Effect of water coordination on competition between π and non-π cation binding sites in aromatic amino acids: L-phenylalanine, L-tyrosine, and L-tryptophan Li+, Na +, and K+ complexes.

Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry
Milan Remko, Stanislava Šoralová

Abstract

Quantum chemistry methods have been applied to charged complexes of the alkali metals Li(+), Na(+), and K(+) with the aromatic amino acids (AAAs) phenylalanine (Phe), tyrosine (Tyr), and tryptophan (Trp). The geometries of 72 different complexes (Phe·M, Tyr·M, Trp·M, M is Li(+), Na(+), or K(+)) were completely optimized at the B3LYP/6-311+G(d,p) level of density functional theory. The solvent effect on the geometry and stability of individual complexes was studied by making use of a microsolvation model. The interaction enthalpies, entropies, and Gibbs energies of nine different complexes of the systems Phe·M, Tyr·M, and Trp·M (M is Li(+), Na(+), or K(+)) were also determined at the B3LYP density functional level of theory. The calculated Gibbs binding energies of the M(+)-AAA complexes follow the order Phe < Tyr < Trp for all three metal cations studied. Among the three AAAs studied, the indole ring of Trp is the best π donor for alkali metal cations. Our calculations demonstrated the existence of strong cation-π interactions between the alkali metals and the aromatic side chains of the three AAAs. These AAAs comprise about 8% of all known protein sequences. Thus, besides the potential for hydrogen-bond interaction, aromatic r...Continue Reading

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Citations

Jan 24, 2013·Proceedings of the National Academy of Sciences of the United States of America·Min LuShohei Koide
Dec 22, 2014·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Md Elius HossainMohammad A Halim
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Apr 24, 2021·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Khrustalev Vladislav VictorovichAkunevich Anastasia Aleksandrovna
Nov 14, 2012·Chemical Reviews·A Subha Mahadevi, G Narahari Sastry
Aug 21, 2020·ACS Chemical Neuroscience·Lakshmi Priya DattaThimmaiah Govindaraju

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