How Symmetry Influences the Dissociation of Protonated Cyclic Peptides
Protonated cyclic dipeptides undergo collision-induced dissociation, and this reaction mechanism strongly depends on the symmetry and the nature of the residues. We review the main dissociation mechanism for a series of cyclic dipeptides, obtained through chemical dynamics simulations. The systems r...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-03-01
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| Series: | Symmetry |
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| Online Access: | https://www.mdpi.com/2073-8994/14/4/679 |
| _version_ | 1797434230819520512 |
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| author | Ariel F. Pérez-Mellor Riccardo Spezia Anne Zehnacker |
| author_facet | Ariel F. Pérez-Mellor Riccardo Spezia Anne Zehnacker |
| author_sort | Ariel F. Pérez-Mellor |
| collection | DOAJ |
| description | Protonated cyclic dipeptides undergo collision-induced dissociation, and this reaction mechanism strongly depends on the symmetry and the nature of the residues. We review the main dissociation mechanism for a series of cyclic dipeptides, obtained through chemical dynamics simulations. The systems range from the symmetrical cyclo-(glycyl-glycyl), with two possible symmetrical protonation sites located on the peptide ring, to cyclo-(tyrosyl-prolyl), where the symmetry of protonation sites on the peptide ring is broken by the dissimilar nature of the different residues. Finally, cyclo-(phenylalanyl-histidyl) shows a completely asymmetric situation, with the proton located on one of the dipeptide side chains, which explains the peculiar fragmentation mechanism induced by shuttling the proton, whose efficiency is strongly dependent on the relative chirality of the residues. |
| first_indexed | 2024-03-09T10:28:16Z |
| format | Article |
| id | doaj.art-82671e316eb648198017aac94b7683bf |
| institution | Directory Open Access Journal |
| issn | 2073-8994 |
| language | English |
| last_indexed | 2024-03-09T10:28:16Z |
| publishDate | 2022-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Symmetry |
| spelling | doaj.art-82671e316eb648198017aac94b7683bf2023-12-01T21:28:16ZengMDPI AGSymmetry2073-89942022-03-0114467910.3390/sym14040679How Symmetry Influences the Dissociation of Protonated Cyclic PeptidesAriel F. Pérez-Mellor0Riccardo Spezia1Anne Zehnacker2CNRS, Institut des Sciences Moléculaires d’Orsay, Université Paris-Saclay, 91405 Orsay, FranceLaboratoire de Chimie Théorique, Sorbonne Université, UMR 7616 CNRS, 4, Place Jussieu, 75005 Paris, FranceCNRS, Institut des Sciences Moléculaires d’Orsay, Université Paris-Saclay, 91405 Orsay, FranceProtonated cyclic dipeptides undergo collision-induced dissociation, and this reaction mechanism strongly depends on the symmetry and the nature of the residues. We review the main dissociation mechanism for a series of cyclic dipeptides, obtained through chemical dynamics simulations. The systems range from the symmetrical cyclo-(glycyl-glycyl), with two possible symmetrical protonation sites located on the peptide ring, to cyclo-(tyrosyl-prolyl), where the symmetry of protonation sites on the peptide ring is broken by the dissimilar nature of the different residues. Finally, cyclo-(phenylalanyl-histidyl) shows a completely asymmetric situation, with the proton located on one of the dipeptide side chains, which explains the peculiar fragmentation mechanism induced by shuttling the proton, whose efficiency is strongly dependent on the relative chirality of the residues.https://www.mdpi.com/2073-8994/14/4/679chiralitymass spectrometrychemical dynamicsquantum chemistry |
| spellingShingle | Ariel F. Pérez-Mellor Riccardo Spezia Anne Zehnacker How Symmetry Influences the Dissociation of Protonated Cyclic Peptides Symmetry chirality mass spectrometry chemical dynamics quantum chemistry |
| title | How Symmetry Influences the Dissociation of Protonated Cyclic Peptides |
| title_full | How Symmetry Influences the Dissociation of Protonated Cyclic Peptides |
| title_fullStr | How Symmetry Influences the Dissociation of Protonated Cyclic Peptides |
| title_full_unstemmed | How Symmetry Influences the Dissociation of Protonated Cyclic Peptides |
| title_short | How Symmetry Influences the Dissociation of Protonated Cyclic Peptides |
| title_sort | how symmetry influences the dissociation of protonated cyclic peptides |
| topic | chirality mass spectrometry chemical dynamics quantum chemistry |
| url | https://www.mdpi.com/2073-8994/14/4/679 |
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