Carbohydrate-DNA interactions at G-quadruplexes: folding and stability changes by attaching sugars at the 5'-end

Chemistry. 2013 Feb 4;19(6):1920-7. doi: 10.1002/chem.201203902. Epub 2013 Jan 11.


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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aptamers, Nucleotide / chemistry*
  • Aptamers, Nucleotide / metabolism
  • Carbohydrates / chemistry*
  • DNA / chemistry*
  • DNA / metabolism
  • G-Quadruplexes
  • Humans
  • Hydrogen Bonding
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Solutions
  • Telomere / chemistry*
  • Telomere / metabolism


  • Aptamers, Nucleotide
  • Carbohydrates
  • Ligands
  • Solutions
  • DNA