Highly Polar Carbohydrates Stack Onto DNA Duplexes Via CH/π Interactions

Description

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.

Abstract

Consejo Superior de Investigaciones Científicas CSIC-PIF06-045

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Ministerio de Ciencia e Innovación CTQ2006-01123, CTQ2007-68014-C02-02, CTQ2009-13705, BFU2007-63287

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Generalitat de Catalunya 2009/SGR/208

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Instituto de Salud Carlos III CB06_01_0019

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