老黄色酶：硝基烯烃的逐步还原及酸式硝基互变异构的催化作用
Old yellow enzyme: stepwise reduction of nitro-olefins and catalysis of aci-nitro tautomerization.
作者信息
Meah Y, Massey V
机构信息
Department of Biological Chemistry, The University of Michigan Medical School, Ann Arbor, MI 48109, USA.
出版信息
Proc Natl Acad Sci U S A. 2000 Sep 26;97(20):10733-8. doi: 10.1073/pnas.190345597.
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.
摘要
老黄色酶已被证明能高效催化与NADPH相关的硝基烯烃还原反应。硝基烯烃的还原反应以逐步方式进行，形成一种可从酶上自由解离的硝酮中间体。第一步涉及从酶还原的黄素向硝基烯烃的C2位进行氢化物转移。硝酮在C1位质子化形成最终的硝基烷烃产物也由该酶催化，并且涉及Tyr-196作为活性位点的酸碱基团。该残基还参与硝基烷烃的酸式-硝基互变异构，这是该酶催化的非氧化还原反应的首个例子。
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