Hydrolytic metalloenzyme models -: Enantioselective hydrolysis of long chain α-amino acid esters by chiral metallomicelles composed of lipophilic L-histidinol

被引：54

作者：

You, JS ^{[1
]}

Yu, XQ ^{[1
]}

Su, XY ^{[1
]}

Wang, T ^{[1
]}

Xiang, QX ^{[1
]}

Yang, M ^{[1
]}

Xie, RG ^{[1
]}

机构：

[1] Sichuan Univ, Dept Chem, Sichuan Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2003年 / 202卷 / 1-2期

基金：

中国国家自然科学基金;

关键词：

enantioselective hydrolysis; alpha-amino acid esters; chiral metallomicelles; L-histidinol; synthesis;

D O I：

10.1016/S1381-1169(03)00199-7

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Chiral metallomicellar supramolecular systems composed of lipophilic L-histidinol have been investigated for their catalytic activities and enantioselectivities in the hydrolysis of N-protected alpha-amino acid esters. Kinetic evidence suggests that the mechanism of the deacylation promoted by ligand 4a with a hydroxyl group and 2a lacking a hydroxyl group is different. The apparent pK(a) of Zn2+ -4a is 6.8 in the micelllar aggregate. The highest enantioselectivity in hydrolysis of R(S)-C-12-Leu-PNP (k(S)/k(R) = 3.01) was obtained with 4a-Zn2+ as catalyst. (C) 2003 Elsevier Science B.V. All rights reserved.

引用

页码：17 / 22

页数：6

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