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

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

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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][BF4]ionic solvents.The D/L-syn-MPS racemate was resolved using a two-phase ionic solvent[BMIM][NTf2]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.

Kinetic resolutionIonic solventEnzymatic resolutionD/L-p-sulphoxyl phenylserine ethyl esterBiphasic reaction system

Fengfan Liu、Zhihao Shi、Jinmei Zhu、Xiaobin Liang、Mingming Liang、Yuanyuan Xie、Weike Su、Jiequn Wu

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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

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

Zhejiang Provincial Key R&D ProjectZhejiang Provincial Key R&D ProjectNational Key R&D Program of ChianNational Natural Science Foundation of ChinaResearch and Application Service Platform Project of API Manufacturing Environmental Protection and Safety Technology in China

2020C030062019-ZJ-JS-032021YFC2100800218082052020-0107-3-1

2023

10.1016/j.gce.2022.10.002

绿色化学工程(英文)
中国科学院过程工程研究所

绿色化学工程(英文)

CSCD
ISSN：
年,卷(期)：2023.4(2)
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