Evidence for an episulfonium ion intermediate in the formation of S-[2-(N7-guanyl) ethyl] glutathione in DNA

…, TM Harris, FP Guengerich

Index: Peterson; Harris; Guengerich Journal of the American Chemical Society, 1988 , vol. 110, # 10 p. 3284 - 3291

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Citation Number: 75

Abstract

Abstract: The carcinogen ethylene dibromide (EDB) is bioactivated via a pathway involving initial conjugation with the tripeptide glutathione (GSH) in a reaction catalyzed by GSH S- transferase. The conjugate then reacts preferentially with DNA guanyl residues to generate S-[2-(Af'-guanyl) ethyl] glutathione. Rates of hydrolysis and alkylation of 4-(p-nitrobenzyl) pyridine with several cysteinyl and homocysteinyl analogues of S-(2-haloethyl) ...