Issue 20, 2005
From the journal:

Chemical Communications

Stereoselective hydroxylation of an achiral cyclopentanecarboxylic acid derivative using engineered P450s BM-3†

Dieter F. Münzer,a   Peter Meinhold,b   Matthew W. Peters,b   Sabine Feichtenhofer,c   Herfried Griengl,a   Frances H. Arnold,*b   Anton Gliederc  and  Anna de Raadt*a  

* Corresponding authors

a Institut für Organische Chemie der Technischen Universität Graz, Stremayrgasse 16, Graz, Austria
E-mail: deraadt@orgc.tu-graz.ac.at
Fax: +43 316 873 8740
Tel: +43 316 873 8751

b Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, USA
E-mail: frances@cheme.caltech.edu
Fax: +1 626 568 8743
Tel: +1 626 395 4162

c Research Centre Applied Biocatalysis, Institut für Molekulare Biotechnologie der Technischen Universität Graz, Petersgasse 14, Graz, Austria
E-mail: a.glieder@tugraz.at
Fax: 43 316 873 4071
Tel: 43 316 873 4074

Abstract

Substrate engineered, achiral carboxylic acid derivative 2 was biohydroxylated with various mutants of cytochrome P450 BM-3 to give two out of the four possible diastereoisomers in high de and ee. The BM-3 mutants exhibit up to 9200 total turnovers for hydroxylation of the engineered substrate, which without the protecting group is not transformed by this enzyme.

Graphical abstract: Stereoselective hydroxylation of an achiral cyclopentanecarboxylic acid derivative using engineered P450s BM-3

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Article information

DOI
https://doi.org/10.1039/B501527H
Article type
Communication
Submitted
02 Feb 2005
Accepted
21 Mar 2005
First published
06 Apr 2005

Chem. Commun., 2005, 2597-2599

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Stereoselective hydroxylation of an achiral cyclopentanecarboxylic acid derivative using engineered P450s BM-3

D. F. Münzer, P. Meinhold, M. W. Peters, S. Feichtenhofer, H. Griengl, F. H. Arnold, A. Glieder and A. de Raadt, Chem. Commun., 2005, 2597 DOI: 10.1039/B501527H

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