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 16 条

[1] Chemo-enzymatic synthesis of a tetra- and octasaccharide fragment of the capsular polysaccharide of Streptococcus pneumoniae type 14
Joosten, JAF
Kamerling, JP
Vliegenthart, JFG
CARBOHYDRATE RESEARCH, 2003, 338 (23) : 2611 - 2627
[2] Synthesis of a hexasaccharide fragment of the capsular polysaccharide of Streptococcus pneumoniae type 3
Lefeber, DJ
Arévalo, EA
Kamerling, JP
Vliegenthart, JFG
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2002, 80 (01): : 76 - 81
[3] Expeditious Synthesis of the Hexasaccharide Repeating Unit of the Capsular Polysaccharide of Streptococcus pneumoniae Type 7A
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[4] Block synthesis of Streptococcus pneumoniae type 14 capsular polysaccharide structures
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[5] Synthesis of tetra- and pentasaccharides corresponding to the capsular polysaccharide of Streptococcus pneumoniae type 9A&L, 9N and 9A
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CARBOHYDRATE RESEARCH, 1999, 319 (1-4) : 1 - 16
[7] Synthesis of oligosaccharides corresponding to Streptococcus pneumoniae type 9 capsular polysaccharide structures
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Oscarson, S
CARBOHYDRATE RESEARCH, 2002, 337 (19) : 1715 - 1722
[8] Capsular polysaccharide of Streptococcus pneumoniae type 19F:: synthesis of the repeating unit
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Russo, G
CARBOHYDRATE RESEARCH, 1998, 311 (04) : 171 - 181
[9] Structure-Reactivity Relationships of Conformationally Armed Disaccharide Donors and Their Use in the Synthesis of a Hexasaccharide Related to the Capsular Polysaccharide from Streptococcus pneumoniae Type 37
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Hamark, Christoffer
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JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (15) : 8123 - 8140
[10] Facile synthesis of a pentasaccharide mimic of a fragment of the capsular polysaccharide of Streptococcus pneumoniae type 15C
Chen Yong-Xiang
Zhao Wei
Zhao Lei
Zhao Yu-Fen
Li Yan-Mei
CARBOHYDRATE RESEARCH, 2008, 343 (04) : 607 - 614

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