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

Autor: Fengfan Liu, Zhihao Shi, Jinmei Zhu, Xiaobin Liang, Mingming Liang, Yuanyuan Xie, Weike Su, Jiequn Wu
Jazyk: angličtina
Rok vydání: 2023
Předmět:
Zdroj: Green Chemical Engineering, Vol 4, Iss 2, Pp 212-216 (2023)
Druh dokumentu: article
ISSN: 2666-9528
DOI: 10.1016/j.gce.2022.10.002
Popis: 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.
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