Lipase catalyzed esterification of glycidol in organic solvents
- Univ. Nova de Lisboa, Oeiras (Portugal). Centro de Tecnologia Quimica e Biologica
The authors studied the resolution of racemic glycidol through esterification with butyric acid catalyzed by porcine pancreatic lipase in organic media. A screening of seven solvents (log P values between 0.49 and 3.0, P being the n-octanol-water partition coefficient of the solvent) showed that neither log P nor the logarithm of the molar solubility of water in the solvent provides good correlations between enantioselectivity and the properties of the organic media. Chloroform was one of the best solvents as regards the enantiometic purity (e.p.) of the ester produced. In this solvent, the optimum temperature for the reaction was determined to be 35C. The enzyme exhibited maximum activity at a water content of 13 [plus minus] 2% (w/w). The enantiomeric purity obtained was 83 [plus minus] 2% of (S)-glycidol butyrate and did not depend on the alcohol concentration or the enzyme water content for values of these parameters up to 200 mM and 25% (w/w), respectively. The reaction was found to follow a BiBi mechanism.
- OSTI ID:
- 6279685
- Journal Information:
- Biotechnology and Bioengineering; (United States), Journal Name: Biotechnology and Bioengineering; (United States) Vol. 42:4; ISSN BIBIAU; ISSN 0006-3592
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ALCOHOLS
BUTYRIC ACID
CARBOXYLESTERASES
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
ENZYME ACTIVITY
ENZYMES
ESTERASES
ESTERIFICATION
HYDROLASES
HYDROXY COMPOUNDS
LIPASES
METABOLISM
MONOCARBOXYLIC ACIDS
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC SOLVENTS
PROPANOLS
PROTEINS
SOLVENTS