Synthesis and Immunological Screening of beta-Linked Mono- and Divalent Mannosides

Chinmoy Mukherjee, K Ranta, J Savolainen, Reko Leino

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    9 Citations (Scopus)

    Abstract

    Three different beta-linked divalent mannosides, along with their corresponding monovalent counterparts, have been designed and chemically synthesized by coupling the corresponding propargyl (propargyl alcohol in the case of the monovalent compounds) and 2-azidoethyl glycosides by using an efficient click chemistry protocol. Crich's beta-mannosylation methodology was applied to the construction of the beta-mannosidic linkages. All the glycosylation reactions gave moderate-to-good yields with high selectivities. A competitive inhibition enzyme-linked immunosorbent assay (ELISA) was performed to determine the inhibition, by the synthesized mannosides, of specific human IgG binding to low-molecular-weight Candida albicans mannan; moderate inhibition capacity was observed for some of the compounds.
    Original languageUndefined/Unknown
    Pages (from-to)2957–2968
    Number of pages12
    JournalEuropean Journal of Organic Chemistry
    Issue number15
    DOIs
    Publication statusPublished - 2012
    MoE publication typeA1 Journal article-refereed

    Keywords

    • Biological activity
    • Click chemistry
    • Glycosylation
    • Medicinal chemistry

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