title: Mycobacterium tuberculosis β-gentiobiosyl diacylglycerides signal through the pattern recognition receptor Mincle: total synthesis and structure activity relationships.
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.
authors: School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Victoria 3010, Australia. sjwill@unimelb.edu.au.
authors: Mark B
authors: MB
authors: Richardson
authors: Shota
authors: S
authors: Torigoe
authors: Sho
authors: S
authors: Yamasaki
authors: Spencer J
authors: SJ
authors: Williams
mesh_terms: D000818:Animals; D003713:Dendritic Cells / Q000187:drug effects / Q000378:metabolism; D004075:Diglycerides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D051379:Mice; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000737:chemistry* / Q000302:isolation & purification; D051192:Receptors, Pattern Recognition / Q000378:metabolism*; D015398:Signal Transduction / Q000187:drug effects*; D013329:Structure-Activity Relationship
chemical_list: D004075:Diglycerides; D051192:Receptors, Pattern Recognition