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Science 12 January 1996:
Vol. 271. no. 5246, pp. 163 - 168
DOI: 10.1126/science.271.5246.163
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Articles

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

Dennis A. Dougherty

Cations bind to the face of an aromatic structure through a surprisingly strong, noncovalent force termed the cation- 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- 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.


The author is in the Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA. E-mail: dad{at}igor.caltech.edu


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Cation-pi interactions in structural biology.
J. P. Gallivan and D. A. Dougherty (1999)
PNAS 96, 9459-9464
   Abstract »    Full Text »    PDF »
Dopamine Transporter: Transmembrane Phenylalanine Mutations Can Selectively Influence Dopamine Uptake and Cocaine Analog Recognition.
Z. Lin, W. Wang, T. Kopajtic, R. S. Revay, and G. R. Uhl (1999)
Mol. Pharmacol. 56, 434-447
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mRNA cap recognition: Dominant role of enhanced stacking interactions between methylated bases and protein aromatic side chains.
G. Hu, P. D. Gershon, A. E. Hodel, and F. A. Quiocho (1999)
PNAS 96, 7149-7154
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The Functional Topography of Transmembrane Domain 3 of the M1 Muscarinic Acetylcholine Receptor, Revealed by Scanning Mutagenesis.
Z.-L. Lu and E. C. Hulme (1999)
J. Biol. Chem. 274, 7309-7315
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Unexpected crucial role of residue 225 in serine proteases.
E. R. Guinto, S. Caccia, T. Rose, K. Futterer, G. Waksman, and E. Di Cera (1999)
PNAS 96, 1852-1857
   Abstract »    Full Text »    PDF »
Novel Insight into the Copper-Ligand Geometry in the Crystal Structure of Ulva pertusa Plastocyanin at 1.6-A Resolution. STRUCTURAL BASIS FOR REGULATION OF THE COPPER SITE BY RESIDUE 88.
N. Shibata, T. Inoue, C. Nagano, N. Nishio, T. Kohzuma, K. Onodera, F. Yoshizaki, Y. Sugimura, and Y. Kai (1999)
J. Biol. Chem. 274, 4225-4230
   Abstract »    Full Text »    PDF »
A Molecular Basis for the Different Local Anesthetic Affinities of Resting Versus Open and Inactivated States of the Sodium Channel.
H.-L. Li, A. Galue, L. Meadows, and D. S. Ragsdale (1999)
Mol. Pharmacol. 55, 134-141
   Abstract »    Full Text »
Oxidized amino acids in the urine of aging rats: potential markers for assessing oxidative stress in vivo.
C. Leeuwenburgh, P. A. Hansen, J. O. Holloszy, and J. W. Heinecke (1999)
Am J Physiol Regulatory Integrative Comp Physiol 276, R128-R135
   Abstract »    Full Text »    PDF »
Siderophore-Mediated Iron Transport: Crystal Structure of FhuA with Bound Lipopolysaccharide.
A. D. Ferguson, E. Hofmann, J. W. Coulton, K. Diederichs, and W. Welte (1998)
Science 282, 2215-2220
   Abstract »    Full Text »
Critical Amino Acid Residues in Transmembrane Span 7 of the Serotonin Transporter Identified by Random Mutagenesis.
K. M. Y. Penado, G. Rudnick, and M. M. Stephan (1998)
J. Biol. Chem. 273, 28098-28106
   Abstract »    Full Text »    PDF »
From ab initio quantum mechanics to molecular neurobiology: A cation-pi binding site in the nicotinic receptor.
W. Zhong, J. P. Gallivan, Y. Zhang, L. Li, H. A. Lester, and D. A. Dougherty (1998)
PNAS 95, 12088-12093
   Abstract »    Full Text »    PDF »
Ionophores and receptors using cation-pi interactions: Collarenes.
H. S. Choi, S. B. Suh, S. J. Cho, and K. S. Kim (1998)
PNAS 95, 12094-12099
   Abstract »    Full Text »    PDF »
A Conserved Element in the Serine Protease Domain of Complement Factor B.
D. E. Hourcade, L. M. Mitchell, and T. J. Oglesby (1998)
J. Biol. Chem. 273, 25996-26000
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Kinetic Evidence That a Radical Transfer Pathway in Protein R2 of Mouse Ribonucleotide Reductase Is Involved in Generation of the Tyrosyl Free Radical.
P. P. Schmidt, U. Rova, B. Katterle, L. Thelander, and A. Graslund (1998)
J. Biol. Chem. 273, 21463-21472
   Abstract »    Full Text »    PDF »
Identification of the CD8 DE Loop as a Surface Functional Epitope. IMPLICATIONS FOR MAJOR HISTOCOMPATIBILITY COMPLEX CLASS I BINDING AND CD8 INHIBITOR DESIGN.
S. Li, S. Choksi, S. Shan, X. Hu, J. Gao, R. Korngold, and Z. Huang (1998)
J. Biol. Chem. 273, 16442-16445
   Abstract »    Full Text »    PDF »


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