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Synthesis of oligosaccharides related to the capsular polysaccharide of Neisseria meningitidis serotype A
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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
Identifiers
URN: urn:nbn:se:su:diva-545ISBN: 91-7155-091-7 (print)OAI: oai:DiVA.org:su-545DiVA: diva2:195289
Public defence
2005-06-10, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 10:00
Opponent
Supervisors
Available from: 2005-05-19 Created: 2005-05-19Bibliographically approved
List of papers
1. Improved Synthesis of 1,3,4,6-tetra-O-acetyl-2-Azido-2-deoxy-α-D-mannopyranose
Open this publication in new window or tab >>Improved Synthesis of 1,3,4,6-tetra-O-acetyl-2-Azido-2-deoxy-α-D-mannopyranose
2005 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 340, no 17, 2675-2676 p.Article in journal (Refereed) Published
Abstract [en]

By improved (anhydrous) work-up conditions of a triflate displacement reaction, the yield in the preparation of the versatile synthetic intermediate 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-d-mannopyranose has been significantly enhanced. This important precursor is now available in three efficient steps from d-glucose.

Place, publisher, year, edition, pages
Elsevier Ltd, 2005
National Category
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-23909 (URN)10.1016/j.carres.2005.09.008 (DOI)
Note
Part of urn:nbn:se:su:diva-545Available from: 2005-05-19 Created: 2005-05-19 Last updated: 2010-11-02Bibliographically approved
2. Synthesis of C-Phosphonate Analogues of Neisseria meningitidis group A Capsular Polysaccharide Structures
Open this publication in new window or tab >>Synthesis of C-Phosphonate Analogues of Neisseria meningitidis group A Capsular Polysaccharide Structures
Manuscript (Other academic)
Identifiers
urn:nbn:se:su:diva-23910 (URN)
Note
Part of urn:nbn:se:su:diva-545Available from: 2005-05-19 Created: 2005-05-19 Last updated: 2010-01-13Bibliographically approved
3. Synthesis of Structures Corresponding to the Capsular Polysaccharide of Neisseria meningitidis Group A
Open this publication in new window or tab >>Synthesis of Structures Corresponding to the Capsular Polysaccharide of Neisseria meningitidis Group A
Show others...
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

6-

 

O

-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

pattern.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2005
National Category
Biochemistry and Molecular Biology
Identifiers
urn:nbn:se:su:diva-23911 (URN)10.1039/B507898A (DOI)
Note
Part of urn:nbn:se:su:diva-545Available from: 2005-05-19 Created: 2005-05-19 Last updated: 2010-10-27Bibliographically approved
4. Synthesis of the Lewis b hexasaccharide and HSA-conjugates thereof
Open this publication in new window or tab >>Synthesis of the Lewis b hexasaccharide and HSA-conjugates thereof
Show others...
2004 (English)In: Glycoconjugate Journal, ISSN 0282-0080, Vol. 21, no 5, 251-256 p.Article in journal (Refereed) Published
Identifiers
urn:nbn:se:su:diva-23912 (URN)10.1023/B:GLYC.0000045097.19353.73 (DOI)
Available from: 2005-05-19 Created: 2005-05-19 Last updated: 2009-04-15Bibliographically approved

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