The biosynthetic gene cluster for the macrolactone ring of the immunosuppressant FK506

European Journal of Biochemistry

Volumn 256, Issue 3, 1998, Pages 528-534

  Motamedi, Haideh ^a   Shafiee, Ali ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

FK506 gene cluster; Modular polyketide synthase; Rapamycin

Indexed keywords

RAPAMYCIN; TACROLIMUS;

ARTICLE; FATTY ACID SYNTHESIS; GENE CLUSTER; GENE SEQUENCE; IMMUNOSUPPRESSIVE TREATMENT; NONHUMAN; OXIDATION; PRIORITY JOURNAL; SIGNAL TRANSDUCTION; STREPTOMYCES;

AMINO ACID SEQUENCE; CHROMOSOME WALKING; DNA, FUNGAL; GENES, FUNGAL; IMMUNOPHILINS; IMMUNOSUPPRESSIVE AGENTS; MODELS, CHEMICAL; MODELS, GENETIC; MOLECULAR SEQUENCE DATA; MULTIENZYME COMPLEXES; OXIDATION-REDUCTION; SIROLIMUS; STREPTOMYCES; TACROLIMUS; TACROLIMUS BINDING PROTEINS;

EID: 0032530781     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1432-1327.1998.2560528.x     Document Type: Article

References (42)

1. Ho, S., Clipstone, N., Timmermann, L., Northrop, J., Graff, I., Florentino, D., Nourse, J. & Crabtree, G. R. (1996) The mechanism of action of cyclosporin A and FK506, Clin. Immunol. Immunopathol. 80, s40-s45.
2. Kino, T., Hatanaka, H., Miyata, S., Inamura, N., Nishiyama, N., Yajima, T., Goto, T., Okuhara, M., Kohsaka, M., Aoki, H. & Ochiai, T. (1987) FK506, a novel immunosuppressant isolated from a Streptomyces, J. Antibiot. (Tokyo) 40, 1256-1265.
3. Motamedi, H., Shafiee, A., Cai, S. J., Streicher, S. L., Arison, B. H. & Miller, R. R. (1996) Characterization of methyltransferase and hydroxylase genes involved in the biosynthesis of the immunosuppressants FK506 and FK520, J. Bacteriol. 178, 5243-5248.
4. Hopwood, D. A. (1997) Genetic contributions to understanding polyketide synthases, Chem. Rev. 97, 2485-2497.
5. Khosla, C. (1997) Harnessing the biosynthetic potential of modular polyketide synthases, Chem. Rev. 97, 2577-2590.
6. Motamedi, H., Cai, S. J., Shafiee, A. & Elliston, K. O. (1997) Structural organization of a multifunctional polyketide synthase involved in biosynthesis of the macrolide immunosuppressant FK506, Eur. J. Biochem. 244, 74-80.
7. Byrne, K. M., Shafiee, A., Nielsen, J. B., Arison, B. H., Monaghan, R. L. & Kaplan, L. (1993) The biosynthesis and enzymology of an immunosuppressant, immunomycin, produced by Streptomyces hygroscopicus var. ascomyceticus, in Developments in industrial microbiology series (Nash, C., Hunter-Cevera, J., Cooper, R., Eveleih, D. E. & Hamill, R., eds) pp. 29-47, Wm. C. Brown Publisher, Iowa.
8. Shafiee, A., Motamedi, H. & Chen, T. (1994) Enzymology of FK506 biosynthesis: Purification and characterization of 31-O-demethyl-FK506-O-methyltransferase from Streptomyces sp. MA6858, Eur. J. Biochem. 225, 764-769.
9. Shafiee, A., Motamedi, H., Dumont, F. J., Arison, B. H. & Miller, R. R. (1997) Chemical and biological characterization of two FK506 analogs produced by targeted gene disruption in Streptomyces sp. MA6548, J. Antibiot. (Tokyo) 50, 418-423.
10. Molnar, I., Aparicio, T. F., Haydock, S. F., Khaw, L. E., Schwecke, T., Konig, A., Staunton, J. & Leadlay, P. F. (1996) Organization of the biosynthetic gene cluster for rapamycin in Streptomyces hygroscopicus: analysis of genes flanking the polyketide synthase genes, Gene (Amst.) 169, 1-7.
11. Sanger, F., Nicklen, S. & Coulson, A. R. (1977) DNA sequencing with chain terminating-inhibitors, Proc. Natl Acad. Sci. USA 74, 5463-5467.
12. Devereux, J., Haeberli, P. & Smithies, O. (1984) A comprehensive set of sequence analysis programs for the VAX, Nucleic Acids Res. 12, 387-395.
13. Motamedi, H., Shafiee, A. & Cai, S. J. (1995) Integrative expression vectors for heterologous gene expression in Streptomyces spp., Gene (Amst.) 160, 25-73.
14. Hatanaka, H., Kino, T., Miyata, S., Inamura, N., Kuroda, A., Goto, T., Tanaka, H. & Okuhara, M. (1988) FR900520 and FR-920523, novel immunosuppressants isolated from a Streptomyces. I. Taxonomy of the producing strain, J. Antibiot. (Tokyo) 411, 592-1601.
15. Schindler, U., Sans, N. & Schroder, J. (1989) Ornithine cyclodeaminase from octopine Ti plasmid Ach5: Identification, DNA sequence, enzyme properties, and comparison with gene and enzyme from the nopaline Ti plasmid C58, J. Bacteriol. 171, 847-854.
16. Schwecke, T., Aparicio, J. F., Molnar, I., Konig, A., Khaw, L. E., Haydock, S. F., Oliynyk, M. Caffrey, P., Cortes, J., Lester, J. B., Bohm, G. A., Staunton, J. & Leadlay, P. F. (1995) The biosynthetic gene cluster for the polyketide immunosuppressant rapamycin, Proc. Natl Acad. Sci. USA 92, 7839-7843.
17. Dieckmann, R., Lee, Y.-O., van Liempt, H., von Dohren, H. & Kleinkauf, H. (1995) Expression of an active adenylate forming domain of peptide synthetases corresponding to acyl-CoA-synthetases, FEBS Lett. 357, 212-216.
18. Nielsen, J. B., Hsu, M., Byrne, K. M. & Kaplan, L. (1992) Biosynthesis of the immunosuppressant immunomycin: The enzymology of pipecolate incorporation, Biochemistry 30, 5789-5796.
19. Write, F. & Bibb, M. J. (1992) Codon usage in the G+C-rich Streptomyces genome, Gene (Amst.) 113, 55-65.
20. Cortes, J., Haydock, S. F., Roberts, G. A., Bevitt, D. J. & Leadlay, P. F. (1990) An unusually large multifunctional polypeptide in the erythromycin producing polyketide synthase of Saccharopolyspora erythraea, Nature 348, 176-178.
21. Donadio, S., Staver, M. J., McAlpine, J. B., Swanson, S. J. & Katz, L. (1991) Modular organization of the genes required for complex polyketide biosynthesis, Science 252, 675-679.
22. Black, P. N., DiRusso, C. D., Metzger, A. K. & Heimert, T. L. (1992) Cloning, sequencing, and expression of the fadD gene of Escherichia coli encoding acyl coenzyme A synthetase, J. Biol. Chem. 267, 25 513-25 520.
23. Fulda, M., Heinz, E. & Wolter, F. P. (1994) The fadD gene of Escherichia coli K12 is located close to red at 39.6 min of the chromosomal map and is a new member of the AMP-binding protein family, Mol. Gen. Genet. 242, 241-249.
24. Black, P. N., Zhang, Q., Weimar, J. D. & DiRusso, C. C. (1997) Mutational analysis of a fatty acyl-Coenzyme A synthetase signature motif identifies seven amino acid residues that modulate fatty acid substrate specificity, J. Biol. Chem. 272, 4896-4903.
25. Smith, S. (1994) The animal fatty acid synthase: one gene, one polypeptide, seven enzymes, FASEB J. 8, 1248-1259.
26. Reynolds, K., Wang, A. P., Fox, K. M., Speedie, M. K., Lam, Y. & Floss, H. G. (1992) Purification and characterization of a novel enoyl Co A reductase from Streptomyces collinus, J. Bacteriol. 174, 3850-3854.
27. Pei, W., Denoya, C. D., Morgenstern, M. R., Skinner, D. D., Wallace, K. K., Digate, R., Patton, S., Banavali, N., Schuler, G., Speedie, M. K. & Reynolds, K. A. (1996) Cloning and characterization of the gene encoding 1-cyclohexenylcarbonyl Coenzyme A reductase from Streptomyces collinus, J. Bacteriol. 178, 6873-6881.
28. Aparicio, J. F. Molnar, I., Schwecke, T., Konig, A., Haydock, S. F., Khaw, L. E., Staunton, J. & Leadlay, P. F. (1996) Organization of the biosynthetic gene cluster for rapamycin in Streptomyces hygroscopicus: analysis of the enzymatic domains in the modular polyketide synthase, Gene (Amst.) 169, 9-16.
29. Borris, R. P., Wicker, L. S., Zink, D. L. & Lien, T. H. (1990) Novel immunosuppressant compounds, European Patent Application, no. 358,508,A2.
30. Joshi, A. K. & Smith, S. (1993) Construction, expression, and characterization of a mutated animal fatty acid synthase deficient in dehydrase function, J. Biol. Chem. 268, 22 508-22 513.
31. Scrutton, N. S., Berry, A. & Perham, R. N. (1990) Redesign of the coenzyme specificity of a dehydrogenase by protein engineering, Nature 343, 38-43.
32. Stachelhaus, T. & Marahiel, M. A. (1995) Modular structure of peptide synthetases revealed by dissection of the multifunctional enzyme GrsA, J. Biol. Chem. 270, 6163-6169.
33. Hutchinson, C. R. (1996) Polyketide synthase gene manipulation: A structure function approach in engineering novel antibiotics, Annu. Rev. Mirobiol. 49, 201-238.
34. McDaniel, R., Ebert-Khosla, S., Hopwood, D. A. & Khosla, C. (1994) Engineered biosynthesis of novel polyketides: actVII and actIV genes encode aromatase and cyclase enzymes, respectively, J. Am. Chem. Soc. 30, 10 855-10 859.
35. Summers, R. G., Wendt-Pienkowski, E., Motamedi, H. & Hutchinson, C. R. (1992) Nucleotide sequence of the tcmII-MnIV region of the tetracenomycin C biosynthetic gene cluster of Streptomyces glaucescens and evidence that the tcmN gene encodes a multifunctional cyclase-dehydratase-O-methyl transferase, J. Bacteriol. 174, 1810-1820.
36. Summers, R. G., Wendt-Pienkowski, E., Motamedi, H. & Hutchinson, C. R. (1993) The tcmVI region of the tetracenomycin C biosynthetic gene cluster of Streptomyces glaucescens encodes the tetracenomycin F1 monooxygenase, tetracenomycin F2 cyclase, and, most likely, a second cyclase, J. Bacteriol. 175, 7571-7580.
37. Motamedi, H. & Hutchinson, C. R. (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.
38. Motamedi, H., Wendt-Pienkowski, E. & Hutchinson, C. R. (1986) Isolation of tetracenomycin C-nonproducing Streptomyces glaucescens mutants, J. Bacteriol. 167, 575-580.
39. Haydock, S. F., Aparicio, J. F., Molnar, I., Schwecke, T., Khaw, L. E., Konig, A., Marsden, A. F. A., Galloway, I. S., Staunton, J. & Leadlay, P. F. (1995) Divergent sequence motifs correlated with the substrate specificity of (methyl) malonyl-CoA: acyl carrier protein transacylase domains in modular polyketide synthases, FEBS Lett. 374, 246-248.
40. Kuhstoss, S., Huber, M., Turner, J. R., Paschal, J. W. & Rao, R. N. (1996) Production of a novel polyketide through the construction of a hybrid polyketide synthase, Gene (Amst.) 183, 231-236.
41. Abraham, R. T. & Wiederrecht, G. J. (1996) Immunopharmacology of rapamycin, Annu. Rev. Immunol. 14, 483-510.
42. Oliynyk, M., Brown, M. J. B., Cortes, J., Staunton, J. & Leadlay, P. F. (1996) A hybrid modular polyketide synthase obtained by domain swapping, Chem. & Biol. 3, 833-839.