Acta Chimica Sinica ›› 1997, Vol. 55 ›› Issue (2): 196-201. Previous Articles     Next Articles

Original Articles

微生物转化芳基丙烯酸类物质不对称合成L-α-氨基酸的新方法

赵健身;杨顺楷   

  1. 中国科学院成都生物研究所
  • 发布日期:1997-02-15

A new asymmetric synthesis of L-α-amino acid via microbial transformation

ZHAO JIANSHEN;YANG SHUNKAI   

  • Published:1997-02-15

A new route to the direct synthesis of L-β-aryl-α-alanine (2) was established by using the red yeast (Rhodotorula rubra, Rhodotorula glutinis) cells containing L-phenylalanine ammonia-lyase (PAL, EC 4.3.1.5) activity to catalyze the addition of ammonia to olefinic bond in trans-β-arylacrylic acid (1). Seven of L-α-amino acid 2 were prepared with the following yields: L-o-nitrophenylalanine (2a, 27.3%), L-m-nitrophenylalanine (2b, 10.2%), L-o-chlorophenylalanine (2c, 68.2%), L-m-chlorophenylalanine (2d, 42.1%), L-m-methylphenylalanine (2e, 49.1%), L-m-aminophenylalanine (2g, 7.9%) and L-4-pyridylalanine (2h, 7.9%), They were all confirmed as L-isomers owing to the positive Cotton effects of their circular dichroism near 215nm. The specific optical rotations of products 2c, 2d and 2e were also comparable to those inliterature. The enantiomeric excess (e. e) value were determined to be no less than 95% on a L-4-hydroxyproline-bonded high-performance ligand exchange column.

Key words: INFRARED SPECTROPHOTOMETRY, NMR SPECTROMETRY, AMMONIA, ACRYLIC ACID P, MICROBIAL TRANSFORMATION, ALANINE P, RHODOTORULA

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