酶法动态动力学拆分制备R-(-)-乙酰基邻氯扁桃酸

化工进展

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

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/Abstract

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

沈萨萨1，姜灵2，陆杰1，于洪巍2. 酶法动态动力学拆分制备R-(-)-乙酰基邻氯扁桃酸[J]. 化工进展.

SHEN Sasa1，JIANG Ling2，LU Jie1，YU Hongwei2. R-(-)-acetyl-o-mandelic acid preparation via enzymatic dynamic kinetic resolution[J]. Chemical Industry and Engineering Progree.