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Molecules 2017, 22(12), 2231; https://doi.org/10.3390/molecules22122231

A Practical Method for the Preparation of 18F-Labeled Aromatic Amino Acids from Nucleophilic [18F]Fluoride and Stannyl Precursors for Electrophilic Radiohalogenation

1
Institute of Neuroscience and Medicine, Nuclear Chemistry (INM-5), Forschungszentrum Jülich GmbH, 52428 Jülich, Germany
2
Institute of Radiochemistry and Experimental Molecular Imaging, University Clinic Cologne, 50931 Cologne, Germany
3
Max Planck Institute for Metabolism Research, Cologne 50931, Germany
*
Authors to whom correspondence should be addressed.
Received: 6 November 2017 / Revised: 5 December 2017 / Accepted: 12 December 2017 / Published: 15 December 2017
(This article belongs to the Section Medicinal Chemistry)
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Abstract

In a recent contribution of Scott et al., the substrate scope of Cu-mediated nucleophilic radiofluorination with [18F]KF for the preparation of 18F-labeled arenes was extended to aryl- and vinylstannanes. Based on these findings, the potential of this reaction for the production of clinically relevant positron emission tomography (PET) tracers was investigated. To this end, Cu-mediated radiofluorodestannylation using trimethyl(phenyl)tin as a model substrate was re-evaluated with respect to different reaction parameters. The resulting labeling protocol was applied for 18F-fluorination of different electron-rich, -neutral and -poor arylstannyl substrates in RCCs of 16–88%. Furthermore, this method was utilized for the synthesis of 18F-labeled aromatic amino acids from additionally N-Boc protected commercially available stannyl precursors routinely applied for electrophilic radiohalogenation. Finally, an automated synthesis of 6-[18F]fluoro-l-m-tyrosine (6-[18F]FMT), 2-[18F]fluoro-l-tyrosine (2-[18F]F-Tyr), 6-[18F]fluoro-l-3,4-dihydroxyphenylalanine (6-[18F]FDOPA) and 3-O-methyl-6-[18F]FDOPA ([18F]OMFD) was established furnishing these PET probes in isolated radiochemical yields (RCYs) of 32–54% on a preparative scale. Remarkably, the automated radiosynthesis of 6-[18F]FDOPA afforded an exceptionally high RCY of 54 ± 5% (n = 5). View Full-Text
Keywords: 18F; radiofluorination; destannylation; positron emission tomography 18F; radiofluorination; destannylation; positron emission tomography
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Zarrad, F.; Zlatopolskiy, B.D.; Krapf, P.; Zischler, J.; Neumaier, B. A Practical Method for the Preparation of 18F-Labeled Aromatic Amino Acids from Nucleophilic [18F]Fluoride and Stannyl Precursors for Electrophilic Radiohalogenation. Molecules 2017, 22, 2231.

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