Journal
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
Volume 97, Issue 24, Pages 10329-10337Publisher
SPRINGER
DOI: 10.1007/s00253-013-5258-2
Keywords
Asymmetric oxidation; Phenyl methyl sulfide; (S)-phenyl methyl sulfoxide; Biphasic system; Rhodococcus sp; CCZU10-1
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Funding
- National Natural Science Foundation of China [21102011]
- Priority Academic Program Development of Jiangsu Higher Education Institutions
- University Student's Science and Technology Creation Foundation of Changzhou University [102006]
- Open Project Program of the State Key Laboratory of Bioreactor Engineering
- Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology [BM2012110]
- Key Laboratory of Guangxi Biorefinery [GXBF11-03]
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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.
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