title: Experimental measurement of carbohydrate-aromatic stacking in water by using a dangling-ended DNA model system.
abstract: 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.
authors.affiliation: Department of Bioorganic Chemistry, Instituto de Investigaciones Químicas, CSIC-Universidad de Sevilla, Sevilla, Spain. jcmorales@iiq.csic.es
authors.forename: Juan C
authors.initials: JC
authors.lastname: Morales
authors.forename: José J
authors.initials: JJ
authors.lastname: Reina
authors.forename: Irene
authors.initials: I
authors.lastname: Díaz
authors.forename: Anna
authors.initials: A
authors.lastname: Aviñó
authors.forename: Pedro M
authors.initials: PM
authors.lastname: Nieto
authors.forename: Ramón
authors.initials: R
authors.lastname: Eritja
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008957:Models, Genetic; D009841:Oligonucleotides / Q000737:chemistry; D013696:Temperature; D013816:Thermodynamics; D014867:Water / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D009841:Oligonucleotides; D014867:Water; D004247:DNA