Fatty acid vinyl esters as acylating agents: A new method for the enzymatic synthesis of monoacylglycerols |
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Authors: | Uwe T Bornscheuer Tsuneo Yamane |
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Affiliation: | (1) Laboratory of Molecular Biotechnology, Department of Applied Biological Sciences, School of Agricultural Sciences, Nagoya University, Chikusa-ku, 464-01 Nagoya, Japan |
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Abstract: | Lipase-catalyzed synthesis of monoacylglycerols (MAG) was performed by transesterification reactions between fatty acid vinyl
esters and either glycerol (1) or 1,2-O-isopropylidene-rac-glycerol (2), without solvents or in the presence ofn-pentane. Vinyl decanoate, vinyl laurate, vinyl stearate and vinyl palmitate have been converted to the corresponding monoacylglycerols.
As expected for the reaction with1, a mixture of mono-, di- and triacylglycerols was synthesized. The highest concentrations of MAG were achieved with vinyl
stearate (30% 2-MAG and 15% 1-MAG). The reactions of fatty acid vinyl esters with the protected glycerol (2) led to the corresponding protected 3-monoacylglycerols with 100% conversion after short reaction times. The subsequent cleavage
of these acetonides was performed by four different methods. The fastest cleavage was found with trifluoroacetic acid as catalyst,
whereas the highest concentration of MAG (100%) was obtained for the boric acid-catalyzed hydrolysis of the acetonides. |
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Keywords: | Cleavage diacylglycerol 2 2-dimethyl-1 3-dioxolane-4-methanol fatty acid vinyl ester 1 2-O-isopropylidene-rac-glycerol lipase monoacylglycerol transesterification |
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