title: 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.
abstract: 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.
authors.affiliation: Discovery Chemistry Research and Technologies, Centro de Investigación Lilly, Avenida de la Industria 30, 28108 Alcobendas, Madrid, Spain.
authors.forename: Paloma
authors.initials: P
authors.lastname: Vidal
authors.forename: Boris
authors.initials: B
authors.lastname: Vauzeilles
authors.forename: Yves
authors.initials: Y
authors.lastname: Blériot
authors.forename: Matthieu
authors.initials: M
authors.lastname: Sollogoub
authors.forename: Pierre
authors.initials: P
authors.lastname: Sinaÿ
authors.forename: Jesús
authors.initials: J
authors.lastname: Jiménez-Barbero
authors.forename: Juan F
authors.initials: JF
authors.lastname: Espinosa
mesh_terms: 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
chemical_list: D004187:Disaccharides; D006027:Glycosides; D005947:Glucose; D005690:Galactose