The flavoprotein-catalyzed reduction of aliphatic nitro-compounds represents a biocatalytic equivalent to the Nef-reaction
The flavoprotein-catalyzed reduction of aliphatic nitro-compounds represents a biocatalytic equivalent to the Nef-reaction
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DOI：
10.1039/b922691e
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发表时间：
2010-04-01
期刊：
影响因子：
9.8
通讯作者：
Faber, Kurt
中科院分区：
文献类型：
--
作者：
Durchschein, Katharina;Silva, Bianca Ferreira-da;Faber, Kurt
从老黄酶家族提纯的黄素蛋白催化的脂肪族仲硝基化合物的生物还原出人意料地提供了相应的羰基化合物，而不是预期的胺，因此代表了相当于Nef反应的生物催化。该途径被证明是通过硝基的初始还原来产生亚硝基的衍生物，亚硝基的自发互变异构化得到更稳定的肟，在第二步中被酶还原以提供一种不稳定的水解亚胺物种，该亚胺物种自发地水解，最终得到一种羰基化合物和氨。
The bioreduction of aliphatic sec-nitro compounds catalyzed by purified flavoproteins from the old-yellow-enzyme family unexpectedly furnished the corresponding carbonyl compounds instead of the expected amines and thus represents a biocatalytic equivalent to the Nef-reaction. The pathway was shown to proceed via initial reduction of the nitro-group to yield the nitroso-derivative, which spontaneously tautomerized to yield the more stable oxime, which was enzymatically reduced in a second step to furnish a hydrolytically unstable imine-species, which spontaneously hydrolyzed to finally give a carbonyl compound and ammonia.