Aromatic-carbohydrate interactions: an NMR and computational study of model systems.
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.
Vandenbussche
Sophie
S
Molecular & Biomolecular Engineering, Université Libre de Bruxelles, Brussels, Belgium.
Díaz
Dolores
D
Fernández-Alonso
María Carmen
MC
Pan
Weidong
W
Vincent
Stéphane P
SP
Cuevas
Gabriel
G
Cañada
Francisco Javier
FJ
Jiménez-Barbero
Jesús
J
Bartik
Kristin
K
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
D024322:Amino Acids, Aromatic; D006027:Glycosides; D010636:Phenols