Nuclear overhauser effect investigation on GM1 ganglioside containing N-glycolyl-neuraminic acid (II(3)Neu5GcGgOse(4)Cer)

The conformational properties of the oligosaccharide chain of GM1 ganglioside containing N-glycolyl-neuraminic acid, beta-Gal-(1-3)-beta-GalNAc-(1-4)-[alpha-Neu5Gc-(2-3)]-beta-Gal-(1-4)-beta-Glc-(1-1)-Cer, were studied through NMR nuclear Overhauser effect investigations on the monomeric ganglioside in dimethylsulfoxide, and on mixed micelles of ganglioside and dodecylphosphocholine in water. Several interresidual contacts for the trisaccharide core -beta-GalNAc-(1-4)-[alpha-Neu5Gc-(2-3)]-beta-Gal- were found to fix the relative orientation of the three saccharides, while the glycosidic linkage of the terminal beta-Gal- was found to be quite mobile as the beta-Gal-(1-3)-beta-GalNAc- disaccharide exists in different conformations. These results are similar to those found for two GM1 gangliosides containing N-acetyl-neuraminic acid and neuraminic acid [1].