Volume 247, 2023

Impact of sodium pyruvate on the electrochemical reduction of NAD+ biomimetics

Abstract

Biomimetics of nicotinamide adenine dinucleotide (mNADH) are promising cost-effective alternatives to their natural counterpart for biosynthetic applications; however, attempts to recycle mNADH often rely on coenzymes or precious metal catalysts. Direct electrolysis is an attractive approach for recycling mNADH, but electrochemical reduction of the oxidized mimetic (mNAD+) primarily results in the formation of an enzymatically inactive dimer. Herein, we find that aqueous electrochemical reduction of an NAD+ mimetic, 1-n-butyl-3-carbamoylpyridinium bromide (1+), to its enzymatically active form, 1,4-dihydro-1-n-butyl nicotinamide (1H), is favored in the presence of sodium pyruvate as a supporting electrolyte. Maximum formation of 1H is achieved in the presence of a large excess of pyruvate in combination with a large excess of a co-supporting electrolyte. Formation of 1H is found to be favored at pH 7, with an optimized product ratio of ∼50/50 dimer/1H observed by cyclic voltammetry. Furthermore, sodium pyruvate is shown to promote electroreductive generation of the 1,4-dihydro form of several additional mNADH as well as NADH itself. This method provides a general strategy for regenerating 1,4-dihydro-nicotinamide mimetics of NADH from their oxidized forms.

Graphical abstract: Impact of sodium pyruvate on the electrochemical reduction of NAD+ biomimetics

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
20 feb. 2023
Accepted
14 mar. 2023
First published
24 mar. 2023

Faraday Discuss., 2023,247, 87-100

Impact of sodium pyruvate on the electrochemical reduction of NAD+ biomimetics

C. Bruggeman, K. Gregurash and D. P. Hickey, Faraday Discuss., 2023, 247, 87 DOI: 10.1039/D3FD00047H

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