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

Autor: Krasikova RN; Institute of Human Brain, Russian Academy of Science, 9, Pavlov strasse, 197376, St.-Petersburg, Russia., Zaitsev VV, Ametamey SM, Kuznetsova OF, Fedorova OS, Mosevich IK, Belokon YN, Vyskocil S, Shatik SV, Nader M, Schubiger PA
Jazyk: angličtina
Zdroj: Nuclear medicine and biology [Nucl Med Biol] 2004 Jul; Vol. 31 (5), pp. 597-603.
DOI: 10.1016/j.nucmedbio.2003.12.010
Abstrakt: 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.
Databáze: MEDLINE