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 3,4-branched phosphorylated trisaccharides corresponding to LPS inner core structure of Neisseria meningitidis and Haemophilius influenzae
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
(English)Manuscript (preprint) (Other academic)
Identifiers
URN: urn:nbn:se:su:diva-29566OAI: oai:DiVA.org:su-29566DiVA: diva2:234187
Available from: 2009-09-06 Created: 2009-09-06 Last updated: 2010-01-25Bibliographically approved
In thesis
1. Synthesis of Bacterial Oligosaccharides from N. meningitidis and Mechanistic Details of Stereoselective Glycosylations Using a Novel Bicyclic Donor
Open this publication in new window or tab >>Synthesis of Bacterial Oligosaccharides from N. meningitidis and Mechanistic Details of Stereoselective Glycosylations Using a Novel Bicyclic Donor
2009 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis includes two parts. The first part, comprising Chapters 3, 4 and 5, describes the synthesis of bacterial oligosaccharides. In Chapters 3 and 4, the synthesis of branched and phosphorylated oligosaccharide structures corresponding to inner core epitopes of the lipopolysaccharide (LPS) of the Gram-negative bacteria N. meningitidis are discussed. A series of different spacer-equipped, phosphorylated and non-phosphorylated, glycosides has been synthesized as a part of a program involving development of a glycoconjugate-based vaccine against meningitis. Chapter 5 describes the synthesis of a tetrasaccharide corresponding to the repeating unit of the extracellular capsular polysaccharide (CPS) found in S. enteritidis. A short and efficient synthetic route to a trisaccharide acceptor corresponding to the common Gal-Man-Rha backbone found in several Salmonella O-antigen is presented. Further more, the synthesis of a novel tyveloside thioglycoside and the final glycosylation to assemble the complete target tetrasaccharide is reported.

The second part, Chapters 6 and 7, describes the development of a novel type of glycosyl donor, a 2N,3O-oxazolidinone protected bicyclic thioglycoside. This donor can be used in stereoselective glycosylations where, by tuning the reaction conditions, either complete α- or β-selectivity can be obtained from the same donor/acceptor system. A mechanistic explanation for this behaviour, involving initial formation of the β-anomer followed by a AgOTf-catalyzed in situ endocyclic anomerization to yield the more stable corresponding α-anomer, has been established. The suggested mechanism was supported by a series of NMR-experiments. Finally, in Chapter 7, the synthesis and use of a galacto-configured 2N,3O-oxazolidinone donor for the synthesis of a serine 2-acetamido 2-deoxy galactoside, a versatile building block for the synthesis of mucin O-glycan core structures, is discussed.

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2009. 76 p.
Keyword
oligosaccharide synthesis, heptose, thioglycoside, glycosylation, Neisseria meningitidis, 2, 3-oxazolidinone
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-29568 (URN)978-91-7155-919-7 (ISBN)
Public defence
2009-10-09, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12, Stockholm, 10:00 (English)
Opponent
Supervisors
Note
At the time of the doctoral defence, the following papers we unpublished and had a status as follows: Paper 1: Manuscript. Paper 5: ManuscriptAvailable from: 2009-09-18 Created: 2009-09-06 Last updated: 2009-09-08Bibliographically approved

Open Access in DiVA

No full text

Search in DiVA

By author/editor
Olsson, Johan
By organisation
Department of Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

urn-nbn

Altmetric score

urn-nbn
Total: 28 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