文献类型：期刊文献

英文题名：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

作者：Li, Ai-Tao[1]; Yu, Hui-Lei[1]; Pan, Jiang[1]; Zhang, Jian-Dong[1]; Xu, Jian-He[1]; Lin, Guo-Qiang[2]

机构：[1] Laboratory of Biocatalysis and Bioprocessing, State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China; [2] Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

年份：2011

卷号：102

期号：2

起止页码：1537

外文期刊名：Bioresource Technology

收录：EI(收录号：20110113543203)

语种：英文

外文关键词：Substrates - Enantioselectivity

摘要：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 (37.8mM and 93.7% ee(S)) in a fed-batch reaction, than by an asymmetric oxidation of PMS (10mM and 80% eeP (S)). The bacterium also displayed fairly good activity (yields, 22.7-43.2%; within 1-8h) 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. ? 2010 Elsevier Ltd.