Enantioselective resolution of 2-(1-hydroxy-3-butenyl)-5-methylfuran by immobilized lipase.
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 degrees C, the ee value of S-1 reached up to above 98% at 52% conversion with an E value of 99.
Yang
Guang
G
Institute of Bioengineering, College of Material Science and Chemical Engineering, Zhejiang University, Hangzhou 310027, China.
Wu
Jianping
J
Xu
Gang
G
Yang
Lirong
L
D000215:Acylation; D004800:Enzymes, Immobilized / Q000378:metabolism*; D004853:Epoxy Resins; D005663:Furans / Q000378:metabolism*; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D012233:Rhizopus / Q000201:enzymology*; D012997:Solvents; D013237:Stereoisomerism; D013696:Temperature
D004800:Enzymes, Immobilized; D004853:Epoxy Resins; D005663:Furans; D012997:Solvents; D008049:Lipase