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Effects of Sugar Functional Groups, Hydrophobicity, and Fluorination on Carbohydrate–DNA Stacking Interactions in Water

 

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Opened Access Effects of Sugar Functional Groups, Hydrophobicity, and Fluorination on Carbohydrate–DNA Stacking Interactions in Water
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Author: 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.
Date: 2014
Published in: Journal of Organic Chemistry, 79 (6), 2419-2429.
Document type: Article
Abstract: 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.
Cite: 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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URI: https://hdl.handle.net/11441/78939

DOI: 10.1021/jo402700y

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