Artículo
Effects of Sugar Functional Groups, Hydrophobicity, and Fluorination on Carbohydrate–DNA Stacking Interactions in Water
Autor/es | Lucas Rodríguez, Ricardo
Peñalver, Pablo Gomez Pinto, Irene Vengut Climent, Empar Matashobya, L. Cousin, J. Sanchez Maldonado, Olivia Reynes, Virginie Aviñó, Anna Eritja Casadellà, Ramón González, Carlos Linclau, Bruno Morales, Juan C. |
Fecha de publicación | 2014 |
Fecha de depósito | 2018-10-01 |
Publicado en |
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Resumen | 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 ... 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. |
Identificador del proyecto | CTQ2007-68014-C02-02
CTQ2009-13705 CTQ2010-20541-C03-01 CTQ2012-35360 2009/SGR/208 CIBER-BNN CB06_01_0019 |
Cita | Lucas Rodríguez, R., Peñalver, P., Gomez Pinto, I., Vengut Climent, E., Matashobya, L., Cousin, J.,...,Morales, J.C. (2014). Effects of Sugar Functional Groups, Hydrophobicity, and Fluorination on Carbohydrate–DNA Stacking Interactions in Water. Journal of Organic Chemistry, 79 (6), 2419-2429. |
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