Bundle D R, Josephson S
Carbohydr Res. 1980 Apr 1;80(1):75-85. doi: 10.1016/s0008-6215(00)85316-1.
The 8-methoxycarbonyloctyl glycoside of the tetrasaccharide hapten, O-alpha-L-rhamnopyranosyl-(1 leads to 2)-O-alpha-L-rhamnopyranosyl-(1 leads to 3)-O-alpha-L-rhamnopyranosyl-(1 leads to 3)-2-acetamido-2-deoxy-beta-D-glucopyranoside and the trisaccharide glycoside 8-methoxycarbonyloctyl O-alpha-L-rhamnopyranosyl-(1 leads to 3)-O-alpha-L-rhamnopyranosyl-(1 leads to 3)-2-acetamido-2-deoxy-beta-D-glucopyranoside were synthesized by sequential Koenigs-Knorr reactions from monosaccharide units. The tetrasaccharide represents the complete skeletal repeating unit of Shigella flexneri serogroup Y lipopolysaccharide. Both oligosaccharide haptens are functionalized for covalent attachment to proteins, cell surfaces, and solid supports. 1H-N.m.r. evidence for the conformations of these oligosaccharides in solution is presented and shown to be consistent with predictions based on the exo-anomeric effect.
四糖半抗原O-α-L-鼠李吡喃糖基-(1→2)-O-α-L-鼠李吡喃糖基-(1→3)-O-α-L-鼠李吡喃糖基-(1→3)-2-乙酰氨基-2-脱氧-β-D-葡萄糖苷的8-甲氧基羰基辛基糖苷以及三糖糖苷8-甲氧基羰基辛基O-α-L-鼠李吡喃糖基-(1→3)-O-α-L-鼠李吡喃糖基-(1→3)-2-乙酰氨基-2-脱氧-β-D-葡萄糖苷由单糖单元通过连续的柯尼希斯-克诺尔反应合成。该四糖代表福氏志贺菌Y血清群脂多糖的完整骨架重复单元。两种寡糖半抗原都经过功能化处理，可共价连接到蛋白质、细胞表面和固体支持物上。给出了这些寡糖在溶液中构象的¹H-N.m.r.证据，并表明其与基于端基异构效应的预测一致。
