Kinetic resolution of (R/S)-propranolol (1-isopropylamino-3-(1-naphtoxy)-2-propanolol) catalyzed by immobilized preparations of Candida antarctica lipase B (CAL-B)

N Biotechnol. 2010 Dec 31;27(6):844-50. doi: 10.1016/j.nbt.2010.07.015. Epub 2010 Aug 3.

Abstract

Enzyme preparations of Candida antarctica B lipase (CAL-B) - immobilized on Eupergit C and partially modified Eupergit C supports - were tested for kinetic resolution of (R/S)-propranolol, using vinyl acetate as acyl donor, and toluene as organic solvent. The effects of (R/S)-propranolol concentration, vinyl acetate concentration and biocatalyst loading on the esterification and resolution of propranolol were studied. Additionally, different types of immobilized lipase derivatives were also evaluated in terms of its selectivity on kinetic resolution of (R,S)-propranolol. These derivatives showed different enantiomeric ratios (E), with high enantiomeric ratios (E=57) with CAL-B immobilized on Eupergit C supports.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Enzymes, Immobilized / metabolism*
  • Esterification
  • Fungal Proteins
  • Lipase / metabolism*
  • Molecular Structure
  • Polymers / chemistry
  • Propranolol / analogs & derivatives*
  • Propranolol / metabolism*
  • Solvents / chemistry
  • Solvents / metabolism
  • Stereoisomerism
  • Toluene / chemistry
  • Toluene / metabolism
  • Vinyl Compounds / chemistry
  • Vinyl Compounds / metabolism

Substances

  • Enzymes, Immobilized
  • Fungal Proteins
  • Polymers
  • Solvents
  • Vinyl Compounds
  • Toluene
  • Eupergit C
  • Propranolol
  • Lipase
  • lipase B, Candida antarctica
  • vinyl acetate