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Science 14 December 1990:
Vol. 250. no. 4987, pp. 1558 - 1560
DOI: 10.1126/science.2274786
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Articles

Science, Vol 250, Issue 4987, 1558-1560
Copyright © 1990 by American Association for the Advancement of Science

articles

Acetylcholine binding by a synthetic receptor: implications for biological recognition

DA Dougherty and DA Stauffer

Arnold and Mabel Beckman Laboratories of Chemical Synthesis, California Institute of Technology, Pasadena 91125.

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.


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