Abstract
We describe a new method for the asymmetric synthesis of [(18)F]fluorinated aromatic alpha-amino acids (FAA) under phase transfer conditions using achiral glycine derivative NiPBPGly and (S)-NOBIN as a novel substrate/catalyst pair. The key alkylation step proceeds under mild conditions. Substituted [(18)F]fluorobenzylbromides were prepared using nucleophilic [(18)F]fluoride and were used as alkylation agents. Two important FAA, 2-[(18)F]fluoro-L-tyrosine (2-FTYR) and 6-[(18)F]fluoro-L-3,4-dihydroxyphenylalanine (6-FDOPA), were synthesized with an ee of 92 and 96%, respectively. The total synthesis time was 110-120 min and radiochemical yields (d.c.) were 25+/-6% for 2-FTYR and 16+/-5% for 6-FDOPA.
Publication types
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Comparative Study
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Evaluation Study
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Research Support, Non-U.S. Gov't
MeSH terms
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2-Naphthylamine / analogs & derivatives*
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2-Naphthylamine / chemistry*
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Animals
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Catalysis
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Dihydroxyphenylalanine / analogs & derivatives*
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Dihydroxyphenylalanine / chemistry*
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Dihydroxyphenylalanine / isolation & purification
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Dihydroxyphenylalanine / pharmacokinetics*
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Fluorine Radioisotopes / chemistry
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Fluorine Radioisotopes / isolation & purification
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Fluorine Radioisotopes / pharmacokinetics
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Glioma / diagnostic imaging
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Glioma / metabolism*
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Isomerism
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Isotope Labeling / methods*
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Metabolic Clearance Rate
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Naphthols / chemistry*
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Organ Specificity
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Phase Transition
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Radionuclide Imaging
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Radiopharmaceuticals / chemical synthesis
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Radiopharmaceuticals / isolation & purification
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Radiopharmaceuticals / pharmacokinetics
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Rats
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Rats, Wistar
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Tissue Distribution
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Tyrosine / chemistry*
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Tyrosine / isolation & purification
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Tyrosine / pharmacokinetics*
Substances
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1-(2-aminonaphth-1-yl)-2-naphthol
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Fluorine Radioisotopes
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Naphthols
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Radiopharmaceuticals
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fluorodopa F 18
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Tyrosine
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Dihydroxyphenylalanine
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2-Naphthylamine