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  • 1.
    Mannerstedt, Karin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Segerstedt, Eva
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olsson, Johan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Oscarson, Stefan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of a common tetrasaccharide motif of Haemophilus influenzae LPS inner core structures2008In: Organic & Biomolecular Chemistry, ISSN 1477-0520, Vol. 6, no 6, p. 1087-1091Article in journal (Refereed)
  • 2.
    Olsson, Johan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of Bacterial Oligosaccharides from N. meningitidis and Mechanistic Details of Stereoselective Glycosylations Using a Novel Bicyclic Donor2009Doctoral 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.

  • 3.
    Olsson, Johan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of oligosaccharides corresponding to the inner core LPS of Neisseria Meningitidis and mechanistic details in glycosylations using a novel bicyclic N-acetylglucosamine donor2007Licentiate thesis, comprehensive summary (Other academic)
  • 4.
    Olsson, Johan D. M.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Lahmann, Martina
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Oscarson, Stefan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Investigations of glycosylation reactions with 2-N-acetyl-2N,3O-oxazolidinone-protected glucosamine donors2008In: The Journal of Organic Chemistry, ISSN 0022-3263, Vol. 73, no 18, p. 7181-7188Article in journal (Refereed)
  • 5.
    Olsson, Johan D M
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Landström, Jens
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rönnols, Jerk
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Oscarson, Stefan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of and molecular dynamics simulations on a tetrasaccharide corresponding to the repeating unit of the capsular polysaccharide from Salmonella enteritidis2009In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 7, no 8, p. 1612-1618Article in journal (Refereed)
  • 6.
    Olsson, Johan D M
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Oscarson, Stefan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of phosphorylated Neisseria meningitidis inner core lipopolysaccharide structures2009In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 20, no 6/8, p. 879-886Article in journal (Refereed)
  • 7.
    Olsson, Johan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lahmann, Martina
    Oscarson, Stefan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of serine substituted 2-N-acetyl 2N,3O-oxazolidinone galactosamine, a key building block for O-glycan synthesisManuscript (preprint) (Other academic)
  • 8.
    Olsson, Johan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Oscarson, Stefan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of 3,4-branched phosphorylated trisaccharides corresponding to LPS inner core structure of Neisseria meningitidis and Haemophilius influenzaeManuscript (preprint) (Other academic)
1 - 8 of 8
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