Chemical and electrochemical oxidation of C8-arylamine adducts of 2'-deoxyguanosine.
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.
Stover
James S
JS
Department of Chemistry, Center in Molecular Toxicology and Vanderbilt Institute of Chemical Biology, Vanderbilt University, VU Station B 351822, Nashville, Tennessee 37235-1822, USA.
Ciobanu
Madalina
M
Cliffel
David E
DE
Rizzo
Carmelo J
CJ
D000588:Amines / Q000737:chemistry* / Q000378:metabolism; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000378:metabolism; D004563:Electrochemistry; D010084:Oxidation-Reduction
D000588:Amines; D003849:Deoxyguanosine