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Acetylcholine Binding by a Synthetic Receptor: Implications for Biological Recognition

Dougherty, Dennis A. and Stauffer, David A. (1990) Acetylcholine Binding by a Synthetic Receptor: Implications for Biological Recognition. Science, 250 (4987). pp. 1558-1560. ISSN 0036-8075. doi:10.1126/science.2274786.

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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 π systems of the aromatic rings (cation-π interaction). Similar interactions may be involved in biological recognition of ACh and other choline derivatives.

Item Type:Article
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Dougherty, Dennis A.0000-0003-1464-2461
Additional Information:© 1990 American Association for the Advancement of Science. Received 17 July 1990; accepted 11 September 1990. Supported by the Office of Naval Research (N000014-88-K-0259) and the National Institutes of Health (GM36356 and GM43936). We thank H. Lester and A. Karlin for helpful discussions and W. L. Jorgensen for providing a copy of the program BOSS. Contribution no. 8174 from the Division of Chemistry and Chemical Engineering, California Institute of Technology.
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Office of Naval Research (ONR)N000014-88-K-0259
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Caltech Division of Chemistry and Chemical Engineering8174
Issue or Number:4987
Record Number:CaltechAUTHORS:20150113-105035358
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Official Citation:Acetylcholine binding by a synthetic receptor: implications for biological recognition DA Dougherty and DA Stauffer Science 14 December 1990: 250 (4987), 1558-1560. [DOI:10.1126/science.2274786]
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:53621
Deposited By: Tony Diaz
Deposited On:13 Jan 2015 19:56
Last Modified:10 Nov 2021 20:04

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