Characterization of the biosynthesis gene cluster for the pyrrole polyether antibiotic calcimycin (A23187) in Streptomyces chartreusis NRRL 3882

Antimicrobial Agents and Chemotherapy

Volumn 55, Issue 3, 2011, Pages 974-982

  Wu, Qiulin ^a   Liang, Jingdan ^a   Lin, Shuangjun ^a   Zhou, Xiufen ^a   Bai, Linquan ^a   Deng, Zixin ^a   Wang, Zhijun ^a  

^a SHANGHAI JIAO TONG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYANTHRANILIC ACID; ALPHA KETOPYRROLE; CALCIMYCIN; DNA; METHYLTRANSFERASE; N METHYLTRANSFERASE; POLYKETIDE SYNTHASE; PYRROLE DERIVATIVE; THIOL ESTER HYDROLASE; THIOL ESTER HYDROLASE II; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GENE; BIOSYNTHESIS; COMPUTER MODEL; CONTROLLED STUDY; DNA MODIFICATION; DNA SEQUENCE; GENE CLUSTER; GENE IDENTIFICATION; GENE MUTATION; GENE SYNTHESIS; MOLECULAR CLONING; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; STREPTOMYCES; STREPTOMYCES CHARTREUSIS;

AMINO ACID SEQUENCE; ANTI-BACTERIAL AGENTS; BACTERIAL PROTEINS; CALCIMYCIN; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; SEQUENCE HOMOLOGY, AMINO ACID; STREPTOMYCES;

EID: 79952348541     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.01130-10     Document Type: Article

References (39)

1. Abbott, B. J., et al. 1979. Microbial transformation of A23187, a divalent cation ionophore antibiotic. Antimicrob. Agents Chemother. 16:808-812.
2. Ansari, M. Z., G. Yadav, R. S. Gokhale, and D. Mohanty. 2004. NRPS-PKS: a knowledge-based resource for analysis of NRPS/PKS megasynthases. Nucleic Acids Res. 32:W405-W413. (Pubitemid 39004076)
3. Bierman, M., et al. 1992. Plasmid cloning vectors for the conjugal transfer of DNA from Escherichia coli to Streptomyces spp. Gene 116:43-49.
4. Black, P. N., C. C. DiRusso, A. K. Metzger, and T. L. Heimert. 1992. Cloning, sequencing, and expression of the fadD gene of Escherichia coli encoding acyl coenzyme A synthetase. J. Biol. Chem. 267:25513-25520.
5. Cerdeno, A. M., M. J. Bibb, and G. L. Challis. 2001. Analysis of the prodiginine biosynthesis gene cluster of Streptomyces coelicolor A3(2): new mechanisms for chain initiation and termination in modular multienzymes. Chem. Biol. 8:817-829.
6. Datsenko, K. A., and B. L. Wanner. 2000. One-step inactivation of chromosomal genes in Escherichia coli K-12 using PCR products. Proc. Natl. Acad. Sci. U. S. A. 97:6640-6645.
7. David, L., and S. Emadzadeh. 1982. Biosynthesis of the ionophorous antibiotic A23187. J. Antibiot. (Tokyo) 35:1616-1617.
8. David, L., and A. Kergomard. 1982. Production by controlled biosynthesis of a novel ionophore antibiotic, cezomycin (demethylamino A23187). J. Antibiot. (Tokyo) 35:1409-1411.
9. Du, L., and L. Lou. 2010. PKS and NRPS release mechanisms. Nat. Prod. Rep. 27:255-278.
10. Frank, B., et al. 2007. Spiroketal polyketide formation in Sorangium: identification and analysis of the biosynthetic gene cluster for the highly cytotoxic spirangienes. Chem. Biol. 14:221-233.
11. Garneau, S., P. C. Dorrestein, N. L. Kelleher, and C. T. Walsh. 2005. Characterization of the formation of the pyrrole moiety during clorobiocin and coumermycin A1 biosynthesis. Biochemistry 44:2770-2780.
12. Gust, B., G. L. Challis, K. Fowler, T. Kieser, and K. F. Chater. 2003. PCR-targeting system in Streptomyces coelicolor. John Innes Center, Norwich, United Kingdom.
13. Heathcote, M. L., J. Staunton, and P. F. Leadlay. 2001. Role of type II thioesterases: evidence for removal of short acyl chains produced by aberrant decarboxylation of chain extender units. Chem. Biol. 8:207-220.
14. Ikeda, H., T. Nonomiya, M. Usami, T. Ohta, and S. Omura. 1999. Organization of the biosynthetic gene cluster for the polyketide anthelmintic macrolide avermectin in Streptomyces avermitilis. Proc. Natl. Acad. Sci. U. S. A. 96:9509-9514.
15. Kieser, T., M. J. Bibb, M. J. Buttner, K. F. Chater, and D. A. Hopwood. 2000. Practical Streptomyces genetics. The John Innes Foundation, Norwich, United Kingdom.
16. Kim, B. S., T. A. Cropp, B. J. Beck, D. H. Sherman, and K. A. Reynolds. 2002. Biochemical evidence for an editing role of thioesterase II in the biosynthesis of the polyketide pikromycin. J. Biol. Chem. 277:48028-48034.
17. 2+ ionophore A23187-mediated apoptosis and demonstration of a high susceptibility for transcriptional repression of cell cycle genes in B lymphoblasts from a patient with Scott syndrome. BMC Genomics 6:146.
18. Li, W., J. Ju, S. R. Rajski, H. Osada, and B. Shen. 2008. Characterization of the tautomycin biosynthetic gene cluster from Streptomyces spiroverticillatus unveiling new insights into dialkylmaleic anhydride and polyketide biosynthesis. J. Biol. Chem. 283:28607-28617.
19. Liu, C. M., et al. 1983. X-14885A, a novel divalent cation ionophore produced by a Streptomyces culture: discovery, fermentation, biological as well as ionophore properties and taxonomy of the producing culture. J. Antibiot. (Tokyo) 36:1118-1122.
20. Liu, C. M., et al. 1979. X-14547A, a new ionophorous antibiotic produced by Streptomyces antibioticus NRRL 8167. Discovery, fermentation, biological properties and taxonomy of the producing culture. J. Antibiot. (Tokyo) 32:95-99.
21. Lorite, M. J., J. Sanjuan, L. Velasco, J. Olivares, and E. J. Bedmar. 1998. Characterization of Bradyrhizobium japonicum pcaBDC genes involved in 4-hydroxybenzoate degradation. Biochim. Biophys. Acta 1397:257-261.
22. Mavrodi, D. V., et al. 1998. A seven-gene locus for synthesis of phenazine-1-carboxylic acid by Pseudomonas fluorescens 2-79. J. Bacteriol. 180:2541-2548. (Pubitemid 28217371)
23. Nowak-Thompson, B., N. Chaney, J. S. Wing, S. J. Gould, and J. E. Loper. 1999. Characterization of the pyoluteorin biosynthetic gene cluster of Pseudomonas fluorescens Pf-5. J. Bacteriol. 181:2166-2174.
24. Pojer, F., S. M. Li, and L. Heide. 2002. Molecular cloning and sequence analysis of the clorobiocin biosynthetic gene cluster: new insights into the biosynthesis of aminocoumarin antibiotics. Microbiology 148:3901-3911. (Pubitemid 36097452)
25. Pressman, B. C. 1976. Biological applications of ionophores. Annu. Rev. Biochem. 45:501-530.
26. Prudhomme, M., G. Dauphin, J. Guyot, and G. Jeminet. 1984. Semisynthesis of A23187 (calcimycin) analogs. II. Introduction of a methyl group on the benzoxazole ring. J. Antibiot. (Tokyo) 37:627-634.
27. Prudhomme, M., G. Dauphin, and G. Jeminet. 1986. Semi-synthesis of A23187 (calcimycin) analogs. III. Modification of benzoxazole ring substituents, ionophorous properties in an organic phase. J. Antibiot. (Tokyo) 39:922-933.
28. Prudhomme, M., J. Guyot, and G. Jeminet. 1986. Semi-synthesis of A23187 (calcimycin) analogs. IV. Cation carrier properties in mitochondria of analogs with modified benzoxazole rings. Antimicrobial activity. J. Antibiot. (Tokyo) 39:934-937.
29. Reed, P. W., and H. A. Lardy. 1972. A23187: a divalent cation ionophore. J. Biol. Chem. 247:6970-6977.
30. Reid, R., et al. 2003. A model of structure and catalysis for ketoreductase domains in modular polyketide synthases. Biochemistry 42:72-79. (Pubitemid 36083852)
31. Sambrook, J., and D. W. Russell. 2001. Molecular cloning: a laboratory manual, 3rd ed. Cold Spring Harbor Laboratory, Cold Spring Harbor, NY.
32. Schubert, H. L., R. M. Blumenthal, and X. Cheng. 2003. Many paths to methyltransfer: a chronicle of convergence. Trends Biochem. Sci. 28:329-335.
33. Thomas, M. G., M. D. Burkart, and C. T. Walsh. 2002. Conversion of L-proline to pyrrolyl-2-carboxyl-S-PCP during undecylprodigiosin and pyoluteorin biosynthesis. Chem. Biol. 9:171-184.
34. Wang, Z. X., S. M. Li, and L. Heide. 2000. Identification of the coumermycin A(1) biosynthetic gene cluster of Streptomyces rishiriensis DSM 40489. Antimicrob. Agents Chemother. 44:3040-3048.
35. Westley, J. W., et al. 1983. Isolation and characterization of a novel polyether antibiotic of the pyrrolether class, antibiotic X-14885A. J. Antibiot. (Tokyo) 36:1275-1278.
36. Yadav, G., R. S. Gokhale, and D. Mohanty. 2003. Computational approach for prediction of domain organization and substrate specificity of modular polyketide synthases. J. Mol. Biol. 328:335-363.
37. Zhang, X., and R. J. Parry. 2007. Cloning and characterization of the pyrrolomycin biosynthetic gene clusters from Actinosporangium vitaminophilum ATCC 31673 and Streptomyces sp. strain UC 11065. Antimicrob. Agents Chemother. 51:946-957.
38. Zhou, Y., et al. 2008. Selective removal of aberrant extender units by a type II thioesterase for efficient FR-008/candicidin biosynthesis in Streptomyces sp. strain FR-008. Appl. Environ. Microbiol. 74:7235-7242.
39. Zmijewski, M. J., Jr. 1980. Biosynthesis of antibiotic A23187. Incorporation of precursors into A23187. J. Antibiot. (Tokyo) 33:447-450.