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  • 1.
    Alpe, Marianne
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of oligosaccharides related to the capsular polysaccharides of Streptococcus pneumoniae serotype 9 and of Cryptococcus neoformans2003Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    In the present investigation, synthesis of oligosaccharides corresponding to structural elements present in the capsular polysaccharides of Streptococcus pneumoniae and Cryptococcus neoformans has been achieved. The first two sections describe the synthesis of spacer-equipped oligosaccharides corresponding to structures from the CPS of Streptococcus pneumoniae serotypes 9N, 9A and 9L, the production of which involved synthetic challenges such as the construction of β-ManNAc and α-GlcA linkages. The former challenge was met by employing azide displacement of a 2-O-triflate substituent on a β-glucoside, whereas the latter task was accomplished utilizing thioethyl glucuronic acid donors in the presence of various promoters. The pentasaccharide product obtained correspond to the complete repeating unit of the CPS of serotype 9A.

    The last two sections of this thesis describe the construction of thioglycoside di- and trisaccharide building blocks containing α-Man, β-Xyl, β-GlcA and 6-O-acetyl motifs, as well as subsequent assembly of these building blocks into oligosaccharides corresponding to the repeating units of the capsular polysaccharide of the yeast Cryptococcus neoformans. The GlcA moiety was introduced via trichloroacetimidate coupling involving the peracetylated glucuronic acid methyl ester donor, after which the subsequent necessary benzylation was performed with the di- and trisaccharides. All of the target oligosaccharides were synthesized as amino-spacer glycosides in order to make conjugation to a carrier protein possible.

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