Immobilization of Amano lipase AK from Pseudomonas fluorescens on different types of chitosan-containing supports: use in the kinetic resolution of rac-indanol

Bioprocess Biosyst Eng. 2021 Apr;44(4):785-792. doi: 10.1007/s00449-020-02487-2. Epub 2021 Jan 3.

Abstract

Amano lipase AK from P. fluorescens was immobilized on different types of chitosan-containing supports. Chitosan lower molecular weight (2.5%), chitosan lower molecular weight/sodium alginate (2.5%/2.5%) and chitosan lower molecular weight/carrageenan (2.5%/2.5%) allowed the highest values of immobilization yields (IY) of 81, 81 and 83%, respectively. Best activity results were achieved using chitosan average molecular weight (5%) and chitosan lower molecular weight/sodium alginate (2.5%/2.5%) as support, with values of 1.40 and 1.30 UpNPB/ggel and with recovery activities of 45.75 and 35.6%, respectively. These derivatives were evaluated in the kinetic resolution of rac-indanol to obtain a key intermediate in the synthesis of a drug used in the treatment of Parkinson's disease. The most efficient derivatives in the kinetic resolution were lipase immobilized on chitosan average molecular weight (5.0%) and chitosan low molecular weight/sodium alginate, the latter leading to obtaining both (S)-indanol and (R)-indanyl acetate with > 99% ee and 50% conversion.

Keywords: Chitosan; Immobilization; Lipase from pseudomonas fluorescens; rac-indanol.

MeSH terms

  • Acetates / chemistry*
  • Alginates / chemistry
  • Carrageenan / chemistry
  • Chemistry, Pharmaceutical / methods*
  • Chitosan / chemistry*
  • Drug Design
  • Enzymes, Immobilized / chemistry
  • Gels
  • Hydrogen-Ion Concentration
  • Kinetics
  • Lipase / chemistry*
  • Molecular Weight
  • Parkinson Disease / drug therapy
  • Powders
  • Pseudomonas fluorescens / metabolism*
  • Selegiline / chemistry

Substances

  • Acetates
  • Alginates
  • Enzymes, Immobilized
  • Gels
  • Powders
  • Selegiline
  • Carrageenan
  • Chitosan
  • Lipase