一种与肿瘤相关糖脂相对应的二聚岩藻糖基乳糖六糖衍生物的合成。

Synthesis of a dimeric Lewis X hexasaccharide derivative corresponding to a tumor-associated glycolipid.

作者信息

Nilsson M, Norberg T

机构信息

Department of Organic Chemistry, Arrhenius Laboratory, University of Stockholm, Sweden.

出版信息

Carbohydr Res. 1988 Nov 15;183(1):71-82. doi: 10.1016/0008-6215(88)80046-6.

DOI:10.1016/0008-6215(88)80046-6

PMID:3233598

Abstract

The dimeric Lewis X hexasaccharide p-trifluoroacetamidophenylethyl O-beta-D-galactopyranosyl-(1----4)-O-[alpha-L-fucopyranosyl-(1----3)]-O- (2- acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----3)-O-beta-D-galactopyrano syl- (1----4)-O-[alpha-L-fucopyranosyl-(1----3)]-2-acetamido-2-deoxy-beta-D- glucopyranoside (14), which is a derivative of a tumor-associated glycolipid, was synthesized from thioglycoside intermediates. A protected disaccharide was used as a key-intermediate for synthesis of the p-nitrophenylethyl glycoside of suitably protected O-beta-D-Galp-(1----4)-O-beta-D-GlcpN-(1----3)-O-beta-D-Galp-(1--- -4)-beta-D- GlcpN, which, after selective deblocking, was di-L-fucosylated and deprotected to give 14.

摘要

二聚体Lewis X六糖对三氟乙酰氨基苯乙基O-β-D-吡喃半乳糖基-(1→4)-O-[α-L-吡喃岩藻糖基-(1→3)]-O-(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基)-(1→3)-O-β-D-吡喃半乳糖基-(1→4)-O-[α-L-吡喃岩藻糖基-(1→3)]-2-乙酰氨基-2-脱氧-β-D-葡萄糖苷(14)，它是一种肿瘤相关糖脂的衍生物，由硫代糖苷中间体合成。一种受保护的二糖被用作关键中间体，用于合成适当保护的O-β-D-吡喃半乳糖基-(1→4)-O-β-D-吡喃葡萄糖胺基-(1→3)-O-β-D-吡喃半乳糖基-(1→4)-β-D-吡喃葡萄糖胺的对硝基苯乙基糖苷，该糖苷在选择性脱保护后进行双-L-岩藻糖基化并脱保护得到14。