A protocol for controlled reactivity shift in the 2,2-difluorovinyl motif used for selective S–18F and C–18F bond formation Article Swipe
Mudasir Maqbool
,
Jimmy E. Jakobsson
,
Santosh Reddy Alluri
,
Vasko Kramer
,
Patrick J. Riss
·
YOU?
·
· 2024
· Open Access
·
· DOI: https://doi.org/10.1038/s42004-024-01132-3
YOU?
·
· 2024
· Open Access
·
· DOI: https://doi.org/10.1038/s42004-024-01132-3
Positron emission tomography (PET) is a powerful imaging technique for biomedical research, drug development and medical diagnosis. The power of PET lies in biochemically selective radiotracers, labelled with positron emitters like fluorine-18 image chemical processes in vivo. A rapid and remarkably efficient, unprecedented protocol to select between S-F and C-F bond formation based on activation of 1,1-difluoroethylene groups followed by selective oxidation or reduction is described. While transition metal mediated conditions can be employed, the reaction proceeds in high yield using unobjectionable chemical reagents amenable to routine radiotracer production. The latter bodes well for facile clinical translation of the method. The new technique affords radiotracers and the labelling reagent 2,2-difluoro-2-(fluoro- 18 F)ethyl 4-methylbenzenesulfonate ( [ 18 F] 1b) in excellent yield. Following oxygenation of the reaction mixture with medical oxygen or air, sulfonyl fluorides are obtained as the primary product. The new protocol was employed in a proof of principle to develop a radiometric assay for quantitation of sulfonylation yield with sulfonyl fluoride reagents. With operational ease and mild conditions, the method bodes a high potential for radiolabelling of biomolecules, known enzyme inhibitors and other temperature-sensitive compounds.
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- Type
- article
- Language
- en
- Landing Page
- http://doi.org/10.1038/s42004-024-01132-3
- OA Status
- gold
- References
- 31
- Related Works
- 10
- OpenAlex ID
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Raw OpenAlex JSON
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https://openalex.org/W4396241999Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.1038/s42004-024-01132-3Digital Object Identifier
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A protocol for controlled reactivity shift in the 2,2-difluorovinyl motif used for selective S–18F and C–18F bond formationWork title
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articleOpenAlex work type
- Language
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enPrimary language
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2024Year of publication
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2024-04-29Full publication date if available
- Authors
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Mudasir Maqbool, Jimmy E. Jakobsson, Santosh Reddy Alluri, Vasko Kramer, Patrick J. RissList of authors in order
- Landing page
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https://doi.org/10.1038/s42004-024-01132-3Publisher landing page
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YesWhether a free full text is available
- OA status
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goldOpen access status per OpenAlex
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https://doi.org/10.1038/s42004-024-01132-3Direct OA link when available
- Concepts
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Reagent, Chemistry, Sulfonyl, Yield (engineering), Combinatorial chemistry, Biomolecule, In vivo, Reactivity (psychology), Radiochemistry, Organic chemistry, Materials science, Biochemistry, Alternative medicine, Metallurgy, Pathology, Medicine, Biology, Biotechnology, AlkylTop concepts (fields/topics) attached by OpenAlex
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0Total citation count in OpenAlex
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31Number of works referenced by this work
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10Other works algorithmically related by OpenAlex
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