Preparation of（S）-（-）-β-hydroxy-benzenepropanoic acid ethyl ester by asymmetric reduction of β-carbonyl phenylpropionate with immobilized CGMCC No.2266

OU Zhimin; YANG Gensheng; GUO Fangyuan

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Preparation of（S）-（-）-β-hydroxy-benzenepropanoic acid ethyl ester by asymmetric reduction of β-carbonyl phenylpropionate with immobilized CGMCC No.2266

更新时间：2025-12-10

- Preparation of（S）-（-）-β-hydroxy-benzenepropanoic acid ethyl ester by asymmetric reduction of β-carbonyl phenylpropionate with immobilized CGMCC No.2266
- CIESC Journal Issue 2, Pages: 421-427(2009)
- 作者机构：
  
  浙江工业大学药学院
- 作者简介：
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- Online First：05 February 2009，
  
  Published：05 February 2009
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OU Zhimin, YANG Gensheng, GUO Fangyuan. Preparation of（S）-（-）-β-hydroxy-benzenepropanoic acid ethyl ester by asymmetric reduction of β-carbonyl phenylpropionate with immobilized CGMCC No.2266[J]. CIESC Journal, 2009, (2): 421-427.
DOI：

OU Zhimin, YANG Gensheng, GUO Fangyuan. Preparation of（S）-（-）-β-hydroxy-benzenepropanoic acid ethyl ester by asymmetric reduction of β-carbonyl phenylpropionate with immobilized CGMCC No.2266[J]. CIESC Journal, 2009, (2): 421-427. DOI：

摘要

在邻苯二甲酸二丁酯中采用固定化酿酒酵母CGMCC No.2266不对称还原β-羰基苯丙酸乙酯制备（S）-（-）-β-羟基苯丙酸乙酯。将干重为430 mg的100 ml菌液50℃预热处理30 min，以2％海藻酸钠固定化得到的直径为2 mm的固定化细胞增殖培养72 h，在300 ml邻苯二甲酸二丁酯中转化17.2 mmol·L-1β-羰基苯丙酸乙酯，摩尔产率和对映体过剩值可以分别达到92.2%和100%。固定化细胞可以较好地重复利用于转化反应10次。产率随底物浓度的增高而降低，分批加入底物可以降低底物浓度过高对反应过程的抑制。

Abstract

(（S）-（-）-β-hydroxy-benzenepropanoic acid ethyl ester was synthesized by asymmetric reduction of β-carbonyl phenylpropionate with immobilized CGMCC No.2266 in dibutyl phthalate.100 ml microbial liquor containing 430 mg（dry weight）biomass preheated at 50℃ for 30 min was immobilized.After re-culturing for 72 h，the immobilized cells of 2 mm diameter prepared by 2% sodium alginate was used to reduce 17.2 mmol·L-1 β-carbonyl phenylpropionate in 300 ml dibutyl phthalate.The yield and enantiomeric excess of（S）-（-）-β-hydroxy-benzenepropanoic acid ethyl ester reached 92.2% and 100% respectively.Immobilized CGMCC No.2266 can be reused in reaction for ten times.The yield decreased with increasing substrate concentration.Batch addition of substrate can reduce inhibition of high concentration substrate.

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