Synthesis, conformational analysis and GalNAc–lectin interactions of a constrained C-glycoside analogue of the TN antigen

Abstract

Highly stereoselective 1,3-dipolar cycloaddition allowed the synthesis of the original stable T_N antigen mimic presenting a constraint on the amino acid part. Two main conformations of the GalNAc moiety were detected by molecular modelling and NMR. A ligand/protein interaction study was performed by saturation transfer difference NMR analyses using two GalNAc-specific model lectins highlighting that the constrained C-glycoside analog was recognized by these proteins as well as the T_N antigen derivative.