制备用于诊断目的的曼氏血吸虫循环阳极抗原的含间隔基二糖、三糖和四糖片段。

Preparation of spacer-containing di-, tri-, and tetrasaccharide fragments of the circulating anodic antigen of Schistosoma mansoni for diagnostic purposes.

作者信息

Halkes K M, Vermeer H J, Slaghek T M, van Hooft P A, Loof A, Kamerling J P, Vliegenthart J F

机构信息

Bijvoet Center, Department of Bio-Organic Chemistry, Utrecht University, The Netherlands.

出版信息

Carbohydr Res. 1998 Jun;309(2):175-88. doi: 10.1016/s0008-6215(98)00125-6.

DOI:10.1016/s0008-6215(98)00125-6

PMID:9741076

Abstract

The chemical synthesis of beta-D-GlcpA-(1-->3)-beta-D-GalpNAc-(1-->O)CH2CH = CH2, beta-D-Galp-NAc-(1-->6)-[beta-D-GlcpA-(1-->3)]-beta-D-GalpNAc-(1-- >O)CH2CH = CH2, and beta-D-GlcpA-(1-->3)-beta-D-GalpNAc-(1-->6)-[beta-D-GlcpA-(1 -->3)] -beta-D-GalpNAc-(1-->O)CH2CH = CH2 is described. These oligosaccharides represent fragments of th circulating anodic antigen, secreted by the parasite Schistosoma mansoni in the circulatory system of the host. The applied synthesis strategy includes the preparation of a non-oxidised backbone oligosaccharide, with a levulinoyl group at O-6 of the beta-D-glucose residue. After the selective removal of the levulinoyl group, the obtained hydroxyl functions were converted into carboxyl groups, using pyridinium dichromate and acetic anhydride in dichloromethane, to afford the desired glucuronic-acid-containing oligosaccharides. Subsequently, the allyl glycosides have been elongated with cysteamine to give the corresponding amine-spacer-containing oligosaccharides.

摘要

本文描述了β-D-葡萄糖醛酸-(1→3)-β-D-乙酰半乳糖胺-(1→O)CH₂CH = CH₂、β-D-乙酰半乳糖胺-(1→6)-[β-D-葡萄糖醛酸-(1→3)]-β-D-乙酰半乳糖胺-(1→O)CH₂CH = CH₂以及β-D-葡萄糖醛酸-(1→3)-β-D-乙酰半乳糖胺-(1→6)-[β-D-葡萄糖醛酸-(1→3)]-β-D-乙酰半乳糖胺-(1→O)CH₂CH = CH₂的化学合成。这些寡糖代表了曼氏血吸虫在宿主体循环系统中分泌的循环阳极抗原的片段。所应用的合成策略包括制备一种非氧化的主链寡糖，其β-D-葡萄糖残基的O-6位带有乙酰丙酸酯基团。在选择性去除乙酰丙酸酯基团后，使用二氯甲烷中的重铬酸吡啶鎓和乙酸酐将所得的羟基官能团转化为羧基，以得到所需的含葡萄糖醛酸的寡糖。随后，烯丙基糖苷用半胱胺进行延长，得到相应的含胺间隔基的寡糖。