Rational design of biologically important chemosensors: a novel receptor for selective recognition of acetylcholine over ammonium cations

Org Lett. 2003 Feb 20;5(4):471-4. doi: 10.1021/ol0273203.


[structure: see text] In consideration of competition between cation-pi and hydrogen bond interaction forces, we designed a novel receptor, 1,3,5-tris(pyrrolyl)benzene, which shows high selectivity for acetylcholine (ACh). The selectivity of the receptor for ACh over other ammonium cations is demonstrated by the ion-selective electrode (ISE) method in buffer solution. The binding free energy of the receptor with ACh in chloroform solution is measured to be 3.65 kcal/mol in the presence of chloride anion by nuclear magnetic resonance spectroscopy, and that in water is estimated to be much greater ( approximately 6 kcal/mol).

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholine / analysis
  • Acetylcholine / chemistry*
  • Acetylcholine / isolation & purification
  • Benzene / chemistry
  • Heterocyclic Compounds, 4 or More Rings / chemistry*
  • Ion-Selective Electrodes
  • Macromolecular Substances
  • Models, Molecular*
  • Molecular Structure
  • Pyrroles / chemistry
  • Quaternary Ammonium Compounds / analysis
  • Quaternary Ammonium Compounds / chemistry*
  • Quaternary Ammonium Compounds / isolation & purification
  • Solutions


  • Heterocyclic Compounds, 4 or More Rings
  • Macromolecular Substances
  • Pyrroles
  • Quaternary Ammonium Compounds
  • Solutions
  • Benzene
  • Acetylcholine