Artículo
Highly Polar Carbohydrates Stack Onto DNA Duplexes Via CH/π Interactions
Autor/es | Lucas Rodríguez, Ricardo
Gómez Pinto, Irene Aviñó, Anna Reina, Jose J. Eritja, Ramón González, Carlos Morales, Juan C. |
Departamento | Universidad de Sevilla. Departamento de Química Orgánica y Farmacéutica |
Fecha de publicación | 2011 |
Fecha de depósito | 2024-01-29 |
Publicado en |
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Resumen | Carbohydrate-nucleic acid contacts are known to be a fundamental part of some drug-DNA recognition processes. Most of these interactions occur through the minor groove of DNA, such as in the calicheamicin or anthracycline ... Carbohydrate-nucleic acid contacts are known to be a fundamental part of some drug-DNA recognition processes. Most of these interactions occur through the minor groove of DNA, such as in the calicheamicin or anthracycline families, or through both minor and major groove binders such as in the pluramycins. Here, we demonstrate that carbohydrate-DNA interactions are also possible through sugar capping of a DNA double helix. Highly polar mono- and disaccharides are capable of CH/π stacking onto the terminal DNA base pair of a duplex as shown by NMR spectroscopy. The energetics of the carbohydrate-DNA interactions vary depending on the stereochemistry, polarity, and contact surface of the sugar involved and also on the terminal base pair. These results reveal carbohydrate-DNA base stacking as a potential recognition motif to be used in drug design, supramolecular chemistry, or biobased nanomaterials. |
Agencias financiadoras | Consejo Superior de Investigaciones Científicas (CSIC) Ministerio de Ciencia e Innovación (MICIN). España Generalitat de Catalunya Instituto de Salud Carlos III |
Identificador del proyecto | CSIC-PIF06-045
CTQ2006-01123 CTQ2007-68014-C02-02 CTQ2009-13705 BFU2007-63287 2009/SGR/208 CB06_01_0019 |
Cita | Lucas Rodríguez, R., Gómez Pinto, I., Aviñó, A., Reina, J.J., Eritja, R., González, C. y Morales, J.C. (2011). Highly Polar Carbohydrates Stack Onto DNA Duplexes Via CH/π Interactions. Journal of the American Chemical Society, 133 (6), 1909-1916. https://doi.org/10.1021/ja108962j. |
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