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
glycolipid, Mincle receptor, corynomycolic acid
NCBI PubMed ID: 25714652Publication DOI: 10.1039/c5cc00085hJournal NLM ID: 9610838Publisher: Cambridge: Royal Society of Chemistry
Correspondence: Williams SJ
; Yamasaki S
Institutions: School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Victoria, Australia, Division of Molecular Immunology, Medical Institute of Bioregulation, Kyushu University, Fukuoka, Japan
Methods: chemical synthesis, biological assays, optical rotation measurement
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