Syntheses of β-D-GalpNAc4SO3-(1→4)-L-IdopA2SO3, a disaccharide fragment of dermatan sulfate, and of its methyl α-L-glycoside derivative

被引：25

作者：

Barroca, N ^{[1
]}

Jacquinet, JC ^{[1
]}

机构：

[1] Univ Orleans, UFR Fac Sci, UPRES A CNRS 6005, Inst Chim Organ & Analyt, F-45067 Orleans, France

来源：

CARBOHYDRATE RESEARCH | 2000年 / 329卷 / 03期

关键词：

glycosylation reactions; 2-deoxy-2-trichloroacetamido-D-galacto derivatives; Dermatan sulfate disaccharides;

D O I：

10.1016/S0008-6215(00)00234-2

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：

The syntheses of sodium (sodium 2-acetamido-2-deoxy-4-O-sulfonato-beta -D-galactopyranosyl)-(1 --> 4)-(sodium 2-O-sulfonato-L-idopyran)uronate, a disaccharide fragment of dermatan sulfate, and of its methyl alpha -L-glycoside derivative are reported for the first time. The use of 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl-alpha -D-galactopyranose, readily prepared from a D-gluco precursor, allowed the stereocontrolled and high yielding coupling with the low reactive 4-hydroxyl group of L-iduronic acid ester derivatives. Classical transformation of the disaccharide products into the target molecules was achieved in high yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：667 / 679

页数：13

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