Abstract
Cyclohexanone monooxygenase (CHMO) catalyzing Baeyer-Villiger oxidation converts cyclic ketones into optically pure lactones, which have been used as building blocks in organic synthesis. A recombinant Escherichia coli BL21(DE3)/pMM4 expressing CHMO originated from Acinetobacter sp. NCIB 9871 was used to produce ε-caprolactone through a simultaneous biocatalyst production and Baeyer-Villiger oxidation (SPO) process. Afed-batch process was designed to obtain high cell density for improvin production of ε-caprolactone. The fed-batch SPO process have the best results, 10.2 g/L of ε-caprolactone and 0.34 g/(L·h) of productivity, corresponding to a 10.5- and 3.4-fold enhancement compared with those of the batch SPO, respectively.
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References
Renz, M. and Meunier, B. (1999), Eur. J. Org. Chem. 4, 737–750.
Kyte, B. G., Rouviere, P., Cheng, Q., and Stewart, J. D. (2004), J. Org. Chem. 69, 12–17.
Roberts, S. M. and Wan, P. W. H. (1998), J. Mol. Catal. B: Enzymat. 4, 111–136.
Strukul, G. (1998), Angew. Chem. Int. Ed. Engl. 37, 1198–1209.
Kelly, D. R., Wan, P. W. H., and Tang, J. (1998), in Biotechnology, vol. 8, Rehm, H. J., Reed, G., Puhler, A., and Stadler, P., eds., Wiley-VCH, Weinheim, Germany pp. 535–587.
Trudgill, P. W. (1990). Methods Enzymol. 37, 70–77.
Willetts, A. (1997), TIBTECH 15, 55–62.
Vogel, M. and Schwarz-Linek, U. (1999), in Bioorganic Chemistry, Diederichsen, U., Lindhorst, T. K., Westermann, B., and Wessjohann, L. A., eds., Wiley-VCH, Weinheim, Germany, pp. 102–110.
Simpson, H. D., Alphand, V., and Furstoss, R. (2001), J. Mol. Catal. B: Enzymat. 16, 101–108.
Doig, S. D., O'Sullivan, L. M., Patel, S., Ward, J. M., and Woodley, J. M. (2001), Enzyme Microb. Technol. 28, 265–274.
Doig, S. D., Simpson, H., Alphand, V., Furstoss, R., and Woodley, J. M. (2003), Enzyme Microb. Technol. 32, 347–355.
Doig, S. D., Avenell, P. J., Bird, P. A., Gallati, P., Lander, K. S., Lye, G. J., Wohlgemuth, R., and Woodley, J. M. (2002), Biotechnol. Prog. 18, 1039–1046.
Mihovilovic, M. D., Muller, B., Kayser, M. M., Stewart, J. D., Frohlich, J., Stanetty, P., and Spreitzer, H. (2001), J. Mol. Catal. B: Enzymat. 11, 349–353.
Martinez, C. A. (2000), PhD thesis, University of Florida, Gainesville.
Walton, A. Z. and Stewart, J. D. (2002), Biotechnol. Prog. 18, 262–268.
Lee, D. H., Kim, M. D., Lee, W. H., Kweon, D. H., and Seo, J. H. (2004), Appl. Microbiol. Biotechnol. 63, 549–552.
Chen, G., Kayser, M. M., Mihovilovic, M. D., Mrstik, M. E., Martinez, C. A., and Stewart, J. D. (1999), N. J. Chem. 23, 827–832.
Kim, M. D., Lee, W. J., Park, K. H., Rhee, K. H., and Seo, J. H. (2002), J. Microbiol. Biotechnol. 12(2) 273–278.
Choi, H. I., Lee, S. Y., Shin, K. S., Lee, W. G., Park, S. J., Chang, H. N., and Chang, Y. K. (2002), Biotechnol. Bioprocess Eng. 7, 371–374.
Laemmli, U. K. (1970), Nature 27, 680–685.
Ramos, J. L., Duque, E., Gallegos, M. t., Godoy, R., Ramos-Gonzalez, I. R., Rojas, A., Teran, W., and Segura, A. (2002), Annu. Rev. Microbiol. 56, 743–768.
White, D. G., Goldmas, J. D., Demple, B., and Levy, S. B. (1997), J. Bacteriol. 179, 6122–6126.
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Lee, WH., Park, YC., Lee, DH. et al. Simultaneous biocatalyst production and baeyer-villiger oxidation for bioonversion of cyclohexanone by recombinant Escherichia coli expressing cyclohexanone monooxygenase. Appl Biochem Biotechnol 123, 827–836 (2005). https://doi.org/10.1385/ABAB:123:1-3:0827
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DOI: https://doi.org/10.1385/ABAB:123:1-3:0827