Lipase-catalysed resolution of gamma- and delta-lactones

J Biotechnol. 1997 Aug 11;56(2):129-33. doi: 10.1016/s0168-1656(97)00107-7.

Abstract

Lipase-catalysed stereoselective hydrolysis of a family of saturated gamma- and delta-lactones was investigated. Increasing the chain length from delta-octalactone to delta-dodecalactone leads to higher enantiomeric excess. Best results were found using a lipase from Pseudomonas species (KW51) yielding highest enantiomeric excesses (greater than 99% ee at 50% conversion, E > 100) at short reaction times (10 h) for delta-undecalactone and delta-dodecalactone. In contrast, gamma-lactones were resolved less efficiently. Highest enantioselectivities (70%ee at 50% conversion, E = 11) were found for gamma-nonalactone. Optimum reaction conditions were found at pH 8 and 12.5 degrees C.

MeSH terms

  • Candida / enzymology
  • Chromobacterium / enzymology
  • Hydrogen-Ion Concentration
  • Hydrolysis
  • Isomerism
  • Lactones / chemistry
  • Lactones / classification
  • Lactones / isolation & purification*
  • Lactones / metabolism
  • Lipase / metabolism*
  • Molecular Structure
  • Pseudomonas / enzymology*
  • Temperature

Substances

  • Lactones
  • Lipase