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Cation-π Interactions in Chemistry and Biology: A New View of Benzene, Phe, Tyr, and Trp

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1126/science.271.5246.163DOIArticle
ORCID:
AuthorORCID
Dougherty, Dennis A.0000-0003-1464-2461
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.
Funders:
Funding AgencyGrant Number
NIHGM43936
Office of Naval Research (ONR)N00014-91-J-1344
Zeneca PharmaceuticalsUNSPECIFIED
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Caltech Arnold and Mabel Beckman Laboratories of Chemical Synthesis9016
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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