Biotechnology and Bioprocess Engineering:BBE

The Korean Society for Biotechnology and Bioengineering (한국생물공학회)
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Enantioselective Hydrolysis of Racemic Styrene Oxide by Epoxide Hydrolase of Rhodosporidium kratochvilovae SYU-08

  • Lee, Ji-Won (Department of Food Science and Technology, Kyungsung University) ;
  • Lee, Eun-Jung (Department of Food Science and Technology, Kyungsung University) ;
  • Yoo, Seung-Sik (Department of Chemical Engineering, Pusan National University) ;
  • Park, Sung-Hoon (Department of Chemical Engineering, Pusan National University) ;
  • Kim, Hee-Sook (Department of Food Science and Technology, Kyungsung University) ;
  • Lee, Eun-Yeol (Department of Food Science and Technology, Kyungsung University)
  • Published : 2003.10.01
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Abstract

Enantioselective hydrolysis for the production of chiral styrene oxide was investigated using the epoxide hydrolase activity of a newly isolated Rhodosporidium kratochvilovae SYU-08. The effects of reaction parameters - 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.

Keywords

References

  1. Curr. Opin. Chem. Biol. v.5 Synthetic applications of epoxide hydrolases Archelas,A.;R.Furstoss https://doi.org/10.1016/S1367-5931(00)00179-4
  2. Biotechnol. Tech. v.12 Kinetic resolution for optically active epoxides by microbial enantioselective hydrolysis Choi,W.J.;E.C.Huh;H.J.Park;E.Y.Lee;C.Y.Choi https://doi.org/10.1023/A:1008825508904
  3. Curr. Opin. Biotechnol. v.12 Microbial epoxide hydrolases for preparative biotransformations Steinreiber,A.;K.Faber https://doi.org/10.1016/S0958-1669(01)00262-2
  4. Tetrahedron. Asymm. v.8 Enantioselective hydrolysis of aryl, alicyclic and aliphatic epoxides by Rhodotorula glutinis Weijers,C.A.G.M. https://doi.org/10.1016/S0957-4166(97)00012-8
  5. J. Biosci. Bioeng. v.88 Biocatalytic production of chiral epichlorohydrin in organic solvent Choi,W.J.;E.Y.Lee;S.J.Yoon;C.Y.Choi https://doi.org/10.1016/S1389-1723(00)80022-5
  6. Biotechnol. Lett. v.20 Biocatalytic resolution of 1,2-epoxyoctane using resting cells of different yeast strains with novel epoxide hydrolase activities Botes,A.L.;C.A.G.M.Weijers;M.S.van Dyk https://doi.org/10.1023/A:1005395817739
  7. Tetrahedron v.50 Chemical and biological synthesis of chiral epoxides Besse,P.;H.Veschambre https://doi.org/10.1016/S0040-4020(01)85362-X
  8. Annu. Rev. Pharmacol. Toxicol. v.20 Molecular properties and biological functions of microsomal epoxide hydrolase Lu,A.Y.H.;G.T.Miwa https://doi.org/10.1146/annurev.pa.20.040180.002501
  9. J. Mol. Catal. B: Enzym. v.6 Epoxide hydrolases from yeasts and other sources: Versatile tools in biocatalysis Weijers,C.A.G.M.;J.A.M.de Bont https://doi.org/10.1016/S1381-1177(98)00123-4
  10. Anal. Chim. Acta v.391 A colorimetric assay suitable for screening epoxide hydrolase activity Zocher,F.;M.M.Enzelberger;U.T.Bornscheuer;B.Hauer;R.D.Schmid https://doi.org/10.1016/S0003-2670(99)00216-0
  11. Angew. Chem. v.112 A versatile periodate-coupled fluorogenic assay for hydrolytic enzymes Badalassi,F.;D.Wahler;G.Klein;P.Crotti;J.L.Reymond https://doi.org/10.1002/1521-3757(20001117)112:22<4233::AID-ANGE4233>3.0.CO;2-Z
  12. Biotechnol. Lett. v.23 Bacterial epoxide hydrolase-catalyzed resolution of a 2,2-disubstituted oxirane: optimization and upscaling Hellstrom,H.;A.Steinreiber;S.F.Mayer;K.Faber https://doi.org/10.1023/A:1005636121060