Carbanion versus hydride transfer mechanisms in flavoprotein-catalyzed dehydrogenations.

Paul F Fitzpatrick

Journal: Bioorganic chemistry 2004;32(3):125-39

PMID: 15110192

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Abstract

The present understanding of the mechanisms by which flavoproteins oxidize amino acid or hydroxy acids to the respective imino or keto acids is reviewed. The observation that many of these enzymes catalyze the elimination of HBr or HCl from the appropriate beta-halogenated substrate was long considered evidence for a carbanion intermediate. Recent structural and mechanistic studies are not compatible with the intermediacy of carbanions in the reactions catalyzed by d-amino acid oxidase and flavocytochrome b(2). In contrast, the data are most consistent with mechanisms involving direct hydride transfer.

Address: Department of Biochemistry and Biophysics, Texas A&M University, College Station, TX 77843-2128, USA. [email protected]

DOI: 10.1016/j.bioorg.2003.02.001

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MeSH Terms: Amino Acids, Carbonates, Catalysis, D-Amino-Acid Oxidase, Electron Transport, Flavoproteins, Halogens, Hydrogen, Hydroxy Acids, L-Lactate Dehydrogenase (Cytochrome), Models, Chemical, Oxidation-Reduction