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Aromatic–Carbohydrate Interactions: An NMR and Computational Study of Model Systems
Author(s) -
Vandenbussche Sophie,
Díaz Dolores,
FernándezAlonso María Carmen,
Pan Weidong,
Vincent Stéphane P.,
Cuevas Gabriel,
Cañada Francisco Javier,
JiménezBarbero Jesús,
Bartik Kristin
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200800247
Subject(s) - chemistry , aromatic amino acids , aromaticity , chemical shift , intermolecular force , computational chemistry , phenol , monosaccharide , solvent , benzene , homonuclear molecule , density functional theory , organic chemistry , molecule , solvent effects , sugar , aqueous solution , enzyme
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 β‐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.