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Here we explore selective radical chemistry to target aromatic residues applying C\u2013H 18F-trifluoromethylation. We report a one-step route to [18F]CF3SO2NH4 from [18F]fluoride and its application to direct [18F]CF3 incorporation at tryptophan or tyrosine residues using unmodified peptides as complex as recombinant human insulin. The fully automated radiosynthesis of octreotide[Trp(2-CF218F)] enables in vivo positron emission tomography imaging.<\/jats:p>","DOI":"10.1021\/jacs.9b11709","type":"journal-article","created":{"date-parts":[[2020,1,8]],"date-time":"2020-01-08T14:17:06Z","timestamp":1578493026000},"page":"1180-1185","source":"Crossref","is-referenced-by-count":101,"title":["18F-Trifluoromethanesulfinate Enables\nDirect C\u2013H 18F-Trifluoromethylation of Native\nAromatic Residues in Peptides"],"prefix":"10.1021","volume":"142","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1843-2189","authenticated-orcid":true,"given":"Choon Wee","family":"Kee","sequence":"first","affiliation":[{"name":"University of Oxford , , 12 Mansfield Road , ,","place":["Oxford, U.K., OX1 3TA"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Osman","family":"Tack","sequence":"additional","affiliation":[{"name":"University of Oxford , , 12 Mansfield Road , ,","place":["Oxford, U.K., OX1 3TA"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Florian","family":"Guibbal","sequence":"additional","affiliation":[{"name":"University of Oxford , , 12 Mansfield Road , ,","place":["Oxford, U.K., OX1 3TA"]},{"name":"University of Oxford , , Headington, ,","place":["Oxford, U.K., OX3 7LJ"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thomas C.","family":"Wilson","sequence":"additional","affiliation":[{"name":"University of Oxford , , 12 Mansfield Road , ,","place":["Oxford, U.K., OX1 3TA"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Patrick G.","family":"Isenegger","sequence":"additional","affiliation":[{"name":"University of Oxford , , 12 Mansfield Road , ,","place":["Oxford, U.K., OX1 3TA"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mateusz","family":"Imio\u0142ek","sequence":"additional","affiliation":[{"name":"University of Oxford , , 12 Mansfield Road , ,","place":["Oxford, U.K., OX1 3TA"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stefan","family":"Verhoog","sequence":"additional","affiliation":[{"name":"University of Oxford , , 12 Mansfield Road , ,","place":["Oxford, U.K., OX1 3TA"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michael","family":"Tilby","sequence":"additional","affiliation":[{"name":"University of Oxford , , 12 Mansfield Road , ,","place":["Oxford, U.K., OX1 3TA"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Giulia","family":"Boscutti","sequence":"additional","affiliation":[{"name":"Invicro Ltd , Du Cane Road , ,","place":["London, U.K., W12 0NN"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sharon","family":"Ashworth","sequence":"additional","affiliation":[{"name":"Invicro Ltd , Du Cane Road , ,","place":["London, U.K., W12 0NN"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Juliette","family":"Chupin","sequence":"additional","affiliation":[{"name":"Invicro Ltd , Du Cane Road , ,","place":["London, U.K., W12 0NN"]},{"name":"Queen Mary University of London , , ,","place":["London, U.K., EC1M 6BQ"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Roxana","family":"Kashani","sequence":"additional","affiliation":[{"name":"Queen Mary University of London , , ,","place":["London, U.K., EC1M 6BQ"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Adeline W. 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