Diversity of C-linked neoglycopeptides for the exploration of subsite-assisted carbohydrate binding interactions

被引：28

作者：

Arya, P

Kutterer, KMK

Qin, HP

Roby, J

Barnes, ML

Kim, JM

Roy, R

机构：

[1] Natl Res Council Canada, Steacie Inst Mol Sci, Ottawa, ON K1A 0R6, Canada

[2] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1998年 / 8卷 / 10期

关键词：

D O I：

10.1016/S0960-894X(98)00182-6

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Diversity of alpha-galactose based C-linked neoglycopeptides (1b, 2b, 3c, 4d, and 5d) has been developed to explore the importance of subsite-assisted carbohydrate binding interactions. Deprotected C-linked neoglycopeptides (1b, 2b, 3c, 4d, and 5d) were synthesized and tested in competitive inhibition assays using a model enzyme-linked lectin (e.g., Maclura pomifera). Compound 2b, with two alpha-galactoside units on the side chain of the lysine residue of the dipeptide backbone, exhibited a remarkable effect with a 2.82-fold increase in its inhibitory properties (IC50 1.48 mM) in comparison to 1b (IC50 4.18 mM). (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1127 / 1132

页数：6

共 30 条

[1] Stereoselective synthesis of NEO-C-glycopeptide building blocks: Towards a flexible and control-oriented design as probes for carbohydrate-protein interactions [J].