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 (Ia), 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) × 10− 4 s− 1. The major products of electrooxidation were separated by HPLC and characterized by GC–MS/MS, 1H NMR and a tentative mechanism for electrooxidation of 2′-deoxyadenosine has been suggested.