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

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dc.contributor.authorLucas, Ricardo
dc.contributor.authorPeñalver, Pablo
dc.contributor.authorGómez-Pinto, Irene
dc.contributor.authorVengut-Climent, Empar
dc.contributor.authorMtashobya, Lewis
dc.contributor.authorCousin, Jonathan
dc.contributor.authorMaldonado, Olivia S
dc.contributor.authorPerez, Violaine
dc.contributor.authorReynes, Virginie
dc.contributor.authorAviñó, Anna
dc.contributor.authorEritja, Ramón
dc.contributor.authorGonzález, Carlos
dc.contributor.authorLinclau, Bruno
dc.contributor.authorMorales, Juan C.
dc.date.accessioned2017-03-09T09:37:12Z
dc.date.available2017-03-09T09:37:12Z
dc.date.issued2014
dc.description.abstractCarbohydrate−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.en_US
dc.description.sponsorshipFinancial support by Ministerio de Economía y Competitividad (Grants CTQ2007-68014-C02-02, CTQ2009-13705, CTQ2010-20541-C03-01, CTQ2012-35360), Generalitat de Catalunya (2009/SGR/208), and Instituto de Salud Carlos III (CIBER-BNN, CB06_01_0019) is gratefully acknowledged. E.V.C. thanks Ministerio de Educación for a FPU fellowshipen_US
dc.identifier.doi10.1021/jo402700y
dc.identifier.urihttp://hdl.handle.net/20.500.11810/4494
dc.language.isoenen_US
dc.publisherAmerican Chemical Societyen_US
dc.titleEffects of Sugar Functional Groups, Hydrophobicity, and Fluorination on Carbohydrate–DNA Stacking Interactions in Wateren_US
dc.typeJournal Article, Peer Revieweden_US
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