Electrochemical oxidation of 2′,3′-dideoxyadenosine at pyrolytic graphite electrode

The oxidation chemistry of 2′,3′-dideoxyadenosine (I) has been studied at a pyrolytic graphite electrode (PGE) in the pH range 2.4–10.9 and a well defined oxidation peak was noticed. The peak potential of the peak was linearly dependent on pH with dEp/dpH as 42 mV/pH. Voltammetric, coulometric, spectral studies and product analysis indicate that the oxidation of (I) occurs in an EC reaction involving 6e−, 6H+ process at pH 7.2 to give allantoin, C–C dimer and dideoxyribose as the major products and a C–O–O–C linked dimer as a minor product. Tentative mechanisms for the formation of the products have also been suggested. A comparison of peak potential value of 2′,3′-dideoxyadenosine with adenosine and 2′-deoxyadensoine indicated that the difference is insignificant which has further been supported by the calculations of difference of energies of lowest unoccupied and highest occupied molecular orbitals.