Literature DB >> 29301394

18F-Trifluoromethylation of Unmodified Peptides with 5-18F-(Trifluoromethyl)dibenzothiophenium Trifluoromethanesulfonate.

Stefan Verhoog1, Choon Wee Kee1, Yanlan Wang1, Tanatorn Khotavivattana1, Thomas C Wilson1, Veerle Kersemans2, Sean Smart2, Matthew Tredwell1, Benjamin G Davis1, Véronique Gouverneur1.   

Abstract

The 18F-labeling of 5-(trifluoromethyl)-dibenzothiophenium trifluoromethanesulfonate, commonly referred to as the Umemoto reagent, has been accomplished applying a halogen exchange 18F-fluorination with 18F-fluoride, followed by oxidative cyclization with Oxone and trifluoromethanesulfonic anhydride. This new 18F-reagent allows for the direct chemoselective 18F-labeling of unmodified peptides at the thiol cysteine residue.

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Year:  2018        PMID： 29301394     DOI： 10.1021/jacs.7b10227

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  17 in total

1.  Fast Protein Footprinting by X-ray Mediated Radical Trifluoromethylation.

Authors:  Ming Cheng; Awuri Asuru; Janna Kiselar; George Mathai; Mark R Chance; Michael L Gross
Journal:  J Am Soc Mass Spectrom       Date:  2020-04-21       Impact factor: 3.109

Review 2.  Chemistry for Positron Emission Tomography: Recent Advances in 11 C-, 18 F-, 13 N-, and 15 O-Labeling Reactions.

Authors:  Xiaoyun Deng; Jian Rong; Lu Wang; Neil Vasdev; Lei Zhang; Lee Josephson; Steven H Liang
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-14       Impact factor: 15.336

3.  Enantioselective catalytic synthesis of α-aryl-α-SCF3-β2,2-amino acids.

Authors:  Andreas Eitzinger; Jean-François Brière; Dominique Cahard; Mario Waser
Journal:  Org Biomol Chem       Date:  2020-01-22       Impact factor: 3.876

4.  An Organometallic Gold(III) Reagent for 18F Labeling of Unprotected Peptides and Sugars in Aqueous Media.

Authors:  James W McDaniel; Julia M Stauber; Evan A Doud; Alexander M Spokoyny; Jennifer M Murphy
Journal:  Org Lett       Date:  2022-07-08       Impact factor: 6.072

Review 5.  Fluorine-18: Radiochemistry and Target-Specific PET Molecular Probes Design.

Authors:  Yunze Wang; Qingyu Lin; Hongcheng Shi; Dengfeng Cheng
Journal:  Front Chem       Date:  2022-06-29       Impact factor: 5.545

6.  Protecting group free radical C-H trifluoromethylation of peptides.

Authors:  Naoko Ichiishi; John P Caldwell; Melissa Lin; Wendy Zhong; Xiaohong Zhu; Eric Streckfuss; Hai-Young Kim; Craig A Parish; Shane W Krska
Journal:  Chem Sci       Date:  2018-04-10       Impact factor: 9.825

7.  Radiosynthesis of the anticancer nucleoside analogue Trifluridine using an automated 18F-trifluoromethylation procedure.

Authors:  Alice King; Andreas Doepner; David Turton; Daniela M Ciobota; Chiara Da Pieve; Anne-Christine Wong Te Fong; Gabriela Kramer-Marek; Yuen-Li Chung; Graham Smith
Journal:  Org Biomol Chem       Date:  2018-04-25       Impact factor: 3.876

Review 8.  The Application of Fluorine-Containing Reagents in Structural Proteomics.

Authors:  Ming Cheng; Chunyang Guo; Michael L Gross
Journal:  Angew Chem Int Ed Engl       Date:  2020-01-16       Impact factor: 15.336

Review 9.  Perfluorocarbons in Chemical Biology.

Authors:  Margeaux A Miller; Ellen M Sletten
Journal:  Chembiochem       Date:  2020-08-05       Impact factor: 3.164

10.  Late-Stage Isotopic Carbon Labeling of Pharmaceutically Relevant Cyclic Ureas Directly from CO2.

Authors:  Antonio Del Vecchio; Fabien Caillé; Arnaud Chevalier; Olivier Loreau; Kaisa Horkka; Christer Halldin; Magnus Schou; Nathalie Camus; Pascal Kessler; Bertrand Kuhnast; Frédéric Taran; Davide Audisio
Journal:  Angew Chem Int Ed Engl       Date:  2018-07-03       Impact factor: 15.336
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