化工进展

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酶法动态动力学拆分制备R-(-)-乙酰基邻氯扁桃酸

沈萨萨1,姜灵2,陆杰1,于洪巍2   

  1. 1江南大学化学与材料工程学院,江苏 无锡 214122;2浙江大学化学工程与生物工程学系,浙江 杭州 310028
  • 出版日期:2014-09-05 发布日期:2014-09-05

R-(-)-acetyl-o-mandelic acid preparation via enzymatic dynamic kinetic resolution

SHEN Sasa1,JIANG Ling2,LU Jie1,YU Hongwei2   

  1. 1School of Chemical and Material Engineering,Jiangnan University,Wuxi 214122,Jiangsu,China;2School of Chemical and Biological Engineering,Zhejiang University,Hangzhou 310028,Zhejiang,China
  • Online:2014-09-05 Published:2014-09-05

摘要: 采用假单胞菌脂肪酶Pseudomonas sp. ECU1011催化乙酰基邻氯扁桃酸进行不对称水解,利用突变后的扁桃酸消旋酶(V29I)对拆分后的产物S-(-)-邻氯扁桃酸进行消旋,消旋后的邻氯扁桃酸经过酰化重新被利用到水解反应中,实现了酶法动态动力学拆分制备R-(-)-乙酰基邻氯扁桃酸。通过对拆分反应、拆分混合物的分离回收以及消旋反应的工艺优化,最终获得光学纯度ee>99.9%的R-(-)-乙酰基邻氯扁桃酸,其收率达80%。本研究建立的R-(-)-乙酰基邻氯扁桃酸的动态动力学拆分工艺,对其工业化应用具有重要的指导意义。

关键词: 酶法动态动力学拆分, 脂肪酶Pseudomonas sp. ECU1011, 扁桃酸消旋酶, 乙酰基邻氯扁桃酸, 邻氯扁桃酸

Abstract: In this study,asymmetric hydrolysis of acetyl chloromandelic acid was catalyzed by Pseudomonas sp. ECU1011,and the S-(-)-chloromandelic acid in the resolution mixture was then racemerized using the mutated mandelate racemase and fed back into the hydrolysis reaction after acylation,realizing enzymatic dynamic kinetic resolution for preparation of R-(-)-acetyl chloromandelic acid. Firstly,the conditions for enzymatic resolution,separation of resolution mixture,and enzymatic racemization were optimized. Subsequently,dynamic kinetic resolution of acetyl chloromandelic acid was conducted under the optimal conditions,obtaining optically pure R-(-)-acetyl chloromandelic acid with final yield of 80%. The conditions for enzymatic resolution,chloromandelic acid recycling and racemization were optimized in this study,leading to preliminary establishment of the dynamic kinetic resolution process for R-(-)-acetyl chloromandelic acid preparation,with guiding significance for future industrial applications.

Key words: enzymatic dynamic kinetic resolution, Pseudomonas sp. ECU1011 lipase, mandelate racemase, R-(-)-acetyl-o-mandelic acid, chloromandelic acid

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