Aromatic Amino Acids-Guanidinium Complexes through Cation-π Interactions

Molecules

Cristina Trujillo²  Ana A. Rodriguez-Sanz¹  Isabel Rozas² 

[1] 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; E-Mail:;Trinity Biomedical Sciences Institute, School of Chemistry, Trinity College Dublin, 152-160 Pearse Street, Dublin 2, Ireland; E-Mail:

关键词: guanidinium cation;    aromatic amino acids;    cation-π interactions;    hydrogen bond;    non-covalent interactions;    aromaticity;   

DOI  :  10.3390/molecules20059214

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.