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Chem Res Toxicol. 2012 Sep 17;25(9):1842-61. doi: 10.1021/tx3000494. Epub 2012 Jul 3.

Intramolecular hydrogen transfer reactions of thiyl radicals from glutathione: formation of carbon-centered radical at Glu, Cys, and Gly.

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1
Department of Pharmaceutical Chemistry, University of Kansas, 2095 Constant Avenue, Lawrence, KA 66047, USA.

Abstract

Glutathione thiyl radicals (GS(•)) were generated in H(2)O and D(2)O by either exposure of GSH to AAPH, photoirradiation of GSH in the presence of acetone, or photoirradiation of GSSG. Detailed interpretation of the fragmentation pathways of deuterated GSH and GSH derivatives during mass spectrometry analysis allowed us to demonstrate that reversible intramolecular H-atom transfer reactions between GS(•) and C-H bonds at Cys[(α)C], Cys[(β)C], and Gly[(α)C] are possible.

PMID:
22712461
PMCID:
PMC3736831
DOI:
10.1021/tx3000494
[Indexed for MEDLINE]
Free PMC Article
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