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Supplement: Aromatic Amino Acids and Related Substances: Chemistry, Biology, Medicine, and Application: SESSION 1

Cation- Interactions Involving Aromatic Amino Acids^1–4,

Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125

^* To whom correspondence should be addressed. E-mail: dadougherty{at}caltech.edu.

The cation- 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- interaction will be described, relying on fundamental, gas phase studies of the effect. Then, several examples of cation- 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- interactions. We will place special emphasis on the binding of quaternary ammonium ions, such as trimethylated Lys and the neurotransmitter acetylcholine.

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