Near-perfect kinetic resolution of racemic p-chlorostyrene oxide by SlEH1, a novel epoxide hydrolase from Solanum lycopersicum with extremely high enantioselectivity.

@article{Hu2019NearperfectKR,
  title={Near-perfect kinetic resolution of racemic p-chlorostyrene oxide by SlEH1, a novel epoxide hydrolase from Solanum lycopersicum with extremely high enantioselectivity.},
  author={Bo-Chun Hu and Die Hu and Chuang Li and X. Xu and Zheng Wen and M. Wu},
  journal={International journal of biological macromolecules},
  year={2019}
}
  • Bo-Chun Hu, Die Hu, +3 authors M. Wu
  • Published 2019
  • Chemistry, Medicine
  • International journal of biological macromolecules
    • An open reading frame of sleh1, a gene encoding for a novel epoxide hydrolase from Solanum lycopersicum (SlEH1), was amplified by RT-PCR and expressed in E. coli BL21(DE3). The substrate spectrum assay showed that E. coli/sleh1 had EH activities towards all tested substrates except for racemic (rac-) 5a, and the highest enantiomeric ratio (E > 200) towards rac-2a, retaining (R)-2a with 99.1% ees and 49.2% yields and affording (R)-2b with 89.8% eep and 46.7% yieldp. Besides, E. coli/sleh1 also… CONTINUE READING
    View on PubMed
    doi.org
    5 Citations
    5 Citations
    Citation Type

    Citation Type

    Efficient kinetic resolution of para-chlorostyrene oxide at elevated concentration by Solanum lycopersicum epoxide hydrolase in the presence of Tween-20
    Highly regio- and enantio-selective hydrolysis of two racemic epoxides by GmEH3, a novel epoxide hydrolase from Glycine max.
    Nearly perfect kinetic resolution of racemic o-nitrostyrene oxide by AuEH2, a microsomal epoxide hydrolase from Aspergillus usamii, with high enantio- and regio-selectivity.
    • Die Hu, Bo-Chun Hu, +4 authors M. Wu
    • Chemistry, Medicine
    • International journal of biological macromolecules
    • 2020
    Manipulating the regioselectivity of a Solanum lycopersicum epoxide hydrolase for the enantioconvergent synthesis of enantiopure alkane- and alkene-1,2-diols
    Greatly enhancing the enantioselectivity of PvEH2, a Phaseolus vulgaris epoxide hydrolase, towards racemic 1,2-epoxyhexane via replacing its partial cap-loop.
    • 1

    References

    SHOWING 1-10 OF 44 REFERENCES
    Asymmetric hydrolysis of styrene oxide by PvEH2, a novel Phaseolus vulgaris epoxide hydrolase with extremely high enantioselectivity and regioselectivity
    • 13
    Stereoselective Hydrolysis of Epoxides by reVrEH3, a Novel Vigna radiata Epoxide Hydrolase with High Enantioselectivity or High and Complementary Regioselectivity.
    • 14
    Enantioconvergent hydrolysis of racemic styrene oxide at high concentration by a pair of novel epoxide hydrolases into (R)-phenyl-1,2-ethanediol
    • 10
    Enantioselective Hydrolysis of Racemic and Meso-Epoxides with Recombinant Escherichia coli Expressing Epoxide Hydrolase from Sphingomonas sp. HXN-200: Preparation of Epoxides and Vicinal Diols in High ee and High Concentration
    • 46
    Directed modification of a novel epoxide hydrolase from Phaseolus vulgaris to improve its enantioconvergence towards styrene epoxides
    • 15
    Improved enantioselective conversion of styrene epoxides and meso-epoxides through epoxide hydrolases with a mutated nucleophile-flanking residue
    • 33
    Improvement in the activity and enantioconvergency of PvEH3, an epoxide hydrolase from Phaseolus vulgaris, for p-chlorostyrene oxide by site-saturation mutagenesis
    • 7
    An Unusual (R)-Selective Epoxide Hydrolase with High Activity for Facile Preparation of Enantiopure Glycidyl Ethers
    • 40
    Enzymatic transformations. Part 58: Enantioconvergent biohydrolysis of styrene oxide derivatives catalysed by the Solanum tuberosum epoxide hydrolase
    • 84
    A novel enantioselective epoxide hydrolase from Agromyces mediolanus ZJB120203: Cloning, characterization and application
    • 23