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Structural Modeling of Djenkolic Acid with Sulfur Replaced by Selenium and Tellurium
The comparative structural modeling of djenkolic acid and its derivatives containing selenium and tellurium in chalcogen sites (Ch = Se, Te) has provided detailed information about the bond lengths and bond angles, filling the gap in what we know about the structural characteristics of these aminoac...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271791/ https://www.ncbi.nlm.nih.gov/pubmed/24747644 http://dx.doi.org/10.3390/molecules19044847 |
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author | Melnikov, Petr Nascimento, Valter A. Silva, Anderson F. Consolo, Lourdes Z. Z. |
author_facet | Melnikov, Petr Nascimento, Valter A. Silva, Anderson F. Consolo, Lourdes Z. Z. |
author_sort | Melnikov, Petr |
collection | PubMed |
description | The comparative structural modeling of djenkolic acid and its derivatives containing selenium and tellurium in chalcogen sites (Ch = Se, Te) has provided detailed information about the bond lengths and bond angles, filling the gap in what we know about the structural characteristics of these aminoacids. The investigation using the molecular mechanics technique with good approximation confirmed the available information on X-ray refinements for the related compounds methionine and selenomethionine, as well as for an estimate made earlier for telluromethionine. It was shown that the Ch-C(3) and Ch-C(4) bond lengths grow in parallel with the increasing anionic radii. Although the distances C-C, C-O, and C-N are very similar, the geometry of conformers is quite different owing to the possibility of rotation about four carbon atoms, hence the remarkable variability observed in dihedral angles. It was shown that the compounds contain a rigid block with two Ch atoms connected through a methylene group. The standard program Gaussian 03 with graphical interface Gaussview 4.1.2 has proved to be satisfactory tool for the structural description of less-common bioactive compositions when direct X-ray results are absent. |
format | Online Article Text |
id | pubmed-6271791 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62717912019-01-02 Structural Modeling of Djenkolic Acid with Sulfur Replaced by Selenium and Tellurium Melnikov, Petr Nascimento, Valter A. Silva, Anderson F. Consolo, Lourdes Z. Z. Molecules Article The comparative structural modeling of djenkolic acid and its derivatives containing selenium and tellurium in chalcogen sites (Ch = Se, Te) has provided detailed information about the bond lengths and bond angles, filling the gap in what we know about the structural characteristics of these aminoacids. The investigation using the molecular mechanics technique with good approximation confirmed the available information on X-ray refinements for the related compounds methionine and selenomethionine, as well as for an estimate made earlier for telluromethionine. It was shown that the Ch-C(3) and Ch-C(4) bond lengths grow in parallel with the increasing anionic radii. Although the distances C-C, C-O, and C-N are very similar, the geometry of conformers is quite different owing to the possibility of rotation about four carbon atoms, hence the remarkable variability observed in dihedral angles. It was shown that the compounds contain a rigid block with two Ch atoms connected through a methylene group. The standard program Gaussian 03 with graphical interface Gaussview 4.1.2 has proved to be satisfactory tool for the structural description of less-common bioactive compositions when direct X-ray results are absent. MDPI 2014-04-17 /pmc/articles/PMC6271791/ /pubmed/24747644 http://dx.doi.org/10.3390/molecules19044847 Text en © 2014 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). |
spellingShingle | Article Melnikov, Petr Nascimento, Valter A. Silva, Anderson F. Consolo, Lourdes Z. Z. Structural Modeling of Djenkolic Acid with Sulfur Replaced by Selenium and Tellurium |
title | Structural Modeling of Djenkolic Acid with Sulfur Replaced by Selenium and Tellurium |
title_full | Structural Modeling of Djenkolic Acid with Sulfur Replaced by Selenium and Tellurium |
title_fullStr | Structural Modeling of Djenkolic Acid with Sulfur Replaced by Selenium and Tellurium |
title_full_unstemmed | Structural Modeling of Djenkolic Acid with Sulfur Replaced by Selenium and Tellurium |
title_short | Structural Modeling of Djenkolic Acid with Sulfur Replaced by Selenium and Tellurium |
title_sort | structural modeling of djenkolic acid with sulfur replaced by selenium and tellurium |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6271791/ https://www.ncbi.nlm.nih.gov/pubmed/24747644 http://dx.doi.org/10.3390/molecules19044847 |
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