Synthesis of 4-[18F]fluoro-L-m-tyrosine: a model analog for the in vivo assessment of central dopaminergic function.
4-[18F]Fluoro-L-m-tyrosine (6), a new analog of L-dopa for probing the presynaptic dopaminergic system by positron emission tomography has been synthesized in good radiochemical yields via the regioselective fluorodemercuration of the 4-mercurio derivatives 4a and 4b with 18F-labeled acetylhypofluorite. The chemical, radiochemical and enantiomeric purities were determined to be greater than 99%. The key step in the synthesis of the precursors 4 was the mercuration of the protected L-m-tyrosine 3. The position of mercuration on the aromatic ring was gleaned from the 13C-NMR spectral data. The non-radiolabeled counterpart of 6 was also synthesized. Structural analyses of all these compounds were carried out by 1H-, 13C-, 19F-NMR and mass spectroscopy.
Perlmutter
M
M
Department of Radiological Sciences, UCLA School of Medicine 90024.
Satyamurthy
N
N
Luxen
A
A
Phelps
M E
ME
Barrio
J R
JR
D005462:Fluorine Radioisotopes; D009682:Magnetic Resonance Spectroscopy; D014055:Tomography, Emission-Computed; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D005462:Fluorine Radioisotopes; C060005:4-fluoro-3-tyrosine; D014443:Tyrosine