Conformational behaviour of glycomimetics: NMR and molecular modelling studies of the C-glycoside analogue of the disaccharide methyl β-d-galactopyranosyl-(1→3)-β-d-glucopyranoside

The conformational behaviour of the C-glycoside β-C-Gal-(1→3)-β-Glc-OMe (1) has been studied using a combination of molecular mechanics and NMR spectroscopy (proton–proton coupling constants and nuclear Overhauser effects). It is shown that the C-disaccharide populates two distinctive conformational families in solution, the normal syn-ψ conformation, which is the predominating conformation of parent O-glycoside 2, and the anti-ψ conformation, which has not been detected for the O-disaccharide.

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