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Yet, we still lack methods to chemically modify each naturally occurring amino acid sidechain. To help address this gap, we show that\n                    <jats:italic>N<\/jats:italic>\n                    ,\n                    <jats:italic>\u03b1<\/jats:italic>\n                    \u2010diaryl oxaziridines expand the scope of bioconjugation methods to chemically modify cysteine, methionine, and tryptophan residues with evidence for additional tyrosine labelling in a proteomic context. Conjugation primarily at tryptophan sites can be accessed by selective cleavage of modifications at other sidechains. The\n                    <jats:italic>N<\/jats:italic>\n                    ,\n                    <jats:italic>\u03b1<\/jats:italic>\n                    \u2010diaryl oxaziridine reagents are accessed through photoisomerization of nitrones, which serve as photocaged reagents, thus providing an additional level of control over reactivity. Initial guiding principles for the design of nitrone reagents are developed by exploring the impact of structure on UV\/Vis absorption, photoisomerization, and reactivity. We identify a nitrone structure that maximizes photoisomerization efficiency, the aqueous stability of the oxaziridine, the extent of amino acid modification, and the stability of the resulting amino acid conjugates. We then translate nitrone reagents to modify proteins in aqueous conditions. Finally, we use nitrones to profile reactive residues across the proteome of a mammalian cell line and find that they expand the proteome coverage.\n                  <\/jats:p>","DOI":"10.1002\/anie.202415976","type":"journal-article","created":{"date-parts":[[2024,11,7]],"date-time":"2024-11-07T14:53:52Z","timestamp":1730991232000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Light\u2010Activated Reactivity of Nitrones with Amino Acids and Proteins"],"prefix":"10.1002","volume":"64","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1563-0382","authenticated-orcid":false,"given":"Kacper","family":"Skakuj","sequence":"first","affiliation":[{"name":"Department of Chemistry University of California, Berkeley  Berkeley CA-94720 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0006-8190-1231","authenticated-orcid":false,"given":"Maximilian","family":"Iglhaut","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of California, Berkeley  Berkeley CA-94720 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1909-4177","authenticated-orcid":false,"given":"Qian","family":"Shao","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of California, Berkeley  Berkeley CA-94720 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Francisco J.","family":"Garcia","sequence":"additional","affiliation":[{"name":"Novartis Biomedical Research  Cambridge MA-02139 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bo\u2010Yang","family":"Huang","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of California, Berkeley  Berkeley CA-94720 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Scott M.","family":"Brittain","sequence":"additional","affiliation":[{"name":"Novartis Biomedical Research  Cambridge MA-02139 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2806-7819","authenticated-orcid":false,"given":"Alexey I.","family":"Nesvizhskii","sequence":"additional","affiliation":[{"name":"Department of Pathology Department of Computational Medicine and Bioinformatics University of Michigan, Ann Arbor  Ann Arbor Michigan 48109 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4933-2623","authenticated-orcid":false,"given":"Markus","family":"Schirle","sequence":"additional","affiliation":[{"name":"Novartis Biomedical Research  Cambridge MA-02139 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1614-8360","authenticated-orcid":false,"given":"Daniel K.","family":"Nomura","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of California, Berkeley  Berkeley CA-94720 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8018-2198","authenticated-orcid":false,"given":"F. 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