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

Stover JS, Ciobanu M, Cliffel DE, Rizzo CJ
J Am Chem Soc. 2007 129 (7): 2074-81

PMID: 17256856 · PMCID: PMC2526121 · DOI:10.1021/ja066404u

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.

MeSH Terms (4)

Amines Deoxyguanosine Electrochemistry Oxidation-Reduction

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