Stereoselective reductase-catalysed deoxygenation of sulfoxides in aerobic and anaerobic bacteria.
Direct and indirect evidence, of unexpected stereoselective reductase-catalysed deoxygenations of sulfoxides, was found. The deoxygenations proceeded simultaneously, with the expected dioxygenase-catalysed asymmetric sulfoxidation of sulfides, during some biotransformations with the aerobic bacterium Pseudomonas putida UV4. Stereoselective reductase-catalysed asymmetric deoxygenation of racemic alkylaryl, dialkyl and phenolic sulfoxides was observed, without evidence of the reverse sulfoxidation reaction, using anaerobic bacterial strains. A purified dimethyl sulfoxide reductase, obtained from the intact cells of the anaerobic bacterium Citrobacter braakii DMSO 11, yielded, from the corresponding racemates, enantiopure alkylaryl sulfoxide and thiosulfinate samples.
Boyd
Derek R
DR
School of Chemistry, The Queen's University of Belfast, Belfast, UK.
Sharma
Narain D
ND
King
Alistair W T
AW
Shepherd
Steven D
SD
Allen
Christopher C R
CC
Holt
Robert A
RA
Luckarift
Heather R
HR
Dalton
Howard
H
D000332:Aerobiosis; D000693:Anaerobiosis; D055162:Biocatalysis; D002954:Citrobacter / Q000201:enzymology*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010088:Oxidoreductases / Q000378:metabolism*; D016958:Pseudomonas putida / Q000201:enzymology*; D012451:Safrole / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism; D013379:Substrate Specificity
D010088:Oxidoreductases; D012451:Safrole; C005746:sulfoxide