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Carbohydrate–DNA Interactions at G‐Quadruplexes: Folding and Stability Changes by Attaching Sugars at the 5′‐End
Author(s) -
GómezPinto Irene,
VengutCliment Empar,
Lucas Ricardo,
Aviñó Anna,
Eritja Ramón,
González Carlos,
Morales Juan Carlos
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201203902
Subject(s) - g quadruplex , chemistry , aptamer , supramolecular chemistry , oligonucleotide , folding (dsp implementation) , dna , stacking , thermal stability , carbohydrate , biochemistry , molecular dynamics , conjugate , combinatorial chemistry , biophysics , stereochemistry , molecule , biology , organic chemistry , computational chemistry , microbiology and biotechnology , electrical engineering , engineering , mathematical analysis , mathematics
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.