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

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

Green Chemical Engineering (Jun 2023)

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

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

Affiliations

Fengfan Liu: 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
Zhihao Shi: 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
Jinmei Zhu: 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
Xiaobin Liang: 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
Mingming Liang: 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
Yuanyuan Xie: 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
Weike Su: 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; Corresponding author.
Jiequn Wu: 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; Corresponding author.

Journal volume & issue: Vol. 4, no. 2
pp. 212 – 216

Abstract

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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.

Published in Green Chemical Engineering

ISSN: 2666-9528 (Online)
Publisher: KeAi Communications Co. Ltd.
Country of publisher: China
LCC subjects: Technology: Chemical technology: Chemical engineering; Science: Chemistry: Organic chemistry: Biochemistry
Website: https://www.keaipublishing.com/en/journals/green-chemical-engineering/

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