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National Institute of Environmental Health Sciences

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Publication Detail

Title: Unusual kinetic isotope effects of deuterium reinforced polyunsaturated fatty acids in tocopherol-mediated free radical chain oxidations.

Authors: Lamberson, Connor R; Xu, Libin; Muchalski, Hubert; Montenegro-Burke, J Rafael; Shmanai, Vadim V; Bekish, Andrei V; McLean, John A; Clarke, Catherine F; Shchepinov, Mikhail S; Porter, Ned A

Published In J Am Chem Soc, (2014 Jan 22)

Abstract: Substitution of -CD2- at the reactive centers of linoleic and linolenic acids reduces the rate of abstraction of D by a tocopheryl radical by as much as 36-fold, compared to the abstraction of H from a corresponding -CH2- center. This H atom transfer reaction is the rate-determining step in the tocopherol-mediated peroxidation of lipids in human low-density lipoproteins, a process that has been linked to coronary artery disease. The unanticipated large kinetic isotope effects reported here for the tocopherol-mediated oxidation of linoleic and linolenic acids and esters suggests that tunneling makes this process favorable.

PubMed ID: 24380377 Exiting the NIEHS site

MeSH Terms: Deuterium/chemistry*; Fatty Acids, Unsaturated/chemistry*; Free Radicals/chemistry; Humans; Kinetics; Lipoproteins, LDL/chemistry; Lipoproteins, LDL/metabolism; Oxidation-Reduction; Tocopherols/chemistry*; Tocopherols/metabolism

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