Synthesis of beta-(1 -> 2)-Linked Oligomannosides

Monika Poláková, Mattias U. Roslund, Filip S. Ekholm, Tiina Saloranta, Reko Leino

    Research output: Contribution to journalArticleScientificpeer-review

    27 Citations (Scopus)

    Abstract

    b-(1 -> 2)-Linked oligomannosides constitute an important class of carbohydrate structures located on the cell surface of several Candida species, including C. albicans. As a result of the immunostimulating properties of such compounds, the upscaling of their synthesis is relevant. In this paper, a highly stereoselective synthesis of beta-(1 -> 2)-linked oligomannosides was performed by further development of and modifications to the methodologies described earlier in the literature. In addition to the synthesis of fully deprotected beta-(1 -> 2)-linked mannobiose and mannotriose, some preliminary modifications to the oligosaccharide core, resulting in close analogues with biological potential, are presented. The fully deprotected products form potential targets for screening against C. albicans and may also result in new model structures for vaccine development. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
    Original languageUndefined/Unknown
    Pages (from-to)870–888
    Number of pages19
    JournalEuropean Journal of Organic Chemistry
    Issue number6
    DOIs
    Publication statusPublished - 2009
    MoE publication typeA1 Journal article-refereed

    Keywords

    • Asymmetric synthesis
    • Glycosylation
    • NMR spectroscopy
    • Oligosaccharides

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