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Molecules 2015, 20(5), 9214-9228; doi:10.3390/molecules20059214

Aromatic Amino Acids-Guanidinium Complexes through Cation-π Interactions

1
Trinity Biomedical Sciences Institute, School of Chemistry, Trinity College Dublin, 152-160 Pearse Street, Dublin 2, Ireland
2
Departamento de Química Física, Facultade de Ciencias, Universidade de Santiago de Compostela, Campus de Lugo, Avda. Alfonso X El Sabio s/n, 27002 Lugo, Spain
*
Author to whom correspondence should be addressed.
Academic Editor: Antonio Frontera
Received: 23 April 2015 / Revised: 11 May 2015 / Accepted: 12 May 2015 / Published: 20 May 2015
(This article belongs to the Special Issue Noncovalent pi-Interactions)
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Abstract

Continuing with our interest in the guanidinium group and the different interactions than can establish, we have carried out a theoretical study of the complexes formed by this cation and the aromatic amino acids (phenylalanine, histidine, tryptophan and tyrosine) using DFT methods and PCM-water solvation. Both hydrogen bonds and cation-π interactions have been found upon complexation. These interactions have been characterized by means of the analysis of the molecular electron density using the Atoms-in-Molecules approach as well as the orbital interactions using the Natural Bond Orbital methodology. Finally, the effect that the cation-π and hydrogen bond interactions exert on the aromaticity of the corresponding amino acids has been evaluated by calculating the theoretical NICS values, finding that the aromatic character was not heavily modified upon complexation. View Full-Text
Keywords: guanidinium cation; aromatic amino acids; cation-π interactions; hydrogen bond; non-covalent interactions; aromaticity guanidinium cation; aromatic amino acids; cation-π interactions; hydrogen bond; non-covalent interactions; aromaticity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Trujillo, C.; Rodriguez-Sanz, A.A.; Rozas, I. Aromatic Amino Acids-Guanidinium Complexes through Cation-π Interactions. Molecules 2015, 20, 9214-9228.

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