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Issue 8, 2012
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Stereoselective synthesis of bulky 1,2-diols with alcohol dehydrogenases

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Abstract

Although biotransformations implementing alcohol dehydrogenases (ADHs) are widespread, enzymes which catalyse the reduction and oxidation of sterically demanding substrates, especially 2-hydroxy ketones, are still rare. To fill this gap eight ADHs were investigated concerning their potential to reduce bulky 2-hydroxy ketones. All of these enzymes showed good activities along with excellent enantio- (ee > 99%) and diastereoselectivities (de > 99%). Due to their differences in substrate preferences and stereoselectivity a broad range of diastereomerically pure 1,2-diols is now accessible via biotransformation. Best results were obtained using the alcohol dehydrogenase from Ralstonia sp. (Cupriavidus sp.) (RADH), which showed a broad substrate range, especially for sterically demanding compounds. Araliphatic 2-hydroxy ketones, like (R)-2-hydroxy-1-phenylpropan-1-one ((R)-2-HPP), were reduced much faster than aliphatic or aromatic aldehydes (e.g. benzaldehyde) under the applied conditions. Additionally (R)- as well as (S)-2-hydroxy ketones were converted with high diastereoselectivities (de > 99%). RADH, which was up to now only studied as a whole cell biocatalyst overexpressed in E. coli, was purified and thoroughly characterised concerning its catalytic properties.

Graphical abstract: Stereoselective synthesis of bulky 1,2-diols with alcohol dehydrogenases

  • This article is part of the themed collection: Biocatalysis
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Supplementary files

Article information


Submitted
28 Feb 2012
Accepted
26 Mar 2012
First published
27 Mar 2012

Catal. Sci. Technol., 2012,2, 1580-1589
Article type
Paper

Stereoselective synthesis of bulky 1,2-diols with alcohol dehydrogenases

J. Kulig, R. C. Simon, C. A. Rose, S. M. Husain, M. Häckh, S. Lüdeke, K. Zeitler, W. Kroutil, M. Pohl and D. Rother, Catal. Sci. Technol., 2012, 2, 1580
DOI: 10.1039/C2CY20120H

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