Hydrolysis of ibuprofen nitrile and ibuprofen amide and deracemisation of ibuprofen using Nocardia corallina B-276

Molecules. 2012 Mar 12;17(3):3148-54. doi: 10.3390/molecules17033148.

Abstract

A novel application of whole cells of Nocardia corallina B-276 for the deracemisation of ibuprofen is reported. This microorganism successfully hydrolysed ibuprofen nitrile to ibuprofen amide, and ibuprofen amide to ibuprofen, using a suspension of cells in a potassium phosphate buffer solution (0.1 M, pH = 7.0). These results can be explained by the presence of NHase and amidase enzymes, but the reactions are not enantioselective and low ee values were obtained. However, (R)-ibuprofen was isolated with > 99% ee by a deracemisation process catalysed by N. corallina B-276. This is the first report of this kind of catalysis with this microorganism.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Amidohydrolases / metabolism
  • Bacterial Proteins / metabolism
  • Biocatalysis
  • Biotransformation
  • Hydro-Lyases / metabolism
  • Hydrolysis
  • Ibuprofen / analogs & derivatives*
  • Ibuprofen / chemistry*
  • Nitriles / chemistry*
  • Nocardia / enzymology
  • Nocardia / metabolism*
  • Stereoisomerism

Substances

  • Amides
  • Bacterial Proteins
  • Nitriles
  • Amidohydrolases
  • Hydro-Lyases
  • nitrile hydratase
  • Ibuprofen