Cation-π Interactions in Chemistry and Biology: A New View of Benzene, Phe, Tyr, and Trp
10.1126/science.271.5246.163
Crossref journal-article
American Association for the Advancement of Science (AAAS)
Science (221)
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.

Bibliography

Dougherty, D. A. (1996). Cation-π Interactions in Chemistry and Biology: A New View of Benzene, Phe, Tyr, and Trp. Science, 271(5246), 163–168.

Authors 1
  1. Dennis A. Dougherty (first)
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Dates
Type When
Created 18 years, 9 months ago (Oct. 27, 2006, 2:30 p.m.)
Deposited 1 year, 7 months ago (Jan. 12, 2024, 6:11 p.m.)
Indexed 15 minutes ago (Aug. 26, 2025, 10:38 a.m.)
Issued 29 years, 7 months ago (Jan. 12, 1996)
Published 29 years, 7 months ago (Jan. 12, 1996)
Published Print 29 years, 7 months ago (Jan. 12, 1996)
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@article{Dougherty_1996, title={Cation-π Interactions in Chemistry and Biology: A New View of Benzene, Phe, Tyr, and Trp}, volume={271}, ISSN={1095-9203}, url={http://dx.doi.org/10.1126/science.271.5246.163}, DOI={10.1126/science.271.5246.163}, number={5246}, journal={Science}, publisher={American Association for the Advancement of Science (AAAS)}, author={Dougherty, Dennis A.}, year={1996}, month=jan, pages={163–168} }