期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 14, 期 26, 页码 7828-7835出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200800335
关键词
carbohydrate-aromatic stacking; carbohydrates; DNA; molecular recognition; stacking interactions
资金
- Ministry of Science and Education [CTQ-2006-01123/BQU]
- Ramon y Cajal
Protein-carbohydrate recognition is of fundamental importance for a large number of biological processes; carbohydrate-aromatic stacking is a widespread, but poorly understood., structural motif in this recognition. We describe, for the first time, the measurement of carbohydrate-aromatic interactions from their contribution to the stability of a dangling-ended DNA model system. We observe clear differences in the energetics of the interactions of several monosaccharides with a benzene moiety depending on the number of hydroxy groups, the stereochemistry, and the presence of a methyl group in the pyranose ring. A fucose-benzene pair is the most stabilizing of the studied series (-0.4 Kcal mol(-1)) and this interaction can be placed in the same range as other more studied interactions with aromatic residues of proteins, such as Phe-Phe, Phe-Met, or Phe-His. The noncovalent forces involved seem to be dispersion forces and nonconventional hydrogen bonds, whereas hydrophobic effects do not seem to drive the interaction.
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