[en] The radiolabeling of (S)-L-4-chlorophenylalanine and (S)-L-(alpha-methyl)-4-chlorophenylalanine were realized with carbon-11 at position beta through a radiochemical synthesis relying on the highly enantioselective reaction between 4-chloro[alpha-C-11]benzyl bromide and the lithium enolate of (S)-1-(t-butyloxycarbonyl)-2-(t-butyl)-3-methyl-1,3-imidazolidine-4-one for (S)-L-[beta-C-11]-4-chlorophenylalanine and of (2S,5S)-1-(t-butyloxycarbonyl)-2-(t-butyl)-3,5-dimethyl-1,3-imidazolidin e-4-one for (S)-L-(alpha-methyl)-[beta-C-11]-4-chlorophenylalanine. Quantities of about 25-35 mCi were obtained at the end of synthesis, ready for injection, after hydrolysis and HPLC purification with a radiochemical yield of 19% corrected to EOB within 45 min. The enantiomeric excesses were shown to be greater than or equal to 97% for both molecules without chiral separation. The radiochemical and the chemical purities of the final compounds were greater than or equal to 98% and the specific activity at the end of synthesis ranged between 250-800 mCi/mu mol.
Research center :
GIGA CRC (Cyclotron Research Center) In vivo Imaging-Aging & Memory - ULiège
Disciplines :
Chemistry Radiology, nuclear medicine & imaging
Author, co-author :
Plenevaux, Alain ; Université de Liège - ULiège > Centre de recherches du cyclotron
Al-Darwich, M. J.
Lemaire, Christian ; Université de Liège - ULiège > Centre de recherches du cyclotron
Delfiore, Guy
Comar, Dominique
Language :
English
Title :
ENANTIOSELECTIVE SYNTHESES OF NCA (S)-L-[BETA-C-11]-4-CHLOROPHENYLALANINE AND (S)-L-(ALPHA-METHYL)-[BETA-C-11]-4-CHLOROPHENYLALANINE
Publication date :
1994
Journal title :
Applied Radiation and Isotopes
ISSN :
0969-8043
Publisher :
Pergamon Press, Oxford, United Kingdom
Volume :
45
Issue :
3
Pages :
361-369
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE]
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