CaltechAUTHORS
  A Caltech Library Service

Cation-pi interactions in aromatics of biological and medicinal interest: Electrostatic potential surfaces as a useful qualitative guide

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

[img]
Preview
PDF
See Usage Policy.

1793Kb

Use this Persistent URL to link to this item: http://resolver.caltech.edu/CaltechAUTHORS:MECpnas96

Abstract

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.


Item Type:Article
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
Record Number:CaltechAUTHORS:MECpnas96
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:MECpnas96
Alternative URL:http://www.pnas.org/cgi/content/abstract/93/20/10566
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:957
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:15 Nov 2005
Last Modified:26 Dec 2012 08:42

Repository Staff Only: item control page