Oxidation chemistry of 2'-deoxyadenosine at pyrolytic graphite electrode.

The electrochemical oxidation of 2'-deoxyadenosine has been investigated in phosphate containing supporting electrolytes in pH range 2-10 at a pyrolytic graphite electrode by cyclic sweep voltammetry, spectral studies, controlled potential electrolysis and related techniques. The oxidation of 2'-deoxyadenosine occurred in a single well-defined oxidation peak (I(a)), over the entire pH range. The electrooxidation occurred by the loss of 6.0+/-0.5 e(-) per mole over the entire pH range. The kinetics of the decay of the UV-absorbing intermediates has been studied and found to follow pseudo first order kinetics having rate constant (k) in the range (5.7-7.7)x10(-4) s(-1). The major products of electrooxidation were separated by HPLC and characterized by GC-MS/MS, (1)H NMR and a tentative mechanism for electrooxidation of 2'-deoxyadenosine has been suggested.