Contributed equally to this work.
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Full Paper
Aromatic–Carbohydrate Interactions: An NMR and Computational Study of Model Systems
Article first published online: 15 MAY 2008
DOI: 10.1002/chem.200800247
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Vandenbussche, S., Díaz, D., Fernández-Alonso, M., Pan, W., Vincent, Stéphane P., Cuevas, G., Cañada, F., Jiménez-Barbero, J. and Bartik, K. (2008), Aromatic–Carbohydrate Interactions: An NMR and Computational Study of Model Systems. Chem. Eur. J., 14: 7570–7578. doi: 10.1002/chem.200800247
Publication History
- Issue published online: 25 AUG 2008
- Article first published online: 15 MAY 2008
- Manuscript Received: 8 FEB 2008
Funded by
- Ministry of Education and Science. Grant Number: CTQ2006-10874-C02-01
- Communauté française de Belgique. Grant Number: ARC2002-7
- European Commission. Grant Number: MRTN-CT2005-019561 DYNAMIC project
Keywords:
- carbohydrates;
- molecular modeling;
- molecular recognition;
- NMR spectroscopy;
- protein–carbohydrate interactions
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.