Nicotinamide cofactor analogues

Nicotinamide cofactor analogues (mNADs) are compounds that mimic the natural nicotinamide adenine dinucleotide cofactors in structure, to explore a mechanism or be used in biocatalysis or other applications.^[1] These nicotinamide cofactor mimics generally retain the nicotinamide moiety with varying substituents.

Background[edit]

Oxidoreductases are enzymes that catalyze the transfer of a hydride ion between a substrate and a cofactor, in many cases, particularly those in metabolic reactions, that cofator is a form of nicotinamide adenine dinucleotide.^[2] Nicotinamide adenine dinucleotide phosphate (NADPH) is used in anabolic reactions while nicotinamide adenine dinucleotide (NAD+) is used in catabolic reactions.^[3]

Analogues[edit]

Unlike the human body, typical chemical reactions are unable to regenerate the cofactor for further use. Synthetic cofactors have been researched to solve this problem. The analogues have been synthesized from similar compounds such as 1,4-dihydronicotinamide. These synthetic cofactors have since been used to better understand the mechanisms of reactions especially when it comes to stereospecificity, which may be enhanced by metal ions. Analogues serve as an alternative to traditional regeneration techniques.^[3]^[4]

References[edit]

^ "Is Simpler Better? Synthetic Nicotinamide Cofactor Analogues for Redox Chemistry", Caroline E. Paul, Isabel W. C. E. Arends, Frank Hollmann, ACS Catal. 2014, 4, 788-797
^ Sellés Vidal, Lara; Kelly, Ciarán L.; Mordaka, Paweł M.; Heap, John T. (February 2018). "Review of NAD(P)H-dependent oxidoreductases: Properties, engineering and application". Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics. 1866 (2): 327–347. doi:10.1016/j.bbapap.2017.11.005. hdl:10044/1/53944. PMID 29129662. S2CID 205856516.
^ ^a ^b Paul, Caroline E.; Arends, Isabel W. C. E.; Hollmann, Frank (2014-03-07). "Is Simpler Better? Synthetic Nicotinamide Cofactor Analogues for Redox Chemistry". ACS Catalysis. 4 (3): 788–797. doi:10.1021/cs4011056. ISSN 2155-5435.
^ Zachos, Ioannis; Döring, Manuel; Tafertshofer, Georg; Simon, Robert C.; Sieber, Volker (2021-06-21). "carba Nicotinamide Adenine Dinucleotide Phosphate: Robust Cofactor for Redox Biocatalysis". Angewandte Chemie International Edition. 60 (26): 14701–14706. doi:10.1002/anie.202017027. ISSN 1433-7851. PMC 8252718. PMID 33719153.

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[1] "Is Simpler Better? Synthetic Nicotinamide Cofactor Analogues for Redox Chemistry", Caroline E. Paul, Isabel W. C. E. Arends, Frank Hollmann, ACS Catal. 2014, 4, 788-797

[2] Sellés Vidal, Lara; Kelly, Ciarán L.; Mordaka, Paweł M.; Heap, John T. (February 2018). "Review of NAD(P)H-dependent oxidoreductases: Properties, engineering and application". Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics. 1866 (2): 327–347. doi:10.1016/j.bbapap.2017.11.005. hdl:10044/1/53944. PMID 29129662. S2CID 205856516.

[:0-3] Paul, Caroline E.; Arends, Isabel W. C. E.; Hollmann, Frank (2014-03-07). "Is Simpler Better? Synthetic Nicotinamide Cofactor Analogues for Redox Chemistry". ACS Catalysis. 4 (3): 788–797. doi:10.1021/cs4011056. ISSN 2155-5435.

[4] Zachos, Ioannis; Döring, Manuel; Tafertshofer, Georg; Simon, Robert C.; Sieber, Volker (2021-06-21). "carba Nicotinamide Adenine Dinucleotide Phosphate: Robust Cofactor for Redox Biocatalysis". Angewandte Chemie International Edition. 60 (26): 14701–14706. doi:10.1002/anie.202017027. ISSN 1433-7851. PMC 8252718. PMID 33719153.

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