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

被引：20

作者：

He, Yu-Cai ^{[1
,2
,3
]}

Ma, Cui-Luan ^{[1
,2
]}

Yang, Zhen-Xing ^{[1
,2
]}

Zhou, Min ^{[1
,2
]}

Xing, Zhen ^{[1
,2
]}

Ma, Jiang-Tao ^{[1
,2
]}

Yu, Hui-Lei ^{[1
,2
]}

机构：

[1] Changzhou Univ, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China

[2] Changzhou Univ, Coll Pharmaceut Engn & Life Sci, Changzhou 213164, Peoples R China

[3] E China Univ Sci & Technol, State Key Lab Bioreactor Engn, Shanghai 200237, Peoples R China

来源：

APPLIED MICROBIOLOGY AND BIOTECHNOLOGY | 2013年 / 97卷 / 24期

基金：

中国国家自然科学基金;

关键词：

Asymmetric oxidation; Phenyl methyl sulfide; (S)-phenyl methyl sulfoxide; Biphasic system; Rhodococcus sp; CCZU10-1; ENANTIOPURE SULFOXIDES; PROCHIRAL SULFIDES; CHIRAL SULFOXIDES; ORGANIC SULFIDES; WHOLE CELLS; RESOLUTION; BIOTRANSFORMATIONS; FUNGI; HYDROPEROXIDES; MONOOXYGENASE;

D O I：

10.1007/s00253-013-5258-2

中图分类号：

Q81 [生物工程学（生物技术）]; Q93 [微生物学];

学科分类号：

071005 ; 0836 ; 090102 ; 100705 ;

摘要：

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.

引用

页码：10329 / 10337

页数：9

共 2 条

[1] 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
Yu-Cai He
Cui-Luan Ma
Zhen-Xing Yang
Min Zhou
Zhen Xing
Jiang-Tao Ma
Hui-Lei Yu
[J]. Applied Microbiology and Biotechnology, 2013, 97 : 10329 - 10337
[2] Biosynthesis of benzoylformic acid from benzoyl cyanide by a newly isolated Rhodococcus sp CCZU10-1 in toluene-water biphasic system
He, Yu-Cai
Zhou, Qiong
Ma, Cui-Luan
Cai, Zhi-Qiang
Wang, Li-Qun
Zhao, Xi-Yue
Chen, Qun
Gao, Da-Zhou
Zheng, Ming
Wang, Xu-Dong
Sun, Quan
[J]. BIORESOURCE TECHNOLOGY, 2012, 115 : 88 - 95

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