Synthesis and conformational analysis of phosphorylated β-(1→2) linked mannosides

Jani Rahkila, Filip S. Ekholm, Rajib Panchadhayee, Ana Ardá, Francisco Javier Cañada, Jesús Jiménez-Barbero, Reko Leino

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    Abstract

    Phosphorylated β-(1→2)-oligomannosides are found on the cell surface of several Candida species, including Candida albicans (an opportunistic pathogen). These molecules are believed to take part in the invasion process of fungal infections, which in the case of C. albicans can lead to severe bloodstream infections and death, and can therefore be considered important from a biological standpoint. Understanding the mechanism of their action requires access to the corresponding oligosaccharide model compounds in pure form. In the present work, synthesis of the model core structures involved in the invasion process of C. albicans, consisting of phosphorylated β-(1→2)-linked mannotriose and tetraose, is reported. In order to elucidate the nature of these molecules in more detail, an extensive NMR-spectroscopic study encompassing complete spectral characterization, conformational analysis and molecular modelling was performed. The obtained results were also compared to similar chemical entities devoid of the charged phosphate group.
    Original languageUndefined/Unknown
    Pages (from-to)58–68
    JournalCarbohydrate Research
    Volume383
    DOIs
    Publication statusPublished - 2014
    MoE publication typeA1 Journal article-refereed

    Keywords

    • Carbohydrates
    • NMR spectroscopy
    • Molecular modeling
    • oligosaccharide synthesis
    • organic chemistry

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