Issue 20, 2013
From the journal:

Chemical Communications

(S)-Selective MenD variants from Escherichia coli provide access to new functionalized chiral α-hydroxy ketones†

Robert Westphal,a   Simon Waltzer,b   Ursula Mackfeld,a   Michael Widmann,c   Jürgen Pleiss,c   Maryam Beigi,b   Michael Müller,b   Dörte Rothera  and  Martina Pohl*a  

* Corresponding authors

a IBG-1: Biotechnology, Forschungszentrum Jülich GmbH, Leo-Brandt-Str. 1, 52425 Jülich, Germany
E-mail: ma.pohl@fz-juelich.de
Fax: +49-(0)2461-61-3870
Tel: +49-(0)2461-61-4388

b Institute of Pharmaceutical Sciences, Albert-Ludwigs-Universität Freiburg, Albertstr. 25, 79104 Freiburg, Germany

c Institute of Technical Biochemistry, University of Stuttgart, Allmandring 31, 70569 Stuttgart, Germany

Abstract

We report the first rationally designed (S)-selective MenD from E. coli for the synthesis of functionalized α-hydroxy ketones. By mutation of two amino acids in the active site stereoselectivity of the (R)-selective EcMenD (ee > 93%) was inverted giving access to (S)-5-hydroxy-4-oxo-5-phenylpentanoate derivatives with stereoselectivities up to 97% ee.

Graphical abstract: (S)-Selective MenD variants from Escherichia coli provide access to new functionalized chiral α-hydroxy ketones

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Article information

DOI
https://doi.org/10.1039/C3CC38607D
Article type
Communication
Submitted
30 Nov 2012
Accepted
22 Jan 2013
First published
22 Jan 2013

Chem. Commun., 2013,49, 2061-2063

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(S)-Selective MenD variants from Escherichia coli provide access to new functionalized chiral α-hydroxy ketones

R. Westphal, S. Waltzer, U. Mackfeld, M. Widmann, J. Pleiss, M. Beigi, M. Müller, D. Rother and M. Pohl, Chem. Commun., 2013, 49, 2061 DOI: 10.1039/C3CC38607D

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