Biotechnology and Bioprocess Engineering:BBE

  • 제11권4호
  • /
  • Pages.282-287
  • /
  • 2006
  • /
  • 1226-8372(pISSN)
  • /
  • 1976-3816(eISSN)
한국생물공학회 (The Korean Society for Biotechnology and Bioengineering)
권호 표지

Purification and Characterization of a Recombinant Caulobacter crescentus Epoxide Hydrolase

  • Hwang, Seung-Ha (Department of Chemical Engineering, Pohang University of Science and Technology) ;
  • Hyun, Hye-Jin (Interdisciplinary Program for Biochemical Engineering and Biotechnology, College of Engineering, Seoul National University) ;
  • Lee, Byoung-Ju (Interdisciplinary Program for Biochemical Engineering and Biotechnology, College of Engineering, Seoul National University) ;
  • Park, Young-Seub (Department of Chemical Engineering, Pohang University of Science and Technology) ;
  • Lee, Eun-Yeol (Department of Food Science and Technology, Kyungsung University) ;
  • Choi, Cha-Yong (Interdisciplinary Program for Biochemical Engineering and Biotechnology, College of Engineering, Seoul National University)
  • 발행 : 2006.08.30
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

A Caulobacter crescentus epoxide hydrolase(CCEH) from a recombinant Escherichia coli was purified to homogeneity using a three-step procedure. The CCEH protein was purified 7.3-fold with a 22.9% yield in overalll activity. The optimal reaction temperature and pH were determined to be $37^{\circ}C$ and pH 8.0, respectively. The addition of 10%(v/v) dimethylsulfoxide as a cosolvent improved the enantioselectivity of CCEH for a batch kinetic resolution of racemic indene oxide.

키워드

참고문헌

  1. Choi, W. J., C. Y. Choi, J. A. De Bont, and C. A. Weijers (2000) Continuous production of enantiopure 1,2- epoxyhexane by yeast epoxide hydrolase in a two-phase membrane bioreactor. Appl. Microbiol. Biotechnol. 54: 641-646 https://doi.org/10.1007/s002530000451
  2. Choi, W. J. and C. Y. Choi (2005) Production of chiral epoxides: Epoxide hydrolase-catalyzed enantioselective hydrolysis. Biotechnol. Bioprocess Eng. 10: 167-179 https://doi.org/10.1007/BF02932009
  3. Breuer, M., K. Ditrich, T. Habicher, B. Hauer, M. Kesseler, R. Stürmer, and T. Zelinski (2004) Industrial methods for the production of optically active intermediates. Angew. Chem. Int. Ed. Engl. 43: 788-824 https://doi.org/10.1002/anie.200300599
  4. Furuhashi, K., M. Shintani, and M. Takagi (1986) Effects of solvents on the production of epoxides by Nocardia corallina B-276. Appl. Microbiol. Biotechnol. 23: 218-223
  5. Panke, S., V. de Lorenzo, A. Kaiser, B. Witholt, and M. G. Wubbolts (1999) Engineering of a stable whole-cell biocatalyst capable of (S)-styrene oxide formation for continuous two-liquid-phase applications. Appl. Environ. Microbiol. 65: 5619-5623
  6. Patel, R. N., C. G. McNamee, A. Banerjee, J. M. Howell, R. S. Robison, and L. J. Szarka (1992) Stereoselective reduction of $\beta$-keto esters by Geotrichum candidum. Enzyme Microb. Technol. 14: 731-738 https://doi.org/10.1016/0141-0229(92)90113-3
  7. Fretland, A. J. and C. J. Omiecinski (2000) Epoxide hydrolases: biochemistry and molecular biology. Chem. Biol. Interact. 129: 41-59 https://doi.org/10.1016/S0009-2797(00)00197-6
  8. Arand, M., B. M. Hallberg, J. Zou, T. Bergfors, F. Oesch, M. J. van der Werf, J. A. M. de Bont, T. A. Jones, and S. L. Mowbray (2003) Structure of Rhodococcus erythropolis limonene-1,2-epoxide hydrolase reveals a novel active site. EMBO J. 22: 2583-2592 https://doi.org/10.1093/emboj/cdg275
  9. Kim, H. S., S. J. Lee, E. J. Lee, J. W. Hwang, S. Park, S. J. K. Kim, and E. Y. Lee (2005) Cloning and characterization of a fish microsomal epoxide hydrolase of Danio rerio and application to kinetic resolution of racemic styrene oxide. J. Mol. Catal., B Enzym. 37: 30-35 https://doi.org/10.1016/j.molcatb.2005.09.003
  10. Nardini, M., I. S. Ridder, H. J. Rozeboom, K. H. Kalk, R. Rink, D. B. Janssen, and B. W. Dijkstra (1999) The X-ray structure of epoxide hydrolase from Agrobacterium radiobacter AD1. An enzyme to detoxify harmful epoxides. J. Biol. Chem. 274: 14579-14586 https://doi.org/10.1074/jbc.274.21.14579
  11. Visser, H., C. A. G. M. Weijers, A. J. J. van Ooyen, and J. C. Verdoes (2002) Cloning, characterization and heterologous expression of epoxide hydrolase-encoding cDNA sequences from yeasts belonging to the genera Rhodotorula and Rhodosporidium. Biotechnol. Lett. 24: 1687-1694 https://doi.org/10.1023/A:1020613803342
  12. Zou, J. Y., B. M. Hallberg, T. Bergfors, F. Oesch, M. Arand, S. L. Mowbray, and T. A. Jones (2000) Structure of Aspergillus niger epoxide hydrolase at 1.8 angstrom resolution: implications for the structure and function of the mammalian microsomal class of epoxide hydrolases. Structure 8: 111-122 https://doi.org/10.1016/S0969-2126(00)00087-3
  13. Kim, H. S., J.-H. Lee, S. Park, and E. Y. Lee (2004) Biocatalytic preparation of chiral epichlorohydrins using recombinant Pichia pastoris expressing epoxide hydrolase of Rhodotorula glutinis. Biotechnol. Bioprocess Eng. 9: 62-64 https://doi.org/10.1007/BF02949324
  14. Lee, J. W., E. J. Lee, S. S. Yoo, S. H. Park, H. S. Kim, and E. Y. Lee (2003) Enantioselective hydrolysis of racemic styrene oxide by epoxide hydrolase of Rhodosporidium kratochvilovae SYU-08. Biotechnol. Bioprocess Eng. 8: 306-308 https://doi.org/10.1007/BF02949223
  15. Argiriadi, M. A., C. Morisseau, B. D. Hammock, and D. W. Christianson (1999) Detoxification of environmental mutagens and carcinogens: Structure-based mechanism and evolution of liver epoxide hydrolase. FASEB J. 13: A1561-A1561
  16. Arand, M., A. Cronin, F. Oesch, S. L. Mowbray, and T. A. Jones (2003) The telltale structures of epoxide hydrolases. Drug Metab. Rev. 35: 365-383 https://doi.org/10.1081/DMR-120026498
  17. Hwang, S., H. Hyun, B. Lee, Y. Park, C. Choi, J. Han, and H. Joo (2006) Screening from the genome databases: Novel epoxide hydrolase from Caulobacter crescentus. J. Microbiol. Biotechnol. 16: 32-36
  18. Osprian, I., W. Kroutil, M. Mischitz, and K. Faber (1997) Biocatalytic resolution of 2-methyl-2-(aryl)alkyloxiranes using novel bacterial epoxide hydrolases. Tetrahedron Asymmetry 8: 65-71 https://doi.org/10.1016/S0957-4166(96)00493-4
  19. 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 https://doi.org/10.1023/A:1008825508904
  20. Morisseau, C., A. Archelas, C. Guitton, D. Faucher, R. Furstoss, and J. C. Baratti (1999) Purification and characterization of a highly enantioselective epoxide hydrolase from Aspergillus niger. Eur. J. Biochem. 263: 386-395 https://doi.org/10.1046/j.1432-1327.1999.00519.x
  21. Monterde, M. I., M. Lombard, A. Archelas, A. Cronin, M. Arand, and R. Furstoss (2004) Enzymatic transformations. Part 58: Enantioconvergent biohydrolysis of styrene oxide derivatives catalysed by the Solanum tuberosum epoxide hydrolase. Tetrahedron Asymmetry 15: 2801-2805 https://doi.org/10.1016/j.tetasy.2004.06.032
  22. Chen, C. S., Y. Fujimoto, G. Girdaukas, and C. J. Sih (1982) Quantitative analyses of biochemical kinetic resolutions of enantiomers. J. Am. Chem. Soc. 104: 7294-7299 https://doi.org/10.1021/ja00389a064
  23. Botes, A. L. (1999) Affinity purification and characterization of a yeast epoxide hydrolase. Biotechnol. Lett. 21: 511-517 https://doi.org/10.1023/A:1005500407152
  24. Kronenburg, N. A. E., M. Mutter, H. Visser, J. A. M. de Bont, and C. A. G. M. Weijers (1999) Purification of an epoxide hydrolase from Rhodotorula glutinis. Biotechnol. Lett. 21: 519-524 https://doi.org/10.1023/A:1005556508061