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Selective oxidation resolution of racemic phenyl methyl sulfoxide with Rhodococcus sp. CCZU10-1

YANG Zhenxing,TAO Zhicheng,HE Yucai,WANG Liqun,ZHANG Yue,XING Zhen,GONG Lei,PAN Xuehe   

  1. Laboratory of Biochemical Engineering,School of Pharmaceutical Engineering and Life Sciences,Changzhou University,Changzhou 213164,Jiangsu,China
  • Online:2014-10-05 Published:2014-10-05

红球菌CCZU10-1选择性氧化拆分外消旋苯甲亚砜的性能

杨振兴,陶志成,何玉财,王利群,张跃,邢震,龚磊,潘雪鹤   

  1. 常州大学制药与生命科学学院生物工程研究室,江苏 常州 213164

Abstract: To efficiently synthesize optically active chiral sulfoxides,Rhodococcus sp. CCZU10-1 was used for the asymmetric resolution of rac-PMSO into (S)-PMSO (ee > 99.9%) in aqueous single-phase system. After optimization,the optimum reaction pH,reaction temperature,shaker speed,co-substrate,cells dosage were 8.0,30℃,180 r/min,galactose (50mmol/L) and 0.08g (wet weight)/mL,respectively. By biotransformation of rac-PMSO (20mmol/L) for 6h under the optimized conditions,(R)-PMSO was completely oxidized into the corresponding sulfone,and (S)-PMSO (ee > 99.9%) was obtained at a high yield of 47.1%. These results would lay the foundation of industrial production of (S)-PMSO.

Key words: Rhodococcus sp., (S)-PMSO, resolution, biotransformation, optimization

摘要: 为了高效地合成高光学纯手性亚砜,在单水相体系中利用Rhodococcus sp. CCZU10-1选择性氧化拆分外消旋苯甲亚砜(rac-PMSO)合成了(S)-PMSO(ee>99.9%)。通过考察反应pH值、反应温度、摇床转速、辅助底物、生物催化剂添加量对催化反应的影响,确定了最适反应条件。结果表明最适反应条件为:反应pH值8.0、反应温度30℃、摇床转速180r/min、辅助底物为半乳糖(50mmol/L)、细胞浓度为0.08g(湿重)/mL。在最适反应条件下生物转化20mmol/L rac-PMSO时,(R)-PMSO完全转化,(S)-PMSO(ee>99.9%)产率为47.1%。因此,研究结果为工业化生产(S)-PMSO奠定了基础。

关键词: 红球菌属, (S)-苯甲亚砜, 拆分, 生物转化, 优化

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