Enantioselective resolution of 2-(1-hydroxy-3-butenyl)-5-methylfuran by immobilized lipase |
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Authors: | Guang Yang Jianping Wu Gang Xu Lirong Yang |
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Institution: | (1) Institute of Bioengineering, College of Material Science and Chemical Engineering, Zhejiang University, Hangzhou, 310027, China |
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Abstract: | An efficient and convenient strategy for synthesis of enantiomerically pure S-2-(1-hydroxy-3-butenyl)-5-methylfuran was for the first time described utilizing a lipase-mediated asymmetric acylation in
organic solvents. Rhizopus arrhizus lipase was chosen as the biocatalyst, and different immobilization methods including sol–gel encapsulation and covalent attachment
were adopted to improve its catalytic characteristics. Various influential factors of the reaction were also investigated.
Finally, the results showed that the lipase covalently attached onto epoxy resin exhibited the highest enantioselectivity
and operational stability. Under optimized reaction conditions, i.e., n-hexane as the solvent, 5/1 (mol/mol) of vinyl acetate to 2-(1-hydroxy-3-butenyl)-5-methylfuran and 30 °C, the ee value of S-1 reached up to above 98% at 52% conversion with an E value of 99. |
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Keywords: | S-2-(1-hydroxy-3-butenyl)-5-methylfuran Lipase Asymmetric acylation Sol– gel encapsulation Covalent attachment |
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