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While the majority of cysteine\u2010based peptide modifications rely on the nucleophilicity of the side chain thiol functionality, umpolung approaches\u2014exploiting instead the electrophilicity of the cystine disulfide\u2014are underexplored. Using structurally diverse sulfinate salts, we have optimized a mild, photochemical strategy for the generation and coupling of carbon\u2010centered radicals with both symmetrical and electronically\u2010distinct, unsymmetrical cystine disulfides using high\u2010throughput experimentation techniques. A library of modified peptides was accessible, as confirmed by qualitative and quantitative analytical data, providing valuable insights into the matched reactivity of specific radical\/disulfide substrate pairings. The method was broadly compatible with a range of unprotected amino acids, including histidine, tryptophan, and tyrosine, and can be used for the functionalization of biologically relevant peptides, as exemplified by the selective, late\u2010stage modification of a semaglutide analogue and the preparation of high\u2010value macrocyclic peptides.<\/jats:p>","DOI":"10.1002\/anie.5484068","type":"journal-article","created":{"date-parts":[[2026,7,7]],"date-time":"2026-07-07T14:10:49Z","timestamp":1783433449000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Harnessing the Reactivity of Sulfinate Salts With Cystine: An Umpolung Approach to Residue\u2010Specific Peptide Modification"],"prefix":"10.1002","volume":"65","author":[{"given":"Joshua M.","family":"Hammond","sequence":"first","affiliation":[{"name":"Research School of Chemistry Australian National University  Canberra Australia"},{"name":"Australian Research 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