Stereoselective Synthesis of the Gal-α-(1→3)-Gal-β-(1→3)-GlcNAc Trisaccharide: a new Ligand for DCAR and Mincle C-Type Lectin Receptors

Chembiochem. 2024 May 2;25(9):e202400026. doi: 10.1002/cbic.202400026. Epub 2024 Apr 8.

Abstract

In this work, we have discovered that the Gal-α-(1→3)-Gal-β-(1→3)-GlcNAc trisaccharide, a fragment of the B antigen Type-1, is a new ligand of two C-type lectin receptors (CLRs) i. e. DCAR and Mincle which are key players in different types of autoimmune diseases. Accordingly, we report here on a straightforward methodology to access pure Gal-α-(1→3)-Gal-β-(1→3)-GlcNAc trisaccharide. A spacer with a terminal primary amine group was included at the reducing end of the GlcNAc residue thus ensuring the further functionalization of the trisaccharide Gal-α-(1→3)-Gal-β-(1→3)-GlcNAc.

Keywords: B Antigen Type-1; C type lectin receptors; DCAR; Mincle; Saccharide synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Humans
  • Lectins, C-Type* / chemistry
  • Lectins, C-Type* / metabolism
  • Ligands
  • Membrane Proteins / chemistry
  • Membrane Proteins / metabolism
  • Receptors, Immunologic*
  • Stereoisomerism
  • Trisaccharides* / chemical synthesis
  • Trisaccharides* / chemistry

Substances

  • Lectins, C-Type
  • Trisaccharides
  • Ligands
  • CLEC4D protein, human
  • Membrane Proteins
  • Receptors, Immunologic