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Asymmetric reduction of racemic sulfoxides by dimethyl sulfoxide reductases from Rhodobacter capsulatus, Escherichia coli and Proteus species

Steven P. Hanlon^1,

Daniel L. Graham^2,

School of Biological Sciences, University of East Anglia, Norwich NR4 7TJ, UK
Zeneca LifeScience Molecules, Belasis Avenue, Billingham, Cleveland TS23 1YN, UK.
Zeneca Pharmaceuticals, Macclesfield, Cheshire, SK10 2NA, UK
Department of Microbiology, The University of Queensland, Brisbane 4072, Australia

ABSTRACT

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.

^*Author for correspondence: Alastair G. McEwan. Tel: +61 7 3365 4878. Fax: +61 7 3365 4620. e-mail: mcewan@biosci.uq.edu.au

Present address: Department of Biochemistry, University College, Gower Street, London WC1E 6BT, UK.

Present address: Molecular Pharmocology Unit, Ninewells Hospital and Medical School, Dundee DD1 9SY, UK.