{"title":"Synthesis of N-Aroyl methylsulfonyl-substituted phenylalanine esters via enzyme-catalyzed dynamic kinetic resolution of azlactones","authors":"Peng Wang, Chunzhi Ju, Lingkai Kong, Jisheng Cai, Guangliang Zhang, Suoqin Zhang","doi":"10.1016/j.tet.2024.134413","DOIUrl":null,"url":null,"abstract":"<div><div>A facile enantioselective synthesis of non-natural phenylalanine esters via dynamic kinetic resolution (DKR) reaction, has been developed. This method entails the utilization of novozym 435 enzyme to catalyze the enantioselective methanolysis of various methylsulfonated azlactone derivatives in organic solvents, providing <em>N</em>-aroyl methylsulfonyl-substituted phenylalanine esters. (ee up to 99 %), which can be further hydrolyzed to obtain the corresponding amino acids.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"171 ","pages":"Article 134413"},"PeriodicalIF":2.1000,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402024005945","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A facile enantioselective synthesis of non-natural phenylalanine esters via dynamic kinetic resolution (DKR) reaction, has been developed. This method entails the utilization of novozym 435 enzyme to catalyze the enantioselective methanolysis of various methylsulfonated azlactone derivatives in organic solvents, providing N-aroyl methylsulfonyl-substituted phenylalanine esters. (ee up to 99 %), which can be further hydrolyzed to obtain the corresponding amino acids.
期刊介绍：
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.
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