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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

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Efficient preparation of optically active ketoprofen by Mucor javanicus lipase immobilized on an inorganic support

K Kato1, Y Gong, T Saito

  • 1Department of Chemistry, National Industrial Research Institute of Nagoya, Hirate-cho, Kita-ku, Nagoya 462-8510, Japan.

Journal of Bioscience and Bioengineering
|October 20, 2005
PubMed

Insights

Lipase M enzyme demonstrated effective enantioselectivity for ketoprofen trifluoroethyl ester. Immobilized Lipase M showed enhanced performance and recyclability for potential industrial applications.

Area of Science:

  • Biocatalysis
  • Enzyme Engineering
  • Organic Synthesis

Background:

  • Enzymatic kinetic resolution is crucial for chiral drug synthesis.
  • Lipases are versatile biocatalysts for enantioselective transformations.
  • Ketoprofen is a widely used non-steroidal anti-inflammatory drug.

Purpose of the Study:

  • To evaluate the enantioselectivity of Lipase M from Mucor javanicus for racemic ketoprofen trifluoroethyl ester.
  • To investigate the effect of immobilization on enzyme performance.
  • To assess the reusability of the immobilized enzyme.

Main Methods:

  • Enzyme screening using racemic ketoprofen trifluoroethyl ester as substrate.
  • Enzyme immobilization on Toyonite 200-A support.
  • Determination of enantioselectivity (E value) and reactivity.
  • Recycling studies of the immobilized enzyme.

Main Results:

  • Lipase M exhibited good enantioselectivity (E=50) for the target ester in a buffered aqueous-organic medium.
  • Immobilization on Toyonite 200-A improved selectivity (E=55) and reactivity.
  • The immobilized enzyme retained activity and selectivity over at least five reuse cycles.

Conclusions:

  • Lipase M is a promising biocatalyst for the enantioselective synthesis of ketoprofen derivatives.
  • Enzyme immobilization enhances stability and reusability, making it suitable for industrial processes.
  • Further optimization could lead to cost-effective production of chiral pharmaceuticals.

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