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@ARTICLE{Zarrad:841351,
author = {Zarrad, Fadi and Zlatopolskiy, Boris and Krapf, Philipp and
Zischler, Johannes and Neumaier, Bernd},
title = {{A} {P}ractical {M}ethod for the {P}reparation of
18{F}-{L}abeled {A}romatic {A}mino {A}cids from
{N}ucleophilic [18{F}]{F}luoride and {S}tannyl {P}recursors
for {E}lectrophilic {R}adiohalogenation},
journal = {Molecules},
volume = {22},
number = {12},
issn = {1420-3049},
address = {Basel},
publisher = {MDPI75390},
reportid = {FZJ-2017-08436},
pages = {2231 -},
year = {2017},
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).},
cin = {INM-5},
ddc = {540},
cid = {I:(DE-Juel1)INM-5-20090406},
pnm = {573 - Neuroimaging (POF3-573)},
pid = {G:(DE-HGF)POF3-573},
typ = {PUB:(DE-HGF)16},
UT = {WOS:000419242400196},
pubmed = {pmid:29244780},
doi = {10.3390/molecules22122231},
url = {https://juser.fz-juelich.de/record/841351},
}