The synthesis and conformational properties of the diastereoisomeric βDGal(1-4)βDGlcNAc(1-6)6-C-CH3-D-Gal trisaccharides

Article abstract of DOI:10.1139/v82-014

The trisaccharide βDGal(1->4)βDGlcNAc(1->6)DGal was known to be bound strongly by the so-called anti-I Ma monoclonal antibody.In order to help assess the conformation about the 1->6 glycosidic linkage that is accepted by the antibody combining site, the conformationally well-defined βDGal(1->4)βDGlcNAc(1->6) derivatives of 7-deoxy-L-glycero-D-galacto-heptopyranose and 7-deoxy-D-glycero-D-galacto-heptopyranose were synthesized.The conformational preferences for these trisaccharides were estabished by 1H nmr spectroscopy and rationalized by computer-assisted molecular modelling.