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Enantioselective resolution of 2-(1-hydroxy-3-butenyl)-5-methylfuran by immobilized lipase

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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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Acknowledgements

The authors would like to thank the Chinese National Natural Science Foundation (No. 20606030 and 20336010), Key Project of Chinese National Programs for Fundamental Research and Development (No. 2003CB716008) and Hi-Tech Research and Development Program of China (No. 2006AA02Z238) for financial support.

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Correspondence to Lirong Yang.

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Yang, G., Wu, J., Xu, G. et al. Enantioselective resolution of 2-(1-hydroxy-3-butenyl)-5-methylfuran by immobilized lipase. Appl Microbiol Biotechnol 81, 847–853 (2009). https://doi.org/10.1007/s00253-008-1713-x

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Keywords

  • S-2-(1-hydroxy-3-butenyl)-5-methylfuran
  • Lipase
  • Asymmetric acylation
  • Sol–gel encapsulation
  • Covalent attachment