Clorobiocin biosynthesis in Streptomyces: Identification of the halogenase and generation of structural analogs

Chemistry and Biology

Volumn 10, Issue 3, 2003, Pages 279-288

  Eustáquio, Alessandra S ^a   Gust, Bertolt ^b   Luft, Thomas ^a   Li, Shu Ming ^a   Chater, Keith F ^b   Heide, Lutz ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

^b JOHN INNES CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA (MICROORGANISMS); STREPTOMYCES;

EID: 0037350329     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(03)00051-6     Document Type: Article

References (40)

1. Maxwell A. DNA gyrase as a drug target. Trends Microbiol. 5:1997;102-109.
2. Maxwell A. The interaction between coumarin drugs and DNA gyrase. Mol. Microbiol. 9:1993;681-686.
3. Lewis R.J., Tsai F.T.F., Wigley D.B. Molecular mechanisms of drug inhibition of DNA gyrase. Bioessays. 18:1996;661-671.
4. 1, clorobiocin, and their analogs on Escherichia coli DNA gyrase and bacterial growth. Antimicrob. Agents Chemother. 22:1982;662-671.
5. Reusser F., Dolak L.A. Novenamine is the active moiety in novobiocin. J. Antibiot. (Tokyo). 39:1986;272-274.
6. Lewis R.J., Singh O.M.P., Smith C.V., Skarzynski T., Maxwell A., Wonacott A.J., Wigley D.B. The nature of inhibition of DNA gyrase by the coumarins and the cyclothialidines revealed by X-ray crystallography. EMBO J. 15:1996;1412-1420.
7. Tsai F.T.F., Singh O.M.P., Skarzynski T., Wonacott A.J., Weston S., Tucker A., Pauptit R.A., Breeze A.L., Poyser J.P., O'Brien R.et al. The high-resolution crystal structure of a 24-kDa gyrase B fragment from E. coli complexed with one of the most potent coumarin inhibitors, clorobiocin. Proteins. 28:1997;41-52.
8. Lafitte D., Lamour V., Tsvetkov P.O., Makarov A.A., Klich M., Deprez P., Moras D., Briand C., Gilli R. DNA gyrase interaction with coumarin-based inhibitors. the role of the hydroxybenzoate isopentenyl moiety and the 5′-methyl group of the noviose Biochemistry. 41:2002;7217-7223.
9. Raad I., Darouiche R., Hachem R., Sacilowski M., Bodey G.P. Antibiotics and prevention of microbial colonization of catheters. Antimicrob. Agents Chemother. 39:1995;2397-2400.
10. Raad I.I., Hachem R.Y., Abi-Said D., Rolston K.V.I., Whimbey E., Buzaid A.C., Legha S. A prospective crossover randomized trial of novobiocin and rifampin prophylaxis for the prevention of intravascular catheter infections in cancer patients treated with interleukin-2. Cancer. 82:1998;403-411.
11. Walsh T.J., Standiford H.C., Reboli A.C., John J.F., Mulligan M.E., Ribner B.S., Montgomerie J.Z., Goetz M.B., Mayhall C.G., Rimland D.et al. Randomized double-blinded trial of rifampin with either novobiocin or trimethoprim-sulfamethoxazole against methicillin-resistant Staphylococcus aureus colonization. prevention of antimicrobial resistance and effect of host factors on outcome Antimicrob. Agents Chemother. 37:1993;1334-1342.
12. Marcu M.G., Schulte T.W., Neckers L. Novobiocin and related coumarins and depletion of heat shock protein 90-dependent signaling proteins. J. Natl. Cancer Inst. 92:2000;242-248.
13. Rappa G., Shyam K., Lorico A., Fodstad O., Sartorelli A.C. Structure-activity studies of novobiocin analogs as modulators of the cytotoxicity of etoposide (VP-16). Oncol. Res. 12:2000;113-119.
14. Thiele A., Pfister M., Erbes M., Cross M., Hänsch M., Hauschildt S. Novobiocin is a novel inducer of CD38 on cells of the myelomonocytic lineage. Biochim. Biophys. Acta. 1542:2002;32-40.
15. Maxwell A., Lawson D.M. The ATP-binding site of type II topoisomerases as a target for antibacterial drugs. Curr. Top. Med. Chem. 3:2003;283-303.
16. Hutchinson C.R. Combinatorial biosynthesis for new drug discovery. Curr. Opin. Microbiol. 1:1998;319-329.
17. Khosla C. Combinatorial biosynthesis of "unnatural" natural products. Gordon E.M., Kerwin J.F. Jr. Combinatorial Chemistry and Molecular Diversity in Drug Discovery. 1998;John Wiley & Sons, New York. 401-417.pp.
18. Steffensky M., Mühlenweg A., Wang Z.-X., Li S.-M., Heide L. Identification of the novobiocin biosynthetic gene cluster of Streptomyces spheroides NCIB 11891. Antimicrob. Agents Chemother. 44:2000;1214-1222.
19. 1 biosynthetic gene cluster of Streptomyces rishiriensis DSM 40489. Antimicrob. Agents Chemother. 44:2000;3040-3048.
20. Pojer F., Li S.-M., Heide L. Molecular cloning and sequence analysis of the clorobiocin biosynthetic gene cluster. new insights into the biosynthesis of aminocoumarin antibiotics Microbiology. 148:2002;3901-3911.
21. Li S.-M., Westrich L., Schmidt J., Kuhnt C., Heide L. Methyltransferase genes in Streptomyces rishiriensis. new coumermycin derivatives from gene-inactivation experiments Microbiology. 148:2002;3317-3326.
22. van Pée K.-H. Microbial biosynthesis of halometabolites. Arch. Microbiol. 175:2001;250-258.
23. Pelzer S., Süssmuth R., Heckmann D., Recktenwald J., Huber P., Jung G., Wohlleben W. Identification and analysis of the balhimycin biosynthetic gene cluster and its use for manipulating glycopeptide biosynthesis in Amycolatopsis mediterranei DSM5908. Antimicrob. Agents Chemother. 43:1999;1565-1573.
24. Puk O., Huber P., Bischoff D., Recktenwald J., Jung G., Süssmuth R.D., van Pée K.-H., Wohlleben W., Pelzer S. Glycopeptide biosynthesis in Amycolatopsis mediterranei DSM5908. function of a halogenase and a haloperoxidase/perhydrolase Chem. Biol. 9:2002;225-235.
25. Chiu H.-T., Hubbard B.K., Shah A.N., Eide J., Fredenburg R.A., Walsh C.T., Khosla C. Molecular cloning and sequence analysis of the complestatin biosynthetic gene cluster. Proc. Natl. Acad. Sci. USA. 98:2001;8548-8553.
26. Nowak-Thompson B., Chaney N., Wing J.S., Gould S.J., Loper J.E. Characterization of the pyoluteorin biosynthetic gene cluster of Pseudomonas fluorescens Pf-5. J. Bacteriol. 181:1999;2166-2174.
27. Datsenko K.A., Wanner B.L. One-step inactivation of chromosomal genes in Escherichia coli K-12 using PCR products. Proc. Natl. Acad. Sci. USA. 97:2000;6640-6645.
28. Gust B., Challis G.L., Fowler K., Kieser T., Chater K.F. PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin. Proc. Natl. Acad. Sci. USA. 100:2003;1541-1546.
29. Kieser, T., Bibb, M.J., Buttner, M.J., Chater, K.F., and Hopwood, D.A. (2000). Practical Streptomyces Genetics. (Norwich, UK: John Innes Foundation).
30. Sasaki T., Igarashi Y., Saito N., Furumai T. TPU-0031-A and B, new antibiotics of the novobiocin group produced by Streptomyces sp. TP-A0556. J. Antibiot. 54:2001;441-447. (Tokyo).
31. Kagan R.M., Clarke S. Widespread occurrence of three sequence motifs in diverse S-adenosylmethionine-dependent methyltransferases suggests a common structure for these enzymes. Arch. Biochem. Biophys. 310:1994;417-427.
32. Gribble G.W. Naturally occurring organohalogen compounds. Acc. Chem. Res. 31:1998;141-152.
33. Dairi T., Nakano T., Aisaka K., Katsumata R., Hasegawa M. Cloning and nucleotide sequence of the gene responsible for chlorination of tetracycline. Biosci. Biotechnol. Biochem. 59:1995;1099-1106.
34. Chen H., Walsh C.T. Coumarin formation in novobiocin biosynthesis. beta-hydroxylation of the aminoacyl enzyme tyrosyl-S-NovH by a cytochrome P450 NovI Chem. Biol. 8:2001;301-312.
35. Berger J., Batcho A.D. Coumarin-glycoside antibiotics. J. Chromatogr. Libr. 15:1978;101-158.
36. Althaus I.W., Dolak L., Reusser F. Coumarins as inhibitors of bacterial DNA gyrase. J. Antibiot. (Tokyo). 41:1988;373-376.
37. Mancy, D., Ninet, L., and Preud'Homme, J. February 1974. Antibiotic 18631 RP. U.S. patent 3,793,147.
38. Sambrook J., Russell D.W. Molecular Cloning. A Laboratory Manual:2001;Cold Spring Harbor Laboratory Press, New York.
39. MacNeil D.J., Gewain K.M., Ruby C.L., Dezeny G., Gibbons P.H., MacNeil T. Analysis of Streptomyces avermitilis genes required for avermectin biosynthesis utilizing a novel integration vector. Gene. 111:1992;61-68.
40. Chadwick D.J. Physical and theoretical aspects of 1H-pyrroles. Pyrroles Part One: The Synthesis, the Physical and Chemical Aspects of the Pyrrole Ring R.A., Jones, The Chemistry of Heterocyclic Compounds In. 1990;John Wiley & Sons, E.C. Taylor and A. Weissberger, eds. (New York., pp. 1-103.