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Paper | Special issue | Vol 82, No. 2, 2010, pp.1217-1228
Published online, 5th August, 2010
DOI: 10.3987/COM-10-S(E)60
2-Amino-3-(5-phenylfuran-2-yl)propionic Acids and 5-Phenylfuran-2-ylacrylic Acids are Novel Substrates of Phenylalanine Ammonia-Lyase

Csaba Paizs, Monica Ioana Toşa, László Csaba Bencze, Jürgen Brem, Florin Dan Irimie, and János Rétey*

*Institute of Organic Chemistry, Karlsruhe Institute of Technology , Richard-Willstätter-Allee, D-76128 Karlsruhe, Germany

Abstract

Both racemic 2-amino-3-(5-phenylfuran-2-yl) propionic acids and 5-phenylfuran-2-yl acrylic acids were synthesized and spectroscopically characterized (UV, EI-MS, 1H-NMR and 13C-NMR). The phenyl group of the 5-phenylfuranyl residue carried no (rac-1a) 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-phenylfuranyl-alanines 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.