Mycobacterium tuberculosis β-gentiobiosyl diacylglycerides signal through the pattern recognition receptor Mincle: Total synthesis and structure activity relationships

Mark B. Richardson, Shota Torigoe, Sho Yamasaki, Spencer J. Williams

    Research output: Contribution to journalArticle

    20 Citations (Scopus)

    Abstract

    Mycobacterium tuberculosis H37Ra produces a range of immunogenic β-gentiobiosyl diacylglycerides. We report the total synthesis of several candidate structures and show that these compounds signal weakly through mouse, but not human, Mincle. Structure-activity relationships reveal a striking dependence upon acyl chain length for gentiobiosyl diacylglyceride signalling through Mincle. Significantly, a truncated β-glucosyl diglyceride was shown to provide potent signalling through both human and mouse Mincle and could activate murine bone marrow derived dendritic cells.

    Original languageEnglish
    Pages (from-to)15027-15030
    Number of pages4
    JournalChemical Communications
    Volume51
    Issue number81
    DOIs
    Publication statusPublished - Aug 20 2015

    Fingerprint

    Pattern Recognition Receptors
    Pattern recognition
    Diglycerides
    Chain length
    Bone
    Dendritic Cells

    All Science Journal Classification (ASJC) codes

    • Catalysis
    • Electronic, Optical and Magnetic Materials
    • Ceramics and Composites
    • Chemistry(all)
    • Surfaces, Coatings and Films
    • Metals and Alloys
    • Materials Chemistry

    Cite this

    Mycobacterium tuberculosis β-gentiobiosyl diacylglycerides signal through the pattern recognition receptor Mincle : Total synthesis and structure activity relationships. / Richardson, Mark B.; Torigoe, Shota; Yamasaki, Sho; Williams, Spencer J.

    In: Chemical Communications, Vol. 51, No. 81, 20.08.2015, p. 15027-15030.

    Research output: Contribution to journalArticle

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