Aromatic Amino Acids-Guanidinium Complexes through Cation-π Interactions
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 sol...
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| Format: | Article |
| Language: | English |
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MDPI AG
2015-05-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/5/9214 |
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| author | Cristina Trujillo Ana A. Rodriguez-Sanz Isabel Rozas |
| author_facet | Cristina Trujillo Ana A. Rodriguez-Sanz Isabel Rozas |
| author_sort | Cristina Trujillo |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-22T19:32:27Z |
| format | Article |
| id | doaj.art-57f4340e8d534b5d9ac9f37ae2a340df |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-22T19:32:27Z |
| publishDate | 2015-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-57f4340e8d534b5d9ac9f37ae2a340df2022-12-21T18:15:04ZengMDPI AGMolecules1420-30492015-05-012059214922810.3390/molecules20059214molecules20059214Aromatic Amino Acids-Guanidinium Complexes through Cation-π InteractionsCristina Trujillo0Ana A. Rodriguez-Sanz1Isabel Rozas2Trinity Biomedical Sciences Institute, School of Chemistry, Trinity College Dublin, 152-160 Pearse Street, Dublin 2, IrelandDepartamento de Química Física, Facultade de Ciencias, Universidade de Santiago de Compostela, Campus de Lugo, Avda. Alfonso X El Sabio s/n, 27002 Lugo, SpainTrinity Biomedical Sciences Institute, School of Chemistry, Trinity College Dublin, 152-160 Pearse Street, Dublin 2, IrelandContinuing 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.http://www.mdpi.com/1420-3049/20/5/9214guanidinium cationaromatic amino acidscation-π interactionshydrogen bondnon-covalent interactionsaromaticity |
| spellingShingle | Cristina Trujillo Ana A. Rodriguez-Sanz Isabel Rozas Aromatic Amino Acids-Guanidinium Complexes through Cation-π Interactions Molecules guanidinium cation aromatic amino acids cation-π interactions hydrogen bond non-covalent interactions aromaticity |
| title | Aromatic Amino Acids-Guanidinium Complexes through Cation-π Interactions |
| title_full | Aromatic Amino Acids-Guanidinium Complexes through Cation-π Interactions |
| title_fullStr | Aromatic Amino Acids-Guanidinium Complexes through Cation-π Interactions |
| title_full_unstemmed | Aromatic Amino Acids-Guanidinium Complexes through Cation-π Interactions |
| title_short | Aromatic Amino Acids-Guanidinium Complexes through Cation-π Interactions |
| title_sort | aromatic amino acids guanidinium complexes through cation π interactions |
| topic | guanidinium cation aromatic amino acids cation-π interactions hydrogen bond non-covalent interactions aromaticity |
| url | http://www.mdpi.com/1420-3049/20/5/9214 |
| work_keys_str_mv | AT cristinatrujillo aromaticaminoacidsguanidiniumcomplexesthroughcationpinteractions AT anaarodriguezsanz aromaticaminoacidsguanidiniumcomplexesthroughcationpinteractions AT isabelrozas aromaticaminoacidsguanidiniumcomplexesthroughcationpinteractions |