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.
Krasikova
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RN
Institute of Human Brain, Russian Academy of Science, 9, Pavlov strasse, 197376, St.-Petersburg, Russia.
Zaitsev
V V
VV
Ametamey
S M
SM
Kuznetsova
O F
OF
Fedorova
O S
OS
Mosevich
I K
IK
Belokon
Y N
YN
Vyskocil
S
S
Shatik
S V
SV
Nader
M
M
Schubiger
P A
PA
D015081:2-Naphthylamine / Q000031:analogs & derivatives* / Q000737:chemistry*; D000818:Animals; D002384:Catalysis; D004295:Dihydroxyphenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000302:isolation & purification / Q000493:pharmacokinetics*; D005462:Fluorine Radioisotopes / Q000737:chemistry / Q000302:isolation & purification / Q000493:pharmacokinetics; D005910:Glioma / Q000000981:diagnostic imaging / Q000378:metabolism*; D007536:Isomerism; D007553:Isotope Labeling / Q000379:methods*; D008657:Metabolic Clearance Rate; D009284:Naphthols / Q000737:chemistry*; D009928:Organ Specificity; D044367:Phase Transition; D011877:Radionuclide Imaging; D019275:Radiopharmaceuticals / Q000138:chemical synthesis / Q000302:isolation & purification / Q000493:pharmacokinetics; D051381:Rats; D017208:Rats, Wistar; D014018:Tissue Distribution; D014443:Tyrosine / Q000737:chemistry* / Q000302:isolation & purification / Q000493:pharmacokinetics*
C493913:1-(2-aminonaphth-1-yl)-2-naphthol; D005462:Fluorine Radioisotopes; D009284:Naphthols; D019275:Radiopharmaceuticals; C043437:fluorodopa F 18; D014443:Tyrosine; D004295:Dihydroxyphenylalanine; D015081:2-Naphthylamine