Neighbouring group participation of C-6 substituents of glucose derivatives on the stereoselectivity of the N-glycosidic linkage of glycopeptides

Article abstract of DOI:10.1515/znb-1999-0519

The first example of a glycopeptide with a direct N-α-glycosidic linkage between the trisaccharide and the amino acid residue was found in the glomerular basement membrane of rats. In connection with the total synthesis of nephritogenoside, glycosyl azides with different protecting groups and carbohydrate chain lengths are synthesized, reduced to the corresponding glycosyl amines and coupled with Z-Asp-OBzl. Remarkable differences in the α:β ratio of the condensation products are observed, caused by neighbouring group participation.