Acetylcholine binding by a synthetic receptor: implications for biological recognition

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Science  14 Dec 1990:
Vol. 250, Issue 4987, pp. 1558-1560
DOI: 10.1126/science.2274786


The neurotransmitter acetylcholine (ACh) is bound with 50-micromolar affinity by a completely synthetic receptor (host) comprising primarily aromatic rings. The host provided an overall hydrophobic binding site, but one that could recognize the positive charge of the quaternary ammonium group of ACh through a stabilizing interaction with the electron-rich pi systems of the aromatic rings (cation-pi interaction). Similar interactions may be involved in biological recognition of ACh and other choline derivatives.