Journal article
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-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 PET imaging.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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- Files:
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(Preview, Accepted manuscript, pdf, 1.2MB, Terms of use)
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- Publisher copy:
- 10.1021/jacs.9b11709
Authors
- Publisher:
- American Chemical Society
- Journal:
- Journal of the American Chemical Society More from this journal
- Volume:
- 142
- Issue:
- 3
- Pages:
- 1180-1185
- Publication date:
- 2020-01-08
- Acceptance date:
- 2020-01-08
- DOI:
- EISSN:
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1520-5126
- ISSN:
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0002-7863
- Language:
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English
- Keywords:
- Pubs id:
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pubs:1081594
- UUID:
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uuid:27c4df26-55b1-43f0-a31f-5c1740c0a6a4
- Local pid:
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pubs:1081594
- Source identifiers:
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1081594
- Deposit date:
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2020-01-10
- ARK identifier:
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2020
- Rights statement:
- © 2020 American Chemical Society
- Notes:
- This is the accepted manuscript version of the article. The final version is available from the American Chemical Society at: https://doi.org/10.1021/jacs.9b11709
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