7420-22-6Relevant articles and documents
Experimental measurement of carbohydrate-aromatic stacking in water by using a dangling-ended DNA model system
Morales, Juan C.,Reina, Jose J.,Diaz, Irene,Avino, Anna,Nieto, Pedro M.,Eritja, Ramon
, p. 7828 - 7835 (2008)
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 interac-tions 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 stabi-lizing 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.