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Synthesis of [3‐ 11 C]phenylpyruvic acid and its use in an enzymatic transamination to [3‐ 11 C]phenylalanine
Author(s) -
Halldin Christer,
Längström Bengt
Publication year - 1986
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580230705
Subject(s) - phenylpyruvic acid , chemistry , transamination , oxazolone , phenylalanine , hydrolysis , dabco , benzaldehyde , organic chemistry , enzyme , stereochemistry , catalysis , amino acid , biochemistry
The synthesis of [3‐ 11 C]phenylpyruvic acid, starting with 11 CO 2 , is reported. This α‐keto acid was prepared via a condensation reaction, using [ 11 C]benzaldehyde (prepared as described elsewhere), and 2‐phenyl‐5‐oxazolone, using diazabicyclooctane (DABCO) as a base. The condensation product, [α‐ 11 C]‐4‐benzylidene‐2‐phenyl‐5‐oxazolone, was converted by basic hydrolysis to give [3‐ 11 C]phenylpyruvic acid in 40 % radiochemical yield, starting with 11 CO 2 , within 40 min. The potential of [3‐ 11 C]phenylpyruvic acid in enzymatic transamination, catalyzed by glutamic/oxaloacetic acid transaminase (GOT) (Ee 2.6.1.1) immobilized on CNBr‐activated Sepharose was also studied.