Molecular recognition of nucleotides in water by scorpiand-type receptors based on nucleobase discrimination

Chemistry. 2014 Mar 24;20(13):3730-41. doi: 10.1002/chem.201303861. Epub 2014 Feb 26.

Abstract

The detection of nucleotides is of crucial importance because they are the basic building blocks of nucleic acids. Scorpiand-based polyamine receptors functionalized with pyridine or anthracene units are able to form stable complexes with nucleotides in water, based on coulombic, π-π stacking, and hydrogen-bonding interactions. This behavior has been rationalized by means of an exploration with NMR spectroscopy and DFT calculations. Binding constants were determined by potentiometry. Fluorescence spectroscopy studies have revealed the potential of these receptors as sensors to effectively and selectively distinguish guanosine-5'-triphosphate (GTP) from adenosine-5'-triphosphate (ATP).

Keywords: molecular recognition; nucleotides; scorpiands; sensors; supramolecular chemistry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine Triphosphate / chemistry*
  • Guanosine Triphosphate / chemistry*
  • Hydrogen Bonding
  • Models, Theoretical
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Nucleotides / chemistry*
  • Spectrometry, Fluorescence / methods
  • Water / chemistry*

Substances

  • Nucleotides
  • Water
  • Guanosine Triphosphate
  • Adenosine Triphosphate