TY - JOUR
T1 - Stereoselective reductase-catalysed deoxygenation of sulfoxides in aerobic and anaerobic bacteria
AU - Boyd, Derek R.
AU - Sharma, Narain D.
AU - King, Alistair W.T.
AU - Shepherd, Steven D.
AU - Allen, Christopher C.R.
AU - Holt, Robert A.
AU - Luckarift, Heather R.
AU - Dalton, Howard
PY - 2004/2/21
Y1 - 2004/2/21
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=1342344950&partnerID=8YFLogxK
U2 - 10.1039/b313714g
DO - 10.1039/b313714g
M3 - Article
C2 - 14770234
AN - SCOPUS:1342344950
SN - 1477-0520
VL - 2
SP - 554
EP - 561
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 4
ER -