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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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