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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
 
 

Catalytic enantioselective synthesis of 18F-fluorinated alpha-amino acids under phase-transfer conditions using (S)-NOBIN.

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.[1]

References

  1. Catalytic enantioselective synthesis of 18F-fluorinated alpha-amino acids under phase-transfer conditions using (S)-NOBIN. Krasikova, R.N., Zaitsev, V.V., Ametamey, S.M., Kuznetsova, O.F., Fedorova, O.S., Mosevich, I.K., Belokon, Y.N., Vyskocil, S., Shatik, S.V., Nader, M., Schubiger, P.A. Nucl. Med. Biol. (2004) [Pubmed]
 
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