18 F-Trifluoromethanesulfinate Enables Direct C-H 18 F-Trifluoromethylation of Native Aromatic Residues in Peptides

F labeling strategies for unmodified peptides with [ F]fluoride require F-labeled prosthetics for bioconjugation more often with cysteine thiols or lysine amines. Here we explore selective radical chemistry to target aromatic residues applying C-H F-trifluoromethylation. We report a one-step route t...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2020-01, Vol.142 (3), p.1180-1185
Main Authors: Kee, Choon Wee, Tack, Osman, Guibbal, Florian, Wilson, Thomas C, Isenegger, Patrick G, Imiołek, Mateusz, Verhoog, Stefan, Tilby, Michael, Boscutti, Giulia, Ashworth, Sharon, Chupin, Juliette, Kashani, Roxana, Poh, Adeline W J, Sosabowski, Jane K, Macholl, Sven, Plisson, Christophe, Cornelissen, Bart, Willis, Michael C, Passchier, Jan, Davis, Benjamin G, Gouverneur, Véronique
Format: Article
Language:English
Subjects:
Chlorofluorocarbons, Methane - chemistry
Fluorine Radioisotopes - chemistry
Methylation
Peptides - chemistry
Positron-Emission Tomography - methods
Radiopharmaceuticals - chemistry
Sulfur Compounds - chemistry
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Summary:F labeling strategies for unmodified peptides with [ F]fluoride require F-labeled prosthetics for bioconjugation more often with cysteine thiols or lysine amines. Here we explore selective radical chemistry to target aromatic residues applying C-H F-trifluoromethylation. We report a one-step route to [ F]CF SO NH from [ F]fluoride and its application to direct [ F]CF incorporation at tryptophan or tyrosine residues using unmodified peptides as complex as recombinant human insulin. The fully automated radiosynthesis of octreotide[Trp(2-CF F)] enables in vivo positron emission tomography imaging.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.9b11709