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脂环族β-氨基酯的首次直接酶促水解:一种制备对映体纯的顺式和反式β-氨基酸的方法。

The first direct enzymatic hydrolysis of alicyclic beta-amino esters: a route to enantiopure cis and trans beta-amino acids.

作者信息

Forró Enikõ, Fülöp Ferenc

机构信息

Institute of Pharmaceutical Chemistry, University of Szeged, 6701 Szeged, PO Box 427, Hungary.

出版信息

Chemistry. 2007;13(22):6397-401. doi: 10.1002/chem.200700257.

Abstract

The first direct enzymatic method is reported for the synthesis of cis and trans beta-amino acid enantiomers through the lipase-catalyzed enantioselective hydrolysis of alicyclic beta-amino esters in organic media. High enantioselectivities (E usually >100) were observed when the Candida antarctica lipase B catalyzed reactions were performed with H2O (0.5 equivalents) in iPr2O at 65 degrees C. The resolved products, obtained in good yields (>or=42%), could be easily separated.

摘要

报道了第一种直接酶法,通过脂肪酶催化的脂环族β-氨基酸酯在有机介质中的对映选择性水解来合成顺式和反式β-氨基酸对映体。当南极假丝酵母脂肪酶B在65℃下于异丙醚中与水(0.5当量)进行催化反应时,观察到了高对映选择性(E通常>100)。以良好的产率(≥42%)获得的拆分产物能够很容易地分离出来。

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