Conformational behaviour of glycomimetics: NMR and molecular modelling studies of the C-glycoside analogue of the disaccharide methyl beta-D-galactopyranosyl-(1-->3)-beta-D-glucopyranoside.
The conformational behaviour of the C-glycoside beta-C-Gal-(1-->3)-beta-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-psi conformation, which is the predominating conformation of parent O-glycoside 2, and the anti-psi conformation, which has not been detected for the O-disaccharide.
Vidal
Paloma
P
Discovery Chemistry Research and Technologies, Centro de Investigación Lilly, Avenida de la Industria 30, 28108 Alcobendas, Madrid, Spain.
Vauzeilles
Boris
B
Blériot
Yves
Y
Sollogoub
Matthieu
M
Sinaÿ
Pierre
P
Jiménez-Barbero
Jesús
J
Espinosa
Juan F
JF
D032701:Biomimetics; D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D005690:Galactose; D005947:Glucose; D006027:Glycosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular
D004187:Disaccharides; D006027:Glycosides; D005947:Glucose; D005690:Galactose