Synthesis of N-Aroyl methylsulfonyl-substituted phenylalanine esters via enzyme-catalyzed dynamic kinetic resolution of azlactones

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-02-01 DOI:10.1016/j.tet.2024.134413

Peng Wang, Chunzhi Ju, Lingkai Kong, Jisheng Cai, Guangliang Zhang, Suoqin Zhang

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.

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一种通过动态动力学解析（DKR）反应简便地对映体选择性合成非天然苯丙氨酸酯的方法已经开发成功。该方法需要利用 novozym 435 酶在有机溶剂中催化各种甲磺化氮内酯衍生物的对映体选择性甲醇分解，从而得到 N-芳酰基甲磺酰基取代的苯丙氨酸酯。(ee高达 99%)，可进一步水解得到相应的氨基酸。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

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.