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Synlett 1998; 1998(6): 631-633
DOI: 10.1055/s-1998-3137
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Kynureninase in Organic Synthesis: Preparation of γ-Hydroxy-α-l-Amino Acids

Tsuyoshi Miura* , Noriko Masuo, Yuki Fusamae, Tetsuya Kajimoto, Yoshiteru Ida
  • *School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan
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Publication Date:
31 December 2000 (online)

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Kynureninase, which is known to catalyze the transaldol reaction between benzaldehyde and kynurenine, accepted many kinds of other aromatic aldehydes and propargyl aldehydes as the substrates to afford novel γ-hydroxy-α-l-amino acids. The l-configuration of the α-carbons was confirmed by an enzymatic method using both d- and l-amino acid oxidases. The stereochemistry of the newly formed chiral center (γ-position) in major isomers was determined to be R-configuration by the observed NOEs in the NMR spectroscopy of lactones derived from the γ-hydroxy-α-l-amino acids.

kynureninase - aromatic aldehyde - propargylaldehyde - γ-(R)-hydroxy-α-l-amino acids - KDO