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Cation-π Interactions Involving Aromatic Amino Acids

Dougherty, Dennis A. (2007) Cation-π Interactions Involving Aromatic Amino Acids. Journal of Nutrition, 137 (6). 1504S-1508S. ISSN 0022-3166. doi:10.1093/jn/137.6.1504s. https://resolver.caltech.edu/CaltechAUTHORS:20200416-145039910

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Abstract

The cation-π interaction is a general, strong, noncovalent binding force that is used throughout nature. The side chains of the aromatic amino acids [phenylalanine (Phe), tyrosine (Tyr), and tryptophan (Trp)] provide a surface of negative electrostatic potential than can bind to a wide range of cations through a predominantly electrostatic interaction. In this brief overview, the fundamental nature of the cation-π interaction will be described, relying on fundamental, gas phase studies of the effect. Then, several examples of cation-π interactions involving aromatic amino acids will be described. These include contributions to protein secondary structure, in which Phe/Tyr/Trp···lysine (Lys)/arginine interactions are common. We will also describe several examples of protein-ligand interactions that make use of cation-π interactions. We will place special emphasis on the binding of quaternary ammonium ions, such as trimethylated Lys and the neurotransmitter acetylcholine.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1093/jn/137.6.1504sDOIArticle
ORCID:
AuthorORCID
Dougherty, Dennis A.0000-0003-1464-2461
Additional Information:© 2007 American Society for Nutrition. Published: 01 June 2007. Published in a supplement to The Journal of Nutrition. Presented at the “Conference on Aromatic Amino Acids and Related Substances: Chemistry, Biology, Medicine, and Application” held July 20–21, 2006 in Vancouver, Canada. The conference was sponsored by Ajinomoto Company, Inc. The organizing committee for the symposium and Guest Editors for the supplement were: Katsuji Takai, Dennis M. Bier, Luc Cynober, Sidney M. Morris, Jr., and Yoshiharu Shimomura. Guest Editor disclosure: Expenses to travel to the meeting were paid by Ajinomoto Company, Inc. for K. Takai, D. M. Bier, L. Cynober, S. M. Morris, Jr., and Y. Shimomura; D. M. Bier has consulted for Ajinomoto Company, Inc. on scientific issues. Supported by the NIH (NS 34407).
Funders:
Funding AgencyGrant Number
NIHNS 34407
Subject Keywords:acetylcholine; amino acids, aromatic; cations; electrostatics; ligands; lysine; phenylalanine; protein structure, secondary; tryptophan; binding (molecular function)
Issue or Number:6
DOI:10.1093/jn/137.6.1504s
Record Number:CaltechAUTHORS:20200416-145039910
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20200416-145039910
Official Citation:Dennis A. Dougherty, Cation-π Interactions Involving Aromatic Amino Acids, The Journal of Nutrition, Volume 137, Issue 6, June 2007, Pages 1504S–1508S, https://doi.org/10.1093/jn/137.6.1504S
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:102588
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:16 Apr 2020 21:59
Last Modified:16 Nov 2021 18:13

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