Resolution of racemic sulfoxides with high productivity and enantioselectivity by a Rhodococcus sp. strain as an alternative to biooxidation of prochiral sulfides for efficient production of enantiopure sulfoxides.
Whole cells of Rhodococcus sp. ECU0066 were used a catalyst for resolution of racemic sulfoxides, as an alternative to asymmetric oxidation of sulfides for efficient production of enantiopure sulfoxides. Racemic sulfoxides were excellent substrates for biotransformation because of their lower biotoxicity compared to sulfides. Determination of apparent kinetic parameters indicated that phenyl methyl sulfide (PMS), but not racemic phenyl methyl sulfoxide (rac-PMSO) caused substrate inhibition. (S)-PMSO was formed at a higher concentration and good enantiomeric excess (37.8 mM and 93.7% ee(S)) in a fed-batch reaction, than by an asymmetric oxidation of PMS (10 mM and 80% eeP (S)). The bacterium also displayed fairly good activity (yields, 22.7-43.2%; within 1-8 h) and enantioselectivity (ee(S)>99.0%) towards para-substituted (methyl and chloro) phenyl methyl sulfoxides and ethyl phenyl sulfoxide, indicating it could be a promising agent for synthetic applications.
Li
Ai-Tao
AT
Laboratory of Biocatalysis and Bioprocessing, State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China.
Yu
Hui-Lei
HL
Pan
Jiang
J
Zhang
Jian-Dong
JD
Xu
Jian-He
JH
Lin
Guo-Qiang
GQ
D002384:Catalysis; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D050296:Microbial Viability; D010084:Oxidation-Reduction; D012240:Rhodococcus / Q000166:cytology / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013440:Sulfides / Q000737:chemistry* / Q000378:metabolism*; D013454:Sulfoxides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D013696:Temperature; D013997:Time Factors
D013440:Sulfides; D013454:Sulfoxides; C417240:methyl phenyl sulfoxide; C093850:methylphenylsulfide