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Cation-π Interactions in Chemistry and Biology: A New View of Benzene, Phe, Tyr, and Trp
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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Cited by
Goetz, D. H., Holmes, M. A., Borregaard, N., Bluhm, M. E., Raymond, K. N., & Strong, R. K. (2002) · Molecular Cell · doi:10.1016/s1097-2765(02)00708-6 · Cited by 1,355
Payne, C. M., Knott, B. C., Mayes, H. B., Hansson, H., Himmel, M. E., Sandgren, M., Ståhlberg, J., & Beckham, G. T. (2015) · Chemical Reviews · doi:10.1021/cr500351c · Cited by 855
Structural Biology and Chemistry of the Terpenoid Cyclases
Christianson, D. W. (2006) · Chemical Reviews · doi:10.1021/cr050286w · Cited by 788
Siderophore-Mediated Iron Transport: Crystal Structure of FhuA with Bound Lipopolysaccharide
Ferguson, A. D., Hofmann, E., Coulton, J. W., Diederichs, K., & Welte, W. (1998) · Science · doi:10.1126/science.282.5397.2215 · Cited by 787
Gallivan, J. P., & Dougherty, D. A. (2000) · Journal of the American Chemical Society · doi:10.1021/ja991755c · Cited by 448
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Metadata
- Authors
- Dougherty, D. A.
- Venue
- Science
- Published
- 1996-01-12
- Volume
- 271
- Issue
- 5246
- Pages
- 163-168
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W2079604571
- Cited by
- 2,656
- References
- 0
- FWCI
- 95.93
- Type
- journal article
- Language
- en
- Open access
- closed
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
