Hydroxylation of macrolactones YC-17 and narbomycin is mediated by the pikC-encoded cytochrome P450 in Streptomyces venezuelae

Chemistry and Biology

Volumn 5, Issue 11, 1998, Pages 661-667

  Xue, Yongquan ^a   Wilson, Daniel ^a   Zhao, Lishan ^b   Liu, Hung Wen ^b   Sherman, David H ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b University of Minnesota   (United States)

Author keywords

Cytochrome P450; Macrolide antibiotics; Narbomycin; Polyketide synthase; YC 17

Indexed keywords

CARBON; CULTURE MEDIUM; CULTURE TECHNIQUE; CYTOCHROME P450; ENZYME SPECIFICITY; ESCHERICHIA COLI; GENE CLUSTER; HIS TAGGED PROTEIN; HYDROXYLATION; MACROLACTONE; METHYMYCIN; MICROBE METABOLISM; NARBOMYCIN; NEOMETHYMYCIN; PIKROMYCIN; SECONDARY METABOLITE;

STREPTOMYCES VENEZUELAE;

EID: 0032213230     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(98)90293-9     Document Type: Article

References (24)

1. Munro, A.W. & Lindsay, J.G. (1996). Bacterial cytochromes P450. Mol. Microbiol. 20, 1115-1125.
2. Haydock, S.F., Dowson, J.A., Dhillon, N., Roberts, G.A., Cortes, J. & Leadlay, P.F. (1991). Cloning and sequence analysis of genes involved in erythromycin biosynthesis in Saccharopolyspora erythraea: sequence similarities between EryG and a family of S-adenosylmethionine-dependent methyltransferases. Mol. Gen. Genet. 230, 120-128.
3. Andersen, J.F. & Hutchinson, C.R. (1992). Characterization of Saccharopolyspora erythraea cytochrome P-450 genes and enzymes, including 6-deoxyerythronolide B hydroxylase. J. Bacteriol. 174, 725-735.
4. Stassi, D., Donadio, S., Staver, M.J. & Katz, L. (1993). Identification of a Saccharopolyspora erythraea gene required for the final hydroxylation step in erythromycin biosynthesis. J. Bacteriol. 175, 182-189.
5. Cupp-Vickery, J.R. & Poulos, T.L. (1995). Structure of cytochrome P450eryF involved in erythromycin biosynthesis. Nat. Struct. Biol. 2, 144-153.
6. Molnar, I., et al., & Leadlay, P.F. (1996). Organisation of the biosynthetic gene cluster for rapamycin in Streptomyces hygroscopicus: analysis of genes flanking the polyketide synthase. Gene 169, 1-7.
7. Schwecke, T., et al. & Leadlay, P.F. (1995). The biosynthetic gene cluster for the polyketide immunosuppressant rapamycin. Proc. Natl Acad. Sci. USA 92, 7839-7843.
8. Inouye, M., Takada, Y., Muto, N., Beppu, T. & Horinouchi, S. (1994). Characterization and expression of a P-450-like mycinamicin biosynthesis gene using a novel Micromonospora-Escherichia coll shuttle cosmid vector. Mol. Gen. Genet. 245, 456-64.
9. Cane, D.E. & Graziani, E.I. (1998). Methymycin biosynthesis: isolation of P450 monooxygenase activity in a cell-free system from Streptomyces venezuelae. J. Am. Chem. Soc. 120, 2682-2683.
10. Xue, Y., Zhao, L., Liu, H.-w. & Sherman, D.H. (1998). A gene cluster for macrolide antibiotic biosynthesis in Streptomyces venezuelae: architecture of metabolic diversity. Proc. Natl Acad. Sci. USA. 95, 12111-12116.
11. Andersen, J.F., Tatsuta, K., Gunji, H., Ishiyama, T. & Hutchinson, C.R. (1993). Substrate specificity of 6-deoxyerythronolide B hydroxylase, a bacterial cytochrome P450 of erythromycin A biosynthesis. Biochemistry 32, 1905-1913.
12. Arisawa, A., Tsunekawa, H., Okamura, K. & Okamoto, R. (1995). Nucleotide sequence analysis of the carbomycin biosynthetic genes including the 3-O-acyltransferase gene from Streptomyces thermotolerans. Biosci. Biotechnol. Biochem. 59, 582-588.
13. Rodriguez, A.M., Olano, C., Mendez, C., Hutchinson, C.R. & Salas, J.A. (1995). A cytochrome P450-like gene possibly involved in oleandomycin biosynthesis by Streptomyces antibioticus. FEMS Microbiol. Lett. 127, 117-120.
14. Ruan, X., Stassi, D., Lax, S. & Katz, L. (1997). A second type I PKS gene cluster isolated from Streptomyces hygroscopicus ATCC29253, a rapamycin-producing strain. Gene 203, 1-9.
15. Molner, I. & Murooka, Y. (1993). Nucleotide sequence analysis of a region upstream of the cholesterol oxidase-oytochrome P450 operon of Streptomyces sp. SA-COO revealing repeating units coding for putative transmembrane and DNA-binding proteins. J. Ferment. Bioeng. 76, 257-263.
16. Kim, C.-G., et al., & Floss, H.G. (1996). Biosynthesis of 3-amino-5-hydroxybenzoic acid, the precursor of mC7N unit in ansamycin antibiotics. J. Am. Chem. Soc. 118, 7486-7491.
17. Stewart, V. (1994). Dual interacting two-component regulatory systems mediate nitrate- and nitrite-regulated gene expression in Escherichia coli. Res. Microbiol. 145, 450-454.
18. Lambalot, R.H., Cane, D.E., Aparicio, J.J. & Katz, L. (1995). Overproduction and characterization of the erythromycin C-12 hydroxylase, EryK. Biochemistry 34, 1858-66.
19. Graziani, E.I, Cane, D.E., Detlach, M.C., Kealey, J.T. & McDaniel, R. (1998). Macrolide biosynthesis: a single cytochrome P450, PickC, is responsible for the hydroxylations that generate methymycin, neomethymycin, and pikromycin in Streptomyces venezuelae. Bioorg. Med. Chem. Lett., in press.
20. Sambrook, J., Fritsch, E.F. & Maniatis, T. (1989). Molecular Cloning: A Laboratory Manual. (2nd edn). Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York.
21. Lambalot, R.H. & Cane, D.E. (1992). Isolation and characterization of 10-deoxymethynolide produced by Streptomyces venezuelae. J. Antibiot. 45, 1981-1982.
22. Maezawa, L., Kinnmaki, A. & Suzuki, M. (1974). Isolation and identification of picronolide, methynolide and neomethynolide produced by Streptomyces venezuelae MCRL-0376. J. Antibiot. 27, 84-85.
23. Bierman, M., Logan, R., O'Brien, K., Seno, E.T., Nagaraja Rao, R. & Schoner, B.E. (1992). Plasmid cloning vectors for the conjugal transfer of DNA from Escherichia coli toStreptomyces spp. Gene 116, 43-49.
24. Cane D.E., Lambalot R.H., Prabhakaran P.C. & Ott W.R. (1993). Macrolide biosynthesis 7. Incorporation of polyketide chain elongation intermediates into methymycin. J. Am. Chem. Soc. 115, 522-526.