Chin. J. Org. Chem. ›› 2006, Vol. 26 ›› Issue (10): 1384-1388. Previous Articles     Next Articles

Original Articles


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

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