Highly enantioselective stereo-inverting sec-alkylsulfatase activity of hyperthermophilic Archaea.
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.
Wallner
Sabine R
SR
Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria.
Nestl
Bettina M
BM
Faber
Kurt
K
D001105:Archaea / Q000201:enzymology*; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism; D013429:Sulfatases / Q000737:chemistry* / Q000378:metabolism; D013696:Temperature
D013429:Sulfatases; C019244:alkylsulfatase