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

Choon Wee Kee | Zendy; Osman Tack | Zendy; Florian Guibbal | Zendy; Thomas C. Wilson | Zendy; Patrick G. Isenegger | Zendy; Mateusz Imiołek | Zendy; Stefan Verhoog | Zendy; Michael J. Tilby | Zendy; Giulia Boscutti | Zendy; Sharon Ashworth | Zendy; Juliette Chupin | Zendy; Roxana Kashani | Zendy; Adeline W. J. Poh | Zendy; Jane Sosabowski | Zendy; Sven Macholl | Zendy; Christophe Plisson | Zendy; Bart Cornelissen | Zendy; Michael C. Willis | Zendy; Jan Passchier | Zendy; Benjamin G. Davis | Zendy; Véronique Gouverneur | Zendy

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

Author(s) -

Choon Wee Kee,

Osman Tack,

Florian Guibbal,

Thomas C. Wilson,

Patrick G. Isenegger,

Mateusz Imiołek,

Stefan Verhoog,

Michael J. Tilby,

Giulia Boscutti,

Sharon Ashworth,

Juliette Chupin,

Roxana Kashani,

Adeline W. J. Poh,

Jane Sosabowski,

Sven Macholl,

Christophe Plisson,

Bart Cornelissen,

Michael C. Willis,

Jan Passchier,

Benjamin G. Davis,

Véronique Gouverneur

Publication year - 2020

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.9b11709

Subject(s) - chemistry , bioconjugation , radiosynthesis , trifluoromethylation , cysteine , combinatorial chemistry , tyrosine , tryptophan , peptide , lysine , amide , amino acid , in vivo , organic chemistry , biochemistry , enzyme , alkyl , microbiology and biotechnology , trifluoromethyl , biology

18 F labeling strategies for unmodified peptides with [ 18 F]fluoride require 18 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 18 F-trifluoromethylation. We report a one-step route to [ 18 F]CF 3 SO 2 NH 4 from [ 18 F]fluoride and its application to direct [ 18 F]CF 3 incorporation at tryptophan or tyrosine residues using unmodified peptides as complex as recombinant human insulin. The fully automated radiosynthesis of octreotide[Trp(2-CF 2 18 F)] enables in vivo positron emission tomography imaging.

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