含有与肠杆菌脂多糖KDO区域相关的3-脱氧-D-甘露-2-辛酮糖酸残基的三糖的合成。

Synthesis of trisaccharides containing 3-deoxy-D-manno-2-octulosonic acid residues related to the KDO-region of enterobacterial lipopolysaccharides.

作者信息

Kosma P, Schulz G, Unger F M, Brade H

机构信息

Institut für Chemie der Universität für Bodenkultur Wien, Vienna, Austria.

出版信息

Carbohydr Res. 1989 Jul 15;190(2):191-201. doi: 10.1016/0008-6215(89)84125-4.

DOI:10.1016/0008-6215(89)84125-4

PMID:2805008

Abstract

Glycosylation of methyl (allyl 7,8-O-carbonyl-3-deoxy-alpha-D-manno-2-octulo-pyranosid)o nate with an alpha-(2----4) linked per-O-acetylated KDO-disaccharide bromide derivative under Helferich conditions afforded a 2:1 mixture of the alpha- and beta-linked trisaccharide derivatives in 50% yield. Removal of the protecting groups gave sodium O-[sodium (3-deoxy-alpha-D-manno-2-octulopyranosyl)onate]-(2----4)-O-[ sodium (3-deoxy-alpha- and -beta-D-manno-2-octulopyranosyl)onate]-(2----4)-sodium (allyl 3-deoxy-alpha-D-manno-2-octulopyranosid)onate. Radical copolymerization of the allyl glycosides afforded artificial antigens, suitable for defining antibody specificities directed against the KDO-region of enterobacterial lipopolysaccharides.

摘要

在Helferich条件下，将甲基（烯丙基7,8-O-羰基-3-脱氧-α-D-甘露-2-辛酮糖酸酯）与α-(2→4)连接的全-O-乙酰化KDO-二糖溴化物衍生物进行糖基化反应，以50%的产率得到α-和β-连接的三糖衍生物的2:1混合物。去除保护基后得到O-[钠（3-脱氧-α-D-甘露-2-辛酮糖基）酸酯]-(2→4)-O-[钠（3-脱氧-α-和-β-D-甘露-2-辛酮糖基）酸酯]-(2→4)-钠（烯丙基3-脱氧-α-D-甘露-2-辛酮糖酸酯）。烯丙基糖苷的自由基共聚合得到了人工抗原，适用于确定针对肠杆菌脂多糖KDO区域的抗体特异性。