Studies on the enantioselectivity in the lipase-catalyzed synthesis of monoacylglycerols from isopropylidene glycerol |
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Authors: | M Heidt U Bornscheuer R D Schmid |
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Institution: | (1) Institut für Technische Biochemie, Universität Stuttgart, 31, 70569 Allmandring, Stuttgart, Germany |
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Abstract: | Summary The regioselective lipase-catalyzed acylation of isopropylidene glycerol using different vinyl esters as acyl donors in toluene was studied. Reaction progress and enantioselectivity were monitored by gas chromatography using a permethylated -cyclodextrin phase. All vinyl esters were completely converted after 20 to 24 h and it was found that the S-enantiomer reacted faster. Lower enantiomeric excess were found using e. g. vinyl palmitate (18 %ee) compared to e. g. vinyl butyrate (42 %ee) with crude lipase from Pseudomonas cepacia. Immobilization using the sol-gel method resulted in higher remaining activities (up to 69%) and increased enantioselectivity E (up to 8.5). |
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