Effects of Sugar Functional Groups, Hydrophobicity, and Fluorination on Carbohydrate鈥揇NA Stacking Interactions in Water

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• 作者：Ricardo Lucas ; Pablo Pe帽alver ; Irene G贸mez-Pinto ; Empar Vengut-Climent ; Lewis Mtashobya ; Jonathan Cousin ; Olivia S. Maldonado ; Violaine Perez ; Virginie Reynes ; Anna Avi帽贸 ; Ram贸n Eritja ; Carlos Gonz谩lez ; Bruno Linclau ; Juan C. Morales
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：March 21, 2014
• 年：2014
• 卷：79
• 期：6
• 页码：2419-2429
• 全文大小：458K
• 年卷期：v.79,no.6(March 21, 2014)
• ISSN：1520-6904

文摘

Carbohydrate鈥揳romatic interactions are highly relevant for many biological processes. Nevertheless, experimental data in aqueous solution relating structure and energetics for sugar鈥揳rene 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鈥揋 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.