Electrochemical Aspects of a NADH/FAD Model System

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Abstract
A model system of the NADH/FAD redox couple has been studied by the use of electrochemical techniques. The system studied was composed of 1-benzyl-1,4-dihydronicotinamide (BNAH) and riboflavin (RF), which were used in place of NADH and FAD respectively, dissolved in a DMSO solution. The results obtained were as follows. RF is reduced either by BNAH or sodium borohydride, obeying a second-order rate law, presumably by the mechanism of hydride-ion transfer. The resultant product is inactive to the electrochemical reduction at a mercury-pool electrode. Entirely different products were produced when RF was reduced electrochemically. RF was reduced at a rate of 1 F/mol at the initial stage of controlled potential electrolysis to form, probably, a dimeric compound, but the latter product underwent further reduction and the total quantity of electricity necessary for the complete reduction exceeded 10 F/mol. Interestingly, the electrolytic reduction gives the same product as that obtained by BNAH when electrolysis is performed in the presence of a sufficient amount of BNAH, indicating that the initial product of electrochemical reduction receives the hydride ion rather than further electrons.

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