N-acetylhexosaminidase inhibitory properties of C-1 homologated GlcNAc- and GalNAc-thiazolines

被引：18

作者：

Amorelli, Benjamin ^{[1
]}

Yang, Chunhua ^{[1
]}

Rempel, Brian ^{[2
]}

Withers, Stephen G. ^{[2
]}

Knapp, Spencer ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA

[2] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2008年 / 18卷 / 09期

关键词：

glycosidase; O-GlcNAcase; Streptomyces plicatus; pyranose conformation; transition state mimic;

D O I：

10.1016/j.bmcl.2008.03.067

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Several C-1 homologated GlcNAc-and GalNAc-thiazolines, as well as a related GalNAc-thiazole, have been prepared. The compounds are analogues of GlcNAc-thiazoline, a potent transition-state-mimicking inhibitor of retaining beta-N-acetylglycosaminidases. Kinetic evaluation of these fused pyranose-heterocycles against the bacterial N-acetylhexosaminidase SpHex suggests active site steric restrictions around the substrate anomeric carbon. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：2944 / 2947

页数：4

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