Kinetic resolution of racemic 1-phenyl 1-propanol by lipase catalyzed enantioselective esterification reaction

Artif Cells Blood Substit Immobil Biotechnol. 2010 Oct;38(5):288-93. doi: 10.3109/10731199.2010.494579.

Abstract

In this study, resolution of (R,S)-1-phenyl 1-propanol by lipase-catalyzed enantioselective esterification was achieved. To investigate the effect of lipase type on enantiomeric excess, three different lipases were used. Novozym 435 exhibited the highest enantioselectivity for resolution of (R,S)-1-phenyl 1-propanol. The effects of carbon length of fatty acids from C12 to C16, which were used as acyl donor, organic solvents with Log P values from 0.5 to 4.5, acyl donor/alcohol molar ratio (1:1, 3:2, 2:1, 3:1), amount of added molecular sieves (0-133.2 kg/m(3)), and temperature (10-60° C) on the enantioselectivity were investigated. The best reaction conditions were comprised of using toluene (Log P= 2.5) as solvent, lauric acid (12C) as acyl donor, 133.2 kg/m(3) molecular sieves at 50° C and acyl donor/alcohol molar ratio as 1:1. Under these conditions, the enantiomeric excess of S enantiomer ee (S) was obtained as 95% for a reaction time of 2.5 hours.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocatalysis*
  • Candida / enzymology
  • Esterification
  • Kinetics
  • Lipase / metabolism*
  • Propanols / chemistry*
  • Propanols / metabolism*
  • Pseudomonas / enzymology
  • Solvents / chemistry
  • Stereoisomerism
  • Substrate Specificity
  • Temperature

Substances

  • Propanols
  • Solvents
  • 1-phenylpropanol
  • Lipase