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

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2020 Jan 9

PMID 31913613

Citations 26

Authors

Choon Wee Kee

Osman Tack

Florian Guibbal

Thomas C Wilson

Patrick G Isenegger

Mateusz Imiolek

Stefan Verhoog

Michael Tilby

Giulia Boscutti

Sharon Ashworth

Juliette Chupin

Roxana Kashani

Adeline W J Poh

Jane K Sosabowski

Sven Macholl

Christophe Plisson

Bart Cornelissen

Michael C Willis

Jan Passchier

Benjamin G Davis

Veronique Gouverneur

Affiliations

Soon will be listed here.

Abstract

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.

Citing Articles

C-H Labeling with [F]Fluoride: An Emerging Methodology in Radiochemistry.

Wright J, Sharninghausen L, Lapsys A, Sanford M, Scott P ACS Cent Sci. 2024; 10(9):1674-1688.

PMID: 39364044 PMC: 11447958. DOI: 10.1021/acscentsci.4c00997.

[F]Trifluoroiodomethane - Enabling Photoredox-mediated Radical [F]Trifluoromethylation for Positron Emission Tomography.

Veth L, Windhorst A, Vugts D Angew Chem Int Ed Engl. 2024; 64(4):e202416901.

PMID: 39349368 PMC: 11753608. DOI: 10.1002/anie.202416901.

Late-stage peptide modification and macrocyclization enabled by tertiary amine catalyzed tryptophan allylation.

Liu Y, Li G, Ma W, Bao G, Li Y, He Z Chem Sci. 2024; 15(28):11099-11107.

PMID: 39027288 PMC: 11253200. DOI: 10.1039/d4sc01244e.

Clickable tryptophan modification for late-stage diversification of native peptides.

Xiao Y, Zhou H, Shi P, Zhao X, Liu H, Li X Sci Adv. 2024; 10(28):eadp9958.

PMID: 38985871 PMC: 11235173. DOI: 10.1126/sciadv.adp9958.

Site-selective -difluoroallylation of unprotected peptides with 3,3-difluoroallyl sulfonium salts.

Ren J, Zhou M, Feng X, Zhao H, Fu X, Zhang X Chem Sci. 2024; 15(26):10002-10009.

PMID: 38966370 PMC: 11220611. DOI: 10.1039/d4sc02681k.

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