Highly selective kinetic resolution of D/L-syn-p-sulfone phenylserine catalyzed by D-threonine aldolase in two-phase ionic solvent  

作　　者：Fengfan Liu Zhihao Shi Jinmei Zhu Xiaobin Liang Mingming Liang Yuanyuan Xie Weike Su Jiequn Wu 

机构地区：[1]National Engineering Research Center for Process Development of Active Pharmaceutical Ingredients,Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals,Zhejiang University of Technology,Hangzhou,310014,China [2]Key Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education and Pharmaceutical Engineering of Zhejiang Province,College of Pharmaceutical Sciences,Zhejiang University of Technology,Hangzhou,310014,China

出　　处：《Green Chemical Engineering》2023年第2期212-216,共5页绿色化学工程（英文）

基　　金：the Zhejiang Provincial Key R&D Project (Nos. 2020C03006 & 2019-ZJ-JS-03);National Key R&D Program of China (2021YFC2100800);the National Natural Science Foundation of China (Project 21808205);Research and Application Service Platform Project of API Manufacturing Environmental Protection and Safety Technology in China (2020-0107-3-1)。

摘　　要：In the chemical synthesis of L-syn-p-methylsulfoxide phenylserine ethyl ester(D-ethyl ester),L-tartaric acid or enzymatic resolution is employed to resolve the racemate,and thus obtain the target compound,and the remaining isomer can be recycled to obtain the raw material.In this study,high-purity L-syn-p-methylsulfoxide phenylserine(L-syn-MPS)was obtained.The kinetics of the D-threonine aldolase enzymatic hydrolysis reaction reveals that D-syn-p-sulfoxylphenylserine resolves well in[BMIM][BF 4]ionic solvents.The D/L-syn-MPS racemate was resolved using a two-phase ionic solvent[BMIM][NTf 2]to afford L-syn-MPS(ee(enantiomeric excess)>99%)and a white solid in 41.7%yield.Therefore,this system is suitable for the separation of insoluble aldehydes and successfully avoids the condensation of hydroxyl aldehydes to form D-anti-MPS.

关 键 词：Kinetic resolution Ionic solvent Enzymatic resolution D/L-p-sulphoxyl phenylserine ethyl ester Biphasic reaction system 

分 类 号：TQ465[化学工程—制药化工]