Enantioselective synthesis of amino acid amides via enzymatic ammoniolysis of amino acid esters

被引：36

作者：

Hacking, MAPJ ^{[1
]}

Wegman, MA ^{[1
]}

Rops, J ^{[1
]}

van Rantwijk, F ^{[1
]}

Sheldon, RA ^{[1
]}

机构：

[1] Delft Univ Technol, Organ Chem & Catalysis Lab, NL-2628 BL Delft, Netherlands

来源：

JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC | 1998年 / 5卷 / 1-4期

关键词：

ammoniolysis; deracemisation; Candida antarctica; lipase; D-phenylglycine amide; dynamic kinetic resolution;

D O I：

10.1016/S1381-1177(98)00025-3

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Ammoniolysis of D,L-phenylglycine methyl ester catalysed by Candida antarctica B lipase (Novozym 435) gave D-phenylglycine amide with 78% ee at 47% conversion. The combination of this reaction with racemisation of the unconverted ester in a single step was investigated. Pyridoxal and salicylaldehyde efficiently catalysed the racemisation of the ester. Because the solubility of the amide was law under the reactions conditions, its racemisation was slow. Ln-process racemisation of the reactant gave D-phenylglycine amide with 73% ee at 85% conversion. (C) 1998 Elsevier Science B.V. All rights reserved.

引用

页码：155 / 157

页数：3