Carbohydrate–DNA Interactions at G-Quadruplexes: Folding and Stability Changes by Attaching Sugars at the 5′-End

Authors

  • Dr. Irene Gómez-Pinto,

    1. Instituto de Química Física “Rocasolano”, CSIC, Serrano 119, 28006 Madrid (Spain)
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  • Empar Vengut-Climent,

    1. Department of Bioorganic Chemistry, Instituto de Investigaciones Químicas, CSIC–Universidad de Sevilla, Americo Vespucio 49, 41092 Sevilla (Spain)
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  • Dr. Ricardo Lucas,

    1. Department of Bioorganic Chemistry, Instituto de Investigaciones Químicas, CSIC–Universidad de Sevilla, Americo Vespucio 49, 41092 Sevilla (Spain)
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  • Dr. Anna Aviñó,

    1. Instituto de Investigación Biomédica de Barcelona, IQAC, CSIC, CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Baldiri Reixac 10, 08028 Barcelona (Spain)
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  • Prof. Dr. Ramón Eritja,

    1. Instituto de Investigación Biomédica de Barcelona, IQAC, CSIC, CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Baldiri Reixac 10, 08028 Barcelona (Spain)
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  • Prof. Dr. Carlos González,

    Corresponding author
    1. Instituto de Química Física “Rocasolano”, CSIC, Serrano 119, 28006 Madrid (Spain)
    • Instituto de Química Física “Rocasolano”, CSIC, Serrano 119, 28006 Madrid (Spain)
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  • Dr. Juan Carlos Morales

    Corresponding author
    1. Department of Bioorganic Chemistry, Instituto de Investigaciones Químicas, CSIC–Universidad de Sevilla, Americo Vespucio 49, 41092 Sevilla (Spain)
    • Department of Bioorganic Chemistry, Instituto de Investigaciones Químicas, CSIC–Universidad de Sevilla, Americo Vespucio 49, 41092 Sevilla (Spain)
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Abstract

Quadruplex DNA structures are attracting an enormous interest in many areas of chemistry, ranging from chemical biology, supramolecular chemistry to nanoscience. We have prepared carbohydrate–DNA conjugates containing the oligonucleotide sequences of G-quadruplexes (thrombin binding aptamer (TBA) and human telomere (TEL)), measured their thermal stability and studied their structure in solution by using NMR and molecular dynamics. The solution structure of a fucose–TBA conjugate shows stacking interactions between the carbohydrate and the DNA G-tetrad in addition to hydrogen bonding and hydrophobic contacts. We have also shown that attaching carbohydrates at the 5′-end of a quadruplex telomeric sequence can alter its folding topology. These results suggest the possibility of modulating the folding of the G-quadruplex by linking carbohydrates and have clear implications in molecular recognition and the design of new G-quadruplex ligands.

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