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Highly enantioselective stereo-inverting sec-alkylsulfatase activity of hyperthermophilic Archaea
Sabine R Wallner1, Bettina M Nestl, Kurt Faber
1Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria.
Abstract:
rac-sec-Alkyl sulfate esters 1a-8a 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.
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