Effects of sugar functional groups, hydrophobicity, and fluorination on carbohydrate-DNA stacking interactions in water
| Autor: | Violaine Perez, Virginie Reynes, Anna Aviñó, Bruno Linclau, Olivia S. Maldonado, Lewis Mtashobya, Ramon Eritja, Ricardo Lucas, Carlos González, Empar Vengut-Climent, Juan C. Morales, Pablo Peñalver, Jonathan Cousin, Irene Gómez-Pinto |
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| Rok vydání: | 2014 |
| Předmět: |
Models
Molecular chemistry.chemical_classification Magnetic Resonance Spectroscopy Aqueous solution Hydrocarbons Fluorinated Chemistry Base pair Organic Chemistry Carbohydrates Stacking Water DNA Carbohydrate Nucleobase chemistry.chemical_compound Crystallography Pyranose Thermodynamics Organic chemistry Monosaccharide Base Pairing Hydrophobic and Hydrophilic Interactions |
| Zdroj: | Digital.CSIC. Repositorio Institucional del CSIC instname idUS. Depósito de Investigación de la Universidad de Sevilla |
| Popis: | Carbohydrate-aromatic interactions are highly relevant for many biological processes. Nevertheless, experimental data in aqueous solution relating structure and energetics for sugar-arene stacking interactions are very scarce. Here, we evaluate how structural variations in a monosaccharide including carboxyl, N-acetyl, fluorine, and methyl groups affect stacking interactions with aromatic DNA bases. We find small differences on stacking interaction among the natural carbohydrates examined. The presence of fluorine atoms within the pyranose ring slightly increases the interaction with the C-G DNA base pair. Carbohydrate hydrophobicity is the most determinant factor. However, gradual increase in hydrophobicity of the carbohydrate does not translate directly into a steady growth in stacking interaction. The energetics correlates better with the amount of apolar surface buried upon sugar stacking on top of the aromatic DNA base pair. © 2014 American Chemical Society. |
| Databáze: | OpenAIRE |
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