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Synthesis and Biochemical Evaluation of Nicotinamide Derivatives as NADH analogues in Ene Reductase.

Nicotinamide and pyridine-containing conjugates have attracted a lot of attention in research as they have found use in a wide range of applications including as redox flow batteries, calcium channel blockers, and in biocatalysis, and metabolism. The interesting redox character of the compounds' pyridine/dihydropyridine system allows them to possess very similar, if not able to mimic, the functions and characteristics of the natural chiral redox agents NAD+/NADH. Considerable interest has been given in designing and synthesizing NAD+/NADH mimics with similar redox properties. In this research, three nicotinamide conjugates were designed, synthesized and characterized. Molecular structures obtained through X-ray crystallography were obtained for two conjugates providing more detail into the bonding and structure of the compounds. The compounds were then further evaluated for biochemical properties and it was found that one of the conjugates possessed similar functions and characteristics to the natural NADH compound. Compound 4 was evaluated in the active enzyme, Enoate Reductase and compared to NADH, it was shown to be successful in reducing the C=C double bond of three substrates and outperformed the natural coenzyme, kinetic data has been reported.

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