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Org Lett. 2003 Feb 20;5(4):471-4.

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

Author information

1
National Creative Research Initiative Center for Superfunctional Materials, Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science and Technology San 31, Hyojadong, Namgu, Pohang, 790-784, Korea.

Abstract

[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).

PMID:
12583746
DOI:
10.1021/ol0273203
[Indexed for MEDLINE]

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