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(18)F-Trifluoromethanesulfinate Enables Direct C–H (18)F-Trifluoromethylation of Native Aromatic Residues in Peptides
[Image: see text] (18)F labeling strategies for unmodified peptides with [(18)F]fluoride require (18)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 (18)F-trifluoromethylat...
| Autores principales: | , , , , , , , , , , , , , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical
Society
2020
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6978814/ https://www.ncbi.nlm.nih.gov/pubmed/31913613 http://dx.doi.org/10.1021/jacs.9b11709 |
| _version_ | 1783490777419087872 |
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| author | Kee, Choon Wee Tack, Osman Guibbal, Florian Wilson, Thomas C. Isenegger, Patrick G. Imiołek, Mateusz Verhoog, Stefan Tilby, Michael Boscutti, Giulia Ashworth, Sharon Chupin, Juliette Kashani, Roxana Poh, Adeline W. J. Sosabowski, Jane K. Macholl, Sven Plisson, Christophe Cornelissen, Bart Willis, Michael C. Passchier, Jan Davis, Benjamin G. Gouverneur, Véronique |
| author_facet | Kee, Choon Wee Tack, Osman Guibbal, Florian Wilson, Thomas C. Isenegger, Patrick G. Imiołek, Mateusz Verhoog, Stefan Tilby, Michael Boscutti, Giulia Ashworth, Sharon Chupin, Juliette Kashani, Roxana Poh, Adeline W. J. Sosabowski, Jane K. Macholl, Sven Plisson, Christophe Cornelissen, Bart Willis, Michael C. Passchier, Jan Davis, Benjamin G. Gouverneur, Véronique |
| author_sort | Kee, Choon Wee |
| collection | PubMed |
| description | [Image: see text] (18)F labeling strategies for unmodified peptides with [(18)F]fluoride require (18)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 (18)F-trifluoromethylation. We report a one-step route to [(18)F]CF(3)SO(2)NH(4) from [(18)F]fluoride and its application to direct [(18)F]CF(3) incorporation at tryptophan or tyrosine residues using unmodified peptides as complex as recombinant human insulin. The fully automated radiosynthesis of octreotide[Trp(2-CF(2)(18)F)] enables in vivo positron emission tomography imaging. |
| format | Online Article Text |
| id | pubmed-6978814 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2020 |
| publisher | American Chemical
Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-69788142020-01-27 (18)F-Trifluoromethanesulfinate Enables Direct C–H (18)F-Trifluoromethylation of Native Aromatic Residues in Peptides Kee, Choon Wee Tack, Osman Guibbal, Florian Wilson, Thomas C. Isenegger, Patrick G. Imiołek, Mateusz Verhoog, Stefan Tilby, Michael Boscutti, Giulia Ashworth, Sharon Chupin, Juliette Kashani, Roxana Poh, Adeline W. J. Sosabowski, Jane K. Macholl, Sven Plisson, Christophe Cornelissen, Bart Willis, Michael C. Passchier, Jan Davis, Benjamin G. Gouverneur, Véronique J Am Chem Soc [Image: see text] (18)F labeling strategies for unmodified peptides with [(18)F]fluoride require (18)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 (18)F-trifluoromethylation. We report a one-step route to [(18)F]CF(3)SO(2)NH(4) from [(18)F]fluoride and its application to direct [(18)F]CF(3) incorporation at tryptophan or tyrosine residues using unmodified peptides as complex as recombinant human insulin. The fully automated radiosynthesis of octreotide[Trp(2-CF(2)(18)F)] enables in vivo positron emission tomography imaging. American Chemical Society 2020-01-08 2020-01-22 /pmc/articles/PMC6978814/ /pubmed/31913613 http://dx.doi.org/10.1021/jacs.9b11709 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. |
| spellingShingle | Kee, Choon Wee Tack, Osman Guibbal, Florian Wilson, Thomas C. Isenegger, Patrick G. Imiołek, Mateusz Verhoog, Stefan Tilby, Michael Boscutti, Giulia Ashworth, Sharon Chupin, Juliette Kashani, Roxana Poh, Adeline W. J. Sosabowski, Jane K. Macholl, Sven Plisson, Christophe Cornelissen, Bart Willis, Michael C. Passchier, Jan Davis, Benjamin G. Gouverneur, Véronique (18)F-Trifluoromethanesulfinate Enables Direct C–H (18)F-Trifluoromethylation of Native Aromatic Residues in Peptides |
| title | (18)F-Trifluoromethanesulfinate Enables
Direct C–H (18)F-Trifluoromethylation of Native
Aromatic Residues in Peptides |
| title_full | (18)F-Trifluoromethanesulfinate Enables
Direct C–H (18)F-Trifluoromethylation of Native
Aromatic Residues in Peptides |
| title_fullStr | (18)F-Trifluoromethanesulfinate Enables
Direct C–H (18)F-Trifluoromethylation of Native
Aromatic Residues in Peptides |
| title_full_unstemmed | (18)F-Trifluoromethanesulfinate Enables
Direct C–H (18)F-Trifluoromethylation of Native
Aromatic Residues in Peptides |
| title_short | (18)F-Trifluoromethanesulfinate Enables
Direct C–H (18)F-Trifluoromethylation of Native
Aromatic Residues in Peptides |
| title_sort | (18)f-trifluoromethanesulfinate enables
direct c–h (18)f-trifluoromethylation of native
aromatic residues in peptides |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6978814/ https://www.ncbi.nlm.nih.gov/pubmed/31913613 http://dx.doi.org/10.1021/jacs.9b11709 |
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