Pozsgay V, Glaudemans C P, Robbins J B, Schneerson R
Laboratory of Developmental and Molecular Immunity, National Institute of Child Health and Human Development, Bethesda, MD 20892.
Carbohydr Res. 1993 Jun 21;244(2):259-73. doi: 10.1016/0008-6215(83)85006-x.
O-(2,4-Di-O-benzoyl-3-O-chloroacetyl-alpha-L-rhamnopyranosyl)-(1--> 2)-O-(3,4,6-tri-O-benzoyl-alpha-D-galactopyranosyl)-(1--> 3)-O-(2-acetamido-4,6-di-O-acetyl-2-deoxy-alpha-D-glucopyranosyl)-(1--> 3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranosyl trichloroacetimidate (1) was synthesized in a stepwise manner, using the following monosaccharide units: 2-(trimethylsilyl)ethyl 2,4-di-O-benzoyl-alpha-L-rhamnopyranoside, 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-beta-D-glucopyranosyl chloride, methyl 3,4,6-tri-O-benzoyl-2-O -(4-methoxybenzyl)-1-thio-beta-D-galactopyranoside, and 2,4-di-O-benzoyl-3-O-chloroacetyl-alpha-L-rhamnopyranosyl chloride. Compound 1 corresponds to a complete tetrasaccharide repeating unit of the O-specific polysaccharide of the lipopolysaccharide of Shigella dysenteriae type 1.
O-(2,4-二-O-苯甲酰基-3-O-氯乙酰基-α-L-鼠李吡喃糖基)-(1→2)-O-(3,4,6-三-O-苯甲酰基-α-D-吡喃半乳糖基)-(1→3)-O-(2-乙酰氨基-4,6-二-O-乙酰基-2-脱氧-α-D-吡喃葡萄糖基)-(1→3)-2,4-二-O-苯甲酰基-α-L-鼠李吡喃糖基三氯乙酰亚胺酯(1)通过逐步合成法制备，使用了以下单糖单元：2-(三甲基硅基)乙基2,4-二-O-苯甲酰基-α-L-鼠李吡喃糖苷、2-叠氮基-4,6-O-亚苄基-3-O-氯乙酰基-2-脱氧-β-D-吡喃葡萄糖基氯、3,4,6-三-O-苯甲酰基-2-O-(4-甲氧基苄基)-1-硫代-β-D-吡喃半乳糖苷甲酯以及2,4-二-O-苯甲酰基-3-O-氯乙酰基-α-L-鼠李吡喃糖基氯。化合物1对应于痢疾志贺氏菌1型脂多糖O-特异性多糖的完整四糖重复单元。
