Site-Specific Deuteration of Polyunsaturated Alkenes

A. V. Smarun, M. Petković, M. S. Shchepinov, D. Vidović

Research output: Contribution to journalArticleResearchpeer-review

14 Citations (Scopus)

Abstract

Selective deuteration of drugs and biologically relevant molecules is becoming increasingly important in the pharmaceutical industry. Site-selective isotopic reinforcement of polyunsaturated fatty acids (PUFAs) at their bis-allylic sites has been identified as a unique approach in preventing oxidative damage in these molecules, which had been linked to neuronal and retinal diseases, atherosclerosis, and aging. Typical methods for preparation of site-selectively deuterated PUFAs require rather long, laborious, and expensive syntheses. In this report, we disclose a very efficient catalytic protocol for site-specific deuteration of PUFAs and analogous poly-alkenes under exceptional kinetic control. Deuterium oxide (D2O) has been identified not only as a deuterium source but also as a crucial component in the overall reaction mechanism responsible for averting the formation of thermodynamically favored side-products.

Original languageEnglish
Pages (from-to)13115-13120
Number of pages6
JournalThe Journal of Organic Chemistry
Volume82
Issue number24
DOIs
Publication statusPublished - 15 Dec 2017

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