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

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.