj 2.819444 0 Td 58.333333 Tz (were ) Tj 40 0 0 40 0 176 Tm 8.175 0 Td 72.222222 Tz (combined. ) Tj 30 0 0 30 0 2547 Tm 41.666667 0 Td 75 Tz (10 ) Tj 30 0 0 30 0 2339 Tm 41.666667 0 Td 72.222222 Tz (15 ) Tj 30 0 0 30 0 1923 Tm 41.6 0 Td 77.777778 Tz (25 ) Tj 30 0 0 30 0 1716 Tm 41.6 0 Td 80.555556 Tz (30 ) Tj 30 0 0 30 0 1507 Tm 41.6 0 Td 77.777778 Tz (35 ) Tj 30 0 0 30 0 1299 Tm 41.566667 0 Td 83.333333 Tz (40 ) Tj 30 0 0 30 0 1091 Tm 41.566667 0 Td 80.555556 Tz (45 ) Tj 30 0 0 30 0 883 Tm 41.6 0 Td 80.555556 Tz (50 ) Tj 30 0 0 30 0 675 Tm 41.6 0 Td 77.777778 Tz (55 ) Tj 30 0 0 30 0 467 Tm 41.633333 0 Td 77.777778 Tz (60 ) Tj 30 0 0 30 0 259 Tm 41.633333 0 Td 75 Tz (65 ) Tj 52.857143 0 0 52.857143 0 2968 Tm 32.691892 0 Td 72.522523 Tz (16 ) Tj 51.428571 0 0 51.428571 0 2919.38394 Tm 26.016667 0 Td 63.734568 Tz (The ) Tj 1.361111 0 Td 45.046296 Tz (relatively ) Tj 2.858333 0 Td 55.092593 Tz (pure ) Tj 1.536111 0 Td 51.006441 Tz (\(12:0\)-p-phosphodiester ) Tj 7.213889 0 Td 43.75 Tz (\(1 ) Tj 0.777778 0 Td 43.425926 Tz (eq.\), ) Tj 1.536111 0 Td 81.018519 Tz (DCC ) Tj 51.428571 0 0 51.428571 0 2875.085427 Tm 25.316667 0 Td 46.180556 Tz (\(2.2 ) Tj 1.341667 0 Td 61.574074 Tz (eq\) ) Tj 1.302778 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 87.5 Tz (DMAP ) Tj 2.313889 0 Td 43.75 Tz (\(0.1 ) Tj 1.322222 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 58.333333 Tz (were ) Tj 1.594444 0 Td 49.907407 Tz (dried ) Tj 1.711111 0 Td 53.472222 Tz (over ) Tj 1.458333 0 Td 56.565657 Tz (phosphorous ) Tj 51.428571 0 0 51.428571 0 2833.971223 Tm 25.297222 0 Td 53.292181 Tz (pentoxide ) Tj 2.994444 0 Td 48.611111 Tz (for ) Tj 1.05 0 Td 53.472222 Tz (12 ) Tj 0.797222 0 Td 49.151235 Tz (hours. ) Tj 1.905556 0 Td 56.442901 Tz (Cyanoethanol ) Tj 4.2 0 Td 43.75 Tz (\(1.1 ) Tj 1.263889 0 Td 46.180556 Tz (eq.\) ) Tj 1.283333 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 50.771605 Tz (dissolved ) Tj 51.428571 0 0 51.428571 0 2789.646772 Tm 25.297222 0 Td 45.37037 Tz (in ) Tj 0.719444 0 Td 54.444444 Tz (dichloromethane ) Tj 5.055556 0 Td 59.41358 Tz (and ) Tj 1.244444 0 Td 49.259259 Tz (dried ) Tj 1.633333 0 Td 53.472222 Tz (with ) Tj 1.497222 0 Td 60.853909 Tz (magnesium ) Tj 3.5 0 Td 45.833333 Tz (sulfate ) Tj 2.1 0 Td 47.530864 Tz (for ) Tj 1.069444 0 Td 51.851852 Tz (12 ) Tj 51.428571 0 0 51.428571 0 2750.44484 Tm 25.277778 0 Td 49.691358 Tz (hours. ) Tj 1.983333 0 Td 62.654321 Tz (The ) Tj 1.302778 0 Td 51.147343 Tz (\(12:0\)-p-phosphodiester ) Tj 7.213889 0 Td 60.493827 Tz (was ) Tj 1.302778 0 Td 50.411523 Tz (dissolved ) Tj 2.877778 0 Td 46.990741 Tz (in ) Tj 0.758333 0 Td 56.712963 Tz (dichlo ) Tj 40 0 0 40 0 2713 Tm 32.525 0 Td 73.148148 Tz (romethane ) Tj 4.2 0 Td 75 Tz (and ) Tj 1.625 0 Td 105.555556 Tz (DCC ) Tj 2.15 0 Td 75 Tz (and ) Tj 1.625 0 Td 111.458333 Tz (DMAP ) Tj 2.925 0 Td 76.041667 Tz (were ) Tj 2.05 0 Td 75 Tz (added ) Tj 2.525 0 Td 56.25 Tz (to ) Tj 0.975 0 Td 62.5 Tz (the ) Tj 1.4 0 Td 62.5 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 2666.168612 Tm 25.297222 0 Td 42.669753 Tz (flask. ) Tj 1.788889 0 Td 62.654321 Tz (The ) Tj 1.361111 0 Td 46.666667 Tz (flask ) Tj 1.633333 0 Td 60.493827 Tz (was ) Tj 1.341667 0 Td 50.771605 Tz (sealed ) Tj 2.061111 0 Td 53.472222 Tz (with ) Tj 1.536111 0 Td 51.851852 Tz (a ) Tj 0.583333 0 Td 57.253086 Tz (septum ) Tj 2.313889 0 Td 59.41358 Tz (and ) Tj 1.283333 0 Td 55.632716 Tz (purged ) Tj 2.294444 0 Td 53.472222 Tz (with ) Tj 51.428571 0 0 51.428571 0 2625.985899 Tm 25.297222 0 Td 50.231481 Tz (nitrogen ) Tj 2.547222 0 Td 46.018519 Tz (after ) Tj 1.497222 0 Td 55.092593 Tz (adding ) Tj 2.1 0 Td 50.771605 Tz (the ) Tj 1.05 0 Td 53.472222 Tz (cyanoethanol ) Tj 4.005556 0 Td 46.090535 Tz (Solution. ) Tj 2.625 0 Td 64.814815 Tz (The ) Tj 1.302778 0 Td 49.016204 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 2583.476433 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.361111 0 Td 44.444444 Tz (stirred ) Tj 2.080556 0 Td 48.611111 Tz (for ) Tj 1.05 0 Td 59.953704 Tz (48 ) Tj 0.952778 0 Td 53.148148 Tz (hours ) Tj 1.808333 0 Td 46.990741 Tz (at ) Tj 0.777778 0 Td 62.384259 Tz (room ) Tj 1.730556 0 Td 50.231481 Tz (temperature. ) Tj 3.869444 0 Td 57.685185 Tz (Water ) Tj 1.944444 0 Td 46.990741 Tz (\(5 ) Tj 0.797222 0 Td 46.180556 Tz (eq.\) ) Tj 40 0 0 40 0 2547 Tm 32.5 0 Td 80.555556 Tz (was ) Tj 1.725 0 Td 75 Tz (added ) Tj 2.5 0 Td 76.388889 Tz (and ) Tj 1.625 0 Td 63.888889 Tz (the ) Tj 1.4 0 Td 62.5 Tz (reaction ) Tj 3.325 0 Td 68.452381 Tz (mixture ) Tj 3.125 0 Td 79.166667 Tz (was ) Tj 1.7 0 Td 57.142857 Tz (stirred ) Tj 2.65 0 Td 62.5 Tz (for ) Tj 1.35 0 Td 72.916667 Tz (an ) Tj 1.125 0 Td 81.25 Tz (addi ) Tj 40 0 0 40 0 2505 Tm 32.5 0 Td 59.722222 Tz (tional ) Tj 2.6 0 Td 79.166667 Tz (24 ) Tj 1.375 0 Td 63.194444 Tz (hours. ) Tj 2.75 0 Td 80.555556 Tz (The ) Tj 1.875 0 Td 65.104167 Tz (contents ) Tj 3.575 0 Td 75 Tz (of ) Tj 1.225 0 Td 63.888889 Tz (the ) Tj 1.6 0 Td 61.979167 Tz (reaction ) Tj 3.475 0 Td 59.166667 Tz (flask ) Tj 2.2 0 Td 75 Tz (were ) Tj 40 0 0 40 0 2464 Tm 32.525 0 Td 80.555556 Tz (vacuum ) Tj 3.175 0 Td 55.729167 Tz (filtered ) Tj 2.875 0 Td 77.777778 Tz (and ) Tj 1.65 0 Td 63.333333 Tz (dried ) Tj 2.15 0 Td 58.333333 Tz (in ) Tj 0.975 0 Td 66.666667 Tz (vacuo. ) Tj 2.65 0 Td 66.666667 Tz (After ) Tj 2.2 0 Td 72.916667 Tz (an ) Tj 1.15 0 Td 61.666667 Tz (extraction ) Tj 4 0 Td 67.708333 Tz (with ) Tj 51.428571 0 0 51.428571 0 2417.386091 Tm 25.297222 0 Td 51.851852 Tz (chloroform/brine ) Tj 5.191667 0 Td 44.290123 Tz (1:1 ) Tj 1.069444 0 Td 43.209877 Tz (\(v/v\), ) Tj 1.730556 0 Td 49.691358 Tz (the ) Tj 1.05 0 Td 55.092593 Tz (coupled ) Tj 2.45 0 Td 53.703704 Tz (product ) Tj 2.411111 0 Td 62.654321 Tz (was ) Tj 1.283333 0 Td 47.800926 Tz (purified ) Tj 51.428571 0 0 51.428571 0 2377.374532 Tm 25.277778 0 Td 61.574074 Tz (by ) Tj 1.011111 0 Td 45.37037 Tz (flash ) Tj 1.652778 0 Td 59.41358 Tz (column ) Tj 2.45 0 Td 56.25 Tz (chromatography ) Tj 4.997222 0 Td 53.148148 Tz (using ) Tj 1.847222 0 Td 73.45679 Tz (40% ) Tj 1.575 0 Td 48.611111 Tz (ethyl ) Tj 1.730556 0 Td 46.585648 Tz (acetate/ ) Tj 51.428571 0 0 51.428571 0 2333.689238 Tm 25.277778 0 Td 57.79321 Tz (hexane ) Tj 2.236111 0 Td 51.041667 Tz (then ) Tj 1.380556 0 Td 52.572016 Tz (switching ) Tj 2.994444 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 73.45679 Tz (80% ) Tj 1.477778 0 Td 47.962963 Tz (ethyl ) Tj 1.594444 0 Td 51.157407 Tz (acetate/hexane ) Tj 4.433333 0 Td 48.611111 Tz (for ) Tj 0.972222 0 Td 55.092593 Tz (a ) Tj 0.525 0 Td 46.990741 Tz (step ) Tj 51.428571 0 0 51.428571 0 2294.169492 Tm 25.297222 0 Td 49.826389 Tz (gradient ) Tj 2.547222 0 Td 45.775463 Tz (elution. ) Tj 51.428571 0 0 51.428571 0 2254.747226 Tm 26.016667 0 Td 52.5 Tz (After ) Tj 1.808333 0 Td 45.121083 Tz (purification, ) Tj 3.791667 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 50.771605 Tz (protected ) Tj 3.013889 0 Td 51.006441 Tz (\(12:0\)-p-phosphodiester ) Tj 51.428571 0 0 51.428571 0 2211.080808 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.4 0 Td 41.481481 Tz (split ) Tj 1.458333 0 Td 46.990741 Tz (into ) Tj 1.380556 0 Td 59.41358 Tz (two ) Tj 1.322222 0 Td 53.240741 Tz (roughly ) Tj 2.469444 0 Td 53.148148 Tz (equal ) Tj 1.808333 0 Td 47.530864 Tz (portions. ) Tj 2.8 0 Td 64.814815 Tz (The ) Tj 1.4 0 Td 37.592593 Tz (first ) Tj 1.322222 0 Td 50.925926 Tz (portion ) Tj 51.428571 0 0 51.428571 0 2166.432099 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 55.092593 Tz (used ) Tj 1.536111 0 Td 46.450617 Tz (for ) Tj 1.011111 0 Td 46.450617 Tz (direct ) Tj 1.866667 0 Td 46.450617 Tz (fluorination ) Tj 3.597222 0 Td 58.738426 Tz (\(Example ) Tj 3.013889 0 Td 50.231481 Tz (7\) ) Tj 0.758333 0 Td 59.41358 Tz (and ) Tj 1.263889 0 Td 50.771605 Tz (the ) Tj 1.069444 0 Td 56.712963 Tz (second ) Tj 51.428571 0 0 51.428571 0 2124.410037 Tm 25.297222 0 Td 49.537037 Tz (portion ) Tj 2.275 0 Td 61.574074 Tz (was ) Tj 1.302778 0 Td 55.902778 Tz (used ) Tj 1.536111 0 Td 47.530864 Tz (for ) Tj 1.030556 0 Td 50.411523 Tz (reduction ) Tj 2.936111 0 Td 52.662037 Tz (followed ) Tj 2.722222 0 Td 59.953704 Tz (by ) Tj 0.913889 0 Td 45.37037 Tz (fluorination. ) Tj 3.791667 0 Td 55.092593 Tz (For ) Tj 51.428571 0 0 51.428571 0 2087.33969 Tm 25.297222 0 Td 48.611111 Tz (reduction, ) Tj 3.091667 0 Td 50.771605 Tz (the ) Tj 1.069444 0 Td 50.411523 Tz (protected ) Tj 2.897222 0 Td 51.147343 Tz (\(12:0\)-p-phosphodiester ) Tj 7.233333 0 Td 40.509259 Tz (\(1 ) Tj 0.758333 0 Td 46.180556 Tz (eq.\) ) Tj 1.302778 0 Td 61.574074 Tz (was ) Tj 51.428571 0 0 51.428571 0 2043.420074 Tm 25.297222 0 Td 50.771605 Tz (dissolved ) Tj 3.033333 0 Td 43.75 Tz (in ) Tj 0.816667 0 Td 59.773663 Tz (THF/water ) Tj 3.480556 0 Td 46.666667 Tz (3:0.1 ) Tj 1.75 0 Td 49.494949 Tz (equivalents ) Tj 3.597222 0 Td 47.800926 Tz (respectively ) Tj 3.713889 0 Td 60.493827 Tz (and ) Tj 51.428571 0 0 51.428571 0 2001.434343 Tm 25.316667 0 Td 58.333333 Tz (sodium ) Tj 2.313889 0 Td 54.208754 Tz (borohydride ) Tj 3.791667 0 Td 42.12963 Tz (\(1 ) Tj 0.777778 0 Td 46.180556 Tz (eq.\) ) Tj 1.322222 0 Td 61.574074 Tz (was ) Tj 1.322222 0 Td 58.333333 Tz (added ) Tj 1.944444 0 Td 46.990741 Tz (to ) Tj 0.797222 0 Td 48.611111 Tz (the ) Tj 1.108333 0 Td 47.800926 Tz (reaction ) Tj 2.527778 0 Td 42.12963 Tz (flask. ) Tj 51.428571 0 0 51.428571 0 1958.755635 Tm 25.297222 0 Td 63.734568 Tz (The ) Tj 1.283333 0 Td 48.206019 Tz (reaction ) Tj 2.45 0 Td 53.703704 Tz (mixture ) Tj 2.372222 0 Td 60.493827 Tz (was ) Tj 1.263889 0 Td 43.981481 Tz (stirred ) Tj 1.983333 0 Td 43.425926 Tz (until ) Tj 1.438889 0 Td 39.969136 Tz (all ) Tj 0.855556 0 Td 58.873457 Tz (sodium ) Tj 2.236111 0 Td 54.503367 Tz (borohydride ) Tj 51.428571 0 0 51.428571 0 1916.105196 Tm 25.297222 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 54.012346 Tz (\(~2 ) Tj 1.302778 0 Td 51.851852 Tz (minutes\) ) Tj 2.741667 0 Td 60.493827 Tz (and ) Tj 1.361111 0 Td 52.932099 Tz (continued ) Tj 3.111111 0 Td 44.155093 Tz (stirring ) Tj 2.372222 0 Td 48.611111 Tz (for ) Tj 1.108333 0 Td 56.712963 Tz (an ) Tj 0.933333 0 Td 63.194444 Tz (addi ) Tj 51.428571 0 0 51.428571 0 1874.599746 Tm 25.277778 0 Td 45.910494 Tz (tional ) Tj 1.963889 0 Td 53.472222 Tz (10 ) Tj 0.875 0 Td 50.636574 Tz (minutes. ) Tj 2.663889 0 Td 57.685185 Tz (Water ) Tj 1.905556 0 Td 46.990741 Tz (\(3 ) Tj 0.777778 0 Td 47.800926 Tz (eq.\) ) Tj 1.361111 0 Td 60.493827 Tz (was ) Tj 1.302778 0 Td 57.685185 Tz (added ) Tj 1.925 0 Td 59.41358 Tz (and ) Tj 1.263889 0 Td 50.771605 Tz (the ) Tj 1.127778 0 Td 48.611111 Tz (reaction ) Tj 40 0 0 40 0 1840 Tm 32.575 0 Td 68.452381 Tz (mixture ) Tj 3.2 0 Td 79.166667 Tz (was ) Tj 1.8 0 Td 57.142857 Tz (stirred ) Tj 2.725 0 Td 72.916667 Tz (an ) Tj 1.225 0 Td 62.083333 Tz (additional ) Tj 4.2 0 Td 70.833333 Tz (10 ) Tj 1.225 0 Td 64.583333 Tz (minutes. ) Tj 3.45 0 Td 65.277778 Tz (All ) Tj 1.55 0 Td 63.020833 Tz (solvents ) Tj 51.428571 0 0 51.428571 0 1793.702703 Tm 25.277778 0 Td 59.953704 Tz (were ) Tj 1.652778 0 Td 59.259259 Tz (removed ) Tj 2.702778 0 Td 43.75 Tz (in ) Tj 0.758333 0 Td 55.740741 Tz (vacuo ) Tj 1.866667 0 Td 58.333333 Tz (and ) Tj 1.263889 0 Td 47.530864 Tz (the ) Tj 1.069444 0 Td 51.041667 Tz (reduced, ) Tj 2.644444 0 Td 50.411523 Tz (protected ) Tj 2.897222 0 Td 48.611111 Tz (\(12:0\)-p- ) Tj 51.428571 0 0 51.428571 0 1754.697561 Tm 25.297222 0 Td 52.777778 Tz (phosphodiester ) Tj 4.647222 0 Td 61.574074 Tz (was ) Tj 1.341667 0 Td 47.800926 Tz (purified ) Tj 2.527778 0 Td 59.953704 Tz (by ) Tj 0.991667 0 Td 44.722222 Tz (flash ) Tj 1.633333 0 Td 59.41358 Tz (column ) Tj 2.411111 0 Td 59.217172 Tz (chromatogra ) Tj 51.428571 0 0 51.428571 0 1711.551122 Tm 25.297222 0 Td 59.41358 Tz (phy ) Tj 1.322222 0 Td 52.5 Tz (using ) Tj 1.788889 0 Td 72.376543 Tz (40% ) Tj 1.555556 0 Td 47.962963 Tz (ethyl ) Tj 1.672222 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.491667 0 Td 51.041667 Tz (then ) Tj 1.458333 0 Td 52.572016 Tz (switching ) Tj 3.072222 0 Td 43.75 Tz (to ) Tj 0.758333 0 Td 74.537037 Tz (80% ) Tj 51.428571 0 0 51.428571 0 1669.138462 Tm 25.297222 0 Td 47.314815 Tz (ethyl ) Tj 1.633333 0 Td 51.157407 Tz (acetate/hexane ) Tj 4.472222 0 Td 48.611111 Tz (for ) Tj 1.011111 0 Td 55.092593 Tz (a ) Tj 0.525 0 Td 47.800926 Tz (step ) Tj 1.341667 0 Td 49.826389 Tz (gradient ) Tj 2.547222 0 Td 45.37037 Tz (elution. ) Tj 52.857143 0 0 52.857143 0 1628.807792 Tm 25.313514 0 Td 62.012012 Tz (The ) Tj 1.456757 0 Td 49.662162 Tz (reduced, ) Tj 2.724324 0 Td 48.698699 Tz (protected ) Tj 2.97027 0 Td 49.627889 Tz (\(12:0\)-p-phosphodiester ) Tj 7.151351 0 Td 40.990991 Tz (\(1 ) Tj 0.889189 0 Td 45.720721 Tz (eq.\) ) Tj 51.428571 0 0 51.428571 0 1585.352287 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 49.259259 Tz (dried ) Tj 1.652778 0 Td 54.282407 Tz (over ) Tj 1.458333 0 Td 55.976431 Tz (phosphorous ) Tj 3.888889 0 Td 53.652263 Tz (pentoxide ) Tj 3.091667 0 Td 46.450617 Tz (for ) Tj 1.088889 0 Td 53.472222 Tz (12 ) Tj 0.836111 0 Td 53.148148 Tz (hours ) Tj 1.788889 0 Td 59.41358 Tz (and ) Tj 1.244444 0 Td 60.493827 Tz (dis ) Tj 40 0 0 40 0 1548 Tm 32.55 0 Td 66.666667 Tz (solved ) Tj 2.6 0 Td 68.287037 Tz (indichloromethane. ) Tj 7.55 0 Td 81.944444 Tz (The ) Tj 1.675 0 Td 61.979167 Tz (reaction ) Tj 3.175 0 Td 59.166667 Tz (flask ) Tj 1.975 0 Td 77.777778 Tz (was ) Tj 1.6 0 Td 64.583333 Tz (sealed ) Tj 2.475 0 Td 77.777778 Tz (and ) Tj 51.428571 0 0 51.428571 0 1501.80198 Tm 25.297222 0 Td 52.932099 Tz (placed ) Tj 2.080556 0 Td 45.37037 Tz (in ) Tj 0.7 0 Td 58.333333 Tz (an ) Tj 0.894444 0 Td 45.37037 Tz (ice ) Tj 0.991667 0 Td 51.851852 Tz (bath ) Tj 1.438889 0 Td 45.37037 Tz (to ) Tj 0.758333 0 Td 52.256944 Tz (maintain ) Tj 2.702778 0 Td 60.763889 Tz (0C. ) Tj 1.672222 0 Td 49.96142 Tz (temperature. ) Tj 3.830556 0 Td 66.435185 Tz (Deoxof ) Tj 51.428571 0 0 51.428571 0 1458.551331 Tm 25.297222 0 Td 50.231481 Tz (luor ) Tj 1.4 0 Td 46.990741 Tz (\(2 ) Tj 0.816667 0 Td 45.37037 Tz (eq.\) ) Tj 1.322222 0 Td 43.75 Tz (in ) Tj 0.797222 0 Td 54.228395 Tz (dichloromethane ) Tj 5.094444 0 Td 61.574074 Tz (was ) Tj 1.361111 0 Td 52.391975 Tz (slowly ) Tj 2.119444 0 Td 58.333333 Tz (added ) Tj 1.963889 0 Td 55.092593 Tz (\(~2 ) Tj 1.244444 0 Td 74.537037 Tz (min ) Tj 51.428571 0 0 51.428571 0 1415 Tm 25.277778 0 Td 44.290123 Tz (utes\). ) Tj 1.711111 0 Td 64.814815 Tz (The ) Tj 1.283333 0 Td 47.530864 Tz (ice ) Tj 0.991667 0 Td 51.041667 Tz (bath ) Tj 1.380556 0 Td 61.574074 Tz (was ) Tj 1.302778 0 Td 59.259259 Tz (removed ) Tj 2.605556 0 Td 59.41358 Tz (and ) Tj 1.186111 0 Td 49.691358 Tz (the ) Tj 1.05 0 Td 48.611111 Tz (reaction ) Tj 2.488889 0 Td 53.703704 Tz (mixture ) Tj 2.372222 0 Td 61.574074 Tz (was ) Tj 40 0 0 40 0 1382 Tm 32.55 0 Td 56.547619 Tz (stirred ) Tj 2.775 0 Td 61.111111 Tz (for ) Tj 1.55 0 Td 68.75 Tz (12 ) Tj 1.225 0 Td 63.194444 Tz (hours. ) Tj 2.675 0 Td 91.666667 Tz (An ) Tj 1.475 0 Td 62.083333 Tz (extraction ) Tj 4.125 0 Td 68.75 Tz (with ) Tj 2.075 0 Td 68.229167 Tz (dichloromethane/ ) Tj 51.428571 0 0 51.428571 0 1332.625815 Tm 25.316667 0 Td 48.251029 Tz (saturated ) Tj 2.936111 0 Td 58.873457 Tz (sodium ) Tj 2.469444 0 Td 51.557239 Tz (bicarbonate ) Tj 3.733333 0 Td 48.611111 Tz (solution ) Tj 2.761111 0 Td 43.209877 Tz (1:1 ) Tj 1.186111 0 Td 46.666667 Tz (\(v/v\) ) Tj 1.75 0 Td 61.574074 Tz (was ) Tj 1.438889 0 Td 64.814815 Tz (per ) Tj 51.428571 0 0 51.428571 0 1293.496644 Tm 25.297222 0 Td 58.333333 Tz (formed ) Tj 2.255556 0 Td 60.493827 Tz (and ) Tj 1.263889 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 51.388889 Tz (organic ) Tj 2.372222 0 Td 48.611111 Tz (layer ) Tj 1.613889 0 Td 61.574074 Tz (was ) Tj 1.302778 0 Td 46.342593 Tz (collected. ) Tj 51.428571 0 0 51.428571 0 1254.527812 Tm 26.016667 0 Td 52.5 Tz (After ) Tj 1.711111 0 Td 52.932099 Tz (drying ) Tj 2.080556 0 Td 43.75 Tz (in ) Tj 0.719444 0 Td 51.851852 Tz (vacuo, ) Tj 2.041667 0 Td 49.691358 Tz (the ) Tj 1.05 0 Td 50.411523 Tz (protected ) Tj 2.897222 0 Td 54.751462 Tz (\(12:0\)-p-monofluoro ) Tj 51.428571 0 0 51.428571 0 1213.697561 Tm 25.297222 0 Td 52.777778 Tz (phosphodiester ) Tj 4.647222 0 Td 61.574074 Tz (was ) Tj 1.341667 0 Td 47.800926 Tz (purified ) Tj 2.527778 0 Td 59.953704 Tz (by ) Tj 0.991667 0 Td 44.722222 Tz (flash ) Tj 1.633333 0 Td 59.41358 Tz (column ) Tj 2.411111 0 Td 59.217172 Tz (chromatogra ) Tj 51.428571 0 0 51.428571 0 1169.551122 Tm 25.297222 0 Td 59.41358 Tz (phy ) Tj 1.322222 0 Td 52.5 Tz (using ) Tj 1.788889 0 Td 72.376543 Tz (40% ) Tj 1.555556 0 Td 47.962963 Tz (ethyl ) Tj 1.672222 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.491667 0 Td 51.041667 Tz (then ) Tj 1.458333 0 Td 52.572016 Tz (switching ) Tj 3.072222 0 Td 43.75 Tz (to ) Tj 0.758333 0 Td 74.537037 Tz (80% ) Tj 51.428571 0 0 51.428571 0 1127.743468 Tm 25.297222 0 Td 47.314815 Tz (ethyl ) Tj 1.555556 0 Td 51.388889 Tz (acetate/hexane ) Tj 4.433333 0 Td 48.611111 Tz (for ) Tj 0.972222 0 Td 55.092593 Tz (a ) Tj 0.486111 0 Td 46.990741 Tz (step ) Tj 1.283333 0 Td 49.826389 Tz (gradient ) Tj 2.508333 0 Td 45.37037 Tz (elution. ) Tj 2.372222 0 Td 56.17284 Tz (For ) Tj 1.127778 0 Td 56.712963 Tz (deprotec ) Tj 51.428571 0 0 51.428571 0 1089.642599 Tm 25.277778 0 Td 44.074074 Tz (tion, ) Tj 1.652778 0 Td 49.691358 Tz (the ) Tj 1.186111 0 Td 50.771605 Tz (protected ) Tj 3.072222 0 Td 52.328431 Tz (\(12:0\)-p-monofluoro-phosphodiester ) Tj 10.966667 0 Td 43.75 Tz (\(1 ) Tj 51.428571 0 0 51.428571 0 1045.777917 Tm 25.297222 0 Td 46.180556 Tz (eq.\) ) Tj 1.361111 0 Td 60.493827 Tz (was ) Tj 1.361111 0 Td 50.411523 Tz (dissolved ) Tj 2.955556 0 Td 45.37037 Tz (in ) Tj 0.777778 0 Td 47.890947 Tz (pyridine. ) Tj 2.858333 0 Td 57.086895 Tz (N-propylamine ) Tj 4.686111 0 Td 55.092593 Tz (\(100 ) Tj 1.555556 0 Td 46.180556 Tz (eq.\) ) Tj 1.361111 0 Td 46.990741 Tz (in ) Tj 51.428571 0 0 51.428571 0 1001.206273 Tm 25.297222 0 Td 50.636574 Tz (pyridine ) Tj 2.566667 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 57.685185 Tz (added ) Tj 1.886111 0 Td 43.75 Tz (to ) Tj 0.7 0 Td 48.611111 Tz (the ) Tj 1.011111 0 Td 48.611111 Tz (reaction ) Tj 2.469444 0 Td 46.018519 Tz (flask ) Tj 1.477778 0 Td 58.333333 Tz (and ) Tj 1.205556 0 Td 49.691358 Tz (the ) Tj 0.991667 0 Td 48.611111 Tz (clear ) Tj 1.575 0 Td 49.016204 Tz (solution ) Tj 51.428571 0 0 51.428571 0 959.848447 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 43.981481 Tz (stirred ) Tj 2.041667 0 Td 47.530864 Tz (for ) Tj 1.088889 0 Td 55.092593 Tz (10 ) Tj 0.836111 0 Td 54.166667 Tz (minutes ) Tj 2.469444 0 Td 43.75 Tz (at ) Tj 0.719444 0 Td 62.384259 Tz (room ) Tj 1.711111 0 Td 50.231481 Tz (temperature. ) Tj 3.811111 0 Td 49.691358 Tz (All ) Tj 1.108333 0 Td 49.016204 Tz (solvents ) Tj 51.428571 0 0 51.428571 0 920.632803 Tm 25.277778 0 Td 59.953704 Tz (were ) Tj 1.633333 0 Td 59.722222 Tz (removed ) Tj 2.702778 0 Td 45.37037 Tz (in ) Tj 0.777778 0 Td 55.740741 Tz (vacuo ) Tj 1.866667 0 Td 46.990741 Tz (to ) Tj 0.758333 0 Td 49.259259 Tz (yield ) Tj 1.633333 0 Td 50.771605 Tz (the ) Tj 1.147222 0 Td 59.751157 Tz (n-propylammonium ) Tj 5.95 0 Td 42.939815 Tz (salt ) Tj 51.428571 0 0 51.428571 0 880.34296 Tm 25.297222 0 Td 58.333333 Tz (of ) Tj 0.972222 0 Td 48.611111 Tz (the ) Tj 1.225 0 Td 51.388889 Tz (\(12:0\)-p-monofluoro-phosphodiester. ) Tj 11.141667 0 Td 71.296296 Tz (An ) Tj 1.205556 0 Td 48.935185 Tz (extraction ) Tj 51.428571 0 0 51.428571 0 833.598226 Tm 25.277778 0 Td 54.282407 Tz (with ) Tj 1.691667 0 Td 52.759259 Tz (chloroform/methanol/brine ) Tj 8.361111 0 Td 44.907407 Tz (1:1.5:1 ) Tj 2.391667 0 Td 47.222222 Tz (\(v/v/v\) ) Tj 2.352778 0 Td 61.574074 Tz (was ) Tj 1.536111 0 Td 63.734568 Tz (per ) Tj 51.428571 0 0 51.428571 0 795.971429 Tm 25.297222 0 Td 58.333333 Tz (formed ) Tj 2.255556 0 Td 45.37037 Tz (to ) Tj 0.7 0 Td 51.446759 Tz (generate ) Tj 2.625 0 Td 48.611111 Tz (the ) Tj 1.011111 0 Td 58.873457 Tz (sodium ) Tj 2.294444 0 Td 42.939815 Tz (salt ) Tj 1.147222 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 48.611111 Tz (the ) Tj 1.030556 0 Td 55.283224 Tz (\(12:0\)-p-monofluo ) Tj 51.428571 0 0 51.428571 0 758 Tm 25.297222 0 Td 50.326797 Tz (rophosphodiester. ) Tj 51.428571 0 0 51.428571 0 678.046358 Tm 32.472222 0 Td 61.574074 Tz (Example ) Tj 2.761111 0 Td 58.333333 Tz (9 ) Tj 51.428571 0 0 51.428571 0 596 Tm 29.380556 0 Td 50.283751 Tz (\(16:0\)-o-difluorophosphodiester ) Tj 31.428571 0 0 31.428571 0 439 Tm 55.236364 0 Td 111.363636 Tz (O ) Tj 31.428571 0 0 31.428571 0 306 Tm 55.236364 0 Td 111.363636 Tz (OH ) Tj 38.571429 0 0 38.571429 0 252 Tm 41.559259 0 Td 97.942387 Tz (CHF ) Tj ET Q endstream endobj 190 0 obj << /Length 1 >> stream q endstream endobj 191 0 obj << /Length 42345 >> stream Q q 0.24 0 0 0.24 0 0 cm BT /F1 1 Tf 3 Tr 62.857143 0 0 62.857143 0 3023 Tm 17.325 0 Td 83.522727 Tz (US ) Tj 1.240909 0 Td 58.333333 Tz (8,022,239 ) Tj 3.388636 0 Td 74.242424 Tz (B2 ) Tj 52.857143 0 0 52.857143 0 2968 Tm 14.264865 0 Td 74.099099 Tz (17 ) Tj 51.428571 0 0 51.428571 0 2917.671214 Tm 7.116667 0 Td 55.976431 Tz (Phosphorous ) Tj 4.025 0 Td 53.030303 Tz (oxychloride ) Tj 3.791667 0 Td 42.12963 Tz (\(1 ) Tj 0.855556 0 Td 46.990741 Tz (eq.\) ) Tj 1.419444 0 Td 61.574074 Tz (was ) Tj 1.4 0 Td 58.333333 Tz (added ) Tj 2.041667 0 Td 46.990741 Tz (to ) Tj 0.836111 0 Td 55.092593 Tz (a ) Tj 0.680556 0 Td 55.740741 Tz (round ) Tj 51.428571 0 0 51.428571 0 2867.324528 Tm 6.338889 0 Td 57.253086 Tz (bottom ) Tj 2.391667 0 Td 46.018519 Tz (flask ) Tj 1.633333 0 Td 58.333333 Tz (and ) Tj 1.341667 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 46.990741 Tz (in ) Tj 0.875 0 Td 49.907407 Tz (tetrahydrofuran ) Tj 4.783333 0 Td 56.17284 Tz (\(THF\). ) Tj 2.313889 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 2818.95449 Tm 6.358333 0 Td 57.037037 Tz (round ) Tj 1.847222 0 Td 56.712963 Tz (bottom ) Tj 2.197222 0 Td 46.666667 Tz (flask ) Tj 1.536111 0 Td 60.493827 Tz (was ) Tj 1.263889 0 Td 51.041667 Tz (then ) Tj 1.4 0 Td 52.391975 Tz (placed ) Tj 2.061111 0 Td 43.75 Tz (in ) Tj 0.661111 0 Td 59.953704 Tz (an ) Tj 0.875 0 Td 46.450617 Tz (ice ) Tj 0.952778 0 Td 52.662037 Tz (bath ) Tj 1.419444 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 53.472222 Tz (maintain ) Tj 51.428571 0 0 51.428571 0 2772.452261 Tm 6.358333 0 Td 51.851852 Tz (a ) Tj 0.544444 0 Td 63.194444 Tz (0C. ) Tj 1.769444 0 Td 50.231481 Tz (temperature. ) Tj 3.908333 0 Td 56.860269 Tz (Hexadecanol ) Tj 4.005556 0 Td 42.12963 Tz (\(1 ) Tj 0.797222 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 50.411523 Tz (dissolved ) Tj 2.936111 0 Td 45.37037 Tz (in ) Tj 0.758333 0 Td 76.697531 Tz (THF ) Tj 51.428571 0 0 51.428571 0 2725.895911 Tm 6.338889 0 Td 54.282407 Tz (with ) Tj 1.497222 0 Td 49.85755 Tz (triethylamine ) Tj 4.083333 0 Td 63.518519 Tz (\(TEA\) ) Tj 2.1 0 Td 42.12963 Tz (\(1 ) Tj 0.777778 0 Td 46.180556 Tz (eq.\) ) Tj 1.283333 0 Td 62.654321 Tz (was ) Tj 1.302778 0 Td 58.981481 Tz (added ) Tj 1.963889 0 Td 55.092593 Tz (dropwise ) Tj 2.858333 0 Td 45.37037 Tz (to ) Tj 0.738889 0 Td 49.691358 Tz (the ) Tj 51.428571 0 0 51.428571 0 2678.215457 Tm 6.358333 0 Td 55.976431 Tz (phosphorous ) Tj 3.830556 0 Td 56.17284 Tz (oxychloride/THF ) Tj 5.191667 0 Td 46.090535 Tz (solution. ) Tj 2.605556 0 Td 64.814815 Tz (Once ) Tj 1.672222 0 Td 39.969136 Tz (all ) Tj 0.836111 0 Td 53.472222 Tz (of ) Tj 0.738889 0 Td 47.530864 Tz (the ) Tj 0.991667 0 Td 66.435185 Tz (hexa ) Tj 51.428571 0 0 51.428571 0 2626 Tm 6.358333 0 Td 60.925926 Tz (decanol/THF/TEA ) Tj 5.658333 0 Td 48.611111 Tz (solution ) Tj 2.527778 0 Td 61.574074 Tz (was ) Tj 1.302778 0 Td 58.981481 Tz (added ) Tj 1.963889 0 Td 57.523148 Tz (\(-20 ) Tj 1.594444 0 Td 46.990741 Tz (min.\), ) Tj 1.905556 0 Td 48.611111 Tz (the ) Tj 1.108333 0 Td 58.333333 Tz (reac ) Tj 40 0 0 40 0 2587 Tm 8.15 0 Td 61.458333 Tz (tion ) Tj 1.75 0 Td 67.857143 Tz (mixture ) Tj 3.05 0 Td 79.166667 Tz (was ) Tj 1.675 0 Td 56.547619 Tz (stirred ) Tj 2.6 0 Td 61.111111 Tz (for ) Tj 1.275 0 Td 72.916667 Tz (an ) Tj 1.075 0 Td 62.5 Tz (additional ) Tj 3.95 0 Td 81.25 Tz (40 ) Tj 1.175 0 Td 69.642857 Tz (minutes ) Tj 3.15 0 Td 56.25 Tz (at ) Tj 0.9 0 Td 77.083333 Tz (0C. ) Tj 51.428571 0 0 51.428571 0 2535.268695 Tm 6.358333 0 Td 87.5 Tz (A ) Tj 0.816667 0 Td 48.206019 Tz (solution ) Tj 2.586111 0 Td 61.574074 Tz (of ) Tj 0.894444 0 Td 55.864198 Tz (o-hydroxybenzaldehyde ) Tj 7.330556 0 Td 42.12963 Tz (\(1 ) Tj 0.836111 0 Td 47.800926 Tz (eq.\) ) Tj 1.4 0 Td 46.990741 Tz (in ) Tj 0.816667 0 Td 77.777778 Tz (THF ) Tj 1.672222 0 Td 61.574074 Tz (was ) Tj 51.428571 0 0 51.428571 0 2485.25641 Tm 6.358333 0 Td 58.333333 Tz (added ) Tj 1.886111 0 Td 55.902778 Tz (dropwise ) Tj 2.819444 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 49.691358 Tz (the ) Tj 1.05 0 Td 48.611111 Tz (reaction ) Tj 2.469444 0 Td 46.666667 Tz (flask ) Tj 1.536111 0 Td 53.06713 Tz (followed ) Tj 2.702778 0 Td 58.333333 Tz (by ) Tj 0.836111 0 Td 79.938272 Tz (TEA ) Tj 1.594444 0 Td 43.75 Tz (\(1 ) Tj 0.738889 0 Td 46.180556 Tz (eq.\) ) Tj 40 0 0 40 0 2443 Tm 8.175 0 Td 58.333333 Tz (in ) Tj 0.875 0 Td 80.208333 Tz (THF. ) Tj 2.15 0 Td 79.166667 Tz (The ) Tj 1.65 0 Td 62.5 Tz (reaction ) Tj 3.25 0 Td 68.452381 Tz (mixture ) Tj 3.05 0 Td 80.555556 Tz (was ) Tj 1.65 0 Td 57.142857 Tz (stirred ) Tj 2.6 0 Td 62.5 Tz (for ) Tj 1.25 0 Td 75 Tz (an ) Tj 1.075 0 Td 62.916667 Tz (additional ) Tj 3.95 0 Td 81.25 Tz (40 ) Tj 51.428571 0 0 51.428571 0 2388.187421 Tm 6.358333 0 Td 54.166667 Tz (minutes ) Tj 2.45 0 Td 45.37037 Tz (at ) Tj 0.719444 0 Td 59.143519 Tz (0C. ) Tj 1.594444 0 Td 57.685185 Tz (Water ) Tj 1.886111 0 Td 42.12963 Tz (\(1 ) Tj 0.719444 0 Td 47.800926 Tz (eq.\) ) Tj 1.263889 0 Td 59.41358 Tz (and ) Tj 1.205556 0 Td 78.858025 Tz (TEA ) Tj 1.594444 0 Td 40.509259 Tz (\(1 ) Tj 0.719444 0 Td 47.800926 Tz (eq.\) ) Tj 1.302778 0 Td 58.333333 Tz (were ) Tj 1.536111 0 Td 58.333333 Tz (added ) Tj 1.905556 0 Td 46.990741 Tz (to ) Tj 40 0 0 40 0 2347 Tm 8.15 0 Td 65.277778 Tz (the ) Tj 1.375 0 Td 61.979167 Tz (reaction ) Tj 3.2 0 Td 69.047619 Tz (mixture ) Tj 3.05 0 Td 75.833333 Tz (which ) Tj 2.475 0 Td 79.166667 Tz (was ) Tj 1.625 0 Td 69.642857 Tz (allowed ) Tj 3.125 0 Td 58.333333 Tz (to ) Tj 0.925 0 Td 58.928571 Tz (stirfor ) Tj 2.65 0 Td 77.083333 Tz (60 ) Tj 1.15 0 Td 69.047619 Tz (minutes ) Tj 40 0 0 40 0 2300 Tm 8.175 0 Td 58.333333 Tz (at ) Tj 0.9 0 Td 79.166667 Tz (0C. ) Tj 2.125 0 Td 81.944444 Tz (The ) Tj 1.65 0 Td 65.104167 Tz (contents ) Tj 3.4 0 Td 72.916667 Tz (of ) Tj 0.975 0 Td 63.888889 Tz (the ) Tj 1.4 0 Td 61.979167 Tz (reaction ) Tj 3.2 0 Td 60 Tz (flask ) Tj 2.025 0 Td 75 Tz (were ) Tj 2 0 Td 66.666667 Tz (then ) Tj 1.875 0 Td 80.555556 Tz (vacuum ) Tj 40 0 0 40 0 2252 Tm 8.175 0 Td 55.208333 Tz (filtered ) Tj 2.95 0 Td 75 Tz (and ) Tj 1.65 0 Td 64.166667 Tz (dried ) Tj 2.25 0 Td 58.333333 Tz (in ) Tj 1.025 0 Td 66.666667 Tz (vacuo. ) Tj 2.7 0 Td 91.666667 Tz (An ) Tj 1.425 0 Td 61.666667 Tz (extraction ) Tj 4.025 0 Td 68.75 Tz (with ) Tj 1.975 0 Td 66.287879 Tz (chloroform? ) Tj 51.428571 0 0 51.428571 0 2199.240629 Tm 6.358333 0 Td 54.166667 Tz (methanol/water ) Tj 4.841667 0 Td 45.37037 Tz (1:1.5:1 ) Tj 2.236111 0 Td 47.222222 Tz (\(v/v/v\) ) Tj 2.275 0 Td 47.800926 Tz (respectively ) Tj 3.694444 0 Td 62.654321 Tz (was ) Tj 1.380556 0 Td 56.893004 Tz (performed ) Tj 51.428571 0 0 51.428571 0 2151.584158 Tm 6.358333 0 Td 58.333333 Tz (and ) Tj 1.361111 0 Td 49.691358 Tz (the ) Tj 1.205556 0 Td 51.006441 Tz (\(16:0\)-o-phosphodiester ) Tj 7.330556 0 Td 62.654321 Tz (was ) Tj 1.419444 0 Td 55.902778 Tz (used ) Tj 1.633333 0 Td 53.240741 Tz (without ) Tj 2.527778 0 Td 48.148148 Tz (further ) Tj 51.428571 0 0 51.428571 0 2108 Tm 6.358333 0 Td 45.121083 Tz (purification. ) Tj 51.428571 0 0 51.428571 0 2059.387909 Tm 7.097222 0 Td 62.654321 Tz (The ) Tj 1.341667 0 Td 44.722222 Tz (relatively ) Tj 2.877778 0 Td 54.282407 Tz (pure ) Tj 1.516667 0 Td 51.006441 Tz (\(16:0\)-o-phosphodiester ) Tj 7.213889 0 Td 43.75 Tz (\(1 ) Tj 0.777778 0 Td 43.425926 Tz (eq.\), ) Tj 1.536111 0 Td 81.018519 Tz (DCC ) Tj 51.428571 0 0 51.428571 0 2008.081556 Tm 6.377778 0 Td 46.990741 Tz (\(2.2 ) Tj 1.341667 0 Td 61.574074 Tz (eq\) ) Tj 1.302778 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 87.5 Tz (DMAP ) Tj 2.313889 0 Td 43.75 Tz (\(0.1 ) Tj 1.322222 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 58.333333 Tz (were ) Tj 1.594444 0 Td 49.907407 Tz (dried ) Tj 1.711111 0 Td 53.472222 Tz (over ) Tj 1.458333 0 Td 56.565657 Tz (phosphorous ) Tj 51.428571 0 0 51.428571 0 1960.961905 Tm 6.358333 0 Td 53.292181 Tz (pentoxide ) Tj 2.994444 0 Td 49.691358 Tz (for ) Tj 1.05 0 Td 56.712963 Tz (12 ) Tj 0.797222 0 Td 49.151235 Tz (hours. ) Tj 1.905556 0 Td 56.442901 Tz (Cyanoethanol ) Tj 4.2 0 Td 43.75 Tz (\(1.1 ) Tj 1.263889 0 Td 47.800926 Tz (eq.\) ) Tj 1.283333 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 51.131687 Tz (dissolved ) Tj 51.428571 0 0 51.428571 0 1910.654501 Tm 6.358333 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 54.228395 Tz (dichloromethane ) Tj 5.036111 0 Td 59.41358 Tz (and ) Tj 1.244444 0 Td 49.259259 Tz (dried ) Tj 1.633333 0 Td 53.472222 Tz (with ) Tj 1.497222 0 Td 61.213992 Tz (magnesium ) Tj 3.5 0 Td 45.833333 Tz (sulfate ) Tj 2.1 0 Td 47.530864 Tz (for ) Tj 1.069444 0 Td 53.472222 Tz (12 ) Tj 51.428571 0 0 51.428571 0 1864.44484 Tm 6.338889 0 Td 49.691358 Tz (hours. ) Tj 1.983333 0 Td 62.654321 Tz (The ) Tj 1.302778 0 Td 51.147343 Tz (\(16:0\)-o-phosphodiester ) Tj 7.213889 0 Td 60.493827 Tz (was ) Tj 1.302778 0 Td 50.411523 Tz (dissolved ) Tj 2.877778 0 Td 46.990741 Tz (in ) Tj 0.758333 0 Td 56.712963 Tz (dichlo ) Tj 40 0 0 40 0 1824 Tm 8.175 0 Td 73.148148 Tz (romethane ) Tj 4.2 0 Td 75 Tz (and ) Tj 1.625 0 Td 105.555556 Tz (DCC ) Tj 2.15 0 Td 75 Tz (and ) Tj 1.625 0 Td 111.458333 Tz (DMAP ) Tj 2.925 0 Td 76.041667 Tz (were ) Tj 2.075 0 Td 74.166667 Tz (added ) Tj 2.5 0 Td 56.25 Tz (to ) Tj 0.975 0 Td 62.5 Tz (the ) Tj 1.4 0 Td 63.020833 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 1772.180879 Tm 6.358333 0 Td 42.669753 Tz (flask. ) Tj 1.788889 0 Td 62.654321 Tz (The ) Tj 1.361111 0 Td 46.666667 Tz (flask ) Tj 1.633333 0 Td 61.574074 Tz (was ) Tj 1.361111 0 Td 50.231481 Tz (sealed ) Tj 2.041667 0 Td 53.472222 Tz (with ) Tj 1.536111 0 Td 51.851852 Tz (a ) Tj 0.583333 0 Td 57.253086 Tz (septum ) Tj 2.313889 0 Td 59.41358 Tz (and ) Tj 1.283333 0 Td 56.712963 Tz (purged ) Tj 2.294444 0 Td 54.282407 Tz (with ) Tj 51.428571 0 0 51.428571 0 1727.976553 Tm 6.358333 0 Td 50.231481 Tz (nitrogen ) Tj 2.547222 0 Td 46.018519 Tz (after ) Tj 1.497222 0 Td 55.092593 Tz (adding ) Tj 2.1 0 Td 50.771605 Tz (the ) Tj 1.05 0 Td 53.472222 Tz (cyanoethanol ) Tj 4.005556 0 Td 46.450617 Tz (Solution. ) Tj 2.625 0 Td 64.814815 Tz (The ) Tj 1.302778 0 Td 49.421296 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 1680.476433 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.361111 0 Td 44.444444 Tz (stirred ) Tj 2.080556 0 Td 48.611111 Tz (for ) Tj 1.05 0 Td 59.953704 Tz (48 ) Tj 0.952778 0 Td 53.148148 Tz (hours ) Tj 1.808333 0 Td 46.990741 Tz (at ) Tj 0.777778 0 Td 62.384259 Tz (room ) Tj 1.730556 0 Td 50.231481 Tz (temperature. ) Tj 3.869444 0 Td 57.685185 Tz (Water ) Tj 1.944444 0 Td 46.990741 Tz (\(5 ) Tj 0.797222 0 Td 46.180556 Tz (eq.\) ) Tj 41.428571 0 0 41.428571 0 1640 Tm 7.868966 0 Td 77.777778 Tz (was ) Tj 1.665517 0 Td 72.413793 Tz (added ) Tj 2.413793 0 Td 73.754789 Tz (and ) Tj 1.568966 0 Td 61.685824 Tz (the ) Tj 1.351724 0 Td 60.344828 Tz (reaction ) Tj 3.210345 0 Td 66.091954 Tz (mixture ) Tj 3.017241 0 Td 76.436782 Tz (was ) Tj 1.641379 0 Td 55.172414 Tz (stirred ) Tj 2.558621 0 Td 61.685824 Tz (for ) Tj 1.303448 0 Td 70.402299 Tz (an ) Tj 1.086207 0 Td 78.448276 Tz (addi ) Tj 40 0 0 40 0 1594 Tm 8.15 0 Td 59.722222 Tz (tional ) Tj 2.6 0 Td 79.166667 Tz (24 ) Tj 1.375 0 Td 63.194444 Tz (hours. ) Tj 2.75 0 Td 80.555556 Tz (The ) Tj 1.875 0 Td 65.104167 Tz (contents ) Tj 3.575 0 Td 75 Tz (of ) Tj 1.225 0 Td 63.888889 Tz (the ) Tj 1.6 0 Td 62.5 Tz (reaction ) Tj 3.475 0 Td 59.166667 Tz (flask ) Tj 2.225 0 Td 75 Tz (were ) Tj 40 0 0 40 0 1548 Tm 8.175 0 Td 81.25 Tz (vacuum ) Tj 3.2 0 Td 55.208333 Tz (filtered ) Tj 2.85 0 Td 77.777778 Tz (and ) Tj 1.65 0 Td 64.166667 Tz (dried ) Tj 2.15 0 Td 60.416667 Tz (in ) Tj 0.975 0 Td 67.361111 Tz (vacuo. ) Tj 2.65 0 Td 66.666667 Tz (After ) Tj 2.225 0 Td 70.833333 Tz (an ) Tj 1.125 0 Td 61.666667 Tz (extraction ) Tj 4 0 Td 68.75 Tz (with ) Tj 51.428571 0 0 51.428571 0 1497.390156 Tm 6.358333 0 Td 51.851852 Tz (chloroform/brine ) Tj 5.191667 0 Td 44.290123 Tz (1:1 ) Tj 1.069444 0 Td 43.209877 Tz (\(v/v\), ) Tj 1.730556 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 54.62963 Tz (coupled ) Tj 2.45 0 Td 53.703704 Tz (product ) Tj 2.411111 0 Td 61.574074 Tz (was ) Tj 1.263889 0 Td 48.206019 Tz (purified ) Tj 51.428571 0 0 51.428571 0 1453.369077 Tm 6.338889 0 Td 61.574074 Tz (by ) Tj 1.011111 0 Td 45.37037 Tz (flash ) Tj 1.652778 0 Td 59.953704 Tz (column ) Tj 2.45 0 Td 56.25 Tz (chromatography ) Tj 4.997222 0 Td 53.148148 Tz (using ) Tj 1.847222 0 Td 73.45679 Tz (40% ) Tj 1.575 0 Td 48.611111 Tz (ethyl ) Tj 1.730556 0 Td 46.585648 Tz (acetate/ ) Tj 51.428571 0 0 51.428571 0 1405.686061 Tm 6.338889 0 Td 57.79321 Tz (hexane ) Tj 2.236111 0 Td 51.041667 Tz (then ) Tj 1.419444 0 Td 51.851852 Tz (switching ) Tj 2.955556 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 73.45679 Tz (80% ) Tj 1.477778 0 Td 47.962963 Tz (ethyl ) Tj 1.594444 0 Td 51.157407 Tz (acetate/hexane ) Tj 4.433333 0 Td 48.611111 Tz (for ) Tj 1.011111 0 Td 51.851852 Tz (a ) Tj 0.486111 0 Td 47.800926 Tz (step ) Tj 51.428571 0 0 51.428571 0 1361.169492 Tm 6.358333 0 Td 49.826389 Tz (gradient ) Tj 2.547222 0 Td 45.775463 Tz (elution. ) Tj 51.428571 0 0 51.428571 0 1318.763906 Tm 7.097222 0 Td 51.851852 Tz (After ) Tj 1.788889 0 Td 45.121083 Tz (purification, ) Tj 3.811111 0 Td 48.611111 Tz (the ) Tj 1.108333 0 Td 50.771605 Tz (protected ) Tj 3.013889 0 Td 51.006441 Tz (\(16:0\)-o-phosphodiester ) Tj 51.428571 0 0 51.428571 0 1271.093671 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.4 0 Td 41.481481 Tz (split ) Tj 1.477778 0 Td 46.180556 Tz (into ) Tj 1.361111 0 Td 59.41358 Tz (two ) Tj 1.341667 0 Td 52.777778 Tz (roughly ) Tj 2.45 0 Td 53.148148 Tz (equal ) Tj 1.808333 0 Td 47.530864 Tz (portions. ) Tj 2.819444 0 Td 63.734568 Tz (The ) Tj 1.380556 0 Td 37.592593 Tz (first ) Tj 1.322222 0 Td 51.388889 Tz (portion ) Tj 51.428571 0 0 51.428571 0 1221.081352 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.380556 0 Td 55.092593 Tz (used ) Tj 1.536111 0 Td 48.611111 Tz (for ) Tj 1.069444 0 Td 45.910494 Tz (direct ) Tj 1.866667 0 Td 46.720679 Tz (fluorination ) Tj 3.577778 0 Td 59.41358 Tz (and ) Tj 1.263889 0 Td 50.771605 Tz (the ) Tj 1.147222 0 Td 55.632716 Tz (second ) Tj 2.197222 0 Td 50 Tz (portion ) Tj 2.333333 0 Td 61.574074 Tz (was ) Tj 51.428571 0 0 51.428571 0 1175.833753 Tm 6.338889 0 Td 55.902778 Tz (used ) Tj 1.633333 0 Td 48.611111 Tz (for ) Tj 1.127778 0 Td 50.411523 Tz (reduction ) Tj 3.013889 0 Td 52.662037 Tz (followed ) Tj 2.8 0 Td 59.953704 Tz (by ) Tj 1.011111 0 Td 46.720679 Tz (fluorination ) Tj 3.655556 0 Td 58.738426 Tz (\(Example ) Tj 3.15 0 Td 44.560185 Tz (10\). ) Tj 51.428571 0 0 51.428571 0 1133.270064 Tm 6.377778 0 Td 50.771605 Tz (Protected ) Tj 3.091667 0 Td 51.006441 Tz (\(16:0\)-o-phosphodiester ) Tj 7.388889 0 Td 40.509259 Tz (\(1 ) Tj 0.933333 0 Td 46.180556 Tz (eq.\) ) Tj 1.477778 0 Td 60.493827 Tz (was ) Tj 1.438889 0 Td 49.907407 Tz (dried ) Tj 1.847222 0 Td 54.282407 Tz (over ) Tj 51.428571 0 0 51.428571 0 1086.271411 Tm 6.358333 0 Td 55.976431 Tz (phosphorous ) Tj 3.85 0 Td 53.652263 Tz (pentoxide ) Tj 3.052778 0 Td 48.611111 Tz (for ) Tj 1.069444 0 Td 55.092593 Tz (12 ) Tj 0.816667 0 Td 53.796296 Tz (hours ) Tj 1.769444 0 Td 58.333333 Tz (and ) Tj 1.225 0 Td 50.771605 Tz (dissolved ) Tj 2.897222 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 56.712963 Tz (dichlo ) Tj 51.428571 0 0 51.428571 0 1037.96 Tm 6.358333 0 Td 53.796296 Tz (romethane. ) Tj 3.363889 0 Td 63.734568 Tz (The ) Tj 1.283333 0 Td 48.611111 Tz (reaction ) Tj 2.508333 0 Td 46.018519 Tz (flask ) Tj 1.516667 0 Td 60.493827 Tz (was ) Tj 1.225 0 Td 50.771605 Tz (sealed ) Tj 1.963889 0 Td 58.333333 Tz (and ) Tj 1.166667 0 Td 53.472222 Tz (placed ) Tj 2.061111 0 Td 45.37037 Tz (in ) Tj 0.7 0 Td 56.712963 Tz (an ) Tj 0.855556 0 Td 46.450617 Tz (ice ) Tj 51.428571 0 0 51.428571 0 993.544021 Tm 6.338889 0 Td 52.662037 Tz (bath ) Tj 1.555556 0 Td 45.37037 Tz (to ) Tj 0.875 0 Td 52.256944 Tz (maintain ) Tj 2.819444 0 Td 51.851852 Tz (0 ) Tj 0.894444 0 Td 55.092593 Tz (C. ) Tj 0.991667 0 Td 49.96142 Tz (temperature. ) Tj 3.927778 0 Td 55.416667 Tz (Deoxofluor ) Tj 3.597222 0 Td 46.990741 Tz (\(2 ) Tj 0.875 0 Td 46.180556 Tz (eq.\) ) Tj 1.380556 0 Td 50.231481 Tz (in ) Tj 51.428571 0 0 51.428571 0 946.927811 Tm 6.358333 0 Td 54.444444 Tz (dichloromethane ) Tj 5.036111 0 Td 62.654321 Tz (was ) Tj 1.283333 0 Td 52.932099 Tz (slowly ) Tj 2.041667 0 Td 58.981481 Tz (added ) Tj 1.905556 0 Td 55.092593 Tz (\(-2 ) Tj 1.205556 0 Td 52.256944 Tz (minutes\) ) Tj 2.644444 0 Td 59.41358 Tz (and ) Tj 1.186111 0 Td 51.388889 Tz (ethanol ) Tj 51.428571 0 0 51.428571 0 903.175258 Tm 6.377778 0 Td 46.990741 Tz (\(0.2 ) Tj 1.341667 0 Td 46.180556 Tz (eq.\) ) Tj 1.322222 0 Td 61.574074 Tz (was ) Tj 1.341667 0 Td 57.685185 Tz (added ) Tj 1.944444 0 Td 45.37037 Tz (to ) Tj 0.777778 0 Td 51.446759 Tz (generate ) Tj 2.663889 0 Td 51.851852 Tz (a ) Tj 0.525 0 Td 44.650206 Tz (catalyst, ) Tj 2.663889 0 Td 55.092593 Tz (HF. ) Tj 1.205556 0 Td 63.734568 Tz (The ) Tj 1.341667 0 Td 47.530864 Tz (ice ) Tj 1.069444 0 Td 53.472222 Tz (bath ) Tj 40 0 0 40 0 862 Tm 8.15 0 Td 80.555556 Tz (was ) Tj 1.875 0 Td 77.380952 Tz (removed ) Tj 3.625 0 Td 75 Tz (and ) Tj 1.725 0 Td 63.888889 Tz (the ) Tj 1.525 0 Td 62.5 Tz (reaction ) Tj 3.425 0 Td 69.047619 Tz (mixture ) Tj 3.3 0 Td 79.166667 Tz (was ) Tj 1.825 0 Td 57.142857 Tz (stirred ) Tj 2.775 0 Td 62.5 Tz (for ) Tj 1.55 0 Td 70.833333 Tz (16 ) Tj 40 0 0 40 0 817 Tm 8.15 0 Td 63.888889 Tz (hours. ) Tj 2.5 0 Td 91.666667 Tz (An ) Tj 1.325 0 Td 61.666667 Tz (extraction ) Tj 3.925 0 Td 68.75 Tz (with ) Tj 1.875 0 Td 66.166667 Tz (dichloromethane/saturated ) Tj 10.125 0 Td 75.694444 Tz (sodium ) Tj 51.428571 0 0 51.428571 0 765.583433 Tm 6.338889 0 Td 51.557239 Tz (bicarbonate ) Tj 3.558333 0 Td 48.611111 Tz (solution ) Tj 2.547222 0 Td 43.209877 Tz (1:1 ) Tj 1.030556 0 Td 46.666667 Tz (\(v/v\) ) Tj 1.536111 0 Td 61.574074 Tz (was ) Tj 1.244444 0 Td 56.532922 Tz (performed ) Tj 3.169444 0 Td 59.41358 Tz (and ) Tj 1.225 0 Td 48.611111 Tz (the ) Tj 0.991667 0 Td 51.851852 Tz (organic ) Tj 51.428571 0 0 51.428571 0 719.202899 Tm 6.358333 0 Td 49.259259 Tz (layer ) Tj 1.652778 0 Td 61.574074 Tz (was ) Tj 1.283333 0 Td 46.342593 Tz (collected. ) Tj 51.428571 0 0 51.428571 0 673.542553 Tm 7.097222 0 Td 51.851852 Tz (After ) Tj 1.866667 0 Td 52.932099 Tz (drying ) Tj 2.275 0 Td 42.12963 Tz (in ) Tj 0.894444 0 Td 52.391975 Tz (vacuo, ) Tj 2.255556 0 Td 48.611111 Tz (the ) Tj 1.186111 0 Td 50.771605 Tz (protected ) Tj 3.091667 0 Td 50.517429 Tz (\(16:0\)-o-difluoro ) Tj 51.428571 0 0 51.428571 0 631.69475 Tm 6.358333 0 Td 52.777778 Tz (phosphodiester ) Tj 4.647222 0 Td 61.574074 Tz (was ) Tj 1.361111 0 Td 47.395833 Tz (purified ) Tj 2.508333 0 Td 59.953704 Tz (by ) Tj 1.011111 0 Td 44.722222 Tz (flash ) Tj 1.613889 0 Td 59.41358 Tz (column ) Tj 2.411111 0 Td 59.217172 Tz (chromatogra ) Tj 51.428571 0 0 51.428571 0 583.551122 Tm 6.358333 0 Td 59.41358 Tz (phy ) Tj 1.322222 0 Td 52.5 Tz (using ) Tj 1.788889 0 Td 72.376543 Tz (40% ) Tj 1.555556 0 Td 47.962963 Tz (ethyl ) Tj 1.672222 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.491667 0 Td 51.041667 Tz (then ) Tj 1.458333 0 Td 52.572016 Tz (switching ) Tj 3.072222 0 Td 43.75 Tz (to ) Tj 0.758333 0 Td 74.537037 Tz (80% ) Tj 51.428571 0 0 51.428571 0 537.748517 Tm 6.358333 0 Td 47.314815 Tz (ethyl ) Tj 1.594444 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.394444 0 Td 48.611111 Tz (for ) Tj 0.972222 0 Td 58.333333 Tz (a ) Tj 0.486111 0 Td 47.800926 Tz (step ) Tj 1.283333 0 Td 49.826389 Tz (gradient ) Tj 2.508333 0 Td 45.775463 Tz (elution. ) Tj 2.372222 0 Td 56.17284 Tz (For ) Tj 1.127778 0 Td 56.712963 Tz (deprotec ) Tj 51.428571 0 0 51.428571 0 494.661853 Tm 6.338889 0 Td 44.074074 Tz (tion, ) Tj 1.613889 0 Td 48.611111 Tz (the ) Tj 1.108333 0 Td 50.411523 Tz (protected ) Tj 2.955556 0 Td 50.130208 Tz (\(16:0\)-o-difluoro-phosphodiester ) Tj 9.858333 0 Td 42.12963 Tz (\(1 ) Tj 0.836111 0 Td 46.180556 Tz (eq.\) ) Tj 51.428571 0 0 51.428571 0 447.829448 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 50.771605 Tz (dissolved ) Tj 2.955556 0 Td 43.75 Tz (in ) Tj 0.719444 0 Td 48.251029 Tz (pyridine. ) Tj 2.819444 0 Td 56.837607 Tz (N-propylamine ) Tj 4.647222 0 Td 55.902778 Tz (\(100 ) Tj 1.516667 0 Td 46.180556 Tz (eq.\) ) Tj 1.322222 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 59.143519 Tz (pyri ) Tj 40 0 0 40 0 405 Tm 8.175 0 Td 67.708333 Tz (dine ) Tj 1.8 0 Td 76.388889 Tz (was ) Tj 1.55 0 Td 75.833333 Tz (added ) Tj 2.4 0 Td 60.416667 Tz (to ) Tj 0.925 0 Td 62.5 Tz (the ) Tj 1.3 0 Td 61.979167 Tz (reaction ) Tj 3.15 0 Td 68.229167 Tz (flaskand ) Tj 3.425 0 Td 65.277778 Tz (the ) Tj 1.325 0 Td 61.666667 Tz (clear ) Tj 1.95 0 Td 63.020833 Tz (solution ) Tj 3.2 0 Td 79.166667 Tz (was ) Tj 51.428571 0 0 51.428571 0 352.82439 Tm 6.377778 0 Td 43.981481 Tz (stirred ) Tj 1.983333 0 Td 48.611111 Tz (for ) Tj 1.088889 0 Td 53.472222 Tz (10 ) Tj 0.816667 0 Td 54.166667 Tz (minutes ) Tj 2.411111 0 Td 45.37037 Tz (at ) Tj 0.719444 0 Td 61.574074 Tz (room ) Tj 1.652778 0 Td 50.501543 Tz (temperature. ) Tj 3.772222 0 Td 50.771605 Tz (All ) Tj 1.088889 0 Td 48.611111 Tz (solvents ) Tj 2.527778 0 Td 58.333333 Tz (were ) Tj 51.428571 0 0 51.428571 0 308.621359 Tm 6.358333 0 Td 60.185185 Tz (removed ) Tj 2.702778 0 Td 43.75 Tz (in ) Tj 0.738889 0 Td 55.092593 Tz (vacuo ) Tj 1.847222 0 Td 45.37037 Tz (to ) Tj 0.7 0 Td 49.907407 Tz (yield ) Tj 1.633333 0 Td 50.771605 Tz (the ) Tj 1.088889 0 Td 59.953704 Tz (n-propylammonium ) Tj 5.930556 0 Td 42.939815 Tz (salt ) Tj 1.186111 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 49.691358 Tz (the ) Tj 51.428571 0 0 51.428571 0 264.533958 Tm 6.377778 0 Td 49.016204 Tz (\(16:0\)-o-difluorophosphodiester. ) Tj 9.625 0 Td 72.916667 Tz (An ) Tj 1.088889 0 Td 48.287037 Tz (extraction ) Tj 3.130556 0 Td 54.282407 Tz (with ) Tj 1.477778 0 Td 58.873457 Tz (chloro ) Tj 51.428571 0 0 51.428571 0 216.381969 Tm 6.358333 0 Td 52.875244 Tz (form/methanol/brine ) Tj 6.241667 0 Td 44.907407 Tz (1:1.5:1 ) Tj 2.119444 0 Td 47.222222 Tz (\(v/v/v\) ) Tj 2.138889 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 56.17284 Tz (performed ) Tj 3.188889 0 Td 43.75 Tz (to ) Tj 0.680556 0 Td 61.574074 Tz (gener ) Tj 51.428571 0 0 51.428571 0 172.743276 Tm 6.358333 0 Td 47.530864 Tz (ate ) Tj 1.127778 0 Td 49.691358 Tz (the ) Tj 1.166667 0 Td 58.333333 Tz (sodium ) Tj 2.391667 0 Td 42.12963 Tz (salt ) Tj 1.263889 0 Td 59.953704 Tz (of ) Tj 0.894444 0 Td 49.691358 Tz (the ) Tj 1.166667 0 Td 49.117477 Tz (\(16:0\)-o-difluorophosphodiester. ) Tj 30 0 0 30 0 2547 Tm 41.666667 0 Td 75 Tz (10 ) Tj 30 0 0 30 0 2339 Tm 41.666667 0 Td 72.222222 Tz (15 ) Tj 30 0 0 30 0 1923 Tm 41.6 0 Td 77.777778 Tz (25 ) Tj 30 0 0 30 0 1716 Tm 41.6 0 Td 80.555556 Tz (30 ) Tj 30 0 0 30 0 1507 Tm 41.6 0 Td 77.777778 Tz (35 ) Tj 30 0 0 30 0 1299 Tm 41.566667 0 Td 83.333333 Tz (40 ) Tj 30 0 0 30 0 1091 Tm 41.566667 0 Td 80.555556 Tz (45 ) Tj 30 0 0 30 0 883 Tm 41.6 0 Td 80.555556 Tz (50 ) Tj 30 0 0 30 0 675 Tm 41.6 0 Td 77.777778 Tz (55 ) Tj 30 0 0 30 0 467 Tm 41.633333 0 Td 77.777778 Tz (60 ) Tj 30 0 0 30 0 259 Tm 41.633333 0 Td 75 Tz (65 ) Tj 52.857143 0 0 52.857143 0 2968 Tm 32.672973 0 Td 74.099099 Tz (18 ) Tj 51.428571 0 0 51.428571 0 2919.323353 Tm 32.297222 0 Td 61.111111 Tz (Example ) Tj 2.8 0 Td 56.712963 Tz (10 ) Tj 51.428571 0 0 51.428571 0 2809 Tm 28.836111 0 Td 52.73569 Tz (\(16:0\)-o-monofluorophosphodiester ) Tj 31.428571 0 0 31.428571 0 2650 Tm 55.236364 0 Td 111.363636 Tz (O ) Tj 31.428571 0 0 31.428571 0 2517 Tm 55.236364 0 Td 111.363636 Tz (OH ) Tj 38.571429 0 0 38.571429 0 2463 Tm 41.611111 0 Td 97.942387 Tz (FHC ) Tj 51.428571 0 0 51.428571 0 2343.683995 Tm 26.036111 0 Td 56.565657 Tz (Phosphorous ) Tj 4.044444 0 Td 52.73569 Tz (oxychloride ) Tj 3.772222 0 Td 43.75 Tz (\(1 ) Tj 0.894444 0 Td 46.180556 Tz (eq.\) ) Tj 1.419444 0 Td 60.493827 Tz (was ) Tj 1.380556 0 Td 58.333333 Tz (added ) Tj 2.041667 0 Td 45.37037 Tz (to ) Tj 0.855556 0 Td 51.851852 Tz (a ) Tj 0.661111 0 Td 55.740741 Tz (round ) Tj 51.428571 0 0 51.428571 0 2298.327456 Tm 25.277778 0 Td 57.253086 Tz (bottom ) Tj 2.391667 0 Td 46.018519 Tz (flask ) Tj 1.633333 0 Td 58.333333 Tz (and ) Tj 1.341667 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 45.37037 Tz (in ) Tj 0.875 0 Td 49.907407 Tz (tetrahydrofuran ) Tj 4.783333 0 Td 56.17284 Tz (\(THF\). ) Tj 2.313889 0 Td 63.734568 Tz (The ) Tj 51.428571 0 0 51.428571 0 2252.961963 Tm 25.297222 0 Td 57.037037 Tz (round ) Tj 1.847222 0 Td 56.712963 Tz (bottom ) Tj 2.197222 0 Td 46.666667 Tz (flask ) Tj 1.536111 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 51.851852 Tz (then ) Tj 1.4 0 Td 52.932099 Tz (placed ) Tj 2.061111 0 Td 45.37037 Tz (in ) Tj 0.680556 0 Td 59.953704 Tz (an ) Tj 0.875 0 Td 46.450617 Tz (ice ) Tj 0.952778 0 Td 52.662037 Tz (bath ) Tj 1.419444 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 53.06713 Tz (maintain ) Tj 51.428571 0 0 51.428571 0 2210.446115 Tm 25.297222 0 Td 51.851852 Tz (a ) Tj 0.544444 0 Td 63.194444 Tz (0C. ) Tj 1.769444 0 Td 50.231481 Tz (temperature. ) Tj 3.908333 0 Td 56.860269 Tz (Hexadecanol ) Tj 3.986111 0 Td 43.75 Tz (\(1 ) Tj 0.816667 0 Td 46.990741 Tz (eq.\) ) Tj 1.341667 0 Td 50.771605 Tz (dissolved ) Tj 2.955556 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 76.697531 Tz (THF ) Tj 51.428571 0 0 51.428571 0 2168.905824 Tm 25.277778 0 Td 54.282407 Tz (with ) Tj 1.497222 0 Td 49.85755 Tz (triethylamine ) Tj 4.083333 0 Td 62.87037 Tz (\(TEA\) ) Tj 2.1 0 Td 42.12963 Tz (\(1 ) Tj 0.758333 0 Td 46.990741 Tz (eq.\) ) Tj 1.302778 0 Td 62.654321 Tz (was ) Tj 1.302778 0 Td 58.333333 Tz (added ) Tj 1.963889 0 Td 55.092593 Tz (dropwise ) Tj 2.858333 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 50.771605 Tz (the ) Tj 51.428571 0 0 51.428571 0 2125.220399 Tm 25.297222 0 Td 55.976431 Tz (phosphorous ) Tj 3.830556 0 Td 56.17284 Tz (oxychloride/THF ) Tj 5.191667 0 Td 45.730453 Tz (solution. ) Tj 2.605556 0 Td 64.814815 Tz (Once ) Tj 1.672222 0 Td 39.969136 Tz (all ) Tj 0.836111 0 Td 53.472222 Tz (of ) Tj 0.738889 0 Td 47.530864 Tz (the ) Tj 0.991667 0 Td 66.435185 Tz (hexa ) Tj 51.428571 0 0 51.428571 0 2078 Tm 25.297222 0 Td 60.925926 Tz (decanol/THF/TEA ) Tj 5.638889 0 Td 48.611111 Tz (solution ) Tj 2.547222 0 Td 61.574074 Tz (was ) Tj 1.302778 0 Td 58.333333 Tz (added ) Tj 1.963889 0 Td 57.523148 Tz (\(-20 ) Tj 1.575 0 Td 46.990741 Tz (min.\), ) Tj 1.925 0 Td 48.611111 Tz (the ) Tj 1.088889 0 Td 59.143519 Tz (reac ) Tj 40 0 0 40 0 2042 Tm 32.5 0 Td 60.416667 Tz (tion ) Tj 1.725 0 Td 68.452381 Tz (mixture ) Tj 3.075 0 Td 79.166667 Tz (was ) Tj 1.675 0 Td 56.547619 Tz (stirred ) Tj 2.6 0 Td 61.111111 Tz (for ) Tj 1.275 0 Td 70.833333 Tz (an ) Tj 1.05 0 Td 62.916667 Tz (additional ) Tj 3.975 0 Td 81.25 Tz (40 ) Tj 1.175 0 Td 69.642857 Tz (minutes ) Tj 3.15 0 Td 56.25 Tz (at ) Tj 0.9 0 Td 77.083333 Tz (0C. ) Tj 51.428571 0 0 51.428571 0 1994.280255 Tm 25.297222 0 Td 87.5 Tz (A ) Tj 0.816667 0 Td 48.206019 Tz (solution ) Tj 2.586111 0 Td 59.953704 Tz (of ) Tj 0.894444 0 Td 55.864198 Tz (o-hydroxybenzaldehyde ) Tj 7.311111 0 Td 43.75 Tz (\(1 ) Tj 0.855556 0 Td 46.990741 Tz (eq.\) ) Tj 1.4 0 Td 45.37037 Tz (in ) Tj 0.816667 0 Td 75.617284 Tz (THF ) Tj 1.672222 0 Td 61.574074 Tz (was ) Tj 51.428571 0 0 51.428571 0 1949.257669 Tm 25.297222 0 Td 58.333333 Tz (added ) Tj 1.886111 0 Td 55.497685 Tz (dropwise ) Tj 2.819444 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 48.611111 Tz (the ) Tj 1.05 0 Td 47.800926 Tz (reaction ) Tj 2.469444 0 Td 46.666667 Tz (flask ) Tj 1.536111 0 Td 53.06713 Tz (followed ) Tj 2.702778 0 Td 58.333333 Tz (by ) Tj 0.836111 0 Td 79.938272 Tz (TEA ) Tj 1.594444 0 Td 43.75 Tz (\(1 ) Tj 0.738889 0 Td 46.180556 Tz (eq.\) ) Tj 40 0 0 40 0 1911 Tm 32.525 0 Td 58.333333 Tz (in ) Tj 0.875 0 Td 80.208333 Tz (THF. ) Tj 2.15 0 Td 79.166667 Tz (The ) Tj 1.65 0 Td 61.979167 Tz (reaction ) Tj 3.25 0 Td 68.452381 Tz (mixture ) Tj 3.05 0 Td 80.555556 Tz (was ) Tj 1.65 0 Td 57.142857 Tz (stirred ) Tj 2.6 0 Td 62.5 Tz (for ) Tj 1.25 0 Td 75 Tz (an ) Tj 1.075 0 Td 62.916667 Tz (additional ) Tj 3.95 0 Td 81.25 Tz (40 ) Tj 51.428571 0 0 51.428571 0 1860.175879 Tm 25.297222 0 Td 54.166667 Tz (minutes ) Tj 2.430556 0 Td 46.990741 Tz (at ) Tj 0.7 0 Td 60.763889 Tz (0C. ) Tj 1.633333 0 Td 57.685185 Tz (Water ) Tj 1.886111 0 Td 42.12963 Tz (\(1 ) Tj 0.719444 0 Td 46.990741 Tz (eq.\) ) Tj 1.263889 0 Td 59.41358 Tz (and ) Tj 1.205556 0 Td 78.858025 Tz (TEA ) Tj 1.594444 0 Td 40.509259 Tz (\(1 ) Tj 0.719444 0 Td 47.800926 Tz (eq.\) ) Tj 1.302778 0 Td 58.333333 Tz (were ) Tj 1.536111 0 Td 58.333333 Tz (added ) Tj 1.905556 0 Td 45.37037 Tz (to ) Tj 40 0 0 40 0 1824 Tm 32.5 0 Td 65.277778 Tz (the ) Tj 1.375 0 Td 61.979167 Tz (reaction ) Tj 3.2 0 Td 68.452381 Tz (mixture ) Tj 3.05 0 Td 75.833333 Tz (which ) Tj 2.475 0 Td 79.166667 Tz (was ) Tj 1.625 0 Td 69.642857 Tz (allowed ) Tj 3.125 0 Td 58.333333 Tz (to ) Tj 0.925 0 Td 50 Tz (stir ) Tj 1.375 0 Td 61.111111 Tz (for ) Tj 1.275 0 Td 77.083333 Tz (60 ) Tj 1.15 0 Td 69.047619 Tz (minutes ) Tj 40 0 0 40 0 1780 Tm 32.525 0 Td 58.333333 Tz (at ) Tj 0.9 0 Td 78.125 Tz (0C. ) Tj 2.125 0 Td 81.944444 Tz (The ) Tj 1.65 0 Td 65.104167 Tz (contents ) Tj 3.4 0 Td 72.916667 Tz (of ) Tj 0.975 0 Td 63.888889 Tz (the ) Tj 1.4 0 Td 60.9375 Tz (reaction ) Tj 3.2 0 Td 60 Tz (flask ) Tj 2.025 0 Td 75 Tz (were ) Tj 2 0 Td 66.666667 Tz (then ) Tj 1.875 0 Td 80.555556 Tz (vacuum ) Tj 40 0 0 40 0 1736 Tm 32.525 0 Td 55.208333 Tz (filtered ) Tj 2.95 0 Td 75 Tz (and ) Tj 1.65 0 Td 64.166667 Tz (dried ) Tj 2.25 0 Td 56.25 Tz (in ) Tj 1.025 0 Td 66.666667 Tz (vacuo. ) Tj 2.7 0 Td 91.666667 Tz (An ) Tj 1.425 0 Td 61.666667 Tz (extraction ) Tj 4.025 0 Td 68.75 Tz (with ) Tj 1.95 0 Td 66.666667 Tz (chloroform? ) Tj 51.428571 0 0 51.428571 0 1688.229091 Tm 25.297222 0 Td 54.166667 Tz (methanol/water ) Tj 4.841667 0 Td 45.37037 Tz (1:1.5:1 ) Tj 2.236111 0 Td 47.222222 Tz (\(v/v/v\) ) Tj 2.275 0 Td 47.530864 Tz (respectively ) Tj 3.694444 0 Td 62.654321 Tz (was ) Tj 1.380556 0 Td 56.532922 Tz (performed ) Tj 52.857143 0 0 52.857143 0 1643.589617 Tm 24.613514 0 Td 56.756757 Tz (and ) Tj 1.324324 0 Td 48.348348 Tz (the ) Tj 1.154054 0 Td 49.764982 Tz (\(16:0\)-o-phosphodiester ) Tj 7.132432 0 Td 60.960961 Tz (was ) Tj 1.418919 0 Td 53.603604 Tz (used ) Tj 1.551351 0 Td 52.252252 Tz (without ) Tj 2.478378 0 Td 46.846847 Tz (further ) Tj 51.428571 0 0 51.428571 0 1604 Tm 25.297222 0 Td 44.871795 Tz (purification. ) Tj 51.428571 0 0 51.428571 0 1546.38394 Tm 26.016667 0 Td 63.734568 Tz (The ) Tj 1.361111 0 Td 45.046296 Tz (relatively ) Tj 2.858333 0 Td 55.092593 Tz (pure ) Tj 1.536111 0 Td 51.006441 Tz (\(16:0\)-o-phosphodiester ) Tj 7.213889 0 Td 43.75 Tz (\(1 ) Tj 0.777778 0 Td 43.425926 Tz (eq.\), ) Tj 1.536111 0 Td 81.018519 Tz (DCC ) Tj 51.428571 0 0 51.428571 0 1500.085427 Tm 25.316667 0 Td 46.180556 Tz (\(2.2 ) Tj 1.341667 0 Td 61.574074 Tz (eq\) ) Tj 1.302778 0 Td 59.41358 Tz (and ) Tj 1.302778 0 Td 87.5 Tz (DMAP ) Tj 2.313889 0 Td 43.75 Tz (\(0.1 ) Tj 1.322222 0 Td 46.990741 Tz (eq.\) ) Tj 1.361111 0 Td 58.333333 Tz (were ) Tj 1.594444 0 Td 49.907407 Tz (dried ) Tj 1.711111 0 Td 53.472222 Tz (over ) Tj 1.458333 0 Td 56.565657 Tz (phosphorous ) Tj 51.428571 0 0 51.428571 0 1456.971223 Tm 25.297222 0 Td 53.292181 Tz (pentoxide ) Tj 2.994444 0 Td 48.611111 Tz (for ) Tj 1.05 0 Td 53.472222 Tz (12 ) Tj 0.797222 0 Td 49.151235 Tz (hours. ) Tj 1.905556 0 Td 56.442901 Tz (Cyanoethanol ) Tj 4.2 0 Td 43.75 Tz (\(1.1 ) Tj 1.263889 0 Td 46.180556 Tz (eq.\) ) Tj 1.283333 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 50.771605 Tz (dissolved ) Tj 51.428571 0 0 51.428571 0 1410.646772 Tm 25.297222 0 Td 45.37037 Tz (in ) Tj 0.719444 0 Td 54.444444 Tz (dichloromethane ) Tj 5.055556 0 Td 59.41358 Tz (and ) Tj 1.244444 0 Td 49.259259 Tz (dried ) Tj 1.633333 0 Td 53.472222 Tz (with ) Tj 1.497222 0 Td 60.853909 Tz (magnesium ) Tj 3.5 0 Td 45.833333 Tz (sulfate ) Tj 2.1 0 Td 47.530864 Tz (for ) Tj 1.069444 0 Td 51.851852 Tz (12 ) Tj 51.428571 0 0 51.428571 0 1369.44484 Tm 25.277778 0 Td 49.691358 Tz (hours. ) Tj 1.983333 0 Td 62.654321 Tz (The ) Tj 1.302778 0 Td 51.147343 Tz (\(16:0\)-o-phosphodiester ) Tj 7.213889 0 Td 60.493827 Tz (was ) Tj 1.302778 0 Td 50.411523 Tz (dissolved ) Tj 2.877778 0 Td 46.990741 Tz (in ) Tj 0.758333 0 Td 56.712963 Tz (dichlo ) Tj 40 0 0 40 0 1330 Tm 32.525 0 Td 73.148148 Tz (romethane ) Tj 4.2 0 Td 75 Tz (and ) Tj 1.625 0 Td 105.555556 Tz (DCC ) Tj 2.15 0 Td 75 Tz (and ) Tj 1.625 0 Td 111.458333 Tz (DMAP ) Tj 2.925 0 Td 76.041667 Tz (were ) Tj 2.05 0 Td 75 Tz (added ) Tj 2.525 0 Td 56.25 Tz (to ) Tj 0.975 0 Td 62.5 Tz (the ) Tj 1.4 0 Td 62.5 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 1280.168612 Tm 25.297222 0 Td 42.669753 Tz (flask. ) Tj 1.788889 0 Td 62.654321 Tz (The ) Tj 1.361111 0 Td 46.666667 Tz (flask ) Tj 1.633333 0 Td 60.493827 Tz (was ) Tj 1.341667 0 Td 50.771605 Tz (sealed ) Tj 2.061111 0 Td 53.472222 Tz (with ) Tj 1.536111 0 Td 51.851852 Tz (a ) Tj 0.583333 0 Td 57.253086 Tz (septum ) Tj 2.313889 0 Td 59.41358 Tz (and ) Tj 1.283333 0 Td 55.632716 Tz (purged ) Tj 2.294444 0 Td 53.472222 Tz (with ) Tj 51.428571 0 0 51.428571 0 1238.985899 Tm 25.297222 0 Td 50.231481 Tz (nitrogen ) Tj 2.547222 0 Td 46.018519 Tz (after ) Tj 1.497222 0 Td 55.092593 Tz (adding ) Tj 2.1 0 Td 50.771605 Tz (the ) Tj 1.05 0 Td 53.472222 Tz (cyanoethanol ) Tj 4.005556 0 Td 46.090535 Tz (Solution. ) Tj 2.625 0 Td 64.814815 Tz (The ) Tj 1.302778 0 Td 49.016204 Tz (reaction ) Tj 51.428571 0 0 51.428571 0 1193.476433 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.361111 0 Td 44.444444 Tz (stirred ) Tj 2.080556 0 Td 48.611111 Tz (for ) Tj 1.05 0 Td 59.953704 Tz (48 ) Tj 0.952778 0 Td 53.148148 Tz (hours ) Tj 1.808333 0 Td 46.990741 Tz (at ) Tj 0.777778 0 Td 62.384259 Tz (room ) Tj 1.730556 0 Td 50.231481 Tz (temperature. ) Tj 3.869444 0 Td 57.685185 Tz (Water ) Tj 1.944444 0 Td 46.990741 Tz (\(5 ) Tj 0.797222 0 Td 46.180556 Tz (eq.\) ) Tj 40 0 0 40 0 1155 Tm 32.5 0 Td 80.555556 Tz (was ) Tj 1.725 0 Td 75 Tz (added ) Tj 2.5 0 Td 76.388889 Tz (and ) Tj 1.625 0 Td 63.888889 Tz (the ) Tj 1.4 0 Td 62.5 Tz (reaction ) Tj 3.325 0 Td 68.452381 Tz (mixture ) Tj 3.125 0 Td 79.166667 Tz (was ) Tj 1.7 0 Td 57.142857 Tz (stirred ) Tj 2.65 0 Td 62.5 Tz (for ) Tj 1.35 0 Td 72.916667 Tz (an ) Tj 1.125 0 Td 81.25 Tz (addi ) Tj 40 0 0 40 0 1112 Tm 32.5 0 Td 59.722222 Tz (tional ) Tj 2.6 0 Td 79.166667 Tz (24 ) Tj 1.375 0 Td 63.194444 Tz (hours. ) Tj 2.75 0 Td 80.555556 Tz (The ) Tj 1.875 0 Td 65.104167 Tz (contents ) Tj 3.575 0 Td 75 Tz (of ) Tj 1.225 0 Td 63.888889 Tz (the ) Tj 1.6 0 Td 61.979167 Tz (reaction ) Tj 3.475 0 Td 59.166667 Tz (flask ) Tj 2.2 0 Td 75 Tz (were ) Tj 40 0 0 40 0 1068 Tm 32.525 0 Td 80.555556 Tz (vacuum ) Tj 3.175 0 Td 55.729167 Tz (filtered ) Tj 2.875 0 Td 77.777778 Tz (and ) Tj 1.65 0 Td 63.333333 Tz (dried ) Tj 2.15 0 Td 58.333333 Tz (in ) Tj 0.975 0 Td 66.666667 Tz (vacuo. ) Tj 2.65 0 Td 66.666667 Tz (After ) Tj 2.2 0 Td 72.916667 Tz (an ) Tj 1.15 0 Td 61.666667 Tz (extraction ) Tj 4 0 Td 67.708333 Tz (with ) Tj 51.428571 0 0 51.428571 0 1019.386091 Tm 25.297222 0 Td 51.851852 Tz (chloroform/brine ) Tj 5.191667 0 Td 44.290123 Tz (1:1 ) Tj 1.069444 0 Td 43.209877 Tz (\(v/v\), ) Tj 1.730556 0 Td 49.691358 Tz (the ) Tj 1.05 0 Td 55.092593 Tz (coupled ) Tj 2.45 0 Td 53.703704 Tz (product ) Tj 2.411111 0 Td 62.654321 Tz (was ) Tj 1.283333 0 Td 47.800926 Tz (purified ) Tj 51.428571 0 0 51.428571 0 977.374532 Tm 25.277778 0 Td 61.574074 Tz (by ) Tj 1.011111 0 Td 45.37037 Tz (flash ) Tj 1.652778 0 Td 59.41358 Tz (column ) Tj 2.45 0 Td 56.25 Tz (chromatography ) Tj 4.997222 0 Td 53.148148 Tz (using ) Tj 1.847222 0 Td 73.45679 Tz (40% ) Tj 1.575 0 Td 48.611111 Tz (ethyl ) Tj 1.730556 0 Td 46.585648 Tz (acetate/ ) Tj 51.428571 0 0 51.428571 0 931.689238 Tm 25.277778 0 Td 57.79321 Tz (hexane ) Tj 2.236111 0 Td 51.041667 Tz (then ) Tj 1.380556 0 Td 52.572016 Tz (switching ) Tj 2.994444 0 Td 45.37037 Tz (to ) Tj 0.719444 0 Td 73.45679 Tz (80% ) Tj 1.477778 0 Td 47.962963 Tz (ethyl ) Tj 1.594444 0 Td 51.157407 Tz (acetate/hexane ) Tj 4.433333 0 Td 48.611111 Tz (for ) Tj 0.972222 0 Td 55.092593 Tz (a ) Tj 0.525 0 Td 46.990741 Tz (step ) Tj 51.428571 0 0 51.428571 0 891.169492 Tm 25.297222 0 Td 49.826389 Tz (gradient ) Tj 2.547222 0 Td 45.775463 Tz (elution. ) Tj 51.428571 0 0 51.428571 0 839.747226 Tm 26.016667 0 Td 52.5 Tz (After ) Tj 1.808333 0 Td 45.121083 Tz (purification, ) Tj 3.791667 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 50.771605 Tz (protected ) Tj 3.013889 0 Td 51.006441 Tz (\(16:0\)-o-phosphodiester ) Tj 51.428571 0 0 51.428571 0 797.080808 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.4 0 Td 41.481481 Tz (split ) Tj 1.458333 0 Td 46.990741 Tz (into ) Tj 1.380556 0 Td 59.41358 Tz (two ) Tj 1.322222 0 Td 53.240741 Tz (roughly ) Tj 2.469444 0 Td 53.148148 Tz (equal ) Tj 1.808333 0 Td 47.530864 Tz (portions. ) Tj 2.8 0 Td 64.814815 Tz (The ) Tj 1.4 0 Td 37.592593 Tz (first ) Tj 1.322222 0 Td 50.925926 Tz (portion ) Tj 51.428571 0 0 51.428571 0 751.428571 Tm 25.277778 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 55.092593 Tz (used ) Tj 1.536111 0 Td 46.450617 Tz (for ) Tj 1.011111 0 Td 46.450617 Tz (direct ) Tj 1.866667 0 Td 46.450617 Tz (fluorination ) Tj 3.597222 0 Td 58.738426 Tz (\(Example ) Tj 2.975 0 Td 53.472222 Tz (9\) ) Tj 0.797222 0 Td 59.41358 Tz (and ) Tj 1.263889 0 Td 50.771605 Tz (the ) Tj 1.069444 0 Td 56.712963 Tz (second ) Tj 51.428571 0 0 51.428571 0 710.410037 Tm 25.297222 0 Td 49.537037 Tz (portion ) Tj 2.275 0 Td 61.574074 Tz (was ) Tj 1.302778 0 Td 55.902778 Tz (used ) Tj 1.536111 0 Td 47.530864 Tz (for ) Tj 1.030556 0 Td 50.411523 Tz (reduction ) Tj 2.936111 0 Td 52.662037 Tz (followed ) Tj 2.722222 0 Td 59.953704 Tz (by ) Tj 0.913889 0 Td 45.37037 Tz (fluorination. ) Tj 3.791667 0 Td 55.092593 Tz (For ) Tj 51.428571 0 0 51.428571 0 672.349282 Tm 25.297222 0 Td 48.287037 Tz (reduction, ) Tj 3.111111 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 49.691358 Tz (protected ) Tj 2.877778 0 Td 51.147343 Tz (\(16:0\)-o-phosphodiester ) Tj 7.233333 0 Td 40.509259 Tz (\(1 ) Tj 0.758333 0 Td 46.990741 Tz (eq.\) ) Tj 1.302778 0 Td 61.574074 Tz (was ) Tj 51.428571 0 0 51.428571 0 629.420074 Tm 25.297222 0 Td 50.771605 Tz (dissolved ) Tj 3.033333 0 Td 43.75 Tz (in ) Tj 0.816667 0 Td 59.773663 Tz (THF/water ) Tj 3.480556 0 Td 46.666667 Tz (3:0.1 ) Tj 1.75 0 Td 49.494949 Tz (equivalents ) Tj 3.597222 0 Td 47.800926 Tz (respectively ) Tj 3.713889 0 Td 60.493827 Tz (and ) Tj 51.428571 0 0 51.428571 0 586.434343 Tm 25.316667 0 Td 58.333333 Tz (sodium ) Tj 2.313889 0 Td 54.208754 Tz (borohydride ) Tj 3.791667 0 Td 42.12963 Tz (\(1 ) Tj 0.777778 0 Td 46.180556 Tz (eq.\) ) Tj 1.322222 0 Td 61.574074 Tz (was ) Tj 1.322222 0 Td 58.333333 Tz (added ) Tj 1.944444 0 Td 46.990741 Tz (to ) Tj 0.797222 0 Td 48.611111 Tz (the ) Tj 1.108333 0 Td 47.800926 Tz (reaction ) Tj 2.527778 0 Td 42.12963 Tz (flask. ) Tj 51.428571 0 0 51.428571 0 543.755635 Tm 25.297222 0 Td 63.734568 Tz (The ) Tj 1.283333 0 Td 48.206019 Tz (reaction ) Tj 2.45 0 Td 53.703704 Tz (mixture ) Tj 2.372222 0 Td 60.493827 Tz (was ) Tj 1.263889 0 Td 43.981481 Tz (stirred ) Tj 1.983333 0 Td 43.425926 Tz (until ) Tj 1.438889 0 Td 39.969136 Tz (all ) Tj 0.855556 0 Td 58.873457 Tz (sodium ) Tj 2.236111 0 Td 54.503367 Tz (borohydride ) Tj 51.428571 0 0 51.428571 0 502.105196 Tm 25.297222 0 Td 50.771605 Tz (dissolved ) Tj 3.013889 0 Td 54.012346 Tz (\(~2 ) Tj 1.302778 0 Td 51.851852 Tz (minutes\) ) Tj 2.741667 0 Td 60.493827 Tz (and ) Tj 1.361111 0 Td 52.932099 Tz (continued ) Tj 3.111111 0 Td 44.155093 Tz (stirring ) Tj 2.372222 0 Td 48.611111 Tz (for ) Tj 1.108333 0 Td 56.712963 Tz (an ) Tj 0.933333 0 Td 63.194444 Tz (addi ) Tj 51.428571 0 0 51.428571 0 459.599746 Tm 25.277778 0 Td 45.910494 Tz (tional ) Tj 1.963889 0 Td 53.472222 Tz (10 ) Tj 0.875 0 Td 50.636574 Tz (minutes. ) Tj 2.663889 0 Td 57.685185 Tz (Water ) Tj 1.905556 0 Td 46.990741 Tz (\(3 ) Tj 0.777778 0 Td 47.800926 Tz (eq.\) ) Tj 1.361111 0 Td 60.493827 Tz (was ) Tj 1.302778 0 Td 57.685185 Tz (added ) Tj 1.925 0 Td 59.41358 Tz (and ) Tj 1.263889 0 Td 50.771605 Tz (the ) Tj 1.127778 0 Td 48.611111 Tz (reaction ) Tj 40 0 0 40 0 426 Tm 32.575 0 Td 68.452381 Tz (mixture ) Tj 3.2 0 Td 79.166667 Tz (was ) Tj 1.8 0 Td 57.142857 Tz (stirred ) Tj 2.725 0 Td 72.916667 Tz (an ) Tj 1.225 0 Td 62.083333 Tz (additional ) Tj 4.2 0 Td 70.833333 Tz (10 ) Tj 1.225 0 Td 64.583333 Tz (minutes. ) Tj 3.45 0 Td 65.277778 Tz (All ) Tj 1.55 0 Td 63.020833 Tz (solvents ) Tj 51.428571 0 0 51.428571 0 377.375921 Tm 25.277778 0 Td 59.953704 Tz (were ) Tj 1.652778 0 Td 59.259259 Tz (removed ) Tj 2.702778 0 Td 43.75 Tz (in ) Tj 0.758333 0 Td 55.740741 Tz (vacuo ) Tj 1.866667 0 Td 58.333333 Tz (and ) Tj 1.263889 0 Td 47.530864 Tz (the ) Tj 1.069444 0 Td 51.041667 Tz (reduced, ) Tj 2.644444 0 Td 50.411523 Tz (protected ) Tj 2.897222 0 Td 48.611111 Tz (\(16:0\)-o- ) Tj 51.428571 0 0 51.428571 0 340.697561 Tm 25.297222 0 Td 52.777778 Tz (phosphodiester ) Tj 4.647222 0 Td 61.574074 Tz (was ) Tj 1.341667 0 Td 47.800926 Tz (purified ) Tj 2.527778 0 Td 59.953704 Tz (by ) Tj 0.991667 0 Td 44.722222 Tz (flash ) Tj 1.633333 0 Td 59.41358 Tz (column ) Tj 2.411111 0 Td 59.217172 Tz (chromatogra ) Tj 51.428571 0 0 51.428571 0 296.551122 Tm 25.297222 0 Td 59.41358 Tz (phy ) Tj 1.322222 0 Td 52.5 Tz (using ) Tj 1.788889 0 Td 72.376543 Tz (40% ) Tj 1.555556 0 Td 47.962963 Tz (ethyl ) Tj 1.672222 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.491667 0 Td 51.041667 Tz (then ) Tj 1.458333 0 Td 52.572016 Tz (switching ) Tj 3.072222 0 Td 43.75 Tz (to ) Tj 0.758333 0 Td 74.537037 Tz (80% ) Tj 51.428571 0 0 51.428571 0 253.449761 Tm 25.297222 0 Td 47.314815 Tz (ethyl ) Tj 1.594444 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.433333 0 Td 48.611111 Tz (for ) Tj 0.972222 0 Td 58.333333 Tz (a ) Tj 0.505556 0 Td 47.800926 Tz (step ) Tj 1.302778 0 Td 50.231481 Tz (gradient ) Tj 2.547222 0 Td 44.965278 Tz (elution. ) Tj 2.333333 0 Td 64.814815 Tz (The ) Tj 1.302778 0 Td 51.041667 Tz (reduced, ) Tj 51.428571 0 0 51.428571 0 215.699746 Tm 25.297222 0 Td 50.05144 Tz (protected ) Tj 3.072222 0 Td 51.147343 Tz (\(16:0\)-o-phosphodiester ) Tj 7.388889 0 Td 42.12963 Tz (\(1 ) Tj 0.933333 0 Td 46.990741 Tz (eq.\) ) Tj 1.497222 0 Td 60.493827 Tz (was ) Tj 1.458333 0 Td 49.907407 Tz (dried ) Tj 1.847222 0 Td 54.282407 Tz (over ) Tj 51.428571 0 0 51.428571 0 171.26747 Tm 25.297222 0 Td 55.976431 Tz (phosphorous ) Tj 3.85 0 Td 53.652263 Tz (pentoxide ) Tj 3.052778 0 Td 48.611111 Tz (for ) Tj 1.069444 0 Td 55.092593 Tz (12 ) Tj 0.797222 0 Td 54.444444 Tz (hours ) Tj 1.788889 0 Td 58.333333 Tz (and ) Tj 1.225 0 Td 50.771605 Tz (dissolved ) Tj 2.897222 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 56.712963 Tz (dichlo ) Tj ET Q endstream endobj 192 0 obj << /Length 1 >> stream q endstream endobj 193 0 obj << /Length 42865 >> stream Q q 0.24 0 0 0.24 0 0 cm BT /F1 1 Tf 3 Tr 62.857143 0 0 62.857143 0 3023 Tm 17.325 0 Td 83.522727 Tz (US ) Tj 1.240909 0 Td 58.333333 Tz (8,022,239 ) Tj 3.388636 0 Td 74.242424 Tz (B2 ) Tj 52.857143 0 0 52.857143 0 2968 Tm 14.245946 0 Td 74.099099 Tz (19 ) Tj 51.428571 0 0 51.428571 0 2913.96 Tm 6.358333 0 Td 53.796296 Tz (romethane. ) Tj 3.363889 0 Td 63.734568 Tz (The ) Tj 1.283333 0 Td 48.611111 Tz (reaction ) Tj 2.508333 0 Td 46.018519 Tz (flask ) Tj 1.516667 0 Td 60.493827 Tz (was ) Tj 1.225 0 Td 50.771605 Tz (sealed ) Tj 1.963889 0 Td 58.333333 Tz (and ) Tj 1.166667 0 Td 53.472222 Tz (placed ) Tj 2.061111 0 Td 45.37037 Tz (in ) Tj 0.7 0 Td 56.712963 Tz (an ) Tj 0.855556 0 Td 46.450617 Tz (ice ) Tj 51.428571 0 0 51.428571 0 2872.544021 Tm 6.338889 0 Td 52.662037 Tz (bath ) Tj 1.555556 0 Td 45.37037 Tz (to ) Tj 0.875 0 Td 52.256944 Tz (maintain ) Tj 2.819444 0 Td 51.851852 Tz (0 ) Tj 0.894444 0 Td 55.092593 Tz (C. ) Tj 0.991667 0 Td 49.96142 Tz (temperature. ) Tj 3.927778 0 Td 55.416667 Tz (Deoxofluor ) Tj 3.597222 0 Td 46.990741 Tz (\(2 ) Tj 0.875 0 Td 46.180556 Tz (eq.\) ) Tj 1.380556 0 Td 50.231481 Tz (in ) Tj 51.428571 0 0 51.428571 0 2826.993663 Tm 6.358333 0 Td 54.444444 Tz (dichloromethane ) Tj 5.191667 0 Td 61.574074 Tz (was ) Tj 1.419444 0 Td 52.932099 Tz (slowly ) Tj 2.197222 0 Td 58.981481 Tz (added ) Tj 2.061111 0 Td 55.092593 Tz (\(-2 ) Tj 1.341667 0 Td 49.331276 Tz (minutes\). ) Tj 2.955556 0 Td 64.814815 Tz (The ) Tj 1.477778 0 Td 46.450617 Tz (ice ) Tj 40 0 0 40 0 2790 Tm 8.15 0 Td 67.708333 Tz (bath ) Tj 1.85 0 Td 77.777778 Tz (was ) Tj 1.6 0 Td 77.380952 Tz (removed ) Tj 3.45 0 Td 75 Tz (and ) Tj 1.525 0 Td 62.5 Tz (the ) Tj 1.325 0 Td 62.5 Tz (reaction ) Tj 3.25 0 Td 68.452381 Tz (mixture ) Tj 3.05 0 Td 80.555556 Tz (was ) Tj 1.65 0 Td 57.142857 Tz (stirred ) Tj 2.575 0 Td 62.5 Tz (for ) Tj 1.35 0 Td 70.833333 Tz (12 ) Tj 40 0 0 40 0 2747 Tm 8.15 0 Td 63.888889 Tz (hours. ) Tj 2.5 0 Td 91.666667 Tz (An ) Tj 1.325 0 Td 61.666667 Tz (extraction ) Tj 3.925 0 Td 68.75 Tz (with ) Tj 1.875 0 Td 66.166667 Tz (dichloromethane/saturated ) Tj 10.125 0 Td 75.694444 Tz (sodium ) Tj 51.428571 0 0 51.428571 0 2697.583433 Tm 6.338889 0 Td 51.557239 Tz (bicarbonate ) Tj 3.558333 0 Td 48.611111 Tz (solution ) Tj 2.547222 0 Td 43.209877 Tz (1:1 ) Tj 1.030556 0 Td 46.666667 Tz (\(v/v\) ) Tj 1.536111 0 Td 61.574074 Tz (was ) Tj 1.244444 0 Td 56.532922 Tz (performed ) Tj 3.169444 0 Td 59.41358 Tz (and ) Tj 1.225 0 Td 48.611111 Tz (the ) Tj 0.991667 0 Td 51.851852 Tz (organic ) Tj 51.428571 0 0 51.428571 0 2653.202899 Tm 6.358333 0 Td 49.259259 Tz (layer ) Tj 1.652778 0 Td 61.574074 Tz (was ) Tj 1.283333 0 Td 46.342593 Tz (collected. ) Tj 51.428571 0 0 51.428571 0 2610.343634 Tm 7.097222 0 Td 51.851852 Tz (After ) Tj 1.691667 0 Td 52.932099 Tz (drying ) Tj 2.061111 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 52.391975 Tz (vacuo, ) Tj 2.061111 0 Td 49.691358 Tz (the ) Tj 1.05 0 Td 50.05144 Tz (protected ) Tj 2.877778 0 Td 54.751462 Tz (\(16:0\)-o-monofluoro ) Tj 51.428571 0 0 51.428571 0 2569.69475 Tm 6.358333 0 Td 52.777778 Tz (phosphodiester ) Tj 4.647222 0 Td 61.574074 Tz (was ) Tj 1.361111 0 Td 47.395833 Tz (purified ) Tj 2.508333 0 Td 59.953704 Tz (by ) Tj 1.011111 0 Td 44.722222 Tz (flash ) Tj 1.613889 0 Td 59.41358 Tz (column ) Tj 2.411111 0 Td 59.217172 Tz (chromatogra ) Tj 51.428571 0 0 51.428571 0 2523.551122 Tm 6.358333 0 Td 59.41358 Tz (phy ) Tj 1.322222 0 Td 52.5 Tz (using ) Tj 1.788889 0 Td 72.376543 Tz (40% ) Tj 1.555556 0 Td 47.962963 Tz (ethyl ) Tj 1.672222 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.491667 0 Td 51.041667 Tz (then ) Tj 1.458333 0 Td 52.572016 Tz (switching ) Tj 3.072222 0 Td 43.75 Tz (to ) Tj 0.758333 0 Td 74.537037 Tz (80% ) Tj 51.428571 0 0 51.428571 0 2480.748517 Tm 6.358333 0 Td 47.314815 Tz (ethyl ) Tj 1.594444 0 Td 50.925926 Tz (acetate/hexane ) Tj 4.394444 0 Td 48.611111 Tz (for ) Tj 0.972222 0 Td 58.333333 Tz (a ) Tj 0.486111 0 Td 47.800926 Tz (step ) Tj 1.283333 0 Td 49.826389 Tz (gradient ) Tj 2.508333 0 Td 45.775463 Tz (elution. ) Tj 2.372222 0 Td 56.17284 Tz (For ) Tj 1.127778 0 Td 56.712963 Tz (deprotec ) Tj 51.428571 0 0 51.428571 0 2439.634615 Tm 6.338889 0 Td 44.074074 Tz (tion, ) Tj 1.652778 0 Td 49.691358 Tz (the ) Tj 1.186111 0 Td 50.771605 Tz (protected ) Tj 3.072222 0 Td 52.328431 Tz (\(16:0\)-o-monofluoro-phosphodiester ) Tj 10.966667 0 Td 45.37037 Tz (\(1 ) Tj 51.428571 0 0 51.428571 0 2393.774032 Tm 6.358333 0 Td 46.180556 Tz (eq.\) ) Tj 1.361111 0 Td 61.574074 Tz (was ) Tj 1.361111 0 Td 50.411523 Tz (dissolved ) Tj 2.955556 0 Td 45.37037 Tz (in ) Tj 0.777778 0 Td 48.611111 Tz (pyridine. ) Tj 2.858333 0 Td 57.086895 Tz (N-propylamine ) Tj 4.686111 0 Td 55.092593 Tz (\(100 ) Tj 1.555556 0 Td 46.180556 Tz (eq.\) ) Tj 1.361111 0 Td 48.611111 Tz (in ) Tj 51.428571 0 0 51.428571 0 2347.204819 Tm 6.358333 0 Td 50.636574 Tz (pyridine ) Tj 2.566667 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 57.685185 Tz (added ) Tj 1.886111 0 Td 43.75 Tz (to ) Tj 0.7 0 Td 48.611111 Tz (the ) Tj 1.011111 0 Td 48.611111 Tz (reaction ) Tj 2.469444 0 Td 46.018519 Tz (flask ) Tj 1.477778 0 Td 58.333333 Tz (and ) Tj 1.205556 0 Td 49.691358 Tz (the ) Tj 0.991667 0 Td 48.611111 Tz (clear ) Tj 1.575 0 Td 49.421296 Tz (solution ) Tj 51.428571 0 0 51.428571 0 2303.853779 Tm 6.338889 0 Td 62.654321 Tz (was ) Tj 1.341667 0 Td 43.981481 Tz (stirred ) Tj 2.041667 0 Td 47.530864 Tz (for ) Tj 1.088889 0 Td 55.092593 Tz (10 ) Tj 0.855556 0 Td 54.166667 Tz (minutes ) Tj 2.45 0 Td 43.75 Tz (at ) Tj 0.738889 0 Td 62.384259 Tz (room ) Tj 1.691667 0 Td 50.501543 Tz (temperature. ) Tj 3.811111 0 Td 50.771605 Tz (All ) Tj 1.108333 0 Td 49.016204 Tz (solvents ) Tj 51.428571 0 0 51.428571 0 2261.629268 Tm 6.338889 0 Td 59.953704 Tz (were ) Tj 1.633333 0 Td 60.185185 Tz (removed ) Tj 2.702778 0 Td 45.37037 Tz (in ) Tj 0.777778 0 Td 56.388889 Tz (vacuo ) Tj 1.866667 0 Td 46.990741 Tz (to ) Tj 0.758333 0 Td 49.259259 Tz (yield ) Tj 1.633333 0 Td 50.771605 Tz (the ) Tj 1.147222 0 Td 59.953704 Tz (n-propylammonium ) Tj 5.95 0 Td 42.939815 Tz (salt ) Tj 51.428571 0 0 51.428571 0 2220.330132 Tm 6.358333 0 Td 58.333333 Tz (of ) Tj 0.972222 0 Td 49.691358 Tz (the ) Tj 1.225 0 Td 51.388889 Tz (\(16:0\)-o-monofluoro-phosphodiester. ) Tj 11.141667 0 Td 71.296296 Tz (An ) Tj 1.205556 0 Td 49.259259 Tz (extraction ) Tj 51.428571 0 0 51.428571 0 2172.537332 Tm 6.338889 0 Td 54.282407 Tz (with ) Tj 1.633333 0 Td 52.62963 Tz (chloroform/methanol/brine ) Tj 8.225 0 Td 46.759259 Tz (\(v/v/v\) ) Tj 2.275 0 Td 61.574074 Tz (was ) Tj 1.419444 0 Td 56.532922 Tz (performed ) Tj 3.363889 0 Td 46.990741 Tz (to ) Tj 51.428571 0 0 51.428571 0 2132.122373 Tm 6.358333 0 Td 51.041667 Tz (generate ) Tj 2.761111 0 Td 50.771605 Tz (the ) Tj 1.225 0 Td 58.333333 Tz (sodium ) Tj 2.430556 0 Td 42.12963 Tz (salt ) Tj 1.283333 0 Td 61.574074 Tz (of ) Tj 0.933333 0 Td 49.691358 Tz (the ) Tj 1.205556 0 Td 55.233494 Tz (\(16:0\)-o-monofluorophos ) Tj 51.428571 0 0 51.428571 0 2092 Tm 6.358333 0 Td 47.727273 Tz (phodiester. ) Tj 51.428571 0 0 51.428571 0 2043.06096 Tm 7.097222 0 Td 57.685185 Tz (These ) Tj 1.963889 0 Td 61.934156 Tz (compounds ) Tj 3.616667 0 Td 58.333333 Tz (were ) Tj 1.633333 0 Td 51.041667 Tz (then ) Tj 1.497222 0 Td 51.851852 Tz (introduced ) Tj 3.344444 0 Td 46.180556 Tz (into ) Tj 1.361111 0 Td 56.712963 Tz (an ) Tj 0.913889 0 Td 56.944444 Tz (aqueous ) Tj 40 0 0 40 0 2007 Tm 8.2 0 Td 61.979167 Tz (Solution ) Tj 3.225 0 Td 62.5 Tz (for ) Tj 1.325 0 Td 62.5 Tz (reaction ) Tj 3.275 0 Td 67.708333 Tz (with ) Tj 1.85 0 Td 61.666667 Tz (autotaxin. ) Tj 51.428571 0 0 51.428571 0 1959.303297 Tm 6.358333 0 Td 53.652263 Tz (Autotaxin ) Tj 3.111111 0 Td 47.260802 Tz (Inactivation ) Tj 3.558333 0 Td 53.06713 Tz (Analysis ) Tj 51.428571 0 0 51.428571 0 1918.203931 Tm 7.097222 0 Td 62.654321 Tz (The ) Tj 1.225 0 Td 47.395833 Tz (efficacy ) Tj 2.391667 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 49.907407 Tz (these ) Tj 1.594444 0 Td 61.934156 Tz (compounds ) Tj 3.480556 0 Td 62.654321 Tz (was ) Tj 1.244444 0 Td 54.768519 Tz (determined ) Tj 3.383333 0 Td 59.953704 Tz (by ) Tj 0.875 0 Td 58.981481 Tz (evalu ) Tj 51.428571 0 0 51.428571 0 1877.636364 Tm 6.358333 0 Td 48.611111 Tz (ating ) Tj 1.769444 0 Td 52.031893 Tz (autotaxin-mediated ) Tj 5.930556 0 Td 50.555556 Tz (hydrolysis ) Tj 3.344444 0 Td 59.953704 Tz (of ) Tj 0.933333 0 Td 49.691358 Tz (the ) Tj 1.225 0 Td 48.251029 Tz (synthetic ) Tj 2.975 0 Td 71.296296 Tz (LPC ) Tj 51.428571 0 0 51.428571 0 1835.906748 Tm 6.358333 0 Td 54.012346 Tz (analog ) Tj 2.197222 0 Td 61.574074 Tz (FS3 ) Tj 1.341667 0 Td 43.75 Tz (at ) Tj 0.758333 0 Td 45.775463 Tz (specific ) Tj 2.411111 0 Td 47.638889 Tz (excitation ) Tj 3.091667 0 Td 58.333333 Tz (and ) Tj 1.263889 0 Td 53.472222 Tz (emission ) Tj 2.8 0 Td 54.503367 Tz (wavelengths ) Tj 51.428571 0 0 51.428571 0 1794.77724 Tm 6.358333 0 Td 47.170782 Tz (resulting ) Tj 2.722222 0 Td 57.523148 Tz (from ) Tj 1.555556 0 Td 52.662037 Tz (cleavage ) Tj 2.683333 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 56.712963 Tz (FS-3 ) Tj 1.555556 0 Td 61.574074 Tz (by ) Tj 0.913889 0 Td 47.962963 Tz (autotaxin. ) Tj 3.013889 0 Td 64.814815 Tz (The ) Tj 1.322222 0 Td 42.12963 Tz (test ) Tj 1.166667 0 Td 58.981481 Tz (proto ) Tj 40 0 0 40 0 1757 Tm 8.175 0 Td 62.5 Tz (col ) Tj 1.4 0 Td 77.777778 Tz (was ) Tj 1.65 0 Td 64.583333 Tz (as ) Tj 1.05 0 Td 61.458333 Tz (follows: ) Tj 52.857143 0 0 52.857143 0 1707 Tm 6.905405 0 Td 70.630631 Tz (MDA-MB-435 ) Tj 4.351351 0 Td 42.882883 Tz (cells ) Tj 1.4 0 Td 58.333333 Tz (were ) Tj 1.475676 0 Td 48.873874 Tz (cultured ) Tj 2.459459 0 Td 42.567568 Tz (at ) Tj 0.624324 0 Td 53.603604 Tz (37 ) Tj 1.097297 0 Td 52.027027 Tz (C. ) Tj 0.756757 0 Td 56.756757 Tz (and ) Tj 1.154054 0 Td 77.252252 Tz (5% ) Tj 1.040541 0 Td 68.318318 Tz (CO, ) Tj 1.362162 0 Td 47.297297 Tz (in ) Tj 51.428571 0 0 51.428571 0 1666.788599 Tm 6.358333 0 Td 55.092593 Tz (Dulbecco's ) Tj 3.519444 0 Td 55.497685 Tz (Modified ) Tj 2.858333 0 Td 53.796296 Tz (Eagle ) Tj 1.827778 0 Td 67.515432 Tz (Medium ) Tj 2.663889 0 Td 75.617284 Tz (\(DMEM\) ) Tj 2.936111 0 Td 55.092593 Tz (\(MediaTech, ) Tj 52.857143 0 0 52.857143 0 1626.00123 Tm 6.205405 0 Td 54.786036 Tz (Herndon, ) Tj 2.837838 0 Td 48.085586 Tz (Va.\) ) Tj 1.362162 0 Td 50.135135 Tz (containing ) Tj 3.235135 0 Td 75.675676 Tz (5% ) Tj 1.135135 0 Td 42.252252 Tz (fetal ) Tj 1.494595 0 Td 53.603604 Tz (bovine ) Tj 2.156757 0 Td 57.387387 Tz (serum ) Tj 1.967568 0 Td 51.151151 Tz (\(Hyclone, ) Tj 51.428571 0 0 51.428571 0 1587.216521 Tm 6.377778 0 Td 56.17284 Tz (Logan, ) Tj 2.255556 0 Td 50.231481 Tz (Utah\), ) Tj 2.080556 0 Td 59.41358 Tz (100 ) Tj 1.263889 0 Td 61.574074 Tz (U/ml ) Tj 1.691667 0 Td 43.897306 Tz (penicillin, ) Tj 3.208333 0 Td 58.333333 Tz (100 ) Tj 1.536111 0 Td 58.333333 Tz (g/ml ) Tj 1.633333 0 Td 52.932099 Tz (streptomycin ) Tj 51.428571 0 0 51.428571 0 1546.005115 Tm 6.377778 0 Td 52.932099 Tz (\(Hyclone, ) Tj 3.208333 0 Td 55.092593 Tz (Logan, ) Tj 2.294444 0 Td 55.092593 Tz (Utah\) ) Tj 1.944444 0 Td 59.41358 Tz (and ) Tj 1.361111 0 Td 59.41358 Tz (292 ) Tj 1.419444 0 Td 55.092593 Tz (ug/ml ) Tj 1.983333 0 Td 54.208754 Tz (L-glutamine ) Tj 3.888889 0 Td 74.537037 Tz (\(Hy ) Tj 51.428571 0 0 51.428571 0 1500.887425 Tm 6.358333 0 Td 48.611111 Tz (clone, ) Tj 1.925 0 Td 55.092593 Tz (Logan, ) Tj 2.138889 0 Td 49.691358 Tz (Utah\). ) Tj 1.925 0 Td 49.907407 Tz (Cells ) Tj 1.652778 0 Td 58.333333 Tz (were ) Tj 1.497222 0 Td 61.574074 Tz (grown ) Tj 1.983333 0 Td 45.37037 Tz (to ) Tj 0.680556 0 Td 71.296296 Tz (~80% ) Tj 1.866667 0 Td 52.5 Tz (confluence ) Tj 3.247222 0 Td 46.990741 Tz (at ) Tj 51.428571 0 0 51.428571 0 1458.4451 Tm 6.338889 0 Td 59.62963 Tz (which ) Tj 1.886111 0 Td 55.092593 Tz (time ) Tj 1.419444 0 Td 50.771605 Tz (the ) Tj 1.011111 0 Td 43.425926 Tz (cells ) Tj 1.458333 0 Td 58.333333 Tz (were ) Tj 1.497222 0 Td 60.493827 Tz (washed ) Tj 2.294444 0 Td 52.5 Tz (twice ) Tj 1.691667 0 Td 52.662037 Tz (with ) Tj 1.419444 0 Td 41.666667 Tz (sterile ) Tj 1.847222 0 Td 55.092593 Tz (phosphate ) Tj 51.428571 0 0 51.428571 0 1415.752577 Tm 6.338889 0 Td 51.041667 Tz (buffered ) Tj 2.722222 0 Td 46.990741 Tz (saline ) Tj 1.944444 0 Td 47.314815 Tz (prior ) Tj 1.691667 0 Td 43.75 Tz (to ) Tj 0.816667 0 Td 48.611111 Tz (the ) Tj 1.127778 0 Td 49.421296 Tz (addition ) Tj 2.644444 0 Td 56.712963 Tz (of ) Tj 0.855556 0 Td 57.685185 Tz (serum ) Tj 2.041667 0 Td 46.180556 Tz (free ) Tj 1.419444 0 Td 93.171296 Tz (DMEM ) Tj 51.428571 0 0 51.428571 0 1377.288575 Tm 6.358333 0 Td 51.203704 Tz (containing ) Tj 3.286111 0 Td 51.58179 Tz (L-glutamine. ) Tj 3.927778 0 Td 54.503367 Tz (Conditioned ) Tj 3.791667 0 Td 64.814815 Tz (medium ) Tj 2.527778 0 Td 62.654321 Tz (was ) Tj 1.302778 0 Td 49.331276 Tz (collected ) Tj 51.428571 0 0 51.428571 0 1336.242274 Tm 6.358333 0 Td 44.722222 Tz (after ) Tj 1.594444 0 Td 57.037037 Tz (24-30 ) Tj 1.925 0 Td 49.151235 Tz (hours, ) Tj 2.061111 0 Td 55.902778 Tz (supplemented ) Tj 4.277778 0 Td 52.662037 Tz (with ) Tj 1.516667 0 Td 72.376543 Tz (20% ) Tj 1.555556 0 Td 51.851852 Tz (ethylene ) Tj 2.702778 0 Td 50.771605 Tz (glycol ) Tj 51.428571 0 0 51.428571 0 1294.496368 Tm 6.358333 0 Td 58.333333 Tz (and ) Tj 1.186111 0 Td 61.574074 Tz (was ) Tj 1.244444 0 Td 43.930041 Tz (clarified ) Tj 2.508333 0 Td 59.953704 Tz (by ) Tj 0.855556 0 Td 48.37963 Tz (centrifugation ) Tj 4.219444 0 Td 42.12963 Tz (at ) Tj 0.641667 0 Td 62.114198 Tz (3000xg ) Tj 2.352778 0 Td 58.333333 Tz (and ) Tj 1.166667 0 Td 59.143519 Tz (4C. ) Tj 1.594444 0 Td 48.611111 Tz (for ) Tj 1.05 0 Td 55.092593 Tz (10 ) Tj 40 0 0 40 0 1257 Tm 8.225 0 Td 66.666667 Tz (min. ) Tj 2.125 0 Td 83.333333 Tz (The ) Tj 2.075 0 Td 75 Tz (media ) Tj 2.775 0 Td 79.166667 Tz (was ) Tj 1.975 0 Td 66.319444 Tz (concentrated ) Tj 5.375 0 Td 77.777778 Tz (~10 ) Tj 1.9 0 Td 63.541667 Tz (fold ) Tj 2.05 0 Td 75 Tz (and ) Tj 1.85 0 Td 64.583333 Tz (buffer ) Tj 51.428571 0 0 51.428571 0 1212.43681 Tm 6.358333 0 Td 57.613169 Tz (exchanged ) Tj 3.286111 0 Td 46.180556 Tz (into ) Tj 1.263889 0 Td 48.611111 Tz (Tris ) Tj 1.361111 0 Td 54.012346 Tz (\(50 ) Tj 1.147222 0 Td 76.697531 Tz (mM, ) Tj 1.555556 0 Td 74.537037 Tz (pH ) Tj 1.088889 0 Td 46.990741 Tz (7.4\) ) Tj 1.302778 0 Td 51.527778 Tz (containing ) Tj 3.266667 0 Td 72.376543 Tz (20% ) Tj 1.497222 0 Td 56.388889 Tz (ethyl ) Tj 51.428571 0 0 51.428571 0 1167.659831 Tm 6.358333 0 Td 56.17284 Tz (ene ) Tj 1.127778 0 Td 49.691358 Tz (glycol ) Tj 1.963889 0 Td 51.851852 Tz (using ) Tj 1.672222 0 Td 56.712963 Tz (an ) Tj 0.758333 0 Td 64.274691 Tz (Amicon ) Tj 2.469444 0 Td 60.763889 Tz (8050 ) Tj 1.575 0 Td 42.939815 Tz (cell ) Tj 1.166667 0 Td 41.589506 Tz (fitted ) Tj 1.633333 0 Td 53.472222 Tz (with ) Tj 1.361111 0 Td 55.092593 Tz (a ) Tj 0.486111 0 Td 73.726852 Tz (PM30 ) Tj 1.886111 0 Td 38.888889 Tz (filter ) Tj 51.428571 0 0 51.428571 0 1125.206125 Tm 6.377778 0 Td 57.407407 Tz (\(MILLIPORE\(R\), ) Tj 5.094444 0 Td 43.75 Tz (Billerica, ) Tj 2.838889 0 Td 50 Tz (Mass.\). ) Tj 2.294444 0 Td 51.851852 Tz (Aliquots ) Tj 2.702778 0 Td 58.333333 Tz (of ) Tj 0.777778 0 Td 52.391975 Tz (concentrated ) Tj 40 0 0 40 0 1091 Tm 8.175 0 Td 67.045455 Tz (conditioned ) Tj 4.675 0 Td 75.833333 Tz (media ) Tj 2.5 0 Td 76.041667 Tz (were ) Tj 2.075 0 Td 63.194444 Tz (stored ) Tj 2.5 0 Td 56.25 Tz (at ) Tj 0.875 0 Td 80.208333 Tz (4C. ) Tj 2.2 0 Td 56.666667 Tz (until ) Tj 2 0 Td 66.666667 Tz (needed. ) Tj 51.428571 0 0 51.428571 0 1043.151351 Tm 7.097222 0 Td 77.777778 Tz (ATX ) Tj 1.711111 0 Td 46.990741 Tz (inhibition ) Tj 3.15 0 Td 61.574074 Tz (was ) Tj 1.419444 0 Td 54.62963 Tz (assayed ) Tj 2.605556 0 Td 52.5 Tz (using ) Tj 1.925 0 Td 55.902778 Tz (FS-3 ) Tj 1.711111 0 Td 54.282407 Tz (\(Echelon ) Tj 2.955556 0 Td 69.135802 Tz (Bio ) Tj 51.428571 0 0 51.428571 0 1000.706468 Tm 6.377778 0 Td 47.890947 Tz (sciences, ) Tj 2.780556 0 Td 41.481481 Tz (Inc., ) Tj 1.438889 0 Td 47.800926 Tz (Salt ) Tj 1.361111 0 Td 58.333333 Tz (Lake ) Tj 1.575 0 Td 46.018519 Tz (City, ) Tj 1.575 0 Td 52.5 Tz (Utah, ) Tj 1.769444 0 Td 70.486111 Tz (USA\) ) Tj 1.866667 0 Td 48.611111 Tz (as ) Tj 0.758333 0 Td 55.092593 Tz (a ) Tj 0.525 0 Td 48.251029 Tz (substrate ) Tj 2.741667 0 Td 60.493827 Tz (and ) Tj 40 0 0 40 0 966 Tm 8.175 0 Td 81.944444 Tz (~10 ) Tj 1.975 0 Td 67.5 Tz (times ) Tj 2.55 0 Td 66.666667 Tz (concentrated ) Tj 5.3 0 Td 67.424242 Tz (conditioned ) Tj 4.975 0 Td 67.916667 Tz (serum-free ) Tj 4.65 0 Td 83.333333 Tz (medium ) Tj 51.428571 0 0 51.428571 0 917 Tm 6.377778 0 Td 70 Tz (\(CCM\) ) Tj 2.411111 0 Td 57.523148 Tz (from ) Tj 1.730556 0 Td 93.981481 Tz (MDA ) Tj 2.002778 0 Td 67.515432 Tz (MB-435 ) Tj 2.780556 0 Td 44.074074 Tz (cells ) Tj 1.652778 0 Td 50.231481 Tz (as ) Tj 0.952778 0 Td 49.691358 Tz (the ) Tj 1.225 0 Td 52.391975 Tz (source ) Tj 2.197222 0 Td 58.333333 Tz (of ) Tj 0.894444 0 Td 65.625 Tz (ATX. ) Tj 51.428571 0 0 51.428571 0 879.564706 Tm 6.358333 0 Td 57.253086 Tz (Assays ) Tj 2.177778 0 Td 59.143519 Tz (were ) Tj 1.516667 0 Td 56.893004 Tz (performed ) Tj 3.169444 0 Td 46.990741 Tz (in ) Tj 0.680556 0 Td 53.240741 Tz (96-well ) Tj 2.333333 0 Td 47.530864 Tz (plates ) Tj 1.866667 0 Td 52.662037 Tz (with ) Tj 1.4 0 Td 89.660494 Tz (CCM ) Tj 1.730556 0 Td 61.574074 Tz (compris ) Tj 51.428571 0 0 51.428571 0 833.464329 Tm 6.358333 0 Td 51.851852 Tz (ing ) Tj 1.05 0 Td 50.05144 Tz (one-third ) Tj 2.819444 0 Td 56.712963 Tz (of ) Tj 0.758333 0 Td 49.691358 Tz (the ) Tj 1.030556 0 Td 42.777778 Tz (total ) Tj 1.438889 0 Td 59.953704 Tz (volume ) Tj 2.294444 0 Td 58.333333 Tz (and ) Tj 1.186111 0 Td 42.777778 Tz (final ) Tj 1.477778 0 Td 55.092593 Tz (FS-3 ) Tj 1.497222 0 Td 59.41358 Tz (and ) Tj 1.205556 0 Td 56.30787 Tz (charcoal ) Tj 51.428571 0 0 51.428571 0 793.826618 Tm 6.377778 0 Td 48.611111 Tz (stripped ) Tj 2.469444 0 Td 43.425926 Tz (fatty ) Tj 1.438889 0 Td 51.041667 Tz (acid ) Tj 1.380556 0 Td 46.180556 Tz (free ) Tj 1.283333 0 Td 76.697531 Tz (BSA ) Tj 1.477778 0 Td 50.694444 Tz (concentrations ) Tj 4.394444 0 Td 59.953704 Tz (of ) Tj 0.816667 0 Td 38.888889 Tz (1 ) Tj 0.427778 0 Td 58.333333 Tz (and ) Tj 1.166667 0 Td 61.574074 Tz (30 ) Tj 0.913889 0 Td 81.018519 Tz (uM ) Tj 1.108333 0 Td 50.231481 Tz (in ) Tj 51.428571 0 0 51.428571 0 751.986996 Tm 6.358333 0 Td 51.851852 Tz (assay ) Tj 1.730556 0 Td 50.231481 Tz (buffer ) Tj 1.963889 0 Td 43.75 Tz (\(1 ) Tj 0.797222 0 Td 97.222222 Tz (mM ) Tj 1.341667 0 Td 55.902778 Tz (each ) Tj 1.516667 0 Td 64.00463 Tz (CaCl ) Tj 1.944444 0 Td 59.41358 Tz (and ) Tj 1.244444 0 Td 59.953704 Tz (MgCl2, ) Tj 2.352778 0 Td 51.851852 Tz (5 ) Tj 0.544444 0 Td 98.842593 Tz (mM ) Tj 1.380556 0 Td 69.135802 Tz (KCl ) Tj 1.613889 0 Td 58.333333 Tz (140 ) Tj 51.428571 0 0 51.428571 0 709.468193 Tm 6.358333 0 Td 100.462963 Tz (mM ) Tj 1.419444 0 Td 56.388889 Tz (NaCl, ) Tj 1.905556 0 Td 59.953704 Tz (50 ) Tj 0.913889 0 Td 100.462963 Tz (mM ) Tj 1.380556 0 Td 47.800926 Tz (Tris ) Tj 1.341667 0 Td 74.537037 Tz (pH ) Tj 1.088889 0 Td 44.074074 Tz (8.0\). ) Tj 1.555556 0 Td 53.20216 Tz (Fluorescence ) Tj 3.986111 0 Td 63.734568 Tz (was ) Tj 1.361111 0 Td 51.851852 Tz (read ) Tj 1.419444 0 Td 45.37037 Tz (at ) Tj 0.738889 0 Td 55.092593 Tz (5 ) Tj 51.428571 0 0 51.428571 0 669.775713 Tm 6.358333 0 Td 56.17284 Tz (minute ) Tj 2.275 0 Td 45.37037 Tz (intervals ) Tj 2.683333 0 Td 59.953704 Tz (by ) Tj 0.952778 0 Td 51.851852 Tz (a ) Tj 0.583333 0 Td 57.118056 Tz (Synergy2 ) Tj 2.975 0 Td 55.092593 Tz (system ) Tj 2.275 0 Td 52.662037 Tz (\(BioTek, ) Tj 2.761111 0 Td 54.372428 Tz (Winooski, ) Tj 51.428571 0 0 51.428571 0 627.75447 Tm 6.358333 0 Td 47.800926 Tz (Vt.\) ) Tj 1.283333 0 Td 52.662037 Tz (with ) Tj 1.4 0 Td 47.314815 Tz (excitation ) Tj 2.955556 0 Td 59.41358 Tz (and ) Tj 1.205556 0 Td 53.06713 Tz (emission ) Tj 2.722222 0 Td 54.208754 Tz (wavelengths ) Tj 3.675 0 Td 58.333333 Tz (of ) Tj 0.777778 0 Td 58.333333 Tz (485 ) Tj 1.186111 0 Td 58.333333 Tz (and ) Tj 1.186111 0 Td 59.41358 Tz (538 ) Tj 51.428571 0 0 51.428571 0 586.620347 Tm 6.358333 0 Td 61.574074 Tz (nm, ) Tj 1.283333 0 Td 46.118234 Tz (respectively. ) Tj 3.811111 0 Td 50 Tz (Results ) Tj 2.275 0 Td 48.611111 Tz (are ) Tj 1.069444 0 Td 61.574074 Tz (shown ) Tj 2.002778 0 Td 46.990741 Tz (at ) Tj 0.777778 0 Td 35.648148 Tz (1 ) Tj 0.447222 0 Td 49.907407 Tz (hour, ) Tj 1.652778 0 Td 46.990741 Tz (at ) Tj 0.7 0 Td 58.981481 Tz (which ) Tj 1.925 0 Td 51.203704 Tz (point ) Tj 51.428571 0 0 51.428571 0 543.227621 Tm 6.358333 0 Td 39.969136 Tz (all ) Tj 0.991667 0 Td 50.501543 Tz (fluorescence ) Tj 3.888889 0 Td 55.555556 Tz (changes ) Tj 2.586111 0 Td 50.231481 Tz (as ) Tj 0.855556 0 Td 58.333333 Tz (a ) Tj 0.583333 0 Td 50.231481 Tz (function ) Tj 2.702778 0 Td 56.712963 Tz (of ) Tj 0.836111 0 Td 54.282407 Tz (time ) Tj 1.575 0 Td 58.333333 Tz (were ) Tj 1.652778 0 Td 42.12963 Tz (linear. ) Tj 51.428571 0 0 51.428571 0 502.236908 Tm 6.377778 0 Td 53.20216 Tz (Fluorescence ) Tj 4.161111 0 Td 50.231481 Tz (readings ) Tj 2.702778 0 Td 59.143519 Tz (were ) Tj 1.75 0 Td 54.12037 Tz (normalized ) Tj 3.538889 0 Td 45.37037 Tz (to ) Tj 0.894444 0 Td 49.537037 Tz (vehicle ) Tj 2.333333 0 Td 49.074074 Tz (control ) Tj 40 0 0 40 0 467 Tm 8.175 0 Td 58.333333 Tz (after ) Tj 1.9 0 Td 62.5 Tz (subtraction ) Tj 4.3 0 Td 70.833333 Tz (of ) Tj 0.925 0 Td 65.277778 Tz (fluorescence ) Tj 4.875 0 Td 58.333333 Tz (in ) Tj 0.85 0 Td 63.888889 Tz (the ) Tj 1.3 0 Td 70.833333 Tz (absence ) Tj 3.125 0 Td 72.916667 Tz (of ) Tj 0.975 0 Td 93.75 Tz (CCM. ) Tj 2.5 0 Td 71.875 Tz (Data ) Tj 40 0 0 40 0 426 Tm 8.175 0 Td 63.888889 Tz (are ) Tj 1.575 0 Td 79.166667 Tz (shown ) Tj 2.8 0 Td 64.583333 Tz (as ) Tj 1.225 0 Td 62.5 Tz (the ) Tj 1.55 0 Td 76.851852 Tz (meantS.D. ) Tj 4.6 0 Td 72.916667 Tz (of ) Tj 1.175 0 Td 56.25 Tz (at ) Tj 1.075 0 Td 57.5 Tz (least ) Tj 2.125 0 Td 62.5 Tz (three ) Tj 2.3 0 Td 59.722222 Tz (wells. ) Tj 2.575 0 Td 81.944444 Tz (The ) Tj 51.428571 0 0 51.428571 0 377.388601 Tm 6.358333 0 Td 46.990741 Tz (inhibition ) Tj 3.188889 0 Td 45.37037 Tz (levels ) Tj 1.963889 0 Td 51.851852 Tz (are ) Tj 1.263889 0 Td 48.251029 Tz (inversely ) Tj 2.994444 0 Td 46.296296 Tz (related ) Tj 2.294444 0 Td 45.37037 Tz (to ) Tj 0.894444 0 Td 49.691358 Tz (the ) Tj 1.244444 0 Td 50.501543 Tz (fluorescence ) Tj 51.428571 0 0 51.428571 0 337.133333 Tm 6.358333 0 Td 57.253086 Tz (change ) Tj 2.197222 0 Td 55.902778 Tz (overtime ) Tj 2.780556 0 Td 60.493827 Tz (and ) Tj 1.205556 0 Td 50.605413 Tz (concentration ) Tj 4.083333 0 Td 58.333333 Tz (and ) Tj 1.166667 0 Td 52.572016 Tz (converted ) Tj 2.936111 0 Td 48.611111 Tz (to ) Tj 0.719444 0 Td 56.481481 Tz (percent ) Tj 51.428571 0 0 51.428571 0 294.846926 Tm 6.358333 0 Td 56.17284 Tz (age ) Tj 1.263889 0 Td 50.771605 Tz (fluorescence ) Tj 3.888889 0 Td 53.472222 Tz (response ) Tj 2.819444 0 Td 45.37037 Tz (to ) Tj 0.816667 0 Td 61.574074 Tz (show ) Tj 1.769444 0 Td 49.691358 Tz (the ) Tj 1.147222 0 Td 47.863248 Tz (effectiveness ) Tj 4.005556 0 Td 59.953704 Tz (of ) Tj 0.875 0 Td 49.691358 Tz (the ) Tj 51.428571 0 0 51.428571 0 253.943765 Tm 6.358333 0 Td 61.934156 Tz (compounds ) Tj 3.558333 0 Td 47.530864 Tz (tested ) Tj 1.925 0 Td 51.851852 Tz (\(low ) Tj 1.497222 0 Td 97.222222 Tz (% ) Tj 0.836111 0 Td 52.256944 Tz (response ) Tj 2.722222 0 Td 43.344907 Tz (reflects ) Tj 2.275 0 Td 46.8107 Tz (effective ) Tj 2.741667 0 Td 52.932099 Tz (inhibi ) Tj 51.428571 0 0 51.428571 0 210 Tm 6.338889 0 Td 43.209877 Tz (tion\). ) Tj 1.652778 0 Td 64.814815 Tz (The ) Tj 1.283333 0 Td 48.148148 Tz (control ) Tj 2.197222 0 Td 60.493827 Tz (was ) Tj 1.244444 0 Td 71.296296 Tz (LPA ) Tj 1.4 0 Td 48.070988 Tz (alone. ) Tj 1.827778 0 Td 64.814815 Tz (The ) Tj 1.283333 0 Td 44.907407 Tz (results ) Tj 2.002778 0 Td 53.472222 Tz (of ) Tj 0.738889 0 Td 49.259259 Tz (these ) Tj 1.613889 0 Td 42.12963 Tz (tests ) Tj 1.419444 0 Td 47.530864 Tz (for ) Tj 51.428571 0 0 51.428571 0 171.287075 Tm 6.338889 0 Td 50.771605 Tz (the ) Tj 1.147222 0 Td 60.648148 Tz (Example ) Tj 2.722222 0 Td 61.574074 Tz (compounds ) Tj 3.519444 0 Td 59.143519 Tz (from ) Tj 1.594444 0 Td 57.685185 Tz (above ) Tj 1.905556 0 Td 59.143519 Tz (were ) Tj 1.575 0 Td 51.851852 Tz (as ) Tj 0.816667 0 Td 48.206019 Tz (follows: ) Tj 30 0 0 30 0 2547 Tm 41.666667 0 Td 75 Tz (10 ) Tj 30 0 0 30 0 2339 Tm 41.666667 0 Td 72.222222 Tz (15 ) Tj 30 0 0 30 0 1923 Tm 41.6 0 Td 77.777778 Tz (25 ) Tj 30 0 0 30 0 1716 Tm 41.6 0 Td 80.555556 Tz (30 ) Tj 30 0 0 30 0 1507 Tm 41.6 0 Td 77.777778 Tz (35 ) Tj 30 0 0 30 0 1299 Tm 41.566667 0 Td 83.333333 Tz (40 ) Tj 30 0 0 30 0 1091 Tm 41.566667 0 Td 80.555556 Tz (45 ) Tj 30 0 0 30 0 883 Tm 41.6 0 Td 80.555556 Tz (50 ) Tj 30 0 0 30 0 675 Tm 41.6 0 Td 77.777778 Tz (55 ) Tj 30 0 0 30 0 467 Tm 41.633333 0 Td 77.777778 Tz (60 ) Tj 30 0 0 30 0 259 Tm 41.633333 0 Td 75 Tz (65 ) Tj 52.857143 0 0 52.857143 0 2968 Tm 32.635135 0 Td 77.252252 Tz (20 ) Tj 38.571429 0 0 38.571429 0 2913 Tm 43.477778 0 Td 101.975309 Tz (TABLE ) Tj 3.292593 0 Td 77.777778 Tz (2 ) Tj 40 0 0 40 0 2843.541139 Tm 35.325 0 Td 54.166667 Tz (Autotaxin ) Tj 3.1 0 Td 48.4375 Tz (Activity ) Tj 2.575 0 Td 54.166667 Tz (Reduction ) Tj 3.15 0 Td 52.083333 Tz (of ) Tj 0.8 0 Td 53.030303 Tz (Exemplified ) Tj 3.7 0 Td 64.814815 Tz (Compounds ) Tj 37.142857 0 0 37.142857 0 2778.231379 Tm 35.996154 0 Td 66.025641 Tz (Example ) Tj 4.657692 0 Td 56.607495 Tz (Concentration ) Tj 6.488462 0 Td 67.307692 Tz (Time ) Tj 3.123077 0 Td 57.58547 Tz (Fluorescence ) Tj 4.361538 0 Td 71.794872 Tz (\(% ) Tj 1.130769 0 Td 58.831909 Tz (Response\) ) Tj 30 0 0 30 0 2719 Tm 46.333333 0 Td 55.555556 Tz (1 ) Tj 5.766667 0 Td 77.777778 Tz (30 ) Tj 1.933333 0 Td 144.444444 Tz (M ) Tj 4.366667 0 Td 77.777778 Tz (O ) Tj 0.966667 0 Td 76.388889 Tz (hour ) Tj 7.666667 0 Td 66.666667 Tz (96.1 ) Tj 30 0 0 30 0 2685 Tm 46.333333 0 Td 55.555556 Tz (1 ) Tj 5.333333 0 Td 75.925926 Tz (100 ) Tj 2.4 0 Td 138.888889 Tz (M ) Tj 4.333333 0 Td 77.777778 Tz (O ) Tj 0.966667 0 Td 76.388889 Tz (hour ) Tj 7.666667 0 Td 66.666667 Tz (94.1 ) Tj 30 0 0 30 0 2652 Tm 46.266667 0 Td 77.777778 Tz (2 ) Tj 6.3 0 Td 72.222222 Tz (3 ) Tj 1.5 0 Td 138.888889 Tz (M ) Tj 4.366667 0 Td 72.222222 Tz (6 ) Tj 0.933333 0 Td 71.111111 Tz (hours ) Tj 7.666667 0 Td 69.444444 Tz (2S.O ) Tj 30 0 0 30 0 2619 Tm 46.266667 0 Td 77.777778 Tz (2 ) Tj 6.3 0 Td 72.222222 Tz (3 ) Tj 1.5 0 Td 138.888889 Tz (M ) Tj 4.333333 0 Td 72.222222 Tz (3 ) Tj 0.966667 0 Td 71.111111 Tz (hours ) Tj 7.666667 0 Td 66.666667 Tz (28.1 ) Tj 28.285714 0 0 28.285714 0 2585 Tm 49.070707 0 Td 82.491582 Tz (2 ) Tj 6.681818 0 Td 76.599327 Tz (3 ) Tj 1.590909 0 Td 147.306397 Tz (M ) Tj 6.151515 0 Td 58.922559 Tz (Ol ) Tj 7.565657 0 Td 75.126263 Tz (47.9 ) Tj 30 0 0 30 0 2552 Tm 46.266667 0 Td 77.777778 Tz (2 ) Tj 6.3 0 Td 72.222222 Tz (3 ) Tj 1.5 0 Td 138.888889 Tz (M ) Tj 4.333333 0 Td 77.777778 Tz (O ) Tj 0.966667 0 Td 76.388889 Tz (hour ) Tj 7.7 0 Td 66.666667 Tz (83.3 ) Tj 30 0 0 30 0 2519 Tm 46.266667 0 Td 77.777778 Tz (2 ) Tj 5.833333 0 Td 77.777778 Tz (30 ) Tj 1.933333 0 Td 144.444444 Tz (M ) Tj 4.4 0 Td 72.222222 Tz (6 ) Tj 0.933333 0 Td 71.111111 Tz (hours ) Tj 7.633333 0 Td 68.055556 Tz (-2.1 ) Tj 30 0 0 30 0 2486 Tm 46.266667 0 Td 77.777778 Tz (2 ) Tj 5.833333 0 Td 77.777778 Tz (30 ) Tj 1.933333 0 Td 144.444444 Tz (M ) Tj 4.366667 0 Td 72.222222 Tz (3 ) Tj 0.966667 0 Td 71.111111 Tz (hours ) Tj 8.166667 0 Td 66.666667 Tz (9.4 ) Tj 28.285714 0 0 28.285714 0 2452 Tm 49.070707 0 Td 82.491582 Tz (2 ) Tj 6.186869 0 Td 82.491582 Tz (30 ) Tj 2.050505 0 Td 153.198653 Tz (M ) Tj 6.186869 0 Td 58.922559 Tz (Ol ) Tj 7.60101 0 Td 75.126263 Tz (35.4 ) Tj 30 0 0 30 0 2419 Tm 46.266667 0 Td 77.777778 Tz (2 ) Tj 5.833333 0 Td 77.777778 Tz (30 ) Tj 1.933333 0 Td 144.444444 Tz (M ) Tj 4.366667 0 Td 77.777778 Tz (O ) Tj 0.966667 0 Td 76.388889 Tz (hour ) Tj 7.666667 0 Td 68.055556 Tz (57.3 ) Tj 30 0 0 30 0 2386 Tm 46.266667 0 Td 72.222222 Tz (3 ) Tj 6.3 0 Td 72.222222 Tz (3 ) Tj 1.5 0 Td 138.888889 Tz (M ) Tj 4.366667 0 Td 72.222222 Tz (6 ) Tj 0.933333 0 Td 71.111111 Tz (hours ) Tj 7.666667 0 Td 70.833333 Tz (34.4 ) Tj 30 0 0 30 0 2353 Tm 46.266667 0 Td 72.222222 Tz (3 ) Tj 6.3 0 Td 72.222222 Tz (3 ) Tj 1.5 0 Td 138.888889 Tz (M ) Tj 4.333333 0 Td 72.222222 Tz (3 ) Tj 0.966667 0 Td 71.111111 Tz (hours ) Tj 7.633333 0 Td 70.833333 Tz (44.8 ) Tj 28.285714 0 0 28.285714 0 2319 Tm 49.070707 0 Td 76.599327 Tz (3 ) Tj 6.681818 0 Td 76.599327 Tz (3 ) Tj 1.590909 0 Td 147.306397 Tz (M ) Tj 6.151515 0 Td 58.922559 Tz (Ol ) Tj 7.636364 0 Td 73.653199 Tz (60.4 ) Tj 30 0 0 30 0 2286 Tm 46.266667 0 Td 72.222222 Tz (3 ) Tj 6.3 0 Td 72.222222 Tz (3 ) Tj 1.5 0 Td 138.888889 Tz (M ) Tj 4.333333 0 Td 77.777778 Tz (O ) Tj 0.966667 0 Td 76.388889 Tz (hour ) Tj 7.666667 0 Td 69.444444 Tz (94.8 ) Tj 30 0 0 30 0 2253 Tm 46.266667 0 Td 72.222222 Tz (3 ) Tj 5.833333 0 Td 77.777778 Tz (30 ) Tj 1.933333 0 Td 144.444444 Tz (M ) Tj 4.4 0 Td 72.222222 Tz (6 ) Tj 0.933333 0 Td 71.111111 Tz (hours ) Tj 7.733333 0 Td 68.055556 Tz (10.4 ) Tj 30 0 0 30 0 2220 Tm 46.266667 0 Td 72.222222 Tz (3 ) Tj 5.833333 0 Td 77.777778 Tz (30 ) Tj 1.933333 0 Td 144.444444 Tz (M ) Tj 4.366667 0 Td 72.222222 Tz (3 ) Tj 0.966667 0 Td 71.111111 Tz (hours ) Tj 7.733333 0 Td 66.666667 Tz (19.0 ) Tj 28.285714 0 0 28.285714 0 2186 Tm 49.070707 0 Td 76.599327 Tz (3 ) Tj 6.186869 0 Td 82.491582 Tz (30 ) Tj 2.050505 0 Td 153.198653 Tz (M ) Tj 6.186869 0 Td 58.922559 Tz (Ol ) Tj 7.60101 0 Td 72.180135 Tz (37.5 ) Tj 30 0 0 30 0 2153 Tm 46.266667 0 Td 72.222222 Tz (3 ) Tj 5.833333 0 Td 77.777778 Tz (30 ) Tj 1.933333 0 Td 144.444444 Tz (M ) Tj 4.366667 0 Td 77.777778 Tz (O ) Tj 0.966667 0 Td 76.388889 Tz (hour ) Tj 7.666667 0 Td 69.444444 Tz (71.9 ) Tj 30 0 0 30 0 2120 Tm 46.233333 0 Td 88.888889 Tz (4 ) Tj 6.333333 0 Td 72.222222 Tz (3 ) Tj 1.5 0 Td 138.888889 Tz (M ) Tj 4.366667 0 Td 72.222222 Tz (6 ) Tj 0.933333 0 Td 71.111111 Tz (hours ) Tj 7.666667 0 Td 69.444444 Tz (21.9 ) Tj 30 0 0 30 0 2087 Tm 46.233333 0 Td 88.888889 Tz (4 ) Tj 6.333333 0 Td 72.222222 Tz (3 ) Tj 1.5 0 Td 138.888889 Tz (M ) Tj 4.333333 0 Td 72.222222 Tz (3 ) Tj 0.966667 0 Td 71.111111 Tz (hours ) Tj 7.666667 0 Td 68.055556 Tz (33.3 ) Tj 28.285714 0 0 28.285714 0 2053 Tm 49.035354 0 Td 94.276094 Tz (4 ) Tj 6.717172 0 Td 76.599327 Tz (3 ) Tj 1.590909 0 Td 147.306397 Tz (M ) Tj 6.151515 0 Td 58.922559 Tz (Ol ) Tj 7.60101 0 Td 73.653199 Tz (SO.O ) Tj 30 0 0 30 0 2020 Tm 46.233333 0 Td 88.888889 Tz (4 ) Tj 6.333333 0 Td 72.222222 Tz (3 ) Tj 1.5 0 Td 138.888889 Tz (M ) Tj 4.333333 0 Td 77.777778 Tz (O ) Tj 0.966667 0 Td 76.388889 Tz (hour ) Tj 7.7 0 Td 88.888889 Tz (813 ) Tj 30 0 0 30 0 1987 Tm 46.233333 0 Td 88.888889 Tz (4 ) Tj 5.866667 0 Td 77.777778 Tz (30 ) Tj 1.933333 0 Td 144.444444 Tz (M ) Tj 4.4 0 Td 72.222222 Tz (6 ) Tj 0.933333 0 Td 71.111111 Tz (hours ) Tj 7.633333 0 Td 68.055556 Tz (-2.1 ) Tj 30 0 0 30 0 1954 Tm 46.233333 0 Td 88.888889 Tz (4 ) Tj 5.866667 0 Td 77.777778 Tz (30 ) Tj 1.933333 0 Td 144.444444 Tz (M ) Tj 4.366667 0 Td 72.222222 Tz (3 ) Tj 0.966667 0 Td 71.111111 Tz (hours ) Tj 8.166667 0 Td 64.814815 Tz (5.2 ) Tj 28.285714 0 0 28.285714 0 1920 Tm 49.035354 0 Td 94.276094 Tz (4 ) Tj 6.222222 0 Td 82.491582 Tz (30 ) Tj 2.050505 0 Td 153.198653 Tz (M ) Tj 6.186869 0 Td 58.922559 Tz (Ol ) Tj 7.671717 0 Td 69.234007 Tz (12.5 ) Tj 30 0 0 30 0 1887 Tm 46.233333 0 Td 88.888889 Tz (4 ) Tj 5.866667 0 Td 77.777778 Tz (30 ) Tj 1.933333 0 Td 144.444444 Tz (M ) Tj 4.366667 0 Td 77.777778 Tz (O ) Tj 0.966667 0 Td 76.388889 Tz (hour ) Tj 7.666667 0 Td 69.444444 Tz (26.0 ) Tj 30 0 0 30 0 1854 Tm 46.266667 0 Td 72.222222 Tz (5 ) Tj 6.3 0 Td 72.222222 Tz (3 ) Tj 1.5 0 Td 138.888889 Tz (M ) Tj 4.366667 0 Td 72.222222 Tz (6 ) Tj 0.933333 0 Td 71.111111 Tz (hours ) Tj 7.666667 0 Td 69.444444 Tz (31.2 ) Tj 30 0 0 30 0 1820 Tm 46.266667 0 Td 72.222222 Tz (5 ) Tj 6.3 0 Td 72.222222 Tz (3 ) Tj 1.5 0 Td 138.888889 Tz (M ) Tj 4.333333 0 Td 72.222222 Tz (3 ) Tj 0.966667 0 Td 71.111111 Tz (hours ) Tj 7.633333 0 Td 70.833333 Tz (42.7 ) Tj 28.285714 0 0 28.285714 0 1787 Tm 49.070707 0 Td 76.599327 Tz (5 ) Tj 6.681818 0 Td 76.599327 Tz (3 ) Tj 1.590909 0 Td 147.306397 Tz (M ) Tj 6.151515 0 Td 58.922559 Tz (Ol ) Tj 7.60101 0 Td 70.707071 Tz (57.1 ) Tj 30 0 0 30 0 1754 Tm 46.266667 0 Td 72.222222 Tz (5 ) Tj 6.3 0 Td 72.222222 Tz (3 ) Tj 1.5 0 Td 138.888889 Tz (M ) Tj 4.333333 0 Td 77.777778 Tz (O ) Tj 0.966667 0 Td 76.388889 Tz (hour ) Tj 7.666667 0 Td 68.055556 Tz (92.5 ) Tj 30 0 0 30 0 1721 Tm 46.266667 0 Td 72.222222 Tz (5 ) Tj 5.833333 0 Td 77.777778 Tz (30 ) Tj 1.933333 0 Td 144.444444 Tz (M ) Tj 4.4 0 Td 72.222222 Tz (6 ) Tj 0.933333 0 Td 71.111111 Tz (hours ) Tj 8.166667 0 Td 64.814815 Tz (9.6 ) Tj 30 0 0 30 0 1687 Tm 46.266667 0 Td 72.222222 Tz (5 ) Tj 5.833333 0 Td 77.777778 Tz (30 ) Tj 1.933333 0 Td 144.444444 Tz (M ) Tj 4.366667 0 Td 72.222222 Tz (3 ) Tj 0.966667 0 Td 71.111111 Tz (hours ) Tj 7.733333 0 Td 66.666667 Tz (12.9 ) Tj 28.285714 0 0 28.285714 0 1654 Tm 49.070707 0 Td 76.599327 Tz (5 ) Tj 6.186869 0 Td 82.491582 Tz (30 ) Tj 2.050505 0 Td 153.198653 Tz (M ) Tj 6.186869 0 Td 58.922559 Tz (Ol ) Tj 7.671717 0 Td 69.234007 Tz (14.3 ) Tj 30 0 0 30 0 1620 Tm 46.266667 0 Td 72.222222 Tz (5 ) Tj 5.833333 0 Td 77.777778 Tz (30 ) Tj 1.933333 0 Td 144.444444 Tz (M ) Tj 4.366667 0 Td 77.777778 Tz (O ) Tj 0.966667 0 Td 76.388889 Tz (hour ) Tj 7.666667 0 Td 68.055556 Tz (24.5 ) Tj 30 0 0 30 0 1587 Tm 46.3 0 Td 72.222222 Tz (6 ) Tj 6.266667 0 Td 72.222222 Tz (3 ) Tj 1.5 0 Td 138.888889 Tz (M ) Tj 4.366667 0 Td 72.222222 Tz (6 ) Tj 0.933333 0 Td 71.111111 Tz (hours ) Tj 7.666667 0 Td 69.444444 Tz (32.7 ) Tj 30 0 0 30 0 1553 Tm 46.3 0 Td 72.222222 Tz (6 ) Tj 6.266667 0 Td 72.222222 Tz (3 ) Tj 1.5 0 Td 138.888889 Tz (M ) Tj 4.333333 0 Td 72.222222 Tz (3 ) Tj 0.966667 0 Td 71.111111 Tz (hours ) Tj 7.633333 0 Td 70.833333 Tz (45.7 ) Tj 28.285714 0 0 28.285714 0 1520 Tm 49.106061 0 Td 76.599327 Tz (6 ) Tj 6.646465 0 Td 76.599327 Tz (3 ) Tj 1.590909 0 Td 147.306397 Tz (M ) Tj 6.151515 0 Td 58.922559 Tz (Ol ) Tj 7.636364 0 Td 72.180135 Tz (61.9 ) Tj 30 0 0 30 0 1487 Tm 46.3 0 Td 72.222222 Tz (6 ) Tj 6.266667 0 Td 72.222222 Tz (3 ) Tj 1.5 0 Td 138.888889 Tz (M ) Tj 4.333333 0 Td 77.777778 Tz (O ) Tj 0.966667 0 Td 76.388889 Tz (hour ) Tj 7.666667 0 Td 69.444444 Tz (95.9 ) Tj 30 0 0 30 0 1454 Tm 46.3 0 Td 72.222222 Tz (6 ) Tj 5.8 0 Td 77.777778 Tz (30 ) Tj 1.933333 0 Td 144.444444 Tz (M ) Tj 4.4 0 Td 72.222222 Tz (6 ) Tj 0.933333 0 Td 71.111111 Tz (hours ) Tj 7.733333 0 Td 65.277778 Tz (18.5 ) Tj 30 0 0 30 0 1420 Tm 46.3 0 Td 72.222222 Tz (6 ) Tj 5.8 0 Td 77.777778 Tz (30 ) Tj 1.933333 0 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0 Td 62.114198 Tz (showed ) Tj 51.428571 0 0 51.428571 0 2454.536585 Tm 6.358333 0 Td 51.851852 Tz (a ) Tj 0.505556 0 Td 49.691358 Tz (reduction ) Tj 2.858333 0 Td 56.712963 Tz (from ) Tj 1.497222 0 Td 63.518519 Tz (94.8% ) Tj 2.061111 0 Td 52.662037 Tz (response ) Tj 2.663889 0 Td 43.75 Tz (at ) Tj 0.641667 0 Td 57.523148 Tz (hour ) Tj 1.477778 0 Td 61.574074 Tz (0 ) Tj 0.525 0 Td 42.12963 Tz (to ) Tj 0.680556 0 Td 61.574074 Tz (34.4% ) Tj 2.041667 0 Td 52.662037 Tz (response ) Tj 51.428571 0 0 51.428571 0 2411.74398 Tm 6.358333 0 Td 45.37037 Tz (at ) Tj 0.719444 0 Td 58.333333 Tz (hour ) Tj 1.594444 0 Td 42.12963 Tz (6\). ) Tj 0.972222 0 Td 54.444444 Tz (Thus, ) Tj 1.866667 0 Td 34.027778 Tz (it ) Tj 0.622222 0 Td 42.12963 Tz (is ) Tj 0.7 0 Td 50.925926 Tz (evident ) Tj 2.352778 0 Td 46.180556 Tz (that ) Tj 1.341667 0 Td 48.611111 Tz (the ) Tj 1.108333 0 Td 48.611111 Tz (inventive ) Tj 2.838889 0 Td 61.934156 Tz (compounds ) Tj 51.428571 0 0 51.428571 0 2371.327103 Tm 6.358333 0 Td 48.148148 Tz (exhibit ) Tj 2.158333 0 Td 48.611111 Tz (excellent ) Tj 2.741667 0 Td 47.530864 Tz (potential ) Tj 2.741667 0 Td 47.530864 Tz (for ) Tj 0.952778 0 Td 50.411523 Tz (autotaxin ) Tj 2.877778 0 Td 45.868946 Tz (inactivation, ) Tj 3.713889 0 Td 54.166667 Tz (particu ) Tj 51.428571 0 0 51.428571 0 2331.567089 Tm 6.358333 0 Td 44.074074 Tz (larly ) Tj 1.555556 0 Td 51.311728 Tz (within ) Tj 2.080556 0 Td 56.712963 Tz (an ) Tj 0.913889 0 Td 56.944444 Tz (aqueous ) Tj 2.644444 0 Td 51.851852 Tz (system, ) Tj 2.391667 0 Td 50.231481 Tz (as ) Tj 0.836111 0 Td 59.953704 Tz (compared ) Tj 3.111111 0 Td 52.662037 Tz (with ) Tj 1.516667 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 72.376543 Tz (LPA ) Tj 51.428571 0 0 51.428571 0 2286.216901 Tm 6.358333 0 Td 49.074074 Tz (control ) Tj 2.488889 0 Td 45.37037 Tz (\(1 ) Tj 1.069444 0 Td 82.638889 Tz (uM ) Tj 1.419444 0 Td 61.574074 Tz (showed ) Tj 2.644444 0 Td 51.851852 Tz (a ) Tj 0.797222 0 Td 56.481481 Tz (minimal ) Tj 2.8 0 Td 58.333333 Tz (change ) Tj 2.527778 0 Td 58.333333 Tz (from ) Tj 1.905556 0 Td 60.277778 Tz (15.6% ) Tj 51.428571 0 0 51.428571 0 2246.891967 Tm 6.358333 0 Td 53.06713 Tz (response ) Tj 2.722222 0 Td 45.37037 Tz (at ) Tj 0.7 0 Td 57.523148 Tz (hour ) Tj 1.536111 0 Td 64.814815 Tz (0 ) Tj 0.544444 0 Td 45.37037 Tz (to ) Tj 0.797222 0 Td 59.953704 Tz (1.0% ) Tj 1.672222 0 Td 52.662037 Tz (response ) Tj 2.702778 0 Td 43.75 Tz (at ) Tj 0.680556 0 Td 56.712963 Tz (hour ) Tj 1.555556 0 Td 41.049383 Tz (6\), ) Tj 0.933333 0 Td 46.990741 Tz (at ) Tj 0.738889 0 Td 41.049383 Tz (least. ) Tj 51.428571 0 0 51.428571 0 2202.820513 Tm 7.097222 0 Td 56.388889 Tz (There ) Tj 1.925 0 Td 44.560185 Tz (are, ) Tj 1.322222 0 Td 56.712963 Tz (of ) Tj 0.836111 0 Td 49.074074 Tz (course, ) Tj 2.352778 0 Td 64.814815 Tz (many ) Tj 1.808333 0 Td 46.254209 Tz (alternative ) Tj 3.247222 0 Td 59.806397 Tz (embodiments ) Tj 4.161111 0 Td 61.574074 Tz (and ) Tj 51.428571 0 0 51.428571 0 2162.050602 Tm 6.358333 0 Td 50.605413 Tz (modifications ) Tj 4.141667 0 Td 59.953704 Tz (of ) Tj 0.797222 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 50.462963 Tz (present ) Tj 2.275 0 Td 50.411523 Tz (invention ) Tj 2.897222 0 Td 58.981481 Tz (which ) Tj 1.963889 0 Td 49.691358 Tz (are ) Tj 1.069444 0 Td 52.256944 Tz (intended ) Tj 2.683333 0 Td 46.990741 Tz (to ) Tj 51.428571 0 0 51.428571 0 2120.700787 Tm 6.338889 0 Td 61.574074 Tz (be ) Tj 0.894444 0 Td 52.256944 Tz (included ) Tj 2.683333 0 Td 51.311728 Tz (within ) Tj 2.041667 0 Td 49.691358 Tz (the ) Tj 1.088889 0 Td 41.589506 Tz (spirit ) Tj 1.633333 0 Td 59.41358 Tz (and ) Tj 1.263889 0 Td 55.092593 Tz (scope ) Tj 1.827778 0 Td 59.953704 Tz (of ) Tj 0.797222 0 Td 42.939815 Tz (this ) Tj 1.244444 0 Td 47.638889 Tz (invention. ) Tj 40 0 0 40 0 2086 Tm 9.125 0 Td 84.375 Tz (What ) Tj 2.25 0 Td 91.666667 Tz (we ) Tj 1.3 0 Td 71.428571 Tz (claimed ) Tj 3.25 0 Td 44.444444 Tz (is: ) Tj 51.428571 0 0 51.428571 0 2039.320942 Tm 7.136111 0 Td 38.888889 Tz (1. ) Tj 0.563889 0 Td 87.5 Tz (A ) Tj 0.622222 0 Td 64.409722 Tz (compound ) Tj 3.188889 0 Td 57.037037 Tz (conforming ) Tj 3.538889 0 Td 46.990741 Tz (to ) Tj 0.680556 0 Td 48.611111 Tz (the ) Tj 0.972222 0 Td 47.530864 Tz (structure ) Tj 2.683333 0 Td 55.092593 Tz (of ) Tj 0.738889 0 Td 57.407407 Tz (Formula ) Tj 2.547222 0 Td 36.944444 Tz (\(II\): ) Tj 35.714286 0 0 35.714286 0 1914.034483 Tm 17.332 0 Td 98 Tz (X ) Tj 15.96 0 Td 43.166667 Tz (\(II\) ) Tj 24.285714 0 0 24.285714 0 1882 Tm 24.211765 0 Td 68.627451 Tz (3 ) Tj 2.923529 0 Td 75.490196 Tz (2 ) Tj 78.571429 0 0 78.571429 0 1808 Tm 7.14 0 Td 82.727273 Tz (/ ) Tj 0.814545 0 Td 75.30303 Tz ('N ) Tj 31.428571 0 0 31.428571 0 1733 Tm 26.027273 0 Td 111.363636 Tz (OH ) Tj 31.428571 0 0 31.428571 0 1866 Tm 26.027273 0 Td 111.363636 Tz (O ) Tj 52.857143 0 0 52.857143 0 1625.058981 Tm 6.886486 0 Td 54.054054 Tz (wherein ) Tj 2.535135 0 Td 69.369369 Tz (R ) Tj 0.605405 0 Td 37.837838 Tz (is ) Tj 0.643243 0 Td 92.492492 Tz (Cls ) Tj 1.92973 0 Td 46.666667 Tz (alkyl ) Tj 1.589189 0 Td 52.027027 Tz (or ) Tj 0.775676 0 Td 46.509009 Tz (alkenyl, ) Tj 2.440541 0 Td 78.828829 Tz (X ) Tj 0.681081 0 Td 39.414414 Tz (is ) Tj 0.643243 0 Td 92.492492 Tz (CHF ) Tj 1.835135 0 Td 52.027027 Tz (or ) Tj 0.775676 0 Td 75.675676 Tz (CHF, ) Tj 51.428571 0 0 51.428571 0 1583.833333 Tm 7.816667 0 Td 58.333333 Tz (and ) Tj 1.205556 0 Td 90.740741 Tz (X ) Tj 0.758333 0 Td 37.268519 Tz (is ) Tj 0.641667 0 Td 50 Tz (located ) Tj 2.255556 0 Td 46.990741 Tz (at ) Tj 0.738889 0 Td 46.990741 Tz (either ) Tj 1.808333 0 Td 49.016204 Tz (position ) Tj 2.547222 0 Td 58.333333 Tz (2 ) Tj 0.544444 0 Td 53.472222 Tz (or ) Tj 0.797222 0 Td 43.75 Tz (4. ) Tj 51.428571 0 0 51.428571 0 1541.700535 Tm 7.097222 0 Td 42.12963 Tz (2. ) Tj 0.7 0 Td 63.734568 Tz (The ) Tj 1.302778 0 Td 64.409722 Tz (compound ) Tj 3.266667 0 Td 55.092593 Tz (of ) Tj 0.777778 0 Td 53.148148 Tz (claim ) Tj 1.808333 0 Td 48.611111 Tz (1 ) Tj 0.525 0 Td 55.555556 Tz (wherein ) Tj 2.508333 0 Td 90.740741 Tz (X ) Tj 0.738889 0 Td 37.268519 Tz (is ) Tj 0.641667 0 Td 50.462963 Tz (located ) Tj 2.275 0 Td 46.990741 Tz (in ) Tj 0.758333 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 58.333333 Tz (4 ) Tj 52.857143 0 0 52.857143 0 1501.05 Tm 6.167568 0 Td 48.085586 Tz (position ) Tj 2.459459 0 Td 57.807808 Tz (and ) Tj 1.210811 0 Td 85.135135 Tz (X ) Tj 0.7 0 Td 37.837838 Tz (is ) Tj 0.643243 0 Td 72.522523 Tz (CHF. ) Tj 51.428571 0 0 51.428571 0 1458.702811 Tm 7.097222 0 Td 42.12963 Tz (3. ) Tj 0.7 0 Td 63.734568 Tz (The ) Tj 1.302778 0 Td 64.409722 Tz (compound ) Tj 3.266667 0 Td 55.092593 Tz (of ) Tj 0.777778 0 Td 53.148148 Tz (claim ) Tj 1.808333 0 Td 48.611111 Tz (1 ) Tj 0.525 0 Td 55.555556 Tz (wherein ) Tj 2.508333 0 Td 90.740741 Tz (X ) Tj 0.738889 0 Td 37.268519 Tz (is ) Tj 0.641667 0 Td 50.462963 Tz (located ) Tj 2.275 0 Td 46.990741 Tz (in ) Tj 0.758333 0 Td 49.691358 Tz (the ) Tj 1.088889 0 Td 55.092593 Tz (2 ) Tj 51.428571 0 0 51.428571 0 1418.028391 Tm 6.358333 0 Td 48.611111 Tz (position ) Tj 2.527778 0 Td 58.333333 Tz (and ) Tj 1.205556 0 Td 90.740741 Tz (X ) Tj 0.758333 0 Td 37.268519 Tz (is ) Tj 0.641667 0 Td 74.537037 Tz (CHF. ) Tj 30 0 0 30 0 2755 Tm 41.833333 0 Td 72.222222 Tz (5 ) Tj 30 0 0 30 0 2547 Tm 41.666667 0 Td 75 Tz (10 ) Tj 30 0 0 30 0 2339 Tm 41.666667 0 Td 72.222222 Tz (15 ) Tj 30 0 0 30 0 1923 Tm 41.6 0 Td 77.777778 Tz (25 ) Tj 30 0 0 30 0 1716 Tm 41.6 0 Td 80.555556 Tz (30 ) Tj 30 0 0 30 0 1507 Tm 41.6 0 Td 77.777778 Tz (35 ) Tj 51.428571 0 0 51.428571 0 2969 Tm 33.541667 0 Td 77.777778 Tz (22 ) Tj 51.428571 0 0 51.428571 0 2916.526658 Tm 26.016667 0 Td 43.75 Tz (4. ) Tj 0.7 0 Td 87.5 Tz (A ) Tj 0.738889 0 Td 59.953704 Tz (method ) Tj 2.352778 0 Td 55.092593 Tz (of ) Tj 0.758333 0 Td 53.06713 Tz (reducing ) Tj 2.722222 0 Td 50.05144 Tz (autotaxin ) Tj 2.877778 0 Td 45.37037 Tz (activity ) Tj 2.372222 0 Td 45.37037 Tz (in ) Tj 0.738889 0 Td 37.808642 Tz (its ) Tj 0.855556 0 Td 44.444444 Tz (ability ) Tj 2.041667 0 Td 46.990741 Tz (to ) Tj 51.428571 0 0 51.428571 0 2877.788618 Tm 25.297222 0 Td 47.314815 Tz (react ) Tj 1.536111 0 Td 53.472222 Tz (with ) Tj 1.419444 0 Td 52.274557 Tz (lysophosphatidylcholine ) Tj 7.369444 0 Td 45.37037 Tz (to ) Tj 0.680556 0 Td 57.523148 Tz (form ) Tj 1.555556 0 Td 51.041667 Tz (lysophosphatidic ) Tj 51.428571 0 0 51.428571 0 2831.700629 Tm 25.297222 0 Td 46.018519 Tz (acid, ) Tj 1.672222 0 Td 47.800926 Tz (said ) Tj 1.419444 0 Td 59.953704 Tz (method ) Tj 2.411111 0 Td 54.768519 Tz (comprising ) Tj 3.519444 0 Td 49.691358 Tz (the ) Tj 1.147222 0 Td 49.151235 Tz (introduction ) Tj 3.830556 0 Td 55.092593 Tz (of ) Tj 0.836111 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 83.179012 Tz (com ) Tj 51.428571 0 0 51.428571 0 2792.861295 Tm 25.297222 0 Td 60.925926 Tz (pound ) Tj 2.138889 0 Td 55.092593 Tz (of ) Tj 0.875 0 Td 53.148148 Tz (claim ) Tj 1.944444 0 Td 48.611111 Tz (1 ) Tj 0.661111 0 Td 50.231481 Tz (within ) Tj 2.1 0 Td 58.333333 Tz (an ) Tj 1.011111 0 Td 56.481481 Tz (aqueous ) Tj 2.683333 0 Td 55.632716 Tz (system ) Tj 2.333333 0 Td 50.771605 Tz (including ) Tj 3.013889 0 Td 59.953704 Tz (an ) Tj 51.428571 0 0 51.428571 0 2749.563204 Tm 25.297222 0 Td 61.033951 Tz (amount ) Tj 2.469444 0 Td 56.712963 Tz (of ) Tj 0.836111 0 Td 50.411523 Tz (autotaxin ) Tj 2.975 0 Td 59.41358 Tz (and ) Tj 1.322222 0 Td 55.092593 Tz (an ) Tj 0.952778 0 Td 61.574074 Tz (amount ) Tj 2.488889 0 Td 56.712963 Tz (of ) Tj 0.855556 0 Td 55.092593 Tz (a ) Tj 0.583333 0 Td 51.851852 Tz (lysophosphatidyl ) Tj 40 0 0 40 0 2713 Tm 32.525 0 Td 61.458333 Tz (choline. ) Tj 51.428571 0 0 51.428571 0 2667.509138 Tm 26.016667 0 Td 43.75 Tz (5. ) Tj 0.719444 0 Td 84.259259 Tz (A ) Tj 0.719444 0 Td 59.953704 Tz (method ) Tj 2.313889 0 Td 59.953704 Tz (of ) Tj 0.816667 0 Td 52.662037 Tz (reducing ) Tj 2.702778 0 Td 50.05144 Tz (autotaxin ) Tj 2.897222 0 Td 44.965278 Tz (activity ) Tj 2.372222 0 Td 45.37037 Tz (in ) Tj 0.719444 0 Td 37.808642 Tz (its ) Tj 0.875 0 Td 43.981481 Tz (ability ) Tj 2.061111 0 Td 43.75 Tz (to ) Tj 51.428571 0 0 51.428571 0 2627.788618 Tm 25.297222 0 Td 47.314815 Tz (react ) Tj 1.536111 0 Td 53.472222 Tz (with ) Tj 1.419444 0 Td 52.274557 Tz (lysophosphatidylcholine ) Tj 7.369444 0 Td 45.37037 Tz (to ) Tj 0.680556 0 Td 57.523148 Tz (form ) Tj 1.555556 0 Td 51.041667 Tz (lysophosphatidic ) Tj 51.428571 0 0 51.428571 0 2582.700629 Tm 25.297222 0 Td 46.018519 Tz (acid, ) Tj 1.672222 0 Td 47.800926 Tz (said ) Tj 1.419444 0 Td 59.953704 Tz (method ) Tj 2.411111 0 Td 54.768519 Tz (comprising ) Tj 3.519444 0 Td 49.691358 Tz (the ) Tj 1.147222 0 Td 49.151235 Tz (introduction ) Tj 3.830556 0 Td 55.092593 Tz (of ) Tj 0.836111 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 83.179012 Tz (com ) Tj 51.428571 0 0 51.428571 0 2543.835742 Tm 25.297222 0 Td 60.925926 Tz (pound ) Tj 2.138889 0 Td 55.092593 Tz (of ) Tj 0.875 0 Td 53.148148 Tz (claim ) Tj 1.905556 0 Td 61.574074 Tz (2 ) Tj 0.7 0 Td 50.231481 Tz (within ) Tj 2.1 0 Td 58.333333 Tz (an ) Tj 1.011111 0 Td 56.481481 Tz (aqueous ) Tj 2.683333 0 Td 55.632716 Tz (system ) Tj 2.333333 0 Td 50.771605 Tz (including ) Tj 3.013889 0 Td 59.953704 Tz (an ) Tj 51.428571 0 0 51.428571 0 2499.563204 Tm 25.297222 0 Td 61.033951 Tz (amount ) Tj 2.469444 0 Td 56.712963 Tz (of ) Tj 0.836111 0 Td 50.411523 Tz (autotaxin ) Tj 2.975 0 Td 59.41358 Tz (and ) Tj 1.322222 0 Td 55.092593 Tz (an ) Tj 0.952778 0 Td 61.574074 Tz (amount ) Tj 2.488889 0 Td 56.712963 Tz (of ) Tj 0.855556 0 Td 55.092593 Tz (a ) Tj 0.583333 0 Td 51.851852 Tz (lysophosphatidyl ) Tj 40 0 0 40 0 2464 Tm 32.525 0 Td 61.458333 Tz (choline. ) Tj 51.428571 0 0 51.428571 0 2417.522936 Tm 26.036111 0 Td 42.12963 Tz (6. ) Tj 0.7 0 Td 81.018519 Tz (A ) Tj 0.7 0 Td 59.953704 Tz (method ) Tj 2.333333 0 Td 59.953704 Tz (of ) Tj 0.816667 0 Td 52.662037 Tz (reducing ) Tj 2.702778 0 Td 50.05144 Tz (autotaxin ) Tj 2.897222 0 Td 44.965278 Tz (activity ) Tj 2.372222 0 Td 43.75 Tz (in ) Tj 0.719444 0 Td 37.808642 Tz (its ) Tj 0.875 0 Td 43.981481 Tz (ability ) Tj 2.061111 0 Td 43.75 Tz (to ) Tj 51.428571 0 0 51.428571 0 2378.788618 Tm 25.297222 0 Td 47.314815 Tz (react ) Tj 1.536111 0 Td 53.472222 Tz (with ) Tj 1.419444 0 Td 52.274557 Tz (lysophosphatidylcholine ) Tj 7.369444 0 Td 45.37037 Tz (to ) Tj 0.680556 0 Td 57.523148 Tz (form ) Tj 1.555556 0 Td 51.041667 Tz (lysophosphatidic ) Tj 51.428571 0 0 51.428571 0 2332.700629 Tm 25.297222 0 Td 46.018519 Tz (acid, ) Tj 1.672222 0 Td 47.800926 Tz (said ) Tj 1.419444 0 Td 59.953704 Tz (method ) Tj 2.411111 0 Td 54.768519 Tz (comprising ) Tj 3.519444 0 Td 49.691358 Tz (the ) Tj 1.147222 0 Td 49.151235 Tz (introduction ) Tj 3.830556 0 Td 55.092593 Tz (of ) Tj 0.836111 0 Td 49.691358 Tz (the ) Tj 1.127778 0 Td 83.179012 Tz (com ) Tj 51.428571 0 0 51.428571 0 2294.842105 Tm 25.297222 0 Td 60.925926 Tz (pound ) Tj 2.138889 0 Td 55.092593 Tz (of ) Tj 0.875 0 Td 53.148148 Tz (claim ) Tj 1.905556 0 Td 58.333333 Tz (3 ) Tj 0.7 0 Td 50.231481 Tz (within ) Tj 2.1 0 Td 58.333333 Tz (an ) Tj 1.011111 0 Td 56.481481 Tz (aqueous ) Tj 2.683333 0 Td 55.632716 Tz (system ) Tj 2.333333 0 Td 50.771605 Tz (including ) Tj 3.013889 0 Td 59.953704 Tz (an ) Tj 51.428571 0 0 51.428571 0 2250.563204 Tm 25.297222 0 Td 61.033951 Tz (amount ) Tj 2.469444 0 Td 56.712963 Tz (of ) Tj 0.836111 0 Td 50.411523 Tz (autotaxin ) Tj 2.975 0 Td 59.41358 Tz (and ) Tj 1.322222 0 Td 55.092593 Tz (an ) Tj 0.952778 0 Td 61.574074 Tz (amount ) Tj 2.488889 0 Td 56.712963 Tz (of ) Tj 0.855556 0 Td 55.092593 Tz (a ) Tj 0.583333 0 Td 51.851852 Tz (lysophosphatidyl ) Tj 40 0 0 40 0 2214 Tm 32.525 0 Td 61.458333 Tz (choline. ) Tj 51.428571 0 0 51.428571 0 2168.254593 Tm 26.016667 0 Td 43.75 Tz (7. ) Tj 0.7 0 Td 87.5 Tz (A ) Tj 0.738889 0 Td 60.493827 Tz (method ) Tj 2.372222 0 Td 56.712963 Tz (of ) Tj 0.777778 0 Td 54.73251 Tz (producing ) Tj 3.15 0 Td 49.691358 Tz (the ) Tj 1.088889 0 Td 64.00463 Tz (compound ) Tj 3.286111 0 Td 55.092593 Tz (of ) Tj 0.797222 0 Td 52.5 Tz (claim ) Tj 1.827778 0 Td 45.37037 Tz (1 ) Tj 0.525 0 Td 82.098765 Tz (com ) Tj 51.428571 0 0 51.428571 0 2129.361446 Tm 25.297222 0 Td 48.148148 Tz (prising ) Tj 2.197222 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 49.259259 Tz (sequential ) Tj 3.15 0 Td 47.962963 Tz (steps ) Tj 1.633333 0 Td 42.12963 Tz (of: ) Tj 52.857143 0 0 52.857143 0 2086.803499 Tm 25.313514 0 Td 47.297297 Tz (a\) ) Tj 0.87027 0 Td 48.085586 Tz (reacting ) Tj 2.591892 0 Td 53.918919 Tz (phosphorus ) Tj 3.575676 0 Td 51.310401 Tz (oxychloride ) Tj 3.689189 0 Td 52.027027 Tz (with ) Tj 1.551351 0 Td 53.603604 Tz (a ) Tj 0.643243 0 Td 95.645646 Tz (C-s ) Tj 2.1 0 Td 42.252252 Tz (fatty ) Tj 48.571429 0 0 48.571429 0 2042 Tm 28.329412 0 Td 51.041667 Tz (alcohol; ) Tj 51.428571 0 0 51.428571 0 2002.776536 Tm 25.997222 0 Td 53.472222 Tz (b\) ) Tj 0.991667 0 Td 48.206019 Tz (reacting ) Tj 2.663889 0 Td 47.530864 Tz (the ) Tj 1.205556 0 Td 46.8107 Tz (resultant ) Tj 2.819444 0 Td 64.409722 Tz (compound ) Tj 3.383333 0 Td 59.953704 Tz (of ) Tj 0.952778 0 Td 48.611111 Tz (step ) Tj 1.497222 0 Td 54.012346 Tz (a ) Tj 1.302778 0 Td 53.472222 Tz (with ) Tj 1.613889 0 Td 58.333333 Tz (a ) Tj 51.428571 0 0 51.428571 0 1964.830911 Tm 26.736111 0 Td 55.092593 Tz (hydroxybenzaldehyde, ) Tj 6.941667 0 Td 51.388889 Tz (thereby ) Tj 2.488889 0 Td 56.018519 Tz (forming ) Tj 2.683333 0 Td 51.851852 Tz (a ) Tj 0.622222 0 Td 60.853909 Tz (phosphodi ) Tj 51.428571 0 0 51.428571 0 1920.589958 Tm 26.755556 0 Td 46.666667 Tz (ester ) Tj 1.555556 0 Td 60.133745 Tz (compound; ) Tj 51.428571 0 0 51.428571 0 1880.300621 Tm 26.016667 0 Td 46.990741 Tz (c\) ) Tj 0.719444 0 Td 49.016204 Tz (reacting ) Tj 2.527778 0 Td 47.800926 Tz (said ) Tj 1.302778 0 Td 52.777778 Tz (phosphodiester ) Tj 4.55 0 Td 64.00463 Tz (compound ) Tj 3.227778 0 Td 53.472222 Tz (with ) Tj 1.438889 0 Td 55.092593 Tz (a ) Tj 0.505556 0 Td 58.796296 Tz (cyanoet ) Tj 51.428571 0 0 51.428571 0 1837.306799 Tm 26.736111 0 Td 54.444444 Tz (hanol ) Tj 1.788889 0 Td 48.611111 Tz (to ) Tj 0.777778 0 Td 57.523148 Tz (form ) Tj 1.575 0 Td 58.333333 Tz (a ) Tj 0.505556 0 Td 50.339506 Tz (phosphotriester ) Tj 4.686111 0 Td 60.133745 Tz (compound; ) Tj 51.428571 0 0 51.428571 0 1796.15443 Tm 26.016667 0 Td 50.231481 Tz (d\) ) Tj 0.855556 0 Td 48.611111 Tz (reacting ) Tj 2.547222 0 Td 49.421296 Tz (said ) Tj 1.4 0 Td 50.123457 Tz (phosphotriester ) Tj 4.725 0 Td 63.599537 Tz (compound ) Tj 3.266667 0 Td 53.472222 Tz (with ) Tj 1.555556 0 Td 66.435185 Tz (Deoxof ) Tj 51.428571 0 0 51.428571 0 1750.564994 Tm 26.755556 0 Td 44.074074 Tz (luor, ) Tj 1.458333 0 Td 54.62963 Tz (wherein ) Tj 2.430556 0 Td 48.611111 Tz (said ) Tj 1.302778 0 Td 48.206019 Tz (reaction ) Tj 2.45 0 Td 53.472222 Tz (with ) Tj 1.419444 0 Td 55.092593 Tz (Deoxofluor ) Tj 3.402778 0 Td 38.888889 Tz (is ) Tj 0.583333 0 Td 49.259259 Tz (optionally ) Tj 51.428571 0 0 51.428571 0 1715.36255 Tm 26.755556 0 Td 54.6875 Tz (preceded ) Tj 2.897222 0 Td 59.953704 Tz (by ) Tj 1.011111 0 Td 53.06713 Tz (reducing ) Tj 2.819444 0 Td 48.611111 Tz (said ) Tj 1.438889 0 Td 50.123457 Tz (phosphotriester ) Tj 4.783333 0 Td 64.00463 Tz (compound ) Tj 51.428571 0 0 51.428571 0 1670.92973 Tm 26.736111 0 Td 54.282407 Tz (with ) Tj 1.594444 0 Td 58.333333 Tz (sodium ) Tj 2.352778 0 Td 52.121914 Tz (borohydride, ) Tj 4.044444 0 Td 50.925926 Tz (thereby ) Tj 2.391667 0 Td 55.092593 Tz (producing ) Tj 3.247222 0 Td 51.851852 Tz (a ) Tj 0.583333 0 Td 50.231481 Tz (fluori ) Tj 52.857143 0 0 52.857143 0 1627.394737 Tm 26.032432 0 Td 51.081081 Tz (nated ) Tj 1.702703 0 Td 58.508509 Tz (compound; ) Tj 3.348649 0 Td 58.858859 Tz (and ) Tj 51.428571 0 0 51.428571 0 1586.004981 Tm 26.016667 0 Td 46.990741 Tz (e\) ) Tj 0.738889 0 Td 50.501543 Tz (deprotecting ) Tj 3.791667 0 Td 49.691358 Tz (the ) Tj 1.069444 0 Td 46.450617 Tz (resultant ) Tj 2.663889 0 Td 47.727273 Tz (fluorinated ) Tj 3.325 0 Td 63.599537 Tz (compound ) Tj 3.227778 0 Td 56.712963 Tz (of ) Tj 0.777778 0 Td 46.990741 Tz (step ) Tj 40 0 0 40 0 1548 Tm 34.4 0 Td 83.333333 Tz (d. ) Tj ET Q 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