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Synthesis of Structures Corresponding to the Capsular Polysaccharide of Neisseria meningitidis Group A
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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2005 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 3, no 20Article in journal (Refereed) Published
Abstract [en]





Four differently substituted trimers of the CPS repeating unit have been synthesised in order to investigate the

dependence on oligosaccharide size, acetylation and mode of phosphorylation of glycoconjugate vaccines against

Neisseria meningitidis


group A. A spacer-containing starting monomer, a H-phosphonate elongating monomer and a




-phosphorylated H-phosphonate cap monomer have been synthesised and coupled together to afford, after

deprotection, the target trimer structures differing in their acetylation and phosphorylation substitution


Place, publisher, year, edition, pages
Royal Society of Chemistry , 2005. Vol. 3, no 20
National Category
Biochemistry and Molecular Biology
URN: urn:nbn:se:su:diva-23911DOI: 10.1039/B507898AOAI: diva2:195287
Part of urn:nbn:se:su:diva-545Available from: 2005-05-19 Created: 2005-05-19 Last updated: 2010-10-27Bibliographically approved
In thesis
1. Synthesis of oligosaccharides related to the capsular polysaccharide of Neisseria meningitidis serotype A
Open this publication in new window or tab >>Synthesis of oligosaccharides related to the capsular polysaccharide of Neisseria meningitidis serotype A
2005 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

In order to find suitable stable vaccine candidates against Neisseria meningitidis group A, several structures related to the capsular polysaccharide have been synthesised. The first part of the thesis describes the synthesis of C-phosphonate analogues starting from glucose. The key step is a Mitsunobu coupling of a methyl C-phosphonate monomer to the 6-hydroxyl group of a 2-acetamido mannose derivative. Contained within this work is a description of an improved synthesis of 2-azido-2-deoxy-D-mannopyranose. The second part outlines the synthesis of structural elements present in the native capsular polysaccharide of Neisseria meningitidis serotype A including different acetylation and phosphorylation patterns. The final chapter describes an improved synthesis of the Lewis b hexasaccharide needed for purification of and interaction studies with the Helicobacter pylori adhesin BabA.

Place, publisher, year, edition, pages
Stockholm: Institutionen för organisk kemi, 2005. 40 p.
National Category
Organic Chemistry
urn:nbn:se:su:diva-545 (URN)91-7155-091-7 (ISBN)
Public defence
2005-06-10, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 10:00
Available from: 2005-05-19 Created: 2005-05-19Bibliographically approved

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