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To overcome this limitation, we developed a thiophilic transition metal-mediated strategy by adapting a three-component reagent system originally conceived for solution-phase synthesis. Systematic screening of copper, zinc and silver salts identified Ag(CF3CO2) and AgNO3 as the most effective promoters of Trt removal. The optimized protocol enabled reproducible and efficient deprotection, provided preliminary mechanistic insight through control experiments, and proved compatible with common Fmoc-SPPS protecting groups and alternative solvents. Furthermore, in situ thiol release enabled direct on-resin S-alkylation with a selected range of aliphatic substituents, including those bearing aromatic moieties, highlighting the utility of the method for the late-stage functionalization of cysteine-containing resin-bound peptides.<\/jats:p>","DOI":"10.1021\/acsomega.6c05277","type":"journal-article","created":{"date-parts":[[2026,9,26]],"date-time":"2026-09-26T04:01:34Z","timestamp":1790395294000},"page":"59327-59338","source":"Crossref","is-referenced-by-count":1,"title":["A Thiophilic Metal-Mediated\nCysteine\n                    <i>S<\/i>\n                    -Detritylation Strategy: Enhancing\nOrthogonality in Solid-Phase\nPeptide Synthesis"],"prefix":"10.1021","volume":"11","author":[{"given":"Salvatore","family":"Mottola","sequence":"first","affiliation":[{"name":"University of Campania Luigi Vanvitelli , , via Vivaldi 43 , ,","place":["Caserta, Italy, 81100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2163-5163","authenticated-orcid":true,"given":"Rosa","family":"Bellavita","sequence":"additional","affiliation":[{"name":"University of Naples Federico II , , via Domenico Montesano 49 , ,","place":["Naples, Italy, 80131"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0002-6662-007X","authenticated-orcid":true,"given":"Ida","family":"Boccino","sequence":"additional","affiliation":[{"name":"University of Naples Federico II , , via Domenico Montesano 49 , ,","place":["Naples, Italy, 80131"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gennaro Maria","family":"Bailo","sequence":"additional","affiliation":[{"name":"University of Naples Federico II , , via Domenico Montesano 49 , ,","place":["Naples, Italy, 80131"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Roberto","family":"Cutolo","sequence":"additional","affiliation":[{"name":"University of Campania Luigi Vanvitelli , , via Vivaldi 43 , ,","place":["Caserta, Italy, 81100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6856-414X","authenticated-orcid":true,"given":"Mariateresa","family":"Giustiniano","sequence":"additional","affiliation":[{"name":"University of Naples Federico II , , via Domenico Montesano 49 , ,","place":["Naples, Italy, 80131"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7849-7024","authenticated-orcid":true,"given":"Stefania","family":"Galdiero","sequence":"additional","affiliation":[{"name":"University of Naples Federico II , , via Domenico Montesano 49 , ,","place":["Naples, Italy, 80131"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paolo","family":"Grieco","sequence":"additional","affiliation":[{"name":"University of Naples Federico II , , via Domenico Montesano 49 , ,","place":["Naples, Italy, 80131"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9286-4433","authenticated-orcid":true,"given":"Salvatore","family":"Di Maro","sequence":"additional","affiliation":[{"name":"University of Campania Luigi Vanvitelli , , via Vivaldi 43 , ,","place":["Caserta, Italy, 81100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4310-9447","authenticated-orcid":true,"given":"Anna","family":"Messere","sequence":"additional","affiliation":[{"name":"University of Campania Luigi Vanvitelli , , via Vivaldi 43 , ,","place":["Caserta, Italy, 81100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9607-229X","authenticated-orcid":true,"given":"Francesco","family":"Merlino","sequence":"additional","affiliation":[{"name":"University of Naples Federico II , , via Domenico Montesano 49 , ,","place":["Naples, Italy, 80131"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,25]]},"reference":[{"key":"2026100610461930800_cit1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules27051601","article-title":"Catch, modify and analyze: methods of chemoselective\nmodification of cysteine-containing peptides","volume":"27","author":"Kowalska","year":"2022","journal-title":"Molecules"},{"key":"2026100610461930800_cit2","doi-asserted-by":"publisher","first-page":"28","DOI":"10.1016\/j.cbpa.2020.04.017","article-title":"Recent advances of thiol-selective bioconjugation reactions","volume":"58","author":"Ochtrop","year":"2020","journal-title":"Curr. 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Protein Res."},{"key":"2026100610461930800_cit25","doi-asserted-by":"publisher","first-page":"445","DOI":"10.1016\/S0008-6215(97)00190-0","article-title":"Detritylation\nof mono- and di-saccharide\nderivatives using ferric chloride hydrate","volume":"303","author":"Ding","year":"1997","journal-title":"Carbohydr.\nRes."},{"key":"2026100610461930800_cit26","doi-asserted-by":"publisher","first-page":"2817","DOI":"10.1016\/S0040-4039(00)00270-7","article-title":"Detritylation with ytterbium triflate","volume":"41","author":"Lu","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"2026100610461930800_cit27","doi-asserted-by":"publisher","first-page":"6805","DOI":"10.1016\/S0040-4020(01)00616-0","article-title":"Efficient and catalytic deprotection\nof triphenylmethyl\nethers with Ce(OTf)4","volume":"57","author":"Khalafi-Nezhad","year":"2001","journal-title":"Tetrahedron"},{"key":"2026100610461930800_cit28","doi-asserted-by":"publisher","first-page":"18","DOI":"10.1016\/j.carres.2014.08.002","article-title":"In(III)\ntriflate-catalyzed detritylation\nand glycosylation by solvent-free ball milling","volume":"397","author":"Kumar","year":"2014","journal-title":"Carbohydr. 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