Synthesis of 4-deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose and their effects on cellular glycosaminoglycan biosynthesis

被引：33

作者：

Berkin, A

Szarek, WA ^{[1
]}

Kisilevsky, R

机构：

[1] Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada

[2] Queens Univ, Dept Pathol, Kingston, ON K7L 3N6, Canada

[3] Queens Univ, Dept Biochem, Kingston, ON K7L 3N6, Canada

[4] Kingston Gen Hosp, Syl & Molly Apps Res Ctr, Kingston, ON K7L 3N6, Canada

来源：

CARBOHYDRATE RESEARCH | 2000年 / 326卷 / 04期

基金：

英国医学研究理事会; 加拿大自然科学与工程研究理事会;

关键词：

glycosaminoglycans; 2-acetamido-2,4-dideoxy-4-fluoro-D-glucopyranose derivatives; 2-acetamido-2,4-dideoxy-4-fluoro-D-galactopyranose derivatives;

D O I：

10.1016/S0008-6215(00)00049-5

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：

4-Deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose were synthesized and evaluated as inhibitors of hepatic glycosaminoglycan biosynthesis. 2-Acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-glucopyranose (16) exhibited a reduction of [H-3]GlcN and [S-35]SO4 incorporation into hepatocyte cellular glycosaminoglycans to 12 and 18%, respectively, of the control cells, at 1.0 mM. Similarly, 2-acetamido-1,3,6-tri-O-acetyl-2,4-dideoxy-4-fluoro-D-gala (31) exhibited a reduction of [H-3]GlcN and [S-35]SO4 incorporation to 1 and 9%. respectively, of the control cells, at 1.0 mM. Unlike 16, 31 exhibited a reduction of [C-14]Leu incorporation into cellular protein to 57% of control cells, at 1.0 mM. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：250 / 263

页数：14

共 41 条

[1] 2-CHLORO-2-DEOXY-D-GLUCOSE AND 2,2-DICHLORO-2-DEOXY-D-ARABINO-HEXOSE [J].