Synthesis of the pentasaccharide related to the repeating unit of the antigen from Shigella dysenteriae type 4 in the form of its methyl ester 2-(trimethylsilyl)ethyl glycoside

被引：17
作者：
Mukhopadhyay, B [1 ]
Roy, N [1 ]
机构：
[1] Indian Assoc Cultivat Sci, Dept Biol Chem, Kolkata 700032, W Bengal, India
来源：
CARBOHYDRATE RESEARCH | 2003年 / 338卷 / 07期
关键词：
synthesis; pentasaccharide repeating unit; Shigella dysenteriae type 4; O-SPECIFIC POLYSACCHARIDE; FLEXNERI SEROTYPE 5A; Y-POLYSACCHARIDE; LINEAR SYNTHESIS; SIDE-CHAIN; FRAGMENT; PART; 2A; LIPOPOLYSACCHARIDE; TETRA;
D O I：
10.1016/S0008-6215(02)00499-8
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Starting from D-mannose, D-glucose and L-fucose, the pentasaccharide derivative methyl 2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl-(1 --> 3)-2-O-acetyl-4,6-O-benzyiidene-alpha-D-mannopyranosyl-(1 --> 3)-2-O-acetyl-6-O-benzyl-4-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-alpha-D-mannopyranosyi-(1 --> 4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-beta-D-glucopyraiiosid]uronate was synthesized. This compound with two alpha-mannopyranosyl units was transformed, via Walden inversion and subsequent deprotection, into the U-D-glucosamine-type target compound, namely methyl alpha-L-fucopyranosyl-(1 --> 3 )-2-acetamido-2-deoxy-alpha-D-glucopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-4-O-(alpha-L-fucopyranosyl)-alpha-D-glucopyranosyl-(1 --> 4)-[2-(trimethylsilyl)ethyl beta-D-glucopyranosid]uronate which is related to the repeating unit of the O-antigen from Shigella dysenteriae type 4. (C) 2003 Elsevier Science Ltd. All rights reserved.
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页码：589 / 596
页数：8
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