Characterization of methyltransferase and hydroxylase genes involved in the biosynthesis of the immunosuppressants FK506 and FK520

Journal of Bacteriology

Volumn 178, Issue 17, 1996, Pages 5243-5248

  Motamedi, Haideh ^a   Shafiee, Ali ^a   Cai, Sheng Jian ^a   Streicher, Stanley L ^a   Arison, Byron H ^a   Miller, Randall R ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASCOMYCIN; IMMUNOSUPPRESSIVE AGENT; METHYLTRANSFERASE; OXYGENASE; TACROLIMUS;

ARTICLE; DRUG HYDROXYLATION; DRUG SYNTHESIS; GENE DISRUPTION; METHYLATION; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; STREPTOMYCES; STREPTOMYCES HYGROSCOPICUS; STREPTOMYCES LIVIDANS;

STREPTOMYCES HYGROSCOPICUS; STREPTOMYCES HYGROSCOPICUS SUBSP. ASCOMYCETICUS; STREPTOMYCES LIVIDANS; STREPTOMYCES SP.;

EID: 0029831399     PISSN: 00219193     EISSN: None     Source Type: Journal    
DOI: 10.1128/jb.178.17.5243-5248.1996     Document Type: Article

References (30)

1. Bibb, M. J., and S. N. Cohen. 1982. Gene expression in Streptomyces: construction and application of promoter-probe plasmid vectors in Streptomyces lividans. Mol. Gen. Genet. 187:265-277.
2. Bibb, M. J., P. R. Findlay, and M. W. Johnson. 1984. The relationship between base composition and codon usage in bacterial genes and its use for the simple and reliable identification of protein-coding sequences. Gene 30:157-166.
3. Byrne, K. M., A. Shafiee, J. B. Nielsen, B. H. Arison, R. L. Monaghan, and L. Kaplan. 1993. The biosynthesis and enzymology of an immunosuppressant, immunomycin, produced by Streptomyces hygroscopicus var. ascomyceticus, p. 29-47. In C. Nash, J. Hunter-Cevera, R. Cooper, D. E. Eveleih, and R. Hamill (ed.), Developments in Industrial Microbiology series, vol. 32. Wm. C. Brown Publisher, Dubuque, Iowa.
4. Decker, H., H. Motamedi, and C. R. Hutchinson. 1993. Nucleotide sequences and heterologous expression of tcmG and tcmP, biosynthetic genes for tetracenomycin C in Streptomyces glaucescens. J. Bacteriol. 175:3876-3886.
5. Devereux, J., P. Haeberli, and O. Smithies. 1984. A comprehensive set of sequence analysis programs for the VAX. Nucleic Acids Res. 12:387-395.
6. Fischer, R. T., R. L. Trazaskos, S. S. Ko, C. S. Brosz, and B. Larsen. 1991. Lanosterol 14α-methyl demethylase. J. Biol. Chem. 266:6124-6132.
7. Garrity, G., B. K. Heimbuch, H. Motamedi, and A. Shafiee. 1993. Genetic relationships among actinomyetes that produce the immunosuppressant macrolidis FK506, FK520/FK523 and rapamycin. J. Ind. Microbiol. 12:42-48.
8. Gewain, K. M., J. L. Occi, F. Foor, and D. J. MacNeil. 1992. Vectors for generating nested deletions and facilitating subcloning G+C-rich DNA between Escherichia coli and Streptomyces sp. Gene 119:149-150.
9. Hatanaka, H., T. Kino, S. Miyata, N. Inamura, A. Kuroda, T. Goto, H. Tanaka, and M. Okuhara. 1988. FR900520 and FR-920523, novel immunosuppressants isolated from a Streptomyces. I. Taxonomy of the producing strain. J. Antibiot. 41:1592-1601.
10. Hopwood, D. A., M. J. Bibb, K. F. Chater, T. Kieser, C. J. Bruton, H. M. Kieser, D. J. Lydiate, C. P. Smith, J. M. Ward, and H. Schrempf. 1985. Genetic manipulation of Streptomyces: a laboratory manual. The John Innes Foundation, Norwich, England.
11. Ingroso, D., A. V. Fowler, J. Bleibaum, and S. Clarke. 1989. Sequence of the D-aspartyl L-isoaspartyl protein methyltransferase from human erythrocytes. Common sequence motifs for protein, DNA, RNA and small molecule S-adenosylmethionine dependent methyltransferases. J. Biol. Chem. 264: 20131-20139.
12. Ishizaki, T., N. Hirayama, H. Shinkawa, O. Nimi, and Y. Murooka. 1989. Nucleotide sequence of the genes for cholesterol oxidase from a Streptomyces sp. J. Bacteriol. 171:596-601.
13. Kino, T., H. Hatanaka, S. Miyata, N. Inamura, N. Nishiyama, T. Yajima, T. Goto, M. Okuhara, M. Kohsaka, H. Aoki, and T. Ochiai. 1987. FK506, a novel immunosuppressant isolated from a Streptomyces. J. Antibiot. 40:1256-1265.
14. Molnar, I., T. F. Aparicio, S. F. Haydock, L. E. Khaw, T. Schwecke, A. Konig, J. Staunton, and P. F. Leadlay. 1996. Organization of the biosynthetic gene cluster for rapamycin in Streptomyces hygroscopicus: analysis of genes flanking the polyketide synthase genes. Gene 169:1-7.
15. Motamedi, H., S. J. Cai, A. Shafiee, and K. O. Elliston. Unpublished data.
16. Motamedi, H., and C. R. Hutchinson. 1987. Cloning and heterologous expression of a gene cluster for the biosynthesis of tetracenomycin C, the anthracycline antitumor antibiotic of Streptomyces glaucescens. Proc. Natl. Acad. Sci. USA 84:4445-4449.
17. Motamedi, H., A. Shafiee, B. H. Arison, and R. R. Miller. Unpublished data.
18. Motamedi, H., A. Shafiee, and S. J. Cai. 1995. Integrative expression vectors for heterologous gene expression in Streptomyces spp. Gene 160:25-73.
19. Nielsen, J. B., M. Hsu, K. M. Byrne, and L. Kaplan. 1992. Biosynthesis of the immunosuppressant immunomycin: the enzymology of pipecolate incorporation. Biochemistry 30:5789-5796.
20. Nishida, H., T. Sakakibara, F. Aoki, T. Saito, K. Ichikawa, T. Inagaki, Y. Kojima, Y. Yamauchi, L. H. Huang, M. A. Guadliana, T. Kaneko, and N. Kojima. 1995. Generation of novel rapamycin structures by microbial manipulations. J. Antibiot. 48:657-666.
21. Omer, C. A., R. Lenstra, P. J. Litle, C. Dean, J. M. Tepperman, K. J. Leto, J. A. Romesser, and D. P. O'Keefe. 1990. Genes for two herbicide-inducible cytochrome P-450s from Streptomyces griseolus. J. Bacteriol. 172:3335-3345.
22. Parsons, W. H., N. H. Sigal, and M. J. Wyvratt. 1993. FK506, a novel immunosuppressant. Ann. N. Y. Acad. Sci. 685:22-36.
23. Rosenberg, M., and D. Court. 1979. Regulatory sequences involved in the promotion and termination of RNA transcription. Annu. Rev. Genet. 13: 319-353.
24. Sambrook, J., E. F. Fritsch, and T. Maniatis. 1989. Molecular cloning: a laboratory manual, 2nd ed. Cold Spring Harbor Laboratory. Cold Spring Harbor, N.Y.
25. Sanger, F., S. Nicklen, and R. Coulson. 1977. DNA sequencing with chain-terminating inhibitors. Proc. Natl. Acad. Sci. USA 74:5463-5467.
26. Schwecke, T., J. F. Aparicio, I. Molnar, A. Konig, L. E. Khaw, S. F. Ilaydock, M. Oliynyk, P. Caffrey, J. Cortes, J. B. Lester, G. A. Bohm, J. Staunton, and P. F. Leadlay. 1995. The biosynthetic gene cluster for the polyketide immunosuppressant rapamycin. Proc. Natl. Acad. Sci. USA 92:7839-7843.
27. Shafiee, A., H. Motamedi, and T. Chen. 1994. Enzymology of FK506 biosynthesis: purification and characterization of 31-O-demethylFK506-O-methyltransferase from Streptomyces sp. MA6858. Eur. J. Biochem. 225:764-769.
28. Summers, R. G., E. Wendt-Pienkowski, H. Motamedi, and C. R. Hutehinson. 1992. Nucleotide sequence of the tcmII-tcmIV region of the tetracinomycin C biosynthetic gene cluster of Streptomyces glaucescens and evidence that the tcmN gene encodes a multifunctional cyclase-dehydratase-O-methyltransferase. J. Bacteriol. 174:1810-1820.
29. soy (soyB) from Streptomyces griseus. Mol. Microbiol. 6:2125-2134.
30. Zalkin, H., and D. J. Ebbole. 1988. Organization and regulation of genes encoding biosynthetic enzymes in Bacillus subtilis. J. Biol. Chem. 263:1595-1598.