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Methods that allow the efficient diversification of peptides with non\u2010canonical modifications are therefore highly sought after. One possible strategy for accessing broadly diversified peptides is on\u2010resin late\u2010stage modification, whereby a functional site\u2014typically an amino acid side chain or the N\u2010terminus\u2014is usually singly modified after peptide chain assembly, while the other functionalities remain protected. Here, we present an on\u2010resin late\u2010stage dual\u2010modification approach. This approach involves a reaction sequence that includes copper\u2010catalyzed S\u2010alkynylation of a resin\u2010bound peptide thiosulfonate, followed by an iridium\u2010catalyzed azide\u2010alkyne click reaction (IrAAC). Thus, peptides with complex non\u2010canonical modifications are obtained. The dual\u2010modification approach is highly modular and compatible with a wide range of alkynes for S\u2010alkynylation and azides for IrAAC. Furthermore, this chemistry can be used to modify complex peptides, such as the 34\u2010amino\u2010acid WW domain. In a structure\u2010activity relationship study of triazole\u2010containing peptide protease inhibitors of the dengue virus, we demonstrate the great potential of the modular on\u2010resin dual\u2010modification of peptide thiosulfonates for modulating peptide\u2010protein interactions.<\/jats:p>","DOI":"10.1002\/anie.8315692","type":"journal-article","created":{"date-parts":[[2026,7,13]],"date-time":"2026-07-13T17:33:43Z","timestamp":1783964023000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Peptide Thioester and Triazole Derivatives Through On\u2010Resin Dual\u2010Modification of Peptide Thiosulfonates"],"prefix":"10.1002","volume":"65","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0926-2181","authenticated-orcid":false,"given":"Marius","family":"Werner","sequence":"first","affiliation":[{"name":"Institute of Organic Chemistry Heidelberg University  Heidelberg Germany"},{"name":"Institute of Pharmacy and Molecular Biotechnology (IPMB) Heidelberg University  Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0003-7598-4024","authenticated-orcid":false,"given":"Agnes","family":"Bergmann","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry Heidelberg University  Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0004-2100-1587","authenticated-orcid":false,"given":"Chenxi","family":"Liu","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry Heidelberg University  Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5839-7675","authenticated-orcid":false,"given":"Mira","family":"Behnam","sequence":"additional","affiliation":[{"name":"Institute of Pharmacy and Molecular Biotechnology (IPMB) Heidelberg University  Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3522-9182","authenticated-orcid":false,"given":"Christian","family":"Klein","sequence":"additional","affiliation":[{"name":"Institute of Pharmacy and Molecular Biotechnology (IPMB) Heidelberg University  Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1176-7018","authenticated-orcid":false,"given":"Franziska","family":"Thomas","sequence":"additional","affiliation":[{"name":"Institute of Organic Chemistry Heidelberg University  Heidelberg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,7,13]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41573\u2010020\u201000135\u20108"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.4155\/fdd\u20102022\u20100005"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2018.01.012"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b13178"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41392\u2010024\u201002107\u20105"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsmedchemlett.3c00037"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.4556652"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.1c05502"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.1c02928"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.3c03070"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/advs.202400640"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010019\u201011395\u20103"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscombsci.5b00087"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201812620"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202509854"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202307782"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c17615"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202201339"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202501229"},{"key":"e_1_2_8_21_1","first-page":"407","volume-title":"Methods in Enzymology","author":"Kenyon G. 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