title: Aromatic-carbohydrate interactions: an NMR and computational study of model systems.
abstract: The interactions of simple carbohydrates with aromatic moieties have been investigated experimentally by NMR spectroscopy. The analysis of the changes in the chemical shifts of the sugar proton signals induced upon addition of aromatic entities has been interpreted in terms of interaction geometries. Phenol and aromatic amino acids (phenylalanine, tyrosine, tryptophan) have been used. The observed sugar-aromatic interactions depend on the chemical nature of the sugar, and thus on the stereochemistries of the different carbon atoms, and also on the solvent. A preliminary study of the solvation state of a model monosaccharide (methyl beta-galactopyranoside) in aqueous solution, both alone and in the presence of benzene and phenol, has also been carried out by monitoring of intermolecular homonuclear solvent-sugar and aromatic-sugar NOEs. These experimental results have been compared with those obtained by density functional theory methods and molecular mechanics calculations.
authors.affiliation: Molecular & Biomolecular Engineering, Université Libre de Bruxelles, Brussels, Belgium.
authors.forename: Sophie
authors.initials: S
authors.lastname: Vandenbussche
authors.forename: Dolores
authors.initials: D
authors.lastname: Díaz
authors.forename: María Carmen
authors.initials: MC
authors.lastname: Fernández-Alonso
authors.forename: Weidong
authors.initials: W
authors.lastname: Pan
authors.forename: Stéphane P
authors.initials: SP
authors.lastname: Vincent
authors.forename: Gabriel
authors.initials: G
authors.lastname: Cuevas
authors.forename: Francisco Javier
authors.initials: FJ
authors.lastname: Cañada
authors.forename: Jesús
authors.initials: J
authors.lastname: Jiménez-Barbero
authors.forename: Kristin
authors.initials: K
authors.lastname: Bartik
mesh_terms: D024322:Amino Acids, Aromatic / Q000737:chemistry*; D003198:Computer Simulation; D006027:Glycosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods* / Q000592:standards; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D012015:Reference Standards; D015203:Reproducibility of Results
chemical_list: D024322:Amino Acids, Aromatic; D006027:Glycosides; D010636:Phenols