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

Sunggoo Yun, Young Ok Kim, Dongwook Kim, Heon Gon Kim, Hyejae Ihm, Jung Kyung Kim, Chi Wan Lee, Woo Jin Lee, Jungjoo Yoon, Kyung Seok Oh, Juyoung Yoon, Su Moon Park, Kwang S. Kim

Research output: Contribution to journalArticlepeer-review

45 Scopus citations

Abstract

(Matrix presented) In consideration of competition between cation-π 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 (∼6 kcal/mol).

Original languageEnglish
Pages (from-to)471-474
Number of pages4
JournalOrganic Letters
Volume5
Issue number4
DOIs
StatePublished - 20 Feb 2003

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