Fengfan Liu , Zhihao Shi , Jinmei Zhu , Xiaobin Liang , Mingming Liang , Yuanyuan Xie , Weike Su , Jiequn Wu
{"title":"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","authors":"Fengfan Liu , Zhihao Shi , Jinmei Zhu , Xiaobin Liang , Mingming Liang , Yuanyuan Xie , Weike Su , Jiequn Wu","doi":"10.1016/j.gce.2022.10.002","DOIUrl":null,"url":null,"abstract":"<div><p>In the chemical synthesis of L-<em>syn</em>-<em>p</em>-methylsulfoxide phenylserine ethyl ester (D-ethyl ester), <span>l</span>-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-<em>syn</em>-<em>p</em>-methylsulfoxide phenylserine (L-<em>syn</em>-MPS) was obtained. The kinetics of the <span>d</span>-threonine aldolase enzymatic hydrolysis reaction reveals that D-<em>syn</em>-<em>p</em>-sulfoxylphenylserine resolves well in [BMIM][BF<sub>4</sub>] ionic solvents. The D/L-<em>syn</em>-MPS racemate was resolved using a two-phase ionic solvent [BMIM][NTf<sub>2</sub>] to afford L-<em>syn</em>-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-<em>anti</em>-MPS.</p></div>","PeriodicalId":66474,"journal":{"name":"Green Chemical Engineering","volume":"4 2","pages":"Pages 212-216"},"PeriodicalIF":9.1000,"publicationDate":"2023-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"1","resultStr":"{\"title\":\"Highly selective kinetic resolution of D/L-syn-p-sulfone phenylserine catalyzed by d-threonine aldolase in two-phase ionic solvent\",\"authors\":\"Fengfan Liu , Zhihao Shi , Jinmei Zhu , Xiaobin Liang , Mingming Liang , Yuanyuan Xie , Weike Su , Jiequn Wu\",\"doi\":\"10.1016/j.gce.2022.10.002\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>In the chemical synthesis of L-<em>syn</em>-<em>p</em>-methylsulfoxide phenylserine ethyl ester (D-ethyl ester), <span>l</span>-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-<em>syn</em>-<em>p</em>-methylsulfoxide phenylserine (L-<em>syn</em>-MPS) was obtained. The kinetics of the <span>d</span>-threonine aldolase enzymatic hydrolysis reaction reveals that D-<em>syn</em>-<em>p</em>-sulfoxylphenylserine resolves well in [BMIM][BF<sub>4</sub>] ionic solvents. The D/L-<em>syn</em>-MPS racemate was resolved using a two-phase ionic solvent [BMIM][NTf<sub>2</sub>] to afford L-<em>syn</em>-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-<em>anti</em>-MPS.</p></div>\",\"PeriodicalId\":66474,\"journal\":{\"name\":\"Green Chemical Engineering\",\"volume\":\"4 2\",\"pages\":\"Pages 212-216\"},\"PeriodicalIF\":9.1000,\"publicationDate\":\"2023-06-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"1\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Green Chemical Engineering\",\"FirstCategoryId\":\"1089\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S2666952822000838\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"ENGINEERING, CHEMICAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Green Chemical Engineering","FirstCategoryId":"1089","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2666952822000838","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"ENGINEERING, CHEMICAL","Score":null,"Total":0}
Highly selective kinetic resolution of D/L-syn-p-sulfone phenylserine catalyzed by d-threonine aldolase in two-phase ionic solvent
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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