Solvent effects in lipase-catalysed transesterification reactions

Acta Chem Scand (Cph). 1990 Nov;44(10):1032-5. doi: 10.3891/acta.chem.scand.44-1032.

Abstract

Porcine pancreatic lipase-catalysed transesterifications of 2,2,2-trifluoroethyl butyrate with racemic 2-octanol and 1-phenylethanol have been studied in different organic solvents. Solvent hydrophobicity (log P -1.1 to 3.3) has only a minor effect on the reaction rate. Independently of the solvent used as the reaction medium, both (R)-2-octyl and (R)-1-phenylethyl butyrates were obtained in high optical purity (ee greater than 90%). Candida cylindracea lipase is active only in the most hydrophobic solvents studied.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Benzyl Alcohols / metabolism
  • Butyrates / metabolism
  • Candida / enzymology
  • Catalysis
  • Esterification* / drug effects
  • Hydrocarbons, Fluorinated
  • Lipase / drug effects*
  • Octanols / metabolism
  • Pancreas / enzymology
  • Solvents / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Swine

Substances

  • Benzyl Alcohols
  • Butyrates
  • Hydrocarbons, Fluorinated
  • Octanols
  • Solvents
  • 2,2,2-trifluoroethyl butyrate
  • 2-octanol
  • methylphenyl carbinol
  • Lipase