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

IF 9.1 Q1 ENGINEERING, CHEMICAL Green Chemical Engineering Pub Date : 2023-06-01 DOI:10.1016/j.gce.2022.10.002

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

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引用次数: 1

Abstract

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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D-苏氨酸醛缩酶在两相离子溶剂中催化D/ l -对砜苯基丝氨酸的高选择性动力学拆分

在L-对甲基亚砜苯基丝氨酸乙酯（D-乙酯）的化学合成中，采用L-酒石酸或酶促拆分来拆分外消旋体，从而获得目标化合物，剩余的异构体可以回收获得原料。本研究获得了高纯度的L-对甲基亚砜苯基丝氨酸（L-syn-MPS）。d-苏氨酸醛缩酶酶水解反应的动力学表明，d-正-磺酰基苯基丝氨酸在[BMIM][BF4]离子溶剂中很好地分解。使用两相离子溶剂[BMIM][NTf2]解析D/L-合-MPS外消旋体，得到L-合-MPS（ee（对映体过量） >； 99%）和白色固体，产率为41.7%。因此，该体系适用于不溶性醛的分离，并成功避免了羟基醛缩合形成D-抗-MPS。

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