SIGNIFICANT ENANTIOSELECTIVITY IN ALANINE ESTER HYDROLYSIS CATALYZED BY IMIDAZOLE ATTACHED BETA-CYCLODEXTRINS

被引：17
作者：
HAMASAKI, K
UENO, A
机构：
来源：
CHEMISTRY LETTERS | 1995年 / 09期
关键词：
D O I：
10.1246/cl.1995.859
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Imidazole-appended beta-cyclodextrins, 3-deoxy-3-imidazolyl-beta-cyclodextrin (3Im-beta CyD) and 6-deoxy-6-imidazolyl-beta-cyclodextrin (6Tm-beta CyD) were synthesized as substrate selective enzyme mimics. 6Im-beta CyD shows marked enantioselectivity in the hydrolysis of Boc-alanine beta-nitrophenyl ester rather than 3Im-beta CyD. This selectivity could be interpreted by transition stability theory.
引用
收藏
页码：859 / 860
页数：2
相关论文
共 15 条
[11]   IDENTIFICATION OF AN ISOPRENYLATED CYSTEINE METHYL-ESTER HYDROLASE ACTIVITY IN BOVINE ROD OUTER SEGMENT MEMBRANES [J].
TAN, EW ;
RANDO, RR .
BIOCHEMISTRY, 1992, 31 (24) :5572-5578
[12]   The stabilization of transition states by cyclodextrins and other catalysts [J].
Tee, OS .
ADVANCES IN PHYSICAL ORGANIC CHEMISTRY, VOL 29, 1994, 29 :1-85
[13]   SELECTIVE SULFONATION OF A SECONDARY HYDROXYL GROUP OF BETA-CYCLODEXTRIN [J].
UENO, A ;
BRESLOW, R .
TETRAHEDRON LETTERS, 1982, 23 (34) :3451-3454
[14]   MECHANISM OF CYCLOAMYLOSE-ACCELERATED CLEAVAGE OF PHENYL ESTERS [J].
VANETTEN, RL ;
CLOWES, GA ;
SEBASTIAN, JF ;
BENDER, ML .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (13) :3253-+
[15]   ACCELERATION OF PHENYL ESTER CLEAVAGE BY CYCLOAMYLOSES - A MODEL FOR ENZYMATIC SPECIFICITY [J].
VANETTEN, RL ;
SEBASTIAN, JF ;
CLOWES, GA ;
BENDER, ML .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (13) :3242-+
12