Biotransformation of heterocyclic dinitriles by Rhodococcus erythropolis and fungal nitrilases

Biotechnol Lett. 2007 Jul;29(7):1119-24. doi: 10.1007/s10529-007-9364-z. Epub 2007 May 4.

Abstract

2,6-Pyridinedicarbonitrile (1a) and 2,4-pyridinedicarbonitrile (2a) were hydrated by Rhodococcus erythropolis A4 to 6-cyanopyridine-2-carboxamide (1b; 83% yield) and 2-cyanopyridine-4-carboxamide (2b; 97% yield), respectively, after 10 min. After 118 h, the intermediates 1b or 2b were transformed into 2,6-pyridinedicarboxamide (1c; 35% yield) and 2,6-pyridinedicarboxylic acid (1d; 60% yield) or 2-cyanopyridine-4-carboxylic acid (2c; 64% yield), respectively. The nitrilase from Fusarium solani afforded cyanocarboxylic acids 1e and 2c after 118 h (yields 95 and 62%, respectively). 3,4-Pyridinedicarbonitrile (3a) and 2,3-pyrazinedicarbonitrile (4a) were inferior substrates of nitrile hydratase and nitrilase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / metabolism
  • Aminohydrolases / metabolism*
  • Biotransformation
  • Chromatography, High Pressure Liquid
  • Fungi / enzymology*
  • Heterocyclic Compounds / chemistry
  • Heterocyclic Compounds / metabolism*
  • Hydrolysis
  • Nitriles / chemistry
  • Nitriles / metabolism*
  • Rhodococcus / enzymology*
  • Substrate Specificity

Substances

  • Amides
  • Heterocyclic Compounds
  • Nitriles
  • Aminohydrolases
  • nitrilase