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

Choon Wee Kee; Osman Tack; Florian Guibbal; Thomas C. Wilson; Patrick G. Isenegger; Mateusz Imiołek; 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; Véronique Gouverneur

doi:10.1021/jacs.9b11709

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

Choon Wee Kee
, Osman Tack
, Florian Guibbal
, Thomas C. Wilson
, Patrick G. Isenegger
, Mateusz Imiołek
, 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

Véronique Gouverneur^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

92 Citations (Scopus)

Abstract

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-CF₂ ¹⁸F)] enables in vivo positron emission tomography imaging.

Original language	English
Pages (from-to)	1180-1185
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	142
Issue number	3
DOIs	https://doi.org/10.1021/jacs.9b11709
Publication status	Published - 22 Jan 2020

Bibliographical note

Publisher Copyright:
Copyright © 2020 American Chemical Society.

Research Groups and Themes

Organic & Biological

Access to Document

10.1021/jacs.9b11709

Handle.net

Persistent link

Cite this

Kee, C. W., Tack, O., Guibbal, F., Wilson, T. C., Isenegger, P. G., Imiołek, M., Verhoog, S., Tilby, M., Boscutti, G., Ashworth, S., Chupin, J., Kashani, R., Poh, A. W. J., Sosabowski, J. K., Macholl, S., Plisson, C., Cornelissen, B., Willis, M. C., Passchier, J., ... Gouverneur, V. (2020). ¹⁸F-Trifluoromethanesulfinate Enables Direct C-H ¹⁸F-Trifluoromethylation of Native Aromatic Residues in Peptides. Journal of the American Chemical Society, 142(3), 1180-1185. https://doi.org/10.1021/jacs.9b11709

@article{db57e08056e64feb9cfb3bf398ba8234,

title = "18F-Trifluoromethanesulfinate Enables Direct C-H 18F-Trifluoromethylation of Native Aromatic Residues in Peptides",

abstract = "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-CF2 18F)] enables in vivo positron emission tomography imaging.",

author = "Kee, \{Choon Wee\} and Osman Tack and Florian Guibbal and Wilson, \{Thomas C.\} and Isenegger, \{Patrick G.\} and Mateusz Imio{\l}ek and Stefan Verhoog and Michael Tilby and Giulia Boscutti and Sharon Ashworth and Juliette Chupin and Roxana Kashani and Poh, \{Adeline W.J.\} and Sosabowski, \{Jane K.\} and Sven Macholl and Christophe Plisson and Bart Cornelissen and Willis, \{Michael C.\} and Jan Passchier and Davis, \{Benjamin G.\} and V{\'e}ronique Gouverneur",

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = jan,

day = "22",

doi = "10.1021/jacs.9b11709",

language = "English",

volume = "142",

pages = "1180--1185",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "3",

}

Kee, CW, Tack, O, Guibbal, F, Wilson, TC, Isenegger, PG, Imiołek, M, Verhoog, S, Tilby, M, Boscutti, G, Ashworth, S, Chupin, J, Kashani, R, Poh, AWJ, Sosabowski, JK, Macholl, S, Plisson, C, Cornelissen, B, Willis, MC, Passchier, J, Davis, BG & Gouverneur, V 2020, '¹⁸F-Trifluoromethanesulfinate Enables Direct C-H ¹⁸F-Trifluoromethylation of Native Aromatic Residues in Peptides', Journal of the American Chemical Society, vol. 142, no. 3, pp. 1180-1185. https://doi.org/10.1021/jacs.9b11709

TY - JOUR

T1 - 18F-Trifluoromethanesulfinate Enables Direct C-H 18F-Trifluoromethylation of Native Aromatic Residues in Peptides

AU - Kee, Choon Wee

AU - Tack, Osman

AU - Guibbal, Florian

AU - Wilson, Thomas C.

AU - Isenegger, Patrick G.

AU - Imiołek, Mateusz

AU - Verhoog, Stefan

AU - Tilby, Michael

AU - Boscutti, Giulia

AU - Ashworth, Sharon

AU - Chupin, Juliette

AU - Kashani, Roxana

AU - Poh, Adeline W.J.

AU - Sosabowski, Jane K.

AU - Macholl, Sven

AU - Plisson, Christophe

AU - Cornelissen, Bart

AU - Willis, Michael C.

AU - Passchier, Jan

AU - Davis, Benjamin G.

AU - Gouverneur, Véronique

PY - 2020/1/22

Y1 - 2020/1/22

N2 - 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-CF2 18F)] enables in vivo positron emission tomography imaging.

AB - 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-CF2 18F)] enables in vivo positron emission tomography imaging.

UR - https://www.scopus.com/pages/publications/85078536958

U2 - 10.1021/jacs.9b11709

DO - 10.1021/jacs.9b11709

M3 - Article (Academic Journal)

C2 - 31913613

AN - SCOPUS:85078536958

SN - 0002-7863

VL - 142

SP - 1180

EP - 1185

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 3

ER -