Dougherty, Dennis A. (1996) Cation-π Interactions in Chemistry and Biology: A New View of Benzene, Phe, Tyr, and Trp. Science, 271 (5246). pp. 163-168. ISSN 0036-8075. doi:10.1126/science.271.5246.163. https://resolver.caltech.edu/CaltechAUTHORS:20200612-115646694
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Abstract
Cations bind to the π face of an aromatic structure through a surprisingly strong, noncovalent force termed the cation-π interaction. The magnitude and generality of the effect have been established by gas-phase measurements and by studies of model receptors in aqueous media. To first order, the interaction can be considered an electrostatic attraction between a positive charge and the quadrupole moment of the aromatic. A great deal of direct and circumstantial evidence indicates that cation-π interactions are important in a variety of proteins that bind cationic ligands or substrates. In this context, the amino acids phenylalanine (Phe), tyrosine (Tyr), and tryptophan (Trp) can be viewed as polar, yet hydrophobic, residues.
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Alternate Title: | Cation-pi Interactions in Chemistry and Biology: A New View of Benzene, Phe, Tyr, and Trp | ||||||||
Additional Information: | © 1996 American Association for the Advancement of Science. Contribution No. 9016 from the Arnold and Mabel Beckman Laboratories of Chemical Synthesis. Supported by NIH (GM43936), the Office of Naval Research (N00014-91-J-1344), and Zeneca Pharmaceuticals. D.A.D. thanks many outstanding students and postdoctoral colleagues for their contributions to this work. | ||||||||
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Issue or Number: | 5246 | ||||||||
DOI: | 10.1126/science.271.5246.163 | ||||||||
Record Number: | CaltechAUTHORS:20200612-115646694 | ||||||||
Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20200612-115646694 | ||||||||
Official Citation: | Cation-π Interactions in Chemistry and Biology: A New View of Benzene, Phe, Tyr, and Trp By Dennis A. Dougherty Science 12 Jan 1996: Vol. 271, Issue 5246, pp. 163-168 DOI: 10.1126/science.271.5246.163 | ||||||||
Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||
ID Code: | 103877 | ||||||||
Collection: | CaltechAUTHORS | ||||||||
Deposited By: | George Porter | ||||||||
Deposited On: | 12 Jun 2020 20:40 | ||||||||
Last Modified: | 16 Nov 2021 18:26 |
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