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Title

Aromatic-carbohydrate interactions: an NMR and computational study of model systems

AuthorsVandenbussche, S.; Díaz, Dolores ; Fernández-Alonso, M. Carmen ; Pan, W.; Vincent, S.P.; Cuevas, Gabriel; Cañada, F. Javier ; Jiménez-Barbero, Jesús ; Bartik, K.
KeywordsCarbohydrates
molecular modeling
molecular recognition
NMR spectroscopy
protein–carbohydrate interactions
Issue Date28-Aug-2008
PublisherWiley-VCH
CitationChemistry - A European Journal, 14 (25) : 7570-7578 (2008)
AbstractThe 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
Description9 páginas, 5 figuras, 2 tablas -- PAGS nros. 7570-7578
Publisher version (URL)http://dx.doi.org/10.1002/chem.200800247
URIhttp://hdl.handle.net/10261/56713
DOI10.1002/chem.200800247
ISSN0947-6539
E-ISSN1521-3765
Appears in Collections:(CIB) Artículos
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