Asymmetric reduction of racemic sulfoxides by dimethyl sulfoxide reductases from Rhodobacter capsulatus, Escherichia coli and Proteus species.
The enantioselective reduction of racemic sulfoxides by dimethyl sulfoxide reductases from Rhodobacter capsulatus, Escherichia coli, Proteus mirabilis and Proteus vulgaris was investigated. Purified dimethyl sulfoxide reductase from Rhodobacter capsulatus catalysed the selective removal of (S)-methyl p-tolyl sulfoxide from a racemic mixture of methyl p-tolyl sulfoxide and resulted in an 88% recovery of enantiomerically pure (R)-methyl p-tolyl sulfoxide. Rhodobacter capsulatus was shown to be able to grow photoheterotrophically in the presence of certain chiral sulfoxides under conditions where a sulfoxide is needed as an electron sink. Whole cells of Rhodobacter capsulatus were shown to catalyse the enantioselective reduction of methyl p-tolyl sulfoxide, ethyl 2-pyridyl sulfoxide, methylthiomethyl methyl sulfoxide and methoxymethyl phenyl sulfoxide. Similarly, whole cells of Escherichia coli, Proteus mirabilis and Proteus vulgaris reduced these sulfoxides but with opposite enantioselectivity.
Hanlon
Steven P
SP
School of Biological Sciences, University of East AngliaNorwich NR4 7TJUK.
Graham
Daniel L
DL
Zeneca LifeScience MoleculesBelasis Avenue, Billingham, Cleveland TS23 1YNUK.
Hogan
Philip J
PJ
Zeneca PharmaceuticalsMacclesfield, Cheshire, SK10 2NAUK.
Holt
Robert A
RA
Zeneca LifeScience MoleculesBelasis Avenue, Billingham, Cleveland TS23 1YNUK.
Reeve
Christopher D
CD
Zeneca LifeScience MoleculesBelasis Avenue, Billingham, Cleveland TS23 1YNUK.
Shaw
Anthony L
AL
Department of Microbiology, The University of QueenslandBrisbane 4072Australia.
McEwan
Alastair G
AG
Department of Microbiology, The University of QueenslandBrisbane 4072Australia.
D000693:Anaerobiosis; D004121:Dimethyl Sulfoxide / Q000378:metabolism; D004926:Escherichia coli / Q000201:enzymology* / Q000378:metabolism; D007506:Iron-Sulfur Proteins; D016877:Oxidants / Q000378:metabolism; D010084:Oxidation-Reduction; D010088:Oxidoreductases / Q000378:metabolism*; D011511:Proteus / Q000201:enzymology* / Q000378:metabolism; D016354:Rhodobacter capsulatus / Q000201:enzymology* / Q000254:growth & development / Q000378:metabolism; D013237:Stereoisomerism; D013454:Sulfoxides / Q000378:metabolism*
D007506:Iron-Sulfur Proteins; D016877:Oxidants; D013454:Sulfoxides; D010088:Oxidoreductases; C045664:dimethyl sulfoxide reductase; D004121:Dimethyl Sulfoxide