{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T20:04:52Z","timestamp":1760385892592,"version":"build-2065373602"},"reference-count":48,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2022,3,25]],"date-time":"2022-03-25T00:00:00Z","timestamp":1648166400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001665","name":"Agence Nationale de la Recherche","doi-asserted-by":"publisher","award":["ANR-14-CE06-0029-01"],"award-info":[{"award-number":["ANR-14-CE06-0029-01"]}],"id":[{"id":"10.13039\/501100001665","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Symmetry"],"abstract":"<jats:p>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.<\/jats:p>","DOI":"10.3390\/sym14040679","type":"journal-article","created":{"date-parts":[[2022,3,27]],"date-time":"2022-03-27T21:31:25Z","timestamp":1648416685000},"page":"679","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["How Symmetry Influences the Dissociation of Protonated Cyclic Peptides"],"prefix":"10.3390","volume":"14","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3134-328X","authenticated-orcid":false,"given":"Ariel F.","family":"P\u00e9rez-Mellor","sequence":"first","affiliation":[{"name":"CNRS, Institut des Sciences Mol\u00e9culaires d\u2019Orsay, Universit\u00e9 Paris-Saclay, 91405 Orsay, France"},{"name":"Laboratoire de Chimie Th\u00e9orique, Sorbonne Universit\u00e9, UMR 7616 CNRS, 4, Place Jussieu, 75005 Paris, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5160-489X","authenticated-orcid":false,"given":"Riccardo","family":"Spezia","sequence":"additional","affiliation":[{"name":"Laboratoire de Chimie Th\u00e9orique, Sorbonne Universit\u00e9, UMR 7616 CNRS, 4, Place Jussieu, 75005 Paris, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5540-0667","authenticated-orcid":false,"given":"Anne","family":"Zehnacker","sequence":"additional","affiliation":[{"name":"CNRS, Institut des Sciences Mol\u00e9culaires d\u2019Orsay, Universit\u00e9 Paris-Saclay, 91405 Orsay, France"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,3,25]]},"reference":[{"unstructured":"Bunker, P.R., and Jensen, R. 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