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Proc Natl Acad Sci U S A. 2000 Sep 26;97(20):10733-8.

Old yellow enzyme: stepwise reduction of nitro-olefins and catalysis of aci-nitro tautomerization.

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1
Department of Biological Chemistry, The University of Michigan Medical School, Ann Arbor, MI 48109, USA.

Abstract

The Old Yellow Enzyme has been shown to catalyze efficiently the NADPH-linked reduction of nitro-olefins. The reduction of the nitro-olefin proceeds in a stepwise fashion, with formation of a nitronate intermediate that is freely dissociable from the enzyme. The first step involves hydride transfer from the enzyme-reduced flavin to carbon 2 of the nitro-olefin. The protonation of the nitronate at carbon 1 to form the final nitroalkane product also is catalyzed by the enzyme and involves Tyr-196 as an active site acid/base. This residue also is involved in aci-nitro tautomerization of nitroalkanes, the first example of a nonredox reaction catalyzed by the enzyme.

PMID:
10995477
PMCID:
PMC27092
DOI:
10.1073/pnas.190345597
[Indexed for MEDLINE]
Free PMC Article
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