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

Nuclear Medicine and Biology
R N KrasikovaP A Schubiger

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.

References

Aug 2, 2002·Applied Radiation and Isotopes : Including Data, Instrumentation and Methods for Use in Agriculture, Industry and Medicine·Lan ZhangYonxian Wang
Aug 2, 2002·Applied Radiation and Isotopes : Including Data, Instrumentation and Methods for Use in Agriculture, Industry and Medicine·E HessH H Coenen

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Citations

Jan 12, 2016·Chemical Reviews·Sean PreshlockVéronique Gouverneur
Nov 29, 2005·Applied Radiation and Isotopes : Including Data, Instrumentation and Methods for Use in Agriculture, Industry and Medicine·Wolfgang WadsakKurt Kletter
May 13, 2009·Applied Radiation and Isotopes : Including Data, Instrumentation and Methods for Use in Agriculture, Industry and Medicine·B ShenG Reischl
Jun 14, 2017·Chemical Society Reviews·Dion van der BornDanielle J Vugts
Nov 29, 2013·Journal of Labelled Compounds & Radiopharmaceuticals·Johannes Ermert, Heinz H Coenen
Dec 14, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Alexander Popkov, Bart De Spiegeleer
Sep 27, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Raisa N Krasikova
May 7, 2009·Lab on a Chip·Arkadij M Elizarov
Mar 11, 2021·EJNMMI Radiopharmacy and Chemistry·Ângela C B NevesAntero J Abrunhosa
May 10, 2013·Journal of Nuclear Medicine : Official Publication, Society of Nuclear Medicine·Lionel C LibertChristian F Lemaire

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