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(S)-(-)-β-羟基苯丙酸乙酯的微生物法合成
引用本文:欧志敏,陈晓彦,杨根生,应国清.(S)-(-)-β-羟基苯丙酸乙酯的微生物法合成[J].工业微生物,2009,39(6):11-15.
作者姓名:欧志敏  陈晓彦  杨根生  应国清
作者单位:浙江工业大学药学院,杭州,310014
基金项目:浙江省科技厅科技计划项目 
摘    要:采用酿酒酵母CGMCC No.2266菌体,不对称还原β-羰基苯丙酸乙酯制备光学纯(S)-(-)-β-羟基苯丙酸乙酯。结果表明:采用初始pH为8.0的液体发酵培养基培养的CGMCCNo.2266菌体经过50℃预热处理30min后用于生物转化获得的(S)-(-)-G-羟基苯丙酸乙酯对映体过剩值可以达到100%ee。确定了合成(S)-(-)-β-羟基苯丙酸乙酯的较佳转化条件为pH7.0,温度30℃,转化时间24h,底物浓度为3.63mmol/L,菌体用量为86g/L(干重/反应体积)。以10%葡萄糖为辅助底物,产率比不加辅助底物时提高了75.4%。在最佳转化条件下反应转化率及(S)-(-)-β-羟基苯丙酸乙酯对映体过剩值可分别达到98.4%和100%ee。

关 键 词:(S)-(-)-β-羟基苯丙酸乙酯  不对称还原  酿酒酵母CGMCC  No.2266

Synthesis of (S)-(-)-Beta-hydroxy-benzenepropanoic acid ethyl ester by microorganism transformation
OU Zhi-min,CHEN Xiao-yan,YANG Gen-sheng,YING Guo-qing.Synthesis of (S)-(-)-Beta-hydroxy-benzenepropanoic acid ethyl ester by microorganism transformation[J].Industrial Microbiology,2009,39(6):11-15.
Authors:OU Zhi-min  CHEN Xiao-yan  YANG Gen-sheng  YING Guo-qing
Institution:(Pharmaceuticals College, Zhejiang University of Technology, Hangzhou 310014,China)
Abstract:Beta-hydroxy-benzenepropanoic acid ethyl ester (HPPE) is an important precursor for the synthesis of chiral pharmaceuticals.The carbonyl asymmetric reduction of β-carbonyl phenylpropionate to (S)-(-)-Beta-hydroxy-benzenepropanoic acid ethyl ester by CGMCC No.2266 was investigated.The enantiometric excess of (S)-(-)-Beta-hydroxy-benzenepropanoic acid ethyl ester could achieve 100%ee by reduction of CGMCC No.2266 cultivated by the liquid medium of intial pH 8.0 and preheated at 50 ℃ for 30 min.The effects of bioconversion conditions on both yield and enantiomeric excess were evaluated.The reaction conditions for the reduction of β-carbonyl phenylpropionate to (S)-(-)-Beta-hydroxy-benzenepropanoic acid ethyl ester were optimized,and the highest yield was achieved when the bioconversion was taken place at pH 7.0 and 30 ℃ for 24 h.The substrate concentration was 3.63 mmol/L and the biomass was 86 g/L(w/v).The experimental data showed that the best co-substrate was glucose and the optimal glucose concentration was 10%.The yield and (S)-(-)-Beta-hydroxy-benzenepropanoic acid ethyl ester enantiometric excess achieved as high as 98.4% and 100%ee,respectively.
Keywords:(S)-(-)-Beta-hydroxy-benzenepropanoic acid ethyl ester  asymmetric reduction  Saccharomyces cerevisiae CGMCC No  2266
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