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.

引用

页码：2629 / 2651

页数：23

共 19 条

[1] DECLINE OF CHILDHOOD HAEMOPHILUS-INFLUENZAE TYPE-B (HIB) DISEASE IN THE HIB VACCINE ERA [J].