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Synthesis of Bacterial Oligosaccharides from N. meningitidis and Mechanistic Details of Stereoselective Glycosylations Using a Novel Bicyclic Donor
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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 [en]
oligosaccharide synthesis, heptose, thioglycoside, glycosylation, Neisseria meningitidis, 2, 3-oxazolidinone
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-29568ISBN: 978-91-7155-919-7 (print)OAI: oai:DiVA.org:su-29568DiVA: diva2:234190
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
List of papers
1. Synthesis of 3,4-branched phosphorylated trisaccharides corresponding to LPS inner core structure of Neisseria meningitidis and Haemophilius influenzae
Open this publication in new window or tab >>Synthesis of 3,4-branched phosphorylated trisaccharides corresponding to LPS inner core structure of Neisseria meningitidis and Haemophilius influenzae
(English)Manuscript (preprint) (Other academic)
Identifiers
urn:nbn:se:su:diva-29566 (URN)
Available from: 2009-09-06 Created: 2009-09-06 Last updated: 2010-01-25Bibliographically approved
2. Synthesis of phosphorylated Neisseria meningitidis inner core lipopolysaccharide structures
Open this publication in new window or tab >>Synthesis of phosphorylated Neisseria meningitidis inner core lipopolysaccharide structures
2009 (English)In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 20, no 6/8, 879-886 p.Article in journal (Refereed) Published
Identifiers
urn:nbn:se:su:diva-29565 (URN)10.1016/j.tetasy.2009.02.017 (DOI)
Available from: 2009-07-22 Created: 2009-07-22 Last updated: 2017-12-13Bibliographically approved
3. Synthesis of and molecular dynamics simulations on a tetrasaccharide corresponding to the repeating unit of the capsular polysaccharide from Salmonella enteritidis
Open this publication in new window or tab >>Synthesis of and molecular dynamics simulations on a tetrasaccharide corresponding to the repeating unit of the capsular polysaccharide from Salmonella enteritidis
Show others...
2009 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 7, no 8, 1612-1618 p.Article in journal (Refereed) Published
Identifiers
urn:nbn:se:su:diva-28937 (URN)10.1039/b823428k (DOI)000265195100014 ()
Available from: 2009-07-22 Created: 2009-07-22 Last updated: 2017-12-13Bibliographically approved
4. Investigations of glycosylation reactions with 2-N-acetyl-2N,3O-oxazolidinone-protected glucosamine donors
Open this publication in new window or tab >>Investigations of glycosylation reactions with 2-N-acetyl-2N,3O-oxazolidinone-protected glucosamine donors
2008 (English)In: The Journal of Organic Chemistry, ISSN 0022-3263, Vol. 73, no 18, 7181-7188 p.Article in journal (Refereed) Published
Identifiers
urn:nbn:se:su:diva-15484 (URN)10.1021/jo800971s (DOI)000259195200030 ()
Available from: 2009-01-02 Created: 2009-01-02 Last updated: 2010-01-25Bibliographically approved
5. Synthesis of serine substituted 2-N-acetyl 2N,3O-oxazolidinone galactosamine, a key building block for O-glycan synthesis
Open this publication in new window or tab >>Synthesis of serine substituted 2-N-acetyl 2N,3O-oxazolidinone galactosamine, a key building block for O-glycan synthesis
(English)Manuscript (preprint) (Other academic)
Identifiers
urn:nbn:se:su:diva-29567 (URN)
Available from: 2009-09-06 Created: 2009-09-06 Last updated: 2010-01-25Bibliographically approved

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