Corynomycolic acid-containing glycolipids signal through the pattern recognition receptor Mincle

An enantioselective synthesis of (+)-corynomycolic acid, and its elaboration to esters of trehalose, glucose and glycerol, is described. Trehalose dicorynomycolate and trehalose monocorynomycolate activate human and mouse Mincle as effectively as trehalose dicorynomycolate (cord factor). Glucose mon...

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Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2015-01, Vol.51 (24), p.5100-5103
Hauptverfasser:	van der Peet, Phillip L, Gunawan, Christian, Torigoe, Shota, Yamasaki, Sho, Williams, Spencer J
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Cell Line Esters Glucose Glycerols Glycolipids - chemistry Glycolipids - pharmacology Human Humans Lectins, C-Type - metabolism Membrane Proteins - metabolism Mice Molecular Conformation Mycolic Acids - chemistry Pattern recognition Receptors, Immunologic - metabolism Rope Signal Transduction - drug effects Stereoisomerism Structure-Activity Relationship Synthesis Trehalose
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Zusammenfassung:	An enantioselective synthesis of (+)-corynomycolic acid, and its elaboration to esters of trehalose, glucose and glycerol, is described. Trehalose dicorynomycolate and trehalose monocorynomycolate activate human and mouse Mincle as effectively as trehalose dicorynomycolate (cord factor). Glucose monomycolate is revealed to be a potent activator of both mouse and human Mincle. Glycerol monocorynomycolate signals through human Mincle, with the activity predominantly residing in the 2'S-isomer.
ISSN:	1359-7345 1364-548X
DOI:	10.1039/c5cc00085h