Site-Specific Deuteration of Polyunsaturated Alkenes

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 oxidati...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-12, Vol.82 (24), p.13115-13120
Main Authors: Smarun, A. V, Petković, M, Shchepinov, M. S, Vidović, D
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Deuterium
Deuterium Oxide - chemistry
Fatty Acids, Unsaturated - chemistry
Models, Molecular
Radiopharmaceuticals
Substrate Specificity
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b02169