Synthesis of racemic [3-11C]phenylalanine and [3-11C]DOPA |
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| Affiliation: | 1. Department of Biological Response and Regulation, Hokkaido University, Sapporo, Hokkaido, Japan;2. Department of Environmental Applied Chemistry, University of Toyama, Toyama, Toyama, Japan;3. Bioproduction Research Institute, National Institute of Advanced Industrial Science and Technology (AIST), Sapporo, Hokkaido, Japan;4. Department of Forensic Medicine, Graduate School of Medicine, Hokkaido University, Sapporo, Hokkaido, Japan;5. Department of Chemistry, School of Science, The University of Tokyo, Tokyo, Japan;6. Laboratory of Molecular and Functional Bio-Imaging, Hokkaido University, Sapporo, Hokkaido, Japan |
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| Abstract: | The synthesis of racemic [3-11C]phenylalanine and [3-11C]DOPA is reported. The [11C]benzaldehyde and [11C]veratraldehyde prepared in a two-step reaction from the corresponding [11C]acid salt and [11C]alcohol, by means of selective oxidation with tetrabutylammonium hydrogen chromate, were reacted with 2-phenyl-5-oxazolone or 2-(4-chloro)phenyl-5-oxazolone in the presence of a tertiary amine to give the corresponding [α-11C]-4-arylene-2-aryl-5-oxazolones. Ring opening of these olefins, hydrogenation, and removal of protecting groups was carried out in one step using hydroiodic acid/phosphorus, with the production of the racemic [3-11C]amino acids in 8–30% radiochemical yield (starting with 11CO2) within 52–60 min (including LC separation). |
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