18F-Trifluoromethanesulfinate enables Direct C–H 18F-Trifluoromethylation of Native Aromatic Residues in Peptides,Journal of the American Chemical Society

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18F-Trifluoromethanesulfinate enables Direct C–H 18F-Trifluoromethylation of Native Aromatic Residues in Peptides
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-01-08 , DOI: 10.1021/jacs.9b11709
Choon Wee Kee ₁ , Osman Tack ₁ , Florian Guibbal _{1,

2} , Thomas C Wilson ₁ , Patrick G Isenegger ₁ , Mateusz Imiołek ₁ , Stefan Verhoog ₁ , Michael Tilby ₁ , Giulia Boscutti ₃ , Sharon Ashworth ₃ , Juliette Chupin _{3,

4} , Roxana Kashani ₄ , Adeline W J Poh ₁ , Jane K Sosabowski ₄ , Sven Macholl _{3,

4} , Christophe Plisson ₃ , Bart Cornelissen ₂ , Michael C Willis ₁ , Jan Passchier ₃ , Benjamin G Davis ₁ , Véronique Gouverneur ₁

Affiliation

18F labeling strategies for unmodified peptides with [18F]fluoride require 18F-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 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.

中文翻译：

18F-三氟甲亚磺酸盐可实现肽中天然芳香残基的直接 C–H 18F-三氟甲基化

用[18F]氟化物对未修饰的肽进行 18F 标记策略需要 18F 标记的假体，以便更频繁地与半胱氨酸硫醇或赖氨酸胺进行生物共轭。在这里，我们探索选择性自由基化学，以应用 C–H 18F-三氟甲基化来靶向芳香族残基。我们报告了一种从[18F]氟化物合成[18F]CF3SO2NH4的一步路线，及其使用与重组人胰岛素一样复杂的未修饰肽直接将[18F]CF3掺入色氨酸或酪氨酸残基的应用。奥曲肽[Trp(2-CF218F)]的全自动放射合成可实现体内正电子发射断层扫描成像。

更新日期：2020-01-08

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