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Chemical and electrochemical oxidation of C8-arylamine adducts of 2'-deoxyguanosine.

ABSTRACT: The electrochemical and chemical oxidation of a series of C8-arylamine adducts of 2'-deoxyguanosine has been examined. The oxidations were found to be reversible by cyclic and square-wave voltammetry in both aqueous buffer and aprotic organic solvent. The mechanism of the oxidation in protic media was either one- or two-electron, depending on the aryl group. The chemical oxidation resulted in guanidinohydantoin and spiroiminodihydantoin rearrangement products similar to those observed for 8-oxo-7,8-dihydro-2'-deoxyguanosine.

SUBMITTER: Stover JS

PROVIDER: S-EPMC2526121 | biostudies-literature | 2007 Feb

REPOSITORIES: biostudies-literature

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Chemical and electrochemical oxidation of C8-arylamine adducts of 2'-deoxyguanosine.

Stover James S JS Ciobanu Madalina M Cliffel David E DE Rizzo Carmelo J CJ

Journal of the American Chemical Society 20070126 7

The electrochemical and chemical oxidation of a series of C8-arylamine adducts of 2'-deoxyguanosine has been examined. The oxidations were found to be reversible by cyclic and square-wave voltammetry in both aqueous buffer and aprotic organic solvent. The mechanism of the oxidation in protic media was either one- or two-electron, depending on the aryl group. The chemical oxidation resulted in guanidinohydantoin and spiroiminodihydantoin rearrangement products similar to those observed for 8-oxo- ...[more]

PMID: 17256856

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