Abstract
The use of enantioselective hydrolysis for preparing chiral epichlorohydrins was investigated using recombinantPichia pastoris with the enantioselective epoxide hydrolase ofRhodotorula glutinis. The rate of the recombinant epoxide hydrolase-catalyzed enantioselective hydrolysis of racemic epichlorohydrins was enhanced by the addition of 5% (v/v) Tween 20. Enantiopure (R)-epichlorohydrins with an enantiopurity of 100%ee and a yield of 26% were obtained within 5 min from 50 mM racemates.
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de Vries, E. J. and D. B. Janssen (2003) Biocatalytic conversion of epoxides.Curr. Opin. Biotechnol. 14: 414–420.
Archelas, A. and R. Furstoss (2001) Synthetic applications of epoxide hydrolases.Curr. Opin. Chem. Biol. 5: 112–119.
Tokunaga, M., J. F. Larrow, F. Kakiuchi, and E. N. Jacobsen (1997) Asymmetric catalysis with water: efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis.Science 277: 936–938.
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.
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.
Weijers, C. A. G. M (1997) Enantioselective hydrolysis of aryl, alicyclic and aliphatic epoxides byRhodotorula glutinis.Tetrahedron Asymmetry 8: 639–647.
Botes, A. L. (1999) Affinity purification and characterization of a yeast epoxide hydrolase.Biotechnol. Lett. 21: 511–517.
Visser, H., S. Vreugdenhil, J. A. M. de Bont, and J. C. Verdoes (2000) Cloning and characterization of an epoxide hydrolase-encoding gene fromRhodotorula glutinis.Appl. Microbiol. Biotechnol. 53: 415–419.
Rink, R., M. Fennema, M. Smids, U. Dehmel, and D. B. Jenssen (1997) Primary structure and catalytic mechanisms of the epoxide hydrolase fromAgrobacterium radiobactor AD1.J. Biol. Chem. 272: 14650–14657.
Lee, S. J., E. J. Lee, C. H. Kim, J. W. Lee, H. S. Kim, and E. Y. Lee (2003) Development of recombinantSaccharomyces cerevisiae expressing epoxide hydrolase for the preparation of chiral phenyl oxirane.Kor. J. Life Sci. 13: 105–109.
Lee, S. J., J. W. Lee, E. J. Lee, H. S. Kim, and E. Y. Lee (2003) Development of functional recombinant epoxide hydrolase for the production of chiral styrene oxide.Proceedings of Current Biotechnology and Bioengineering (XII). April 11–12. Busan, Korea.
Kronenburg, N. A. E. and J. A. M. de Bont (2001) Effects of detergents on specific activity and enantioselectivity of the epoxide hydrolase fromRhodotorula glutinis.Enzyme Microb. Technol. 28: 210–217.
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Kim, H.S., Lee, JH., Park, S. et al. Biocatalytic preparation of chiral epichlorohydrins using recombinantPichia pastoris expressing epoxide hydrolase ofRhodotorula glutinis . Biotechnol Bioproc E 9, 62–64 (2004). https://doi.org/10.1007/BF02949324
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DOI: https://doi.org/10.1007/BF02949324