TY - JOUR
T1 - Carbanion versus hydride transfer mechanisms in flavoprotein-catalyzed dehydrogenations
AU - Fitzpatrick, Paul F.
PY - 2004/6
Y1 - 2004/6
N2 - 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 β-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 b2. In contrast, the data are most consistent with mechanisms involving direct hydride transfer.
AB - 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 β-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 b2. In contrast, the data are most consistent with mechanisms involving direct hydride transfer.
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U2 - 10.1016/j.bioorg.2003.02.001
DO - 10.1016/j.bioorg.2003.02.001
M3 - Review article
C2 - 15110192
AN - SCOPUS:1942485882
VL - 32
SP - 125
EP - 139
JO - Bioorganic Chemistry
JF - Bioorganic Chemistry
SN - 0045-2068
IS - 3
ER -