2-AMINO-3-(5-PHENYLFURAN-2-YL)PROPIONIC ACIDS AND 5-PHENYLFURAN-2-YLACRYLIC ACIDS ARE NOVEL SUBSTRATES OF PHENYLALANINE AMMONIA-LYASE

摘要

Both racemic 2-amino-3-(5-phenylfuran-2-yl)propionic acids and 5-phenylfuran-2-ylacrylic acids were synthesized and spectroscopically characterized (UV, EI-MS, ~1H-NMR and ~(13)C-NMR). The phenyl group of the 5-phenylfuranyl residue carried no (rac-la) para-Br (rac-1b) or Cl para or ortho (rac-1c, d) substituents. The novel furanylalanines were used as substrates of recombinant phenylalanine ammonia-lyase (PAL). When 50% of the racemic 5-phenylfuranylalanines were converted into the corresponding acrylates, the D-enantiomers of the substrates could be isolated. The L-enantiomers could be prepared from the substituted acrylates when the PAL reaction was reversed in the presence of 6 M ammonia at pH 10.