Rational design of biologically important chemosensors: a novel receptor for selective recognition of acetylcholine over ammonium cations.
[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).
Yun
Sunggoo
S
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.
Kim
Young-Ok
YO
Kim
Dongwook
D
Kim
Heon Gon
HG
Ihm
Hyejae
H
Kim
Jung Kyung
JK
Lee
Chi-Wan
CW
Lee
Woo Jin
WJ
Yoon
Jungjoo
J
Oh
Kyung Seok
KS
Yoon
Juyoung
J
Park
Su-Moon
SM
Kim
Kwang S
KS
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
D006576:Heterocyclic Compounds, 4 or More Rings; D046911:Macromolecular Substances; D011758:Pyrroles; D000644:Quaternary Ammonium Compounds; D012996:Solutions; D001554:Benzene; D000109:Acetylcholine