Synthesis of sn-1 substituted PC bearing perdeuteradted elaidic acid

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Synthesis of sn-1 substituted PC bearing perdeuteradted elaidic acid Molecular Organization in Phospholipid Bilayers Containing Trans Fatty Acids Studied by Solid State 2H NMR Stephen R. Wassall1 and Stephanie E. Sen2 Departments of Physics1 and Chemistry and Chemical Biology2, IUPUI Trans fatty acids (TFA) are “manmade” unsaturated fatty acids produced during the partial hydrogenation of vegetable oils that differ from “natural “ cis unsaturated fatty acids (CFA) in the disposition of the hydrogens on carbon C=C double bonds. Changes in dynamical structure of the phospholipid molecules into which they incorporate following dietary consumption of “fast” foods are potentially the origin of detrimental health effects. Trans Cis Our approach is to apply solid state 2H NMR, complemented by MD simulations, to non-invasively compare molecular organization in model membranes prepared from deuterated analogs of phosphatidylcholine (PC) containing trans elaidic (t18:1) or cis oleic (c18:1) acid. The focus here is the synthesis of sn-1 substituted PC bearing perdeuterated [2H33]t18:1 acid that will be employed to directly probe the conformation of the TFA. Synthesis of sn-1 substituted PC bearing perdeuteradted elaidic acid