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Enantioselective hydrolysis of racemic styrene oxide by epoxide hydrolase ofRhodosporidium kratochvilovae SYU-08

Abstract

Enantioselective hydrolysis for the production of chiral styrene oxide was investigated using the epoxide hydrolase activity of a newly isolatedRhodosporidium kratochvilovae SYU-08. The effects of reaction prameters—buffer type, pH, temperature, initial substrate concentrations, phenyl-1,2-ethanediol concentrations on hydrolysis rate, and enantioselectivity—were analyzed. Optically active (S)-styrene oxide with an enantiomeric excess higher than 99 % was obtained from its racemate with a yield of 38 % (theoretically 50% maximum yield) from an initial concentration of 80 mM.

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References

  1. [1]

    Archelas, A. and R. Furstoss (2001) Synthetic applications of epoxide hydrolases.Curr. Opin. Chem. Biol. 5: 112–119.

  2. [2]

    Besse, P. and H. Veschambre (1994) Chemical and biological synthesis of chiral epoxides.Tetrahedron 50: 8885–8927.

  3. [3]

    Choi, W. J., E. C. Huh, H. J. Park, E. Y. Lee, and C. Y. Choi (1998) Kinetic resolution for optically active epoxides by microbial enantioselective hydrolysis.Biotechnol. Tech. 12: 225–228.

  4. [4]

    Steinreiber, A. and K. Faber (2001) Microbial epoxide hydrolases for preparative biotransformations.Curr. Opin. Biotechnol. 12: 552–558.

  5. [5]

    Weijers, C. A. G. M. (1997) Enantioselective hydrolysis of aryl, alicyclic and aliphatic epoxides byRhodotorula glutinis.Tetrahedron. Asymm. 8: 639–647.

  6. [6]

    Choi, W. J., E. Y. Lee, S. J. Yoon, and C. Y. Choi (1999) Biocatalytic production of chiral epichlorohydrin in organic solvent.J. Biosci. Bioeng. 88: 339–341.

  7. [7]

    Botes, A. L., C. A. G. M. Weijers, and M. S. van Dyk (1998) Biocatalytic resolution of 1,2-epoxyoctane using resting cells of different yeast strains with novel epoxide hydrolase activities.Biotechnol. Lett. 20: 421–426.

  8. [8]

    Lu, A. Y. H. and G. T. Miwa (1980) Molecular properties and biological functions of microsomal epoxide hydrolase.Annu. Rev. Pharmacol. Toxicol. 20: 513–531.

  9. [9]

    Weijers, C. A. G. M. and J. A. M. de Bont (1999) Epoxide hydrolases from yeasts and other sources: Versatile tools in biocatalysis.J. Mol. Catal. B: Enzym. 6: 199–214.

  10. [10]

    Zocher, F., M. M. Enzelberger, U. T. Bornscheuer, B. Hauer, and R. D. Schmid (1999) A colorimetric assay suitable for screening epoxide hydrolase activity.Anal. Chim. Acta 391: 345–351.

  11. [11]

    Badalassi, F., D. Wahler, G. Klein, P. Crotti, and J.-L. Reymond (2000) A versatile periodate-coupled fluorogenic assay for hydrolytic enzymes.Angew. Chem. 112: 4233–4236.

  12. [12]

    Hellström, H., A. Steinreiber, S. F. Mayer, and K. Faber (2001) Bacterial epoxide hydrolase-catalyzed resolution of a 2,2-disubstituted oxirane: optimization and upscaling.Biotechnol. Lett. 23: 169–173.

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Correspondence to Eun Yeol Lee.

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Lee, J.W., Lee, E.J., Yoo, S.S. et al. Enantioselective hydrolysis of racemic styrene oxide by epoxide hydrolase ofRhodosporidium kratochvilovae SYU-08. Biotechnol. Bioprocess Eng. 8, 306–308 (2003). https://doi.org/10.1007/BF02949223

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Keywords

  • enantioselective hydrolysis
  • epoxide hydrolase
  • Rhodosporidium kratochvilovae
  • chiral styrene oxide