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Issue 4, 2010
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The flavoprotein-catalyzed reduction of aliphatic nitro-compounds represents a biocatalytic equivalent to the Nef-reaction

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Abstract

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.

Graphical abstract: The flavoprotein-catalyzed reduction of aliphatic nitro-compounds represents a biocatalytic equivalent to the Nef-reaction

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Supplementary files

Article information


Submitted
30 Oct 2009
Accepted
23 Dec 2009
First published
08 Feb 2010

Green Chem., 2010,12, 616-619
Article type
Paper

The flavoprotein-catalyzed reduction of aliphatic nitro-compounds represents a biocatalytic equivalent to the Nef-reaction

K. Durchschein, B. Ferreira-da Silva, S. Wallner, P. Macheroux, W. Kroutil, S. M. Glueck and K. Faber, Green Chem., 2010, 12, 616
DOI: 10.1039/B922691E

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