Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Synthesis of the Lewis b hexasaccharide and HSA-conjugates thereof
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Show others and affiliations
2004 (English)In: Glycoconjugate Journal, ISSN 0282-0080, E-ISSN 1573-4986, Vol. 21, no 5, 251-256 p.Article in journal (Refereed) Published
Place, publisher, year, edition, pages
2004. Vol. 21, no 5, 251-256 p.
Identifiers
URN: urn:nbn:se:su:diva-23912DOI: 10.1023/B:GLYC.0000045097.19353.73OAI: oai:DiVA.org:su-23912DiVA: diva2:195288
Available from: 2005-05-19 Created: 2005-05-19 Last updated: 2017-12-13Bibliographically 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
Identifiers
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
Opponent
Supervisors
Available from: 2005-05-19 Created: 2005-05-19Bibliographically approved
2. Synthesis of biologically active oligosaccharides of the Lewis b family and investigations towards the synthesis of glycoclusters
Open this publication in new window or tab >>Synthesis of biologically active oligosaccharides of the Lewis b family and investigations towards the synthesis of glycoclusters
2009 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The gastric pathogen Helicobacter pylori is a Gram negative bacterium which may cause diseases such as peptic ulceration and gastric adenocarcinoma. It colonises a host by attaching to the gastric epithelial cells, an attachment mediated by outer membrane proteins on the bacterial surface, e.g, the blood group antigen binding adhesin, BabA. This adhesin recognises and binds to specific carbohydrates, Lewis blood group antigens, on the epithelial cell walls.

This thesis presents the synthesis of three oligosaccharides of the Lewis family. A new and improved block synthesis of a Leb hexasaccharide and synthesis of HSA-conjugates thereof are described. Also presented are the syntheses of a Leb pentasaccharide and a B-Leb heptasaccharide via linear routes. The latter strategy is designed to enable the synthesis of other Lewis blood group antigens by only minor changes in protection patterns.

Investigations have been made towards finding a route for the synthesis of glycoclusters using of unprotected carbohydrates. The biologically active dendrimers will be used in examinations of binding to galectin-3, an important animal lectin abundant in nature.

The thesis also includes an efficient synthesis of an oxazolidinone protected thioethyl LacNAc disaccharide, and its ability as a donor has been examined.

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2009. 58 p.
Keyword
Carbohydrates, Lewis b, lactosamine, dendrimers, oxazolidinone
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-26684 (URN)978-91-628-7780-4 (ISBN)
Public defence
2009-05-08, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 10:00 (English)
Opponent
Supervisors
Available from: 2009-04-17 Created: 2009-04-07 Last updated: 2009-04-15Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full text
By organisation
Department of Organic Chemistry
In the same journal
Glycoconjugate Journal

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 76 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf