Issue 4, 2010
From the journal:

Green Chemistry

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

Katharina Durchschein,a   Bianca Ferreira-da Silva,a   Silvia Wallner,b   Peter Macheroux,b   Wolfgang Kroutil,a   Silvia Maria Gluecka  and  Kurt Faber*a  

* Corresponding authors

a Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, Austria
E-mail: Kurt.Faber@Uni-Graz.at
Fax: +43-316-380-9840
Tel: +43-316-380-5332

b Institute of Biochemistry, Graz University of Technology, Petersgasse 12, Graz, Austria

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

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B922691E
Article type
Paper
Submitted
30 Oct 2009
Accepted
23 Dec 2009
First published
08 Feb 2010

Green Chem., 2010,12, 616-619

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements