Hydroxylation of indole by PikC cytochrome P450 from Streptomyces venezuelae and engineering its catalytic activity by site-directed mutagenesis

Journal of Microbiology and Biotechnology

Volumn 16, Issue 6, 2006, Pages 974-978

  Lee, Sang Kil ^a   Park, Je Won ^b   Park, Sung Ryeol ^b   Ahn, Jong Seog ^c   Choi, Cha Yong ^a   Yoon, Yeo Joon ^b  

^a Seoul National University   (South Korea)

^b Ewha Womans University   (South Korea)

^c Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

Author keywords

Cytochrome P450 monooxygenase; Indigo; Indole hydroxylating; PikC; Site directed mutagenesis; Streptomyces venezuelae

Indexed keywords

CYTOCHROME P450; INDOLE; MUTANT PROTEIN; PIKROMYCIN; UNSPECIFIC MONOOXYGENASE;

ARTICLE; CATALYSIS; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME ENGINEERING; ENZYME KINETICS; GENE CONVERSION; HYDROXYLATION; NONHUMAN; NUCLEOTIDE SEQUENCE; SITE DIRECTED MUTAGENESIS; STREPTOMYCES VENEZUELAE; WILD TYPE;

STREPTOMYCES; STREPTOMYCES VENEZUELAE;

EID: 33745624271     PISSN: 10177825     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (25)

1. Betlach, M. C., J. T. Kealey, M. C. Betlach, G. W. Ashley, and R. McDaniel. 1998. Characterization of the macrolide P-450 hydroxylase from Streptomyces venezuelae which converts narbomycin to picromycin. Biochemistry 37: 14937-14942.
2. Bhushan, B., S. K. Samanta, and R. K. Jain. 2000. Indigo production by naphthalene-degrading bacteria. Lett. Appl. Microbiol. 31: 5-9.
3. Bradford, M. M. 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72: 248-254.
4. DeMoss, R. D. and K. Moser. 1969. Tryptophanase in diverse bacterial species. J. Bacteriol. 98: 167-171.
5. Eaton, R. W. and P. J. Chapman. 1995. Formation of indigo and related compounds from indolecarboxylic acids by aromatic acid-degrading bacteria: Chromogenic reactions for cloning genes encoding dioxygenases that act on aromatic acids. J. Bacteriol 177: 6983-6988.
6. Gillam, E. M. J., L. M. Notley, H. Cai, J. J. DeVoss, and F. P. Guengerich. 2000. Oxidation of indole by cytochrome P450 enzymes. Biochemistry 39: 13817-13824.
7. Hoessel, R., S. Leclerc, J. A. Endicott, M. E. M. Nobel, A. Lawrie, P. Tunnah, M. Leost, E. Damiens, D. Marie, D. Marko, E. Niederberger, W. Tang, G. Eisenbrand, and L. Meijer. 1999. Indirubin, the active constituent of a Chinese antileukaemia medicine, inhibits cyclin-dependent kinases. Nat. Cell Biol. 1: 60-67.
8. Hong, J. S. J., S. H. Park, C. Y. Choi, J. K. Sohng, and Y. J. Yoon. 2004. New olivosyl derivatives of methymycin/pikromycin from an engineered strain of Streptomyces venezuelae. FEMS Microbiol. Lett. 238: 391-399.
9. Hong, J. S. J., W. S. Kim, S. K. Lee, H. S. Koh, H. S. Park, S. J. Park, Y. S. Kim, and Y. J. Yoon. 2005. The role of a second protein (DesVIII) in glycosylation for the biosynthesis of hybrid macrolide antibiotics in Streptomyces venezuelae. J. Microbiol. Biotechnol. 15: 640-645.
10. Koehler, C. S. W. 1999. Synthetic dyes and the German chemical industry. Today's Chemist Work 8: 85-91.
11. Lee, S. K., D. B. Basnet, J. S. J. Hong, W S. Jung, C. Y. Choi, H. C. Lee, J. K. Sohng, K. G. Ryu, D. J. Kim, J. S. Ahn, B. S. Kim, H. C. Oh, D. H. Sherman, and Y. J. Yoon. 2005. Structural diversification of macrolactones by substrate-flexible cytochrome P450 monooxygenases. Adv. Synth. Catal. 347: 1369-1378.
12. Lee, S. K., C. Y. Choi, J. S. Ahn, J. Y. Cho, C. S. Park, and Y. J. Yoon. 2004. Identification of a cytochrome P450 hydroxylase gene involved in rifamycin biosynthesis by Amycolatopsis mediterranei S699. J. Microbiol. Biotechnol. 14:35 6-362.
13. Li, Q. S., U. Schwaneberg, P. Fischer, and R. D. Schmid. 2000. Directed evolution of the fatty-acid hydroxylase P450 BM-3 into an indole-hydroxylating catalyst. Chem. Eur. J. 6: 1531-1 536.
14. Maugard, T., E. Enaud, P. Choisy, and M. D. Legoy. 2001. Identification of an indigo precursor from leaves of Isatis tinctoria (Woad). Phytochemistry 58: 897-904.
15. Narhi, L. O. and A. J. Fulco. 1986. Characterization of a catalytically self-sufficient 119,000-dalton cytochrome P-450 monooxygenase induced by barbiturates in Bacillus megaterium. J. Biol. Chem. 261: 7160-7169.
16. Narhi, L. O., L. P. Wen, and A. J. Fulco. 1988. Characterization of the protein expressed in Escherichia coli by a recombinant plasmid containing the Bacillus megaterium cytochrome P-450 BM-3 gene. Mol. Cell. Biochem. 79: 63-71.
17. O'Connor, K. E., A. D. Dobson, and S. Hartmans. 1997. Indigo formation by microorganisms expressing styrene monooxygenase activity. Appl. Environ. Microbiol. 63: 4287-4 291.
18. Ramachandra, M., R. Seetharam, M. H. Emptage, and F. S. Sariaslani. 1991. Purification and characterization of a soybean flour-inducible ferredoxin reductase of Streptomyces griseus. J. Bacteriol. 173: 7106-7112.
19. Rix, U., C. Fischer, L. L. Remsing, and J. Rohr. 2002. Modification of post-PKS tailoring steps through combinatorial biosynthesis. Nat. Prod. Rep. 19: 542-580.
20. Sambrook, J., E. Fritsch, and T. Maniatis. 1989. Molecular Cloning: A Laboratory Mannual. 3rd Ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York, U.S.A.
21. Thompson, J. D., D. G. Higgins, and T. J. Gibson. 1994. CLUSTAL W: Improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res. 22: 4673-4680.
22. Xue, Y. and D. H. Sherman. 2001. Biosynthesis and combinatorial biosynthesis of pikromycin-related macrolides in Streptomyces venezuelae. Metab. Eng. 3: 15-26.
23. Xue, Y., D. Wilson, L. Zhao, H.-W. Liu, and D. H. Sherman. 1998. Hydroxylation of macrolactones YC-17 and narbomycin is mediated by the pikC-encoded cytochrome P450 in Streptomyces venezuelae. Chem, Biol. 5: 661-667.
24. Yoon, Y. J., B. J. Beck, B. S. Kim, H. Y. Kang, K. A. Reynolds, and D. H. Sherman. 2002. Generation of multiple bioactive macrolides by hybrid modular polyketide synthases in Streptomyces venezuelae. Chem. Biol. 9: 203-214.
25. Zhang, Q. and D. H. Sherman. 2001. Isolation and structure determination of novamethymycin, a new bioactive metabolite of the methymycin biosynthetic pathway in Streptomyces venezuelae. J. Nat. Prod. 64: 1447-1450.