Mass transport limitations reduce the effective stereospecificity in enzyme-catalyzed kinetic resolution

Org Lett. 2000 May 18;2(10):1373-6. doi: 10.1021/ol005639m.

Abstract

[reaction-see text] The kinetic resolution of seudenol catalyzed by Candida antarctica lipase B in hexane was investigated. Large differences in reaction rate and stereospecificity were observed when different enzyme preparations were used. These differences were ascribed to mass transport limitations which reduced both reaction rate and stereospecificity. Lyophilized enzyme preparations were more apt to give this problem than immobilized preparations. Further, low substrate concentrations enhanced the effect. Thus, high alcohol concentrations and enzyme immobilization can be recommended.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Candida / enzymology
  • Enzymes / metabolism*
  • Enzymes, Immobilized
  • Fungal Proteins
  • Kinetics
  • Lipase / metabolism*
  • Stereoisomerism*
  • Substrate Specificity

Substances

  • Enzymes
  • Enzymes, Immobilized
  • Fungal Proteins
  • Novozyme 435
  • Lipase