流感嗜血杆菌脂多糖中含L-甘油-D-甘露庚糖的寡糖结构的合成。

Synthesis of L-glycero-D-manno-heptopyranose-containing oligosaccharide structures found in lipopolysaccharides from Haemophilus influenzae.

作者信息

Bernlind C, Oscarson S

机构信息

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

出版信息

Carbohydr Res. 1997 Jan 17;297(3):251-60. doi: 10.1016/s0008-6215(96)00275-3.

DOI:10.1016/s0008-6215(96)00275-3

PMID:9060188

Abstract

Syntheses are described of the tetrasaccharide 2-(4-trifluoroacetamidophenyl)ethyl O-(beta-D-galactopyranosyl)-(1-->2)-O- (L-glycero-alpha-D-manno-heptopyranosyl)-(1-->2)-O-(L-glycero-alpha-D- manno-heptopyranosyl)-(1-->3)-L-glycero-alpha-D-manno-heptopyranoside (20) and the three trisaccharides 2-(4-trifluoroacetamidophenyl)ethyl O-(L-glycero-alpha-D-manno-heptopyranosyl)-(1-->2)-O-(L-glycero-alpha-D- manno-heptopyranosyl)-(1-->3)-L-glycero-alpha-D-manno-heptopyranoside (17), 2-(4-trifluoroacetamidophenyl)ethyl O-(beta-D-glucopyranosyl)-(1-->4)- O-(beta-D-glucopyranosyl)-(1-->4)-L-glycero-alpha-D-manno-heptopyrano side (5), and 2-(4-trifluoro-acetamidophenyl)ethyl O-(beta-D-galactopyranosyl)-(1-->4)-O-(beta-D-glucopyranosyl)-(1-->4)- L-glycero-alpha-D-manno-heptopyranoside (8), corresponding to structures found in the lipooligosaccharides of Haemophilus influenzae.

摘要

描述了四糖2-(4-三氟乙酰氨基苯基)乙基O-(β-D-吡喃半乳糖基)-(1→2)-O-(L-甘油-α-D-甘露庚吡喃糖基)-(1→2)-O-(L-甘油-α-D-甘露庚吡喃糖基)-(1→3)-L-甘油-α-D-甘露庚吡喃糖苷(20)以及三种三糖2-(4-三氟乙酰氨基苯基)乙基O-(L-甘油-α-D-甘露庚吡喃糖基)-(1→2)-O-(L-甘油-α-D-甘露庚吡喃糖基)-(1→3)-L-甘油-α-D-甘露庚吡喃糖苷(17)、2-(4-三氟乙酰氨基苯基)乙基O-(β-D-吡喃葡萄糖基)-(1→4)-O-(β-D-吡喃葡萄糖基)-(1→4)-L-甘油-α-D-甘露庚吡喃糖苷(5)和2-(4-三氟乙酰氨基苯基)乙基O-(β-D-吡喃半乳糖基)-(1→4)-O-(β-D-吡喃葡萄糖基)-(1→4)-L-甘油-α-D-甘露庚吡喃糖苷(8)的合成，它们与流感嗜血杆菌脂寡糖中发现的结构相对应。