From glycomimetics to novel multivalent ligands. Synthesis and potential applications

MARÍA LAURA UHRIG

Simposio; 30th International Carbohydrate Symposium; 2022

International Carbohydrate Organization

Thioglycosides and thiodisaccharides are still considered interesting synthetic targets for carbohydrate chemists due to their potential applications in the Glycobiology field. As the anomeric oxygen is replaced by a sulfur atom, they are considered carbohydrate mimetics given that this replacement does not interfere with recognition events. In this presentation, we will focus on our latest results on the synthesis of multivalent ligands bearing S-GlcNAc and S-AllNAc residues attached to resorcinarene scaffolds by CuAAC reaction. These compounds led to self-assembled multivalent systems which showed increased affinity to wheat germ agglutinin (WGA). Also, the same macrocycle was selected for the attachment of the beta-S-GlcA(1→3)GlcNAc thiodisaccharide, a mimetic for the repeating unit disaccharide of hyaluronic acid. The resulting octavalent ligand showed to interact with langerin, a human C-type lectin which plays an important role in viral infections. Besides, in our way to (1→3) thiodisaccharides, we detected a vinyl azide intermediate, which showed to react with 1-thioaldoses to give a peculiar class of 2,3-dideoxy-2-azido-(1→2) thiodisaccharides by an addition reaction. This result expands the possibilities for the access to carbohydrate-modified derivatives of unique structures.