Highly enantioselective oxidation of phenyl methyl sulfide and its derivatives into optically pure (S)-sulfoxides with Rhodococcus sp. CCZU10-1 in an n-octane–water biphasic system

Enantiopure sulfoxides can be prepared via the asymmetric oxidation of sulfides using sulfide monooxygenases. The n -octane–water biphasic system was chosen for the bio-oxidation of a water-insoluble phenyl methyl sulfide (PMS) by Rhodococcus sp. CCZU10-1. In this n -octane–water system, the optimum reaction conditions were obtained. ( S )-phenyl methyl sulfoxide (( S )-PMSO) with >99.9 % enantiomeric excess formed at 55.3 mM in the n -octane–water biphasic system. Using fed-batch method, a total of 118 mM ( S )-PMSO accumulated in 1-L reaction mixture after the 7th feed, and no ( R )-PMSO and sulfone were detected. Moreover, Rhodococcus sp. CCZU10-1 displayed fairly good activity and enantioselectivity toward other sulfides. In conclusion, Rhodococcus sp. CCZU10-1 is a promising biocatalyst for synthesizing highly optically active sulfoxides.