CALB-Catalyzed Two-Step Alcoholytic Desymmetrization of 3-Methylglutaric Diazolides in MTBE

Ting Yi Wu, Yuan Rong Lai, Shau Wei Tsai*

*此作品的通信作者

研究成果: 期刊稿件文章同行評審

2 引文 斯高帕斯(Scopus)

摘要

Optically pure 3-substituted glutarates can be prepared from the alcoholic ring-opening of cyclic anhydride derivatives, esterification of 3-substituted glutaric acid, and hydrolysis, alcoholysis, aminolysis, and ammonolysis of the diester derivatives via hydrolases or organocatalysts. Unfortunately, most of them mainly focus on the first-step desymmetrization, leading to the difficulty on producing optically pure enantiomers. As a general trend in lipase-catalyzed desymmetrization of 3-methylglutarates, poorer enantiomeric excesses with lower chemical yields were found, as the methyl substituent is relatively small to induce a high enzyme stereodiscrimination. The two-step desymmetrization for CALB-catalyzed alcoholysis of 3-methylglutaric di-1,2,4-triazolide 1a in anhydrous MTBE is first developed to increase the enzyme activity in each reaction step. The enantioselectivity for the second-step kinetic resolution is furthermore improved by using 3-methylglutaric dipyrazolide 1b as the substrate. The kinetic and thermodynamic analysis is, moreover, addressed for shedding insights into the desymmetrization process.

原文英語
頁(從 - 到)578-592
頁數15
期刊Applied Biochemistry and Biotechnology
185
發行號3
DOIs
出版狀態已出版 - 01 07 2018

文獻附註

Publisher Copyright:
© 2018, Springer Science+Business Media, LLC, part of Springer Nature.

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