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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页码：2629 / 2651

页数：23

相关论文

共 19 条

[11] Immunogenicity in a mouse model of a conjugate vaccine made with a synthetic single repeating unit of type 14 pneumococcal polysaccharide coupled to CRM197 [J].

Mawas, F ;

Niggemann, J ;

Jones, C ;

Corbel, MJ ;

Kamerling, JP ;

Vliegenthart, JFG .

INFECTION AND IMMUNITY, 2002, 70 (09) :5107-5114

[12] Chemoenzymic synthesis of oligosaccharide fragments of the capsular polysaccharide of Streptococcus pneumoniae type 14 [J].

Michalik, D ;

Vliegenthart, JFG ;

Kamerling, JP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (17) :1973-1981

[13] β-1,4-galactosyltransferase-catalyzed synthesis of the branched tetrasaccharide repeating unit of Streptococcus pneumoniae type 14 [J].

Niggemann, J ;

Kamerling, JP ;

Vliegenthart, JFG .

BIOORGANIC & MEDICINAL CHEMISTRY, 1998, 6 (09) :1605-1612

[14] Application of β-1,4-galactosyltransferase in the synthesis of complex branched-chain oligosaccharide mimics of fragments of the capsular polysaccharide of Streptococcus pneumoniae type 14 [J].

Niggemann, J ;

Kamerling, JP ;

Vliegenthart, JFG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (18) :3011-3020

[15] Randomised trial of 23-valent pneumococcal capsular polysaccharide vaccine in prevention of pneumonia in middle-aged and elderly people [J].

Örtqvist, Å ;

Hedlund, J ;

Burman, LÅ ;

Elbel, N ;

Höfer, M ;

Leinonen, M ;

Lindblad, I ;

Sundelöf, B ;

Kalin, M .

LANCET, 1998, 351 (9100) :399-403

[16] Safety and immunogenicity of heptavalent pneumococcal vaccine conjugated to CRM197 in United States infants [J].

Rennels, MB ;

Edwards, KM ;

Keyserling, HL ;

Reisinger, KS ;

Hogerman, DA ;

Madore, DV ;

Chang, I ;

Paradiso, PR ;

Malinoski, FJ ;

Kimura, A .

PEDIATRICS, 1998, 101 (04) :604-611

[17] Meningococcal serogroup C conjugate vaccine is immunogenic in infancy and primes for memory [J].

Richmond, P ;

Borrow, R ;

Miller, E ;

Clark, S ;

Sadler, F ;

Fox, A ;

Begg, N ;

Morris, R ;

Cartwright, K .

JOURNAL OF INFECTIOUS DISEASES, 1999, 179 (06) :1569-1572

[18] CONSIDERATIONS FOR FORMULATING THE 2ND-GENERATION PNEUMOCOCCAL CAPSULAR POLYSACCHARIDE VACCINE WITH EMPHASIS ON THE CROSS-REACTIVE TYPES WITHIN GROUPS [J].

ROBBINS, JB ;

AUSTRIAN, R ;

LEE, CJ ;

RASTOGI, SC ;

SCHIFFMAN, G ;

HENRICHSEN, J ;

MAKELA, PH ;

BROOME, CV ;

FACKLAM, RR ;

TIESJEMA, RH ;

PARKE, JC .

JOURNAL OF INFECTIOUS DISEASES, 1983, 148 (06) :1136-1159

[19] GLYCOSYLIMIDATES .8. SYNTHESIS OF 1-THIOGLYCOSIDES [J].

SCHMIDT, RR ;

STUMPP, M .

LIEBIGS ANNALEN DER CHEMIE, 1983, (07) :1249-1256