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有机化学
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有机化学 ›› 2006, Vol. 26 ›› Issue (10): 1384-1388. 上一篇    下一篇

研究论文

有机相酶催化氨解反应拆分制备(R)-4-氯-3-羟基丁酸乙酯

金勇a， 吴坚平a，徐刚a，杨立荣*,a,b   

  1. (a浙江大学化学与生物工程学系 杭州 310027)
    (b江南大学工业生物技术教育部重点实验室 无锡 214036)
  • 收稿日期:2006-01-17 修回日期:2006-03-20 发布日期:2006-09-19
  • 通讯作者: 杨立荣

Preparation of (R)-Ethyl 4-Chloro-3-hydroxybutanoate throughEnzymatic Ammonolysis in Organic Media

JIN Yonga,WU Jian-Pinga,XU Ganga,YANG Li-Rong*,a,b   

  1. (a Department of Chemical and Biochemical Engineering, Zhejiang University, Hangzhou 310027)
    (b Key Laboratory of Industrial Biotechnology, Ministry of Educa-tion, Jiangnan University, Wuxi 214036 )
  • Received:2006-01-17 Revised:2006-03-20 Published:2006-09-19
  • Contact: YANG Li-Rong

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通过脂肪酶催化的氨解反应拆分4-氯-3-羟基丁酸乙酯. 经过对脂肪酶及反应溶剂的筛选, 确定最佳脂肪酶及溶剂分别为Novozym435和二氧六环; 并在该反应体系中考察了温度、底物浓度、酶浓度与摇床转速对反应的影响. 综合考虑反应的反应速度和对映体选择率, 确定较佳的反应条件为: 温度30 ℃、底物浓度0.5 mol/L、酶量10 mg/mL、摇床转速200 n/min. 反应35 h后, ee可以达到99%以上, 此时转化率为57.7%.

关键词: 4-氯-3-羟基丁酸乙酯, 拆分, 脂肪酶, 氨解

The lipase-catalyzed resolution of ethyl 4-chloro-3-hydroxybutanoate (CHBE) by aminolysis was carried out to prepare (R)-4-chloro-3-hydroxybutanoate. Through screening of lipases, lipase Novozym435 was found to show the highest activity and enantioselectivity for the ammonolysis of CHBE. The effect of different solvents on the ammonolysis was investigated. And 1,4-dioxane was found to be the most optimum solvent. The influence of various factors on the enzymatic resolution was studied. The optimal temperature was 30 ℃. 99% ee value of (R)-CHBE and 57.7% conversion of CHBE could be achieved at 35 h when the concentration of enzyme was 10 mg/mL and the concentration of substrate was 0.5 mol/L.

Key words: 4-chloro-3-hydroxybutanoate, resolution, ammonolysis, lipase