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Published on: July 1, 2012
The indole side chain of tryptophan as a versatile pi-donor
Jiaxin Hu1, Leonard J Barbour, George W Gokel
1Division of Bioorganic Chemistry, Bioorganic Chemistry Program, and Department of Molecular Biology & Pharmacology, Washington University School of Medicine, 660 South Euclid Avenue, Campus Box 8103, St. Louis, Missouri 63110, USA.
Abstract:
Single-armed, 15- and 18-membered lariat ether receptor systems having indolylethyl side arms bind Na+ and K+ in the ring. The indole residue serves as a pi-donor to the ring-bound cation. Whether the five- or six-membered ring interacts most directly with Na+ or K+ depends on whether the sidearm is attached to indole's 3- or 5-position. This suggests that structural as well as electronic factors are important in pi-complexation of alkali metal cations.
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