Mecozzi, Sandro and West, Anthony P., Jr. and Dougherty, Dennis A. (1996) Cation-pi interactions in aromatics of biological and medicinal interest: Electrostatic potential surfaces as a useful qualitative guide. Proceedings of the National Academy of Sciences of the United States of America, 93 (20). pp. 10566-10571. ISSN 0027-8424 http://resolver.caltech.edu/CaltechAUTHORS:MECpnas96
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The cation-pi interaction is an important, general force for molecular recognition in biological receptors. Through the sidechains of aromatic amino acids, novel binding sites for cationic ligands such as acetylcholine can be constructed. We report here a number of calculations on prototypical cation-pi systems, emphasizing structures of relevance to biological receptors and prototypical heterocycles of the type often of importance in medicinal chemistry. Trends in the data can be rationalized using a relatively simple model that emphasizes the electrostatic component of the cation-pi interaction. In particular, plots of the electrostatic potential surfaces of the relevant aromatics provide useful guidelines for predicting cation-pi interactions in new systems.
|Additional Information:||Copyright © 1996 by the National Academy of Sciences. Communicated by Robert H. Grubbs, California Institute of Technology, Pasadena, CA, July 11, 1996 (received for review March 15, 1996). We thank the Office of Naval Research and Zeneca Pharmaceuticals for financial support. The publication costs of this article were defrayed in part by page charge payment. This article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. §1734 solely to indicate this fact.|
|Subject Keywords:||aromatic amino acid, molecular recognition, hydrophobic binding, quadrupole-moment, active-site, receptor, benzene, water, mechanism, models, ion|
|Usage Policy:||No commercial reproduction, distribution, display or performance rights in this work are provided.|
|Deposited By:||Tony Diaz|
|Deposited On:||15 Nov 2005|
|Last Modified:||26 Dec 2012 08:42|
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