Chromatography, High Pressure Liquid; Dihydroxyphenylalanine/analogs & derivatives/chemical synthesis/isolation & purification; Fluorine Radioisotopes; Indicators and Reagents; Isotope Labeling/methods; Molecular Structure
Abstract :
[en] METHODS: A trimethylammonium veratraldehyde triflate was synthesized and used as a precursor for the asymmetric synthesis of 6-[18F]fluoro-L-dopa. RESULTS: Its nucleophilic fluorination with 18F-fluoride produced by the 18O(p,n)18F nuclear reaction on enriched 18O-water led to the corresponding no-carrier-added [18F]fluoroveratraldehyde (45 +/- 5% EOB). Diiodosilane was used to prepare the corresponding [18F]fluorobenzyl iodide (36.5 +/- 5.3% EOB). Akylation of (S)-1-tert-boc-2-tert-butyl-3-methyl-4-imidazolidinone with this electrophilic agent, hydrolysis and purification by preparative high-pressure liquid chromatography made 6-[18F]fluoro-L-dopa ready for human injection, in a 23% +/- 6% decay-corrected radiochemical yield. The enantiomeric purity and the specific activity were above 96% and 1 Ci/mumole respectively. CONCLUSION: Through this procedure, starting from 250 mCi of 18F-fluoride, multimillicurie amounts (32 +/- 8.5 mCi) of no-carrier-added 6-[18F]fluoro-L-dopa are now available at the end of synthesis (90 min) with a good radiochemical purity (more than 98%).
Research center :
GIGA CRC (Cyclotron Research Center) In vivo Imaging-Aging & Memory - ULiège
Disciplines :
Chemistry
Author, co-author :
Lemaire, Christian ; Université de Liège - ULiège > Centre de recherches du cyclotron
Damhaut, Philippe
Plenevaux, Alain ; Université de Liège - ULiège > Centre de recherches du cyclotron
Comar, Dominique
Language :
English
Title :
Enantioselective synthesis of 6-[fluorine-18]-fluoro-L-dopa from no-carrier-added fluorine-18-fluoride.
Publication date :
1994
Journal title :
Journal of Nuclear Medicine
ISSN :
0161-5505
eISSN :
1535-5667
Publisher :
Society of Nuclear Medicine, Reston, United States - Virginia
Volume :
35
Issue :
12
Pages :
1996-2002
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE]