title: Rational design of biologically important chemosensors: a novel receptor for selective recognition of acetylcholine over ammonium cations.
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).
authors.affiliation: 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.
authors.forename: Sunggoo
authors.initials: S
authors.lastname: Yun
authors.forename: Young-Ok
authors.initials: YO
authors.lastname: Kim
authors.forename: Dongwook
authors.initials: D
authors.lastname: Kim
authors.forename: Heon Gon
authors.initials: HG
authors.lastname: Kim
authors.forename: Hyejae
authors.initials: H
authors.lastname: Ihm
authors.forename: Jung Kyung
authors.initials: JK
authors.lastname: Kim
authors.forename: Chi-Wan
authors.initials: CW
authors.lastname: Lee
authors.forename: Woo Jin
authors.initials: WJ
authors.lastname: Lee
authors.forename: Jungjoo
authors.initials: J
authors.lastname: Yoon
authors.forename: Kyung Seok
authors.initials: KS
authors.lastname: Oh
authors.forename: Juyoung
authors.initials: J
authors.lastname: Yoon
authors.forename: Su-Moon
authors.initials: SM
authors.lastname: Park
authors.forename: Kwang S
authors.initials: KS
authors.lastname: Kim
mesh_terms: D000109:Acetylcholine / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification; D001554:Benzene / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry*; D017736:Ion-Selective Electrodes; D046911:Macromolecular Substances; D008958:Models, Molecular; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification; D012996:Solutions
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; D046911:Macromolecular Substances; D011758:Pyrroles; D000644:Quaternary Ammonium Compounds; D012996:Solutions; D001554:Benzene; D000109:Acetylcholine