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Issue 14, 2005
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Highly enantioselective stereo-inverting sec-alkylsulfatase activity of hyperthermophilic Archaea

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Abstract

rac-sec-Alkyl sulfate esters 1a8a were resolved in low to excellent enantioselectivities with E-values up to >200 using whole cells of aerobically-grown hyperthermophilic sulfur-metabolizers, such as Sulfolobus solfataricus DSM 1617, Sulfolobus shibatae DSM 5389 and, most notably, Sulfolobus acidocaldarius DSM 639. Significantly enhanced selectivities were obtained using cells grown on sucrose-enriched Brock-medium. The stereochemical course of this biohydrolysis was shown to proceed with strict inversion of configuration, thus the preferred (R)-enantiomers were converted into the corresponding (S)-sec-alcohols to furnish a homochiral product mixture.

Graphical abstract: Highly enantioselective stereo-inverting sec-alkylsulfatase activity of hyperthermophilic Archaea

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Supplementary files

Article information


Submitted
11 Apr 2005
Accepted
24 May 2005
First published
21 Jun 2005

Org. Biomol. Chem., 2005,3, 2652-2656
Article type
Paper

Highly enantioselective stereo-inverting sec-alkylsulfatase activity of hyperthermophilic Archaea

S. R. Wallner, B. M. Nestl and K. Faber, Org. Biomol. Chem., 2005, 3, 2652
DOI: 10.1039/B504883D

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