Molecular Simulation of the Separation of Some Amino Acid Enantiomers by β-Cyclodextrin in Gas-Phase
The complexes formed by β-cyclodextrin and some amino acids (alanine, valine, leucine, and isoleucine) in vacuo are studied by molecular mechanics and dynamics simulations. These methods have been improved with respect to our previous studies with amino acids, regarding the determination of molecula...
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| Format: | Article |
| Language: | English |
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Frontiers Media S.A.
2020-09-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2020.00823/full |
| _version_ | 1819057195921178624 |
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| author | Elena Alvira |
| author_facet | Elena Alvira |
| author_sort | Elena Alvira |
| collection | DOAJ |
| description | The complexes formed by β-cyclodextrin and some amino acids (alanine, valine, leucine, and isoleucine) in vacuo are studied by molecular mechanics and dynamics simulations. These methods have been improved with respect to our previous studies with amino acids, regarding the determination of molecular structures or initial enantiomer dispositions in the molecular dynamics trajectories. The greatest contribution to the interaction energy is from the van der Waals term, although the discrimination between enantiomers is due mainly to the electrostatic contribution. The lowest energy structures of the complexes obtained from molecular mechanics are inclusion complexes in which the carboxylic end of amino acids is pointing toward the narrow (D-) or wide rim (L-) of β-cyclodextrin. The position probability density provided by molecular dynamics also confirms inclusion complex formation, because the guests spend most time inside the cavity of β-cyclodextrin along its axis, with the carboxylic end pointing toward the narrow rim. The L-amino acids are the first eluted enantiomers in all cases and chiral discrimination increases with the size of guests, except leucine, which has the lowest capacity to discriminate. During the simulation, Ala and Val remain in weakly enantioselective regions, while Leu and Ile stay in zones with great chiral selectivity. |
| first_indexed | 2024-12-21T13:35:27Z |
| format | Article |
| id | doaj.art-b990bdfe759f4542afc66bf0d89f5955 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-21T13:35:27Z |
| publishDate | 2020-09-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-b990bdfe759f4542afc66bf0d89f59552022-12-21T19:02:11ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462020-09-01810.3389/fchem.2020.00823575627Molecular Simulation of the Separation of Some Amino Acid Enantiomers by β-Cyclodextrin in Gas-PhaseElena AlviraThe complexes formed by β-cyclodextrin and some amino acids (alanine, valine, leucine, and isoleucine) in vacuo are studied by molecular mechanics and dynamics simulations. These methods have been improved with respect to our previous studies with amino acids, regarding the determination of molecular structures or initial enantiomer dispositions in the molecular dynamics trajectories. The greatest contribution to the interaction energy is from the van der Waals term, although the discrimination between enantiomers is due mainly to the electrostatic contribution. The lowest energy structures of the complexes obtained from molecular mechanics are inclusion complexes in which the carboxylic end of amino acids is pointing toward the narrow (D-) or wide rim (L-) of β-cyclodextrin. The position probability density provided by molecular dynamics also confirms inclusion complex formation, because the guests spend most time inside the cavity of β-cyclodextrin along its axis, with the carboxylic end pointing toward the narrow rim. The L-amino acids are the first eluted enantiomers in all cases and chiral discrimination increases with the size of guests, except leucine, which has the lowest capacity to discriminate. During the simulation, Ala and Val remain in weakly enantioselective regions, while Leu and Ile stay in zones with great chiral selectivity.https://www.frontiersin.org/article/10.3389/fchem.2020.00823/fullcyclodextrinsamino acidsenantiomersmolecular mechanicsmolecular dynamicsinclusion complex |
| spellingShingle | Elena Alvira Molecular Simulation of the Separation of Some Amino Acid Enantiomers by β-Cyclodextrin in Gas-Phase Frontiers in Chemistry cyclodextrins amino acids enantiomers molecular mechanics molecular dynamics inclusion complex |
| title | Molecular Simulation of the Separation of Some Amino Acid Enantiomers by β-Cyclodextrin in Gas-Phase |
| title_full | Molecular Simulation of the Separation of Some Amino Acid Enantiomers by β-Cyclodextrin in Gas-Phase |
| title_fullStr | Molecular Simulation of the Separation of Some Amino Acid Enantiomers by β-Cyclodextrin in Gas-Phase |
| title_full_unstemmed | Molecular Simulation of the Separation of Some Amino Acid Enantiomers by β-Cyclodextrin in Gas-Phase |
| title_short | Molecular Simulation of the Separation of Some Amino Acid Enantiomers by β-Cyclodextrin in Gas-Phase |
| title_sort | molecular simulation of the separation of some amino acid enantiomers by β cyclodextrin in gas phase |
| topic | cyclodextrins amino acids enantiomers molecular mechanics molecular dynamics inclusion complex |
| url | https://www.frontiersin.org/article/10.3389/fchem.2020.00823/full |
| work_keys_str_mv | AT elenaalvira molecularsimulationoftheseparationofsomeaminoacidenantiomersbybcyclodextriningasphase |