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

Chem Commun (Camb). 2015 Mar 25;51(24):5100-3. doi: 10.1039/c5cc00085h.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line
  • Glycolipids / chemistry*
  • Glycolipids / pharmacology*
  • Humans
  • Lectins, C-Type / metabolism*
  • Membrane Proteins / metabolism*
  • Mice
  • Molecular Conformation
  • Mycolic Acids / chemistry*
  • Receptors, Immunologic / metabolism*
  • Signal Transduction / drug effects*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • CLEC4D protein, human
  • Clecsf8 protein, mouse
  • Glycolipids
  • Lectins, C-Type
  • Membrane Proteins
  • Mycolic Acids
  • Receptors, Immunologic
  • corynomycolic acid