A host-vector system for analysis and manipulation of rifamycin polyketide biosynthesis in Amycolatopsis mediterranei

Microbiology

Volumn 145, Issue 9, 1999, Pages 2335-2341

  Hu, Zhihao ^a   Hunziker, Daniel ^a   Hutchinson, C Richard ^c   Khosla, Chaitan ^a,b  

^a Stanford University   (United States)

^b STANFORD UNIVERSITY   (United States)

^c UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Amycolatopsis; Polyketide synthase; Rifamycin

Indexed keywords

POLYKETIDE; RIFAMYCIN;

ARTICLE; BACTERIAL GENETICS; BIOSYNTHESIS; DELETION MUTANT; ELECTROPORATION; GENE CLUSTER; GENETIC ANALYSIS; GENETIC ENGINEERING; GENETIC MANIPULATION; MARKER GENE; NONHUMAN; PRIORITY JOURNAL;

AMYCOLATOPSIS MEDITERRANEI;

EID: 0032866337     PISSN: 13500872     EISSN: None     Source Type: Journal    
DOI: 10.1099/00221287-145-9-2335     Document Type: Article

References (41)

1. Arora, S. K. (1985). Correlation of structure and activity in ansamycins: structure, conformation, and interactions of antibiotic rifamycin S. J Med Chem 28, 1099-1102.
2. Arora, S. K. & Main, P. (1984). Correlation of structure and activity in ansamycin: molecular structure of cyclized rifamycin SV. J Antibiot 37, 178-181.
3. August, P. R., Tang, L., Yoon, Y. J. & 9 other authors (1998). Biosynthesis of the ansamycin antibiotic rifamycin. Deductions from the molecular analysis of the rif biosynthetic gene cluster of Amycolatopsis mediterranei S699. Chem Biol 5, 69-79.
4. Bacchi, A., Pelizzi, G., Nebuloni, M. & Ferrari, P. (1998). Comprehensive study on structure-activity relationships of rifamycins: discussion of molecular and crystal structure and spectroscopic and thermochemical properties of rifamycin O. J Med Chem 41, 2319-2332.
5. Barna, J. C. J. & Williams, D. H. (1984). The structure and mode of action of glycopeptide antibiotics of the vancomycin group. Annu Rev Microbiol 38, 339-357.
6. Bartolucci, C., Cellai, L., Marzano, M. & 8 other authors (1995). Structure-activity relationships in open ansa-chain rifamycin S derivatives as inhibitors of HIV-1 reverse transcriptase. Farmaco 50, 587-593.
7. Bedford, D., Jacobsen, J. R., Luo, G., Cane, D. E. & Khosla, C. (1996). A functional chimeric modular polyketide synthase generated via domain replacement. Chem Biol 3, 827-831.
8. Cane, D. E., Walsh, C. T. & Khosla, C. (1998). Harnessing the biosynthetic code. Combinations, permutations, mutations. Science 282, 63-68.
9. Cole, S. T. (1996). Rifamycin resistance in mycobacteria. Res Microbiol 147, 48-52.
10. Donadio, S., McAlpine, J. B., Sheldon, P. J., Jackson, M. & Katz, L. (1993). An erythromycin analog produced by reprogramming of polyketide synthesis. Proc Natl Acad Sci USA 90, 7119-7123.
11. Flett, F., Mersinias. V. & Smith, C. P. (1997). High efficiency intergeneric conjugal transfer of plasmid DNA from Escherichia coli to methyl DNA-restricting streptomycetes. FEMS Microbiol Lett 155, 233-239.
12. Ghisalba, O. & Nuesch, J. (1981). A genetic approach to the biosynthesis of the rifamycin-chromophore in Nocardia mediterranei. IV. Identification of 3-amino-5-hydroxybenzoic acid as a direct precursor of the seven-carbon amino starter-unit. J Antibiot 34, 64-71.
13. Ghisalba, O., Fuhrer, H., Richter, W. J. & Moss, S.(1981). A genetic approach to the biosynthesis of the rifamycin-chromophore in Nocardia mediterranei. III. Isolation and identification of an early aromatic ansamycin-precursor containing the seven-carbon amino starter-unit and three initial acetate/propionate-units of the ansa chain. J Antibiot 34, 59-63.
14. 7N-unit) of ansamitocin, a group of novel maytansinoid antibiotics. J Antibiot 35, 1415-1417.
15. Hunziker, D., Yu, T. W., Hutchinson, C. R., Floss, H. G. & Khosla, C. (1998). Primer unit specificity in rifamycin biosynthesis principally resides in the later stages of the biosynthetic pathway. J Am Chem Soc 120, 1092-1093.
16. Kao, C. M., Katz, L. & Khosla, C. (1994). Engineered biosynthesis of a complete macrolactone in a heterologous host. Science 265, 509-512.
17. Kao, C. M., Pieper, R., Cane, D. E. & Khosla, C. (1996). Evidence for two catalytically independent clusters of active sites in a functional modular polyketide synthase. Biochemistry 135, 12363-12368.
18. 7N units in rifamycin and related antibiotics. J Biol Chem 273, 6030-6040.
19. Lal, R., Lal, S. & Grund, E. (1991). Construction of a hybrid plasmid capable of replication in Amycolatopsis mediterranei. Appl Environ Microbiol 57, 665-671.
20. Lal, R., Khanna, R., Dhingra, N., Khanna, M. & Lal, S. (1998). Development of an improved cloning vector and transformation system in Amycolatopsis mediterranei (Nocardia mediterranei). J Antibiot 51, 161-169.
21. Lowder, J. F. & Johnson, R. S. (1987). The generation of the rifamycin binding site in the beta subunit of E. coli RNA polymerase through subunit interactions. Biochem Biophys Res Commun 147, 1129-1136.
22. McDaniel, R., Ebert-Khosla, S., Hopwood, D. A. & Khosla, C. (1993). Engineered biosynthesis of novel polyketides. Science 262, 1546-1550.
23. Madon, J. & Hutter, R. (1991). Transformation system for Amycolatopsis (Nocardia) mediterranei : direct transformation of mycelium with plasmid DNA. J Bacteriol 173, 6325-6331.
24. Malpartida, F., Zalacain, M., Jimenen, A. & Davies, J. (1983). Molecular cloning and expression in Streptomyces lividans of a hygromycin B phosphotransferase gene from Streptomyces hygroscopicus. Biochem Biophys Res Commun 117, 6-12.
25. Marsden, A. F., Wilkinson, B., Cortes, J., Dunster, N. J., Staunton, J. & Leadlay, P. F. (1998). Engineering broader specificity into an antibiotic-producing polyketide synthase. Science 279, 199-202.
26. Matsushima, P., McHenney, M. A. & Baltz, R. H. (1987). Efficient transformation of Amycolatopsis orientalis (Nocardia orientalis) protoplasts by Streptomyces plasmids. J Bacteriol 169, 2298-2300.
27. Moretti, P., Hintermann, G. & Huttler, R. (1985). Isolation and characterization of an extrachromosomal element from Nocardia mediterranei. Plasmid 14, 126-133.
28. Nadkarni, S. R., Patel, M. V., Chatterjee, S., Vijayakumar, E. K. S., Desikan, K. R., Blumbach, J. & Ganguli, B. N. (1994). Balhimycin, a new glycopeptide antibiotics produced by Amycolatopsis sp. Y-86, 21022. Taxonomy, production, isolation and biological activity. J Antibiot 47, 334-341.
29. Pelzer, S., Reichert, W., Huppert, M., Heckmann, D. & Wohlleben, W. (1997). Cloning and analysis of a peptide synthetase gene of the balhimycin producer Amycolatopsis mediterranei DSM5908 and development of a gene disruption/replacement system. J Biotechnol 56, 115-128.
30. Riva, S., Fietta, A. & Silvestri, L. G. (1972). Mechanism of action of a rifamycin derivative (AF-013) which is active on the nucleic acid polymerases insensitive to rifampicin. Biochem Biophys Res Commun 49, 1263-1271.
31. Rowe, C. J., Cortes, J., Gaisser, S., Staunton, J. & Leadlay, P. F. (1998). Construction of new vectors for high-level expression in actinomycetes. Gene 216, 215-223.
32. Ruan, X., Pereda, A., Stassi, D. L. & 8 other authors (1997). Acyltransferase domain substitutions in erythromycin polyketide synthase yield novel erythromycin derivatives. J Bacteriol 179, 6416-6425.
33. Sambrook, J., Fritsch, E. F. & Maniatis, T. (1989). Molecular Cloning: a Laboratory Manual, 2nd edn. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory.
34. Schupp, T. & Diver, M. (1986). Protoplast preparation and regeneration in Nocardia mediterranei. FEMS Microbiol Lett 36, 159-165.
35. Schupp, T., Toupet, C., Engel, N. & Goff, S. (1998). Cloning and sequence analysis of the putative rifamycin polyketide synthase gene cluster from Amycolatopsis mediterranei. FEMS Microbiol Lett 157, 201-207.
36. Sensi, P., Margalith, P. & Timbal, M. T. (1959). Rifamycin, a new antibiotic. Preliminary report. Farm Ed Sci 14, 146-147.
37. Tang, L., Yoon, Y. J., Choi, C. Y. & Hutchinson, C. R. (1998). Characterization of the enzymatic domains in the modular polyketide synthase involved in rifamycin B biosynthesis by Amycolatopsis mediterranei. Gene 216, 255-265.
38. Ueno, M., Iijima, M., Masuda, T., Kinoshita, N., Iinuma, H., Naganawa, H., Hamada, M., Ishizuka, M. & Takeuchi, T. (1992). Dethymicin, a novel immunosuppressant isolated from an Amycolatopsis. Fermentation, isolation, physico-chemical properties and biological activities. J Antibiot 12, 1819-1826.
39. Van Wageningen, A. M., Kirkpatrick, P. N., Williams, D. H., Harris, B. R., Kershaw, J. K., Lennard, N. J., Jones, M., Jones, S. J. & Solenberg, P. J. (1998). Sequencing and analysis of genes involved in the biosynthesis of a vancomycin group antibiotic. Chem Biol 5, 133-162.
40. Vrijbloed, J. W., Madon, J. & Dijkhuizen, L. (1994). A plasmid from the methylotrophic actinomycete Amycolatopsis methanolica capable of site-specific integration. J Bacteriol 176, 7087-7090.
41. Yu, T.-W., Shen, Y., Doi-Katayama, Y., Tang, L., Park, C., Moore, B. S., Hutchinson, C. R. & Floss, H. G. (1999). Direct evidence that the rifamycin polyketide synthase assembles polyketide chains processively. Proc Natl Acad Sci USA (in press).