Biosynthesis of the anti-parasitic agent megalomicin: Transformation of erythromycin to megalomicin in Saccharopolyspora erythraea

Molecular Microbiology

Volumn 37, Issue 4, 2000, Pages 752-762

  Volchegursky, Yanina ^a   Zhihao, Hu ^a   Katz, Leonard ^a   McDaniel, Robert ^a  

^a KOSAN BIOSCIENCES INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIPARASITIC AGENT; BACTERIAL DNA; ERYTHROMYCIN; MEGALOMICIN; POLYKETIDE SYNTHASE;

ARTICLE; BACTERIAL GENE; BACTERIAL METABOLISM; BIOSYNTHESIS; DNA SEQUENCE; GENE CLUSTER; MOLECULAR CLONING; NONHUMAN; PRIORITY JOURNAL; SACCHAROPOLYSPORA; STREPTOMYCES LIVIDANS;

ANTI-BACTERIAL AGENTS; ANTIPARASITIC AGENTS; BASE SEQUENCE; CARBOHYDRATES; DNA PRIMERS; ERYTHROMYCIN; MULTIGENE FAMILY; SACCHAROPOLYSPORA;

ACTINOBACTERIA (CLASS); BACTERIA (MICROORGANISMS); MICROMONOSPORA MEGALOMICEA; MICROMONOSPORA MELANOSPOREA; SACCHAROPOLYSPORA ERYTHRAEA; STREPTOMYCES LIVIDANS; UNCULTURED ACTINOMYCETE;

EID: 0033852319     PISSN: 0950382X     EISSN: None     Source Type: Journal    
DOI: 10.1046/j.1365-2958.2000.02059.x     Document Type: Article

References (51)

1. Alarcon, B., Lacal, J.C., Fernandez-Souza, J.M., and Carrasco, L. (1984) Screening for new compounds with antiherpes activity. Antiviral Res 4: 231-243.
2. Alarcon, B., Gonzalez, E., and Carrasco, L. (1988) Megalomycin C, a macrolide antibiotic that blocks protein glycosylation and shows antiviral activity. FEBS Lett 231: 207-211.
3. Altschul, S.F., Gish, W., Miller, W., Myers, E.W., and Lipman, D.J. (1990) Basic local alignment search tool. J Mol Biol 215: 403-410.
4. Andersen, J.F., and Hutchinson, C.R. (1992) Characterization of Saccharopolyspora erythraea cytochrome P-450 genes and enzymes, including 6-deoxyerythronolide B hydroxylase. J Bacteriol 174: 725-735.
5. Arisawa, A., Kawamura, N., Tsunekawa, H., Okamura, K., Tone, H., and Okamoto, R. (1993) Cloning and nucleotide sequences of two genes involved in the 4″-O-acylation of macrolide antibiotics from Streptomyces thermotolerans. Biosci Biotechnol Biochem 57: 2020-2025.
6. Arisawa, A., Kawamura, N., Takeda, K., Tsunekawa, H., Okamura, K., and Okamoto, R. (1994) Cloning of the macrolide antibiotic biosynthesis gene acyA, which encodes 3-O-acyltransferase, from Streptomyces thermotolerans and its use for direct fermentative production of a hybrid macrolide antibiotic. Appl Environ Microbiol 60: 2657-2660.
7. Bierman, M., Logan, R., O'Brien, K., Seno, E.T., Nagaraja, R., and Schoner, B.E. (1992) Plasmid cloning vectors for the conjugal transfer of DNA from Escherichia coli to Streptomyces spp. Gene 116: 43-49.
8. Bisang, C., Long, P.F., Cortés, J., Westcott, J., Crosby, J., Matharu, A.-L., et al. (1999) A chain initiation factor common to both modular and aromatic polyketide synthases. Nature 401: 502-505.
9. Bonay, P., Munro, S., Fresno, M., and Alarcon, B. (1996) Intra-Golgi transport inhibition by megalomicin. J Biol Chem 271: 3719-3726.
10. Bonay, P., Fresno, M., and Alarcon, B. (1997) Megalomicin disrupts lysosomal functions. J Cell Sci 110: 1839-1849.
11. Bonay, P., Duran-Chica, I., Fresno, M., Alarcon, B., and Alcina, A. (1998) Antiparasitic effects of the intra-Golgi transport inhibitor megalomicin. Antimicrob Agents Chemother 42: 2668-2673.
12. Brünker, P., Minas, W., Kallio, P.T., and Bailey, J.E. (1998) Genetic engineering of an industrial strain of Saccharopolyspora erythraea for stable expression of the Vitreoscilla haemoglobin gene (vhb). Microbiology 144: 2441-2448.
13. Butler, A.R., Bate, N., and Cundliffe, E. (1999) Impact of thioesterase activity on tylosin biosynthesis in Streptomyces fradiae. Chem Biol 6: 287-292.
14. Cane, D.E., Walsh, C.T., and Khosla, C. (1998) Harnessing the biosynthetic code: combinations, permutations, and mutations. Science 282: 63-68.
15. Cortés, J., Haydock, S.F., Roberts, G.A., Bevitt, D.J., and Leadlay, P.F. (1990) An unusually large multifunctional polypeptide in the erythromycin-producing polyketide synthase of Saccharopolyspora erythraea. Nature 348: 176-178.
16. Dhillon, N., Hale, R.S., Cortes, J., and Leadlay, P.F. (1989) Molecular characterization of a gene from Saccharopolyspora erythraea (Streptomyces erythraeus) which is involved in erythromycin biosynthesis. Mol Microbiol 3: 1405-1414.
17. Donadio, S., and Katz, L. (1992) Organization of the enzymatic domains in the multifunctional polyketide synthase involved in erythromycin formation in Saccharopolyspora erythraea. Gene 111: 51-60.
18. Donadio, S., and Staver, M.J. (1993) IS1136, an insertion element in the erythromycin gene cluster of Saccharopolyspora erythraea. Gene 126: 147-151.
19. Donadio, S., Staver, M.J., McAlpine, J.B., Swanson, S.J., and Katz, L. (1991) Modular organization of genes required for complex polyketide biosynthesis. Science 252: 675-679.
20. Epp, J.K., Huber, M., Turner, J.R., Goodson, T., and Schoner, B.E. (1989) Production of a hybrid macrolide antibiotic in Streptomyces ambofaciens and Streptomyces lividans by introduction of a cloned carbomycin biosynthetic gene from Streptomyces thermotolerans. Gene 85: 293-301.
21. Gaisser, S., Böhm, G.A., Cortés, J., and Leadlay, P.F. (1997) Analysis of seven genes from the eryAI-eryK region of the erythromycin biosynthetic gene cluster in Saccharpolyspora erythraea. Mol Gen Genet 256: 239-251.
22. Gokhale, R.S., Tsuji, S.Y., Cane, D.E., and Khosla, C. (1999) Dissecting and exploiting intermodular communication in polyketide synthases. Science 284: 482-485.
23. Gu, H., Wang, Y., Xu, X., Wei, X., and Fong, M. (1996) Increase of the expression of midecamycin 4′-hydroxyl propionyltransferase gene (mpt) by a promoter-like fragment from the midecamycin producing strain. Chin J Biotechnol 12: 147-152.
24. Hara, O., and Hutchinson, C.R. (1992) A macrolide 3-O-acyltransferase gene from the midecamycin-producing species Streptomyces mycarofaciens. J Bacteriol 174: 5141-5144.
25. Haydock, S.F., Dowson, J.A., Dhillon, N., Roberts, G.A., Cortes, J., and Leadlay, P.F. (1991) Cloning and sequence analysis of the 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.
26. Hopwood, D.A., Bibb, M.J., Chater, K.F., Kieser, T., Bruton, C.J., Kieser, H.M., et al. (1985) Genetic Manipulation of Streptomyces: A Laboratory Manual. Norwich, UK: The John Innes Foundation.
27. Kakavas, S.J., Katz, L., and Stassi, D. (1997) Identification and characterization of the niddamycin polyketide synthase genes from Streptomyces caelestis. J Bacteriol 179: 7515-7522.
28. Kao, C.M., Luo, G., Katz, L., Cane, D.E., and Khosla, C. (1994a) Engineered biosynthesis of atriketide lactone from an incomplete modular polyketide synthase. J Am Chem Soc 116: 11612-11613.
29. Kao, C.M., Katz, L., and Khosla, C. (1994b) Engineered biosynthesis of a complete macrolactone in a heterologous host. Science 265: 509-512.
30. Katz, L. (1997) Manipulation of modular polyketide synthases. Chem Rev 97: 2557-2576.
31. Kuhstoss, S., Huber, M., Turner, J.R., Paschal, J.W., and Rao, R.N. (1996) Production of a novel polyketide through the construction of a hybrid polyketide synthase. Gene 183: 231-236.
32. McDaniel, R., Thamchaipenet, A., Gustafsson, C., Fu, H., Betlach, M., Betlach, M., et al. (1999) Multiple genetic modifications of the erythromycin gene cluster to produce a library of novel 'unnatural' natural products. Proc Natl Acad Sci USA 96: 1846-1851.
33. Nakagawa, A., and Omura, S. (1984) Structure and stereo-chemistry of macrolides. In Macrolide Antibiotics. Omura, S. (ed.). New York: Academic Press, pp. 37-84.
34. Olano, C., Lomovskaya, N., Fonstein, L., Roll, J.T., and Hutchinson, C.R. (1999) A two-plasmid system for the glycosylation of polyketide antibiotics: bioconversion of ε-rhodomycinone to rhodomycin D. Chem Biol 6: 845-855.
35. Pereda, A., Summers, R., and Katz, L. (1997) Nucleotide sequence of the ermE distal flank of the biosynthesis cluster in Saccaropolyspora erythraea. Gene 193: 65-71.
36. Sambrook, J., Fritsch, E.F., and Maniatis, T. (1989). Molecular Cloning: a Laboratory Manual. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory Press.
37. Schwecke, T., Aparicio, J.F., Molnar, I., Konig, A., Khaw, L.E., Haydock, S.F., et al. (1995) The biosynthetic gene cluster for the polyketide immunosuppressant rapamycin. Proc Natl Acad Sci USA 92: 7839-7843.
38. Shah, S., Xue, Q., Tang, L., Carney, J.R., Betlach, M., and McDaniel, R. (2000) Cloning, characterization and heterologous expression of a polyketide synthase and P-450 oxidase involved in the biosynthesis of the antibiotic oleandomycin. J Antibiotics 53: 502-508.
39. Stassi, D., Donadio, S., Staver, M.J., and Katz, L. (1993) Identification of a Saccharopolyspora erythraea gene required for the final hydroxylation step in erythromycin biosynthesis. J Bacteriol 175: 182-189.
40. Summers, R.G., Donadio, S., Staver, M.J., Wendt-Pienkowski, E., Hutchinson, C.R., and Katz, L. (1997) Sequencing and mutagenesis of genes from the erythromycin biosynthetic gene cluster of Saccharopolyspora erythraea that are involved in L-mycarose and D-desosamine production. Microbiology 143: 3251-3262.
41. Tang, L., Fu, H., Betlach, M.C., and McDaniel, R. (1999) Elucidating the mechanism of chain termination switching in the picromycin/methymycin polyketide synthase. Chem Biol 6: 553-558.
42. Tang, L., Fu, H., and McDaniel, R. (2000) Formation of functional heterologous complexes using subunits from the picromycin, erythromycin, and oleandomycin polyketide synthases. Chem Biol 7: 77-84.
43. van Wageningen, A., Kirkpatrick, P., Williams, D., Harris, B., Kershaw, J., Lennard, N., et al. (1998) Sequencing and analysis of genes involved in the biosynthesis of a vancomycin group antibiotic. Chem Biol 3: 155-162.
44. Weber, J.M., Leung, J.O., Maine, G.T., Potenz, R.H., Paulus, T.J., and DeWitt, J.P. (1990) Organization of a cluster of erythromycin genes in Saccharopolyspora erythraea. J Bacteriol 172: 2372-2383.
45. Weber, J.M., Leung, J.O., Swanson, S.J., Idler, K.B., and McAlpine, J.B. (1991) An erythromycin derivative produced by targeted gene disruption in Saccharopolyspora erythraea. Science 252: 114-117.
46. Weinstein, M.J., Wagman, G.H., Marquez, J.A., Testa, R.T., Oden, E., and Waitz, J.A. (1969) Megalomicin, a new macrolide antibiotic complex produced by Micromonospora. J Antibiot 22: 253-258.
47. Xue, Q., Ashley, G., Hutchinson, C.R., and Santi, D.V. (1999) A multi-plasmid approach to preparing large libraries of polyketides. Proc Natl Acad Sci USA 96: 11740-11745.
48. Xue, Y., Zhao, L., Liu, H.-W., and Sherman, D.H. (1998) A gene cluster for the macrolide antibiotic biosynthesis in Streptomyces venezuelae: architecture of metabolic diversity. Proc Natl Acad Sci USA 95: 12111-12116.
49. Zhao, L., Sherman, D.H., and Liu, H.-W. (1998) Biosynthesis of desosamine: construction of a new methymycin/ neomethymycin analogue by deletion of a desosamine biosynthetic gene. J Am Chem Soc 120: 10256-10257.
50. Ziermann, R., and Betlach, M.C. (1999) Recombinant polyketide synthesis in Streptomyces: Engineering of improved host strains. Biotechniques 26: 106-110.
51. Ziermann, R., and Betlach, M. (2000) A two-vector system for the production of recombinant polyketides in Streptomyces. J Ind Microbiol Biotech 24: 46-50.