Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (08): 1439-1444. Previous Articles     Next Articles




  1. (中南大学药学院 长沙 410013)
  • 收稿日期:2007-12-26 修回日期:2008-02-13 发布日期:2008-08-18
  • 通讯作者: 马大友

Nitrile Biotransformations for Asymmetric Synthesis of β-Amino Acid and β-Amino Acid Amide

MA, Da-You   

  1. (School of Pharmacy, Central South University, Changsha 410013)
  • Received:2007-12-26 Revised:2008-02-13 Published:2008-08-18
  • Contact: MA, Da-You

Rhodococcus erythropolis AJ270, a nitrile hydratase/amidase-containing microbial whole-cell catalyst, is able to catalyze the hydrolysis of a number of β-amino-β-phenyl-propionitrile derivatives under very mild conditions to produce the corresponding β-amino acids and β-amino acid amides. Both the efficiency and enantioselectivity of biocatalysis, however, were strongly dependent upon the structures of both nitrile and amide substrates. While biotransformations of racemic 3-amino-3-phenylpropionitrile gave low enantioselectivity, their N-methylated derivatives underwent moderate enantioselective biocatalytic reactions to afford the corresponding S-β-amino acids and R-β-amino acid amides. N-Bulky group substitution dra-matically slowed down the biotransformations.

Key words: nitrile hydratase, β-amino acid amide, amidase, β-amino acid, enantioselective biotransformation