Full Library of (Bis-allyl)-deuterated Arachidonic Acids: Synthesis and Analytical Verification

摘要

abstract_textpDeuteration at bis-allylic positions slows down hydrogen abstraction, thereby reducing the rate of polyunsaturated fatty acids (PUFA) oxidation. Arachidonic acid undergoes oxidation through both enzymatic and non-enzymatic mechanisms, giving rise to a range of important products with variable biological activity, including pro-and anti-inflammatory properties. We report on the synthesis and verification of a full library of arachidonic acids variably deuterated at the bis-allylic (C7, C10, C13) positions: 7,7-D-2-arachidonic acid, 10,10-D-2-arachidonic acid, 13,13-D-2-arachidonic acid, 7,7,10,10-D-4-arachidonic acid, 7,7,13,13-D-4-arachidonic acid, 10,10,13,13-D-4-arachidonic acid, and 7,7,10,10,13,13-D-6-arachidonic acid isotopologues. The library is intended to be useful for determining the relative importance of enzymatic versus non-enzymatic oxidation at particular sites in vivo./p/abstract_text