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Here, we report the preparation, properties, and applications of chemically stable internal diazo peptides. Peptidyl phosphoranylidene\u2010esters and amides were found to react with triflyl azide primarily to novel 3,4\u2010disubstituted triazolyl\u2010peptides. Nonaflyl azide instead furnished diazo peptides, which are chemically stable from pH\u20051\u201314 as amides and from pH\u20051\u20138 as esters. Thus, diazo peptides prepared by solid phase peptide synthesis were stable to final deprotection with 95\u2009% trifluoroacetic acid. Diazo peptides with the recognition sequence of caspase\u20103 were identified as specific, covalent, and irreversible inhibitors of this enzyme at low nanomolar concentrations. A fluorescent diazo peptide entered living cells enabling microscopic imaging and quantification of apoptotic cells via flow cytometry. Thus, internal diazo peptides constitute a novel class of activity\u2010based probes and enzyme inhibitors useful in chemical biology and medicinal chemistry.<\/jats:p>","DOI":"10.1002\/anie.202411006","type":"journal-article","created":{"date-parts":[[2024,10,9]],"date-time":"2024-10-09T04:20:19Z","timestamp":1728447619000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Chemically Stable Diazo Peptides as Selective Probes of Cysteine Proteases in Living Cells"],"prefix":"10.1002","volume":"63","author":[{"given":"Juliane","family":"Wahl","sequence":"first","affiliation":[{"name":"Institute of Pharmacy, Medicinal Chemistry Freie Universit\u00e4t Berlin  K\u00f6nigin-Luise-Str. 2+4 14195 Berlin Germany"}]},{"family":"Ahsanullah","sequence":"additional","affiliation":[{"name":"Institute of Pharmacy, Medicinal Chemistry Freie Universit\u00e4t Berlin  K\u00f6nigin-Luise-Str. 2+4 14195 Berlin Germany"}]},{"given":"Hana","family":"Zupan","sequence":"additional","affiliation":[{"name":"Institute of Chemistry and Biochemistry Freie Universit\u00e4t Berlin  Arnimallee 22 14195 Berlin Germany"}]},{"given":"Franziska","family":"Gottschalk","sequence":"additional","affiliation":[{"name":"Institute of Pharmacy, Medicinal Chemistry Freie Universit\u00e4t Berlin  K\u00f6nigin-Luise-Str. 2+4 14195 Berlin Germany"}]},{"given":"Andreas","family":"Nerlich","sequence":"additional","affiliation":[{"name":"Department of Infectious Diseases, Respiratory Medicine and Critical Care Charit\u00e9\u2014Universit\u00e4tsmedizin Berlin, Corporate Member of Freie Universit\u00e4t Berlin and Humboldt-Universit\u00e4t zu Berlin  10117 Berlin Germany"}]},{"given":"Christoph","family":"Arkona","sequence":"additional","affiliation":[{"name":"Institute of Pharmacy, Medicinal Chemistry Freie Universit\u00e4t Berlin  K\u00f6nigin-Luise-Str. 2+4 14195 Berlin Germany"}]},{"given":"Andreas C.","family":"Hocke","sequence":"additional","affiliation":[{"name":"Department of Infectious Diseases, Respiratory Medicine and Critical Care Charit\u00e9\u2014Universit\u00e4tsmedizin Berlin, Corporate Member of Freie Universit\u00e4t Berlin and Humboldt-Universit\u00e4t zu Berlin  10117 Berlin Germany"}]},{"given":"Bettina G.","family":"Keller","sequence":"additional","affiliation":[{"name":"Institute of Chemistry and Biochemistry Freie Universit\u00e4t Berlin  Arnimallee 22 14195 Berlin Germany"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6678-3165","authenticated-orcid":false,"given":"J\u00f6rg","family":"Rademann","sequence":"additional","affiliation":[{"name":"Institute of Pharmacy, Medicinal Chemistry Freie Universit\u00e4t Berlin  K\u00f6nigin-Luise-Str. 2+4 14195 Berlin Germany"}]}],"member":"311","published-online":{"date-parts":[[2024,11,5]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"The tetrapeptide Gly\u2212Gly\u2212Gly\u2212Gly\u2212OEt was diazotized and the crystalline product was investigated by elemental analysis in"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19040370215"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.188301601173"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/p19900001005"},{"key":"e_1_2_3_5_1","unstructured":"\u00a0"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-291X(77)91199-8"},{"key":"e_1_2_3_7_2","first-page":"821","volume":"80","author":"Shaw E.","year":"1981","journal-title":"Meth. 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