Synthesis of 6-[18F] and 4-[18F]fluoro-L-m-tyrosines via regioselective radiofluorodestannylation.
The regioselective radiofluorodestannylation of 6-trimethylstannyl-L-m-tyrosine derivative 6 with [18F]F2 and [18F]acetyl hypofluorite afforded, after acid hydrolysis, 6-[18F]fluoro-L-m-tyrosine (8a) in radiochemical yields of 23 and 17%, respectively. Similarly, 4-[18F]fluoro-L-m-tyrosine (13a) was synthesized in 11% radiochemical yield from the corresponding 4-trimethylstannyl-L-m-tyrosine derivative 11 using [18F]F2. The structural analyses of precursors (6,11), intermediates, and the final products (after 18F decay), were carried out by 1H, 13C, 19F, 119Sn-NMR and high resolution mass spectroscopy.
Namavari
M
M
Department of Radiological Sciences, UCLA School of Medicine 90024.
Satyamurthy
N
N
Phelps
M E
ME
Barrio
J R
JR
D005462:Fluorine Radioisotopes; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D005462:Fluorine Radioisotopes; C060005:4-fluoro-3-tyrosine; C080704:6-fluoro-3-tyrosine; D014443:Tyrosine