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.
School of Biological Sciences, University of East AngliaNorwich NR4 7TJUK.
Steven P
SP
Hanlon
Zeneca LifeScience MoleculesBelasis Avenue, Billingham, Cleveland TS23 1YNUK.
Daniel L
DL
Graham
Zeneca PharmaceuticalsMacclesfield, Cheshire, SK10 2NAUK.
Philip J
PJ
Hogan
Zeneca LifeScience MoleculesBelasis Avenue, Billingham, Cleveland TS23 1YNUK.
Robert A
RA
Holt
Zeneca LifeScience MoleculesBelasis Avenue, Billingham, Cleveland TS23 1YNUK.
Christopher D
CD
Reeve
Department of Microbiology, The University of QueenslandBrisbane 4072Australia.
Anthony L
AL
Shaw
Department of Microbiology, The University of QueenslandBrisbane 4072Australia.
Alastair G
AG
McEwan
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