Old Yellow Enzyme: Stepwise reduction of nitro-olefins and catalysis of aci-nitro tautomerization

Meah Y.; Massey V.

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Old Yellow Enzyme: Stepwise reduction of nitro-olefins and catalysis of aci-nitro tautomerization

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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. References: 14

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《Proceedings of the National Academy of Sciences of the United States of America》 |2000年第20期|10733-10738|共6页
作者
Meah Y.; Massey V.;
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Univ Michigan, Sch Med, Dept Biol Chem, Ann Arbor, MI 48109, USA, .;

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收录信息美国《科学引文索引》(SCI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
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正文语种英语
中图分类自然科学总论;
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1. Old yellow enzyme: reduction of nitrate esters, glycerin trinitrate, and propylene 1,2-dinitrate. [J] . Meah Y, Brown BJ, Chakraborty SMassey V Proceedings of the National Academy of Sciences of the United States of America . 2001,第15期

机译：Old yellow enzyme: reduction of nitrate esters, glycerin trinitrate, and propylene 1,2-dinitrate.
2. Bioorganometallic Chemistry at the Interface with Biocatalysis: Chemoselective Reduction of Biomimetic NAD+ Cofactors with Cp*Rh(bpy)H+, Tandem Catalysis with 1,4-NADH-Dependent Enzymes, Chiral Synthesis, Organotin Metabolites, and DFT Mechanism Studies [J] . Marrone Alessandro, Fish Richard H. Organometallics . 2023,第4期

机译：Bioorganometallic Chemistry at the Interface with Biocatalysis: Chemoselective Reduction of Biomimetic NAD+ Cofactors with Cp*Rh(bpy)H+, Tandem Catalysis with 1,4-NADH-Dependent Enzymes, Chiral Synthesis, Organotin Metabolites, and DFT Mechanism Studies
3. ChemInform Abstract: Controlling Factors of Stepwise Versus Concerted Reductive Cleavages. Illustrative Examples in the Electrochemical Reductive Breaking of Nitrogen‐Halogen Bonds in Aromatic N‐Halosultams. [J] . C. P. ANDRIEUX, E. DIFFERDING, M. ROBERTJ.‐M. SAVEANT Chem Inform . 1993,第47期

机译：ChemInform Abstract: Controlling Factors of Stepwise Versus Concerted Reductive Cleavages. Illustrative Examples in the Electrochemical Reductive Breaking of Nitrogen‐Halogen Bonds in Aromatic N‐Halosultams.
4. Bifunctional Catalysis: Direct Reductive Amination of Aliphatic Ketones with an Iridium-Phosphate Catalyst [O] . Barbara Villa-Marcos, Chaoqun Li, Keith R. Mulholland, 2010

机译：Bifunctional Catalysis: Direct Reductive amination of aliphatic Ketones with an Iridium-phosphate Catalyst

Old Yellow Enzyme: Stepwise reduction of nitro-olefins and catalysis of aci-nitro tautomerization

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