Chemo-enzymatic synthesis of tetra-, penta-, and hexasaccharide fragments of the capsular polysaccharide of Streptococcus pneumoniae type 14

被引：12
|
作者：
Joosten, JAF [1 ]
Lazet, BJ [1 ]
Kamerling, JP [1 ]
Vliegenthart, JFG [1 ]
机构：
[1] Univ Utrecht, Bijvoet Ctr, Dept Bioorgan Chem, Sect Glycosci & Biocatalysis, NL-3584 CH Utrecht, Netherlands
来源：
CARBOHYDRATE RESEARCH | 2003年 / 338卷 / 23期
关键词：
carbohydrates; Streptococcus pneumoniae; oligosaccharide synthesis;
D O I：
10.1016/S0008-6215(03)00292-1
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：
The chemo-enzymatic synthesis is described of beta-D-Glcp-(1-->6)-[beta-D-Galp-(1-->4)]-beta-D-Glcp NAc-(1-->3)-beta-D-Galp-(1--> O(CH2)(6)NH2 (1), beta-D-Glcp-(1-->6)-[beta-D-Galp-(1-->4)-beta-D-Glcp NAc-(1-->3)-beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->O(CH2)(6)NH2 (2), beta-D-Galp-(1 -->4)-beta-D-Glcp NAc-(1-->3)-beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->O(CH2)(6)NH2 (3), and beta-D-Galp-(1-->4)-beta-D-Glcp NAc-(1--> 3)-beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->6)-[beta-D-Galp-(1-->4)-beta-D-Glcp NAc-(1-->O(CH2)(6)NH2 (4), representing fragments of the repeating unit of the Streptococcuspneumoniae serotype 14 capsular polysaccharide. Linear intermediate oligosaccharides 5-8 were synthesized via chemical synthesis, followed by enzymatic galactosylation using bovine milk beta-1,4-galactosyltransferase as a catalyst. The title oligosaccharides form suitable compounds for conjugation with carrier proteins, to be tested as potential vaccines in animal models. (C) 2003 Elsevier Ltd. All rights reserved.
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收藏
页码：2629 / 2651
页数：23
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