Solvent effects in lipase-catalysed transesterification reactions.
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.
Kanerva
L T
LT
Department of Chemistry, University of Turku, Finland.
Vihanto
J
J
Halme
M H
MH
Loponen
J M
JM
Euranto
E K
EK
D000818:Animals; D001592:Benzyl Alcohols / Q000378:metabolism; D002087:Butyrates / Q000378:metabolism; D002175:Candida / Q000201:enzymology; D002384:Catalysis; D004951:Esterification / Q000187:drug effects; D006845:Hydrocarbons, Fluorinated; D008049:Lipase / Q000187:drug effects*; D000442:Octanols / Q000378:metabolism; D010179:Pancreas / Q000201:enzymology; D012997:Solvents / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013552:Swine
D001592:Benzyl Alcohols; D002087:Butyrates; D006845:Hydrocarbons, Fluorinated; D000442:Octanols; D012997:Solvents; C067942:2,2,2-trifluoroethyl butyrate; C067943:2-octanol; C002017:methylphenyl carbinol; D008049:Lipase