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Issue 81, 2015
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Mycobacterium tuberculosis β-gentiobiosyl diacylglycerides signal through the pattern recognition receptor Mincle: total synthesis and structure activity relationships

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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.

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

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The article was received on 10 Jun 2015, accepted on 20 Aug 2015 and first published on 20 Aug 2015


Article type: Communication
DOI: 10.1039/C5CC04773K
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Chem. Commun., 2015,51, 15027-15030

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

    M. B. Richardson, S. Torigoe, S. Yamasaki and S. J. Williams, Chem. Commun., 2015, 51, 15027
    DOI: 10.1039/C5CC04773K

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