A thorough experimental study of CH/π interactions in water: quantitative structure–stability relationships for carbohydrate/aromatic complexes. Issue 11 (12th August 2015)

• Record Type: Journal Article
• Authors: Jiménez-Moreno, Ester; Jiménez-Osés, Gonzalo; Gómez, Ana M.; Santana, Andrés G.; Corzana, Francisco; Bastida, Agatha; Jiménez-Barbero, Jesus; Asensio, Juan Luis
• Is Part Of: Chemical science. Volume 6:Issue 11(2015:Nov.)
• Page Start: 6076
• Page End: 6085
• Publication Date: 2015-08-12
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c5sc02108a
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A dynamic combinatorial analysis of carbohydrate/aromatic complexes clarifies the structural determinants and origins of these important interactions in water. Abstract : CH/π interactions play a key role in a large variety of molecular recognition processes of biological relevance. However, their origins and structural determinants in water remain poorly understood. In order to improve our comprehension of these important interaction modes, we have performed a quantitative experimental analysis of a large data set comprising 117 chemically diverse carbohydrate/aromatic stacking complexes, prepared through a dynamic combinatorial approach recently developed by our group. The obtained free energies provide a detailed picture of the structure–stability relationships that govern the association process, opening the door to the rational design of improved carbohydrate-based ligands or carbohydrate receptors. Moreover, this experimental data set, supported by quantum mechanical calculations, has contributed to the understanding of the main driving forces that promote complex formation, underlining the key role played by coulombic and solvophobic forces on the stabilization of these complexes. This represents the most quantitative and extensive experimental study reported so far for CH/π complexes in water.