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

Maksim A. Fomich, Andrei V. Bekish, Dragoslav Vidovic, Connor R. Lamberson, Ivan L. Lysenko, Peter Lawrence, J. Thomas Brenna, Olga L. Sharko, Vadim V. Shmanai, Mikhail S. Shchepinov

Research output: Contribution to journalArticleResearchpeer-review

9 Citations (Scopus)

Abstract

Deuteration 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-D2-arachidonic acid, 10,10-D2-arachidonic acid, 13,13-D2-arachidonic acid, 7,7,10,10-D4-arachidonic acid, 7,7,13,13-D4-arachidonic acid, 10,10,13,13-D4-arachidonic acid, and 7,7,10,10,13,13-D6-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.

Original languageEnglish
Pages (from-to)4758-4764
Number of pages7
JournalChemistrySelect
Volume1
Issue number15
DOIs
Publication statusPublished - 1 Jan 2016
Externally publishedYes

Keywords

  • fatty acids
  • isotope effects
  • lipids
  • mass spectrometry
  • NMR spectroscopy

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