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F-Trifluoromethanesulfinate Enables Direct C-H F-Trifluoromethylation of Native Aromatic Residues in Peptides. | LitMetric
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]CFSONH 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-CFF)] enables in vivo positron emission tomography imaging.
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