Stereoselective reductase-catalysed deoxygenation of sulfoxides in aerobic and anaerobic bacteria

Derek R. Boyd, Narain D. Sharma, Alistair W.T. King, Steven D. Shepherd, Christopher C.R. Allen, Robert A. Holt, Heather R. Luckarift, Howard Dalton

Research output: Contribution to journalArticleScientificpeer-review

31 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)554-561
JournalOrganic and Biomolecular Chemistry
Issue number4
Publication statusPublished - 21 Feb 2004
MoE publication typeA1 Journal article-refereed


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