Molecular cloning and sequence analysis of the clorobiocin biosynthetic gene cluster: New insights into the biosynthesis of aminocoumarin antibiotics

Microbiology

Volumn 148, Issue 12, 2002, Pages 3901-3911

  Pojer, Florence ^a   Li, Shu Ming ^a   Heide, Lutz ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

Aldolase; Coumermycin A1; Novobiocin; Retro aldol reaction

Indexed keywords

ANTIBIOTIC AGENT; BENZOIC ACID DERIVATIVE; CLOROBIOCIN; COUMAMYCIN A1; NOVOBIOCIN; UNCLASSIFIED DRUG;

ANTIBIOTIC BIOSYNTHESIS; BIOSYNTHESIS; CATALYSIS; CONTROLLED STUDY; COSMID; FEEDING; GENE CLUSTER; GENE DELETION; GENE INACTIVATION; GENE PROBE; GENETIC SCREENING; MOLECULAR CLONING; MOLECULAR LIBRARY; MUTANT; NONHUMAN; NUCLEOTIDE SEQUENCE; OPEN READING FRAME; PRIORITY JOURNAL; REACTION ANALYSIS; REVIEW; SEQUENCE ANALYSIS; STREPTOMYCES; STREPTOMYCES ROSEOCHROMOGENES;

ACTINOBACTERIA (CLASS); PROKARYOTA; STREPTOMYCES; STREPTOMYCES MARITIMUS; STREPTOMYCES ROSEOCHROMOGENES; UNCULTURED ACTINOMYCETE;

EID: 0036953085     PISSN: 13500872     EISSN: None     Source Type: Journal    
DOI: 10.1099/00221287-148-12-3901     Document Type: Review

References (36)

1. Achterholt, S., Priefert, H. & Steinbuchel, A. (2000). Identification of Amycolatopsis sp. strain HR167 genes, involved in the bioconversion of ferulic acid to vanillin. Appl Microbiol Biotechnol 54, 799-807.
2. Ali, J. A., Jackson, A. P., Howells, A. J. & Maxwell, A. (1993). The 43-kilodalton N-terminal fragment of the DNA gyrase B protein hydrolyzes ATP and binds coumarin drugs. Biochemistry 32, 2717-2724.
3. Berger, J. & Batcho, A. D. (1978). Coumarin-glycoside antibiotics. J Chromatogr Libr 15, 101-159.
4. Bunton, C. A., Kenner, G. W., Robinson, M. J. T. & Webster, B. R. (1963). Experiments related to the biosynthesis of novobiocin and other coumarins. Tetrahedron 19, 1001-1010.
5. Cerdeno, A. M., Bibb, M. J. & Challis, G. L. (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. Chen, H. & Walsh, C. T. (2001). Coumarin formation in novobiocin biosynthesis: β-hydroxylation of the aminoacyl enzyme tyrosyl-S-NovH by a cytochrome P450 NovI. Chem Biol 8, 301-312.
7. Galm, U., Schimana, J., Fiedler, H. P., Schmidt, J., Li, S.-M. & Heide, L. (2002). Cloning and analysis of the simocyclinone biosynthetic gene cluster of Streptomyces antibioticus Tü 6040. Arch Microbiol 178, 102-114.
8. Gasson, M. J., Kitamura, Y., McLauchlan, W. R., Narbad, A., Parr, A. J., Parsons, E. L. H., Payne, J., Rhodes, M. J. C. & Walton, N. J. (1998). Metabolism of ferulic acid to vanillin. A bacterial gene of the enoyl-SCoA hydratase/isomerase superfamily encodes an enzyme for the hydration and cleavage of a hydroxycinnamic acid SCoA thioester. J Biol Chem 273, 4163-4170.
9. Hertweck, C. & Moore, B. S. (2000). A plant-like biosynthesis of benzoyl-CoA in the marine bacterium Streptomyces maritimus. Tetrahedron 56, 9115-9120.
10. Hinman, J. W., Caron, E. L & Hoeksema, H. (1957). Novobiocin. V. Carbamyl migration and isonovobiocin. J Am Chem Soc 79, 5321-5322.
11. 2-rich atmosphere. J Antibiot (Tokyo) 55, 341-342.
12. Hooper, D. C., Wolfson, J. S., McHugh, G. L., Winters, M. B. & Swartz, M. N. (1982). Effects of novobiocin, coumermycin A1, clorobiocin, and their analogs on Escherichia coli DNA gyrase and bacterial growth. Antimicrob Agents Chemother 22, 662-671.
13. Horinouchi, S. & Beppu, T. (1995). Autoregulators. Biotechnology 28, 103-119.
14. Kieser, T., Bibb, M. J., Buttner, M. J., Chater, K. F. & Hopwood, D. A. (2000). Practical Streptomyces Genetics. Norwich: John Innes Foundation.
15. Kominek, L. A. & Sebek, O. K. (1974). Biosynthesis of novobiocin and related coumarin antibiotics. Dev Ind Microbiol 15, 60-69.
16. Lafitte, D., Lamour, V., Tsvetkov, P. O., Makarov, A. A., Klich, M., Deprez, P., Moras, D., Briand, C. & Gilli, R. (2002). DNA gyrase interaction with coumarin-based inhibitors: the role of the hydroxybenzoate isopentenyl moiety and the 5′-methyl group of the noviose. Biochemistry 41, 7217-7223.
17. Lewis, R. J., Singh, O. M., Smith, C. V., Skarzynski, T., Maxwell, A., Wonacott, A. J. & Wigley, D. B. (1996). The nature of inhibition of DNA gyrase by the coumarins and the cyclothialidines revealed by X-ray crystallography. EMBO J 15, 1412-1420.
18. Li, S.-M., Hennig, S. & Heide, L. (1998). Biosynthesis of the dimethylallyl moiety of novobiocin via a non-mevalonate pathway. Tetrahedron Lett 39, 2717-2720.
19. Li, S.-M., Westrich, L., Schmidt, J., Kuhnt, C. & Heide, L. (2002). Methyltransferase genes in Streptomyces rishiriensis: new coumermycin derivatives from gene-inactivation experiments. Microbiology 148, 3317-3326.
20. Lombo, F., Siems, K., Brana, A. F., Mendez, C., Bindseil, K. & Salas, J. A. (1997). Cloning and insertional inactivation of Streptomyces argillaceus genes involved in the earliest steps of biosynthesis of the sugar moieties of the antitumor polyketide mithramycin. J Bacteriol 179, 3354-3357.
21. Mancy, D., Ninet, L. & Preud Homme, J. (1974). Antibiotic 18. 631 RP. United States Patent Office, no. 3793147.
22. Maxwell, A. (1993). The interaction between coumarin drugs and DNA gyrase. Mol Microbiol 9, 681-686.
23. Maxwell, A. (1999). DNA gyrase as a drug target. Biochem Soc Trans 27, 48-53.
24. Nowak-Thompson, B., Chaney, N., Wing, J. S., Gould, S. J. & Loper, J. E. (1999). Characterization of the pyoluteorin biosynthetic gene cluster of Pseudomonas fluorescens Pf-5. J Bacteriol 181, 2166-2174.
25. Peschke, U., Schmidt, H., Zhang, H. Z. & Piepersberg, W. (1995). Molecular characterization of the lincomycin-production gene cluster of Streptomyces lincolnensis 78-11. Mol Microbiol 16, 1137-1156.
26. Queener, S. W., Sebek, O. K. & Vezina, C. (1978). Mutants blocked in antibiotic synthesis. Annu Rev Microbiol 32, 593-636.
27. Sambrook, J. & Russell, D. (2001). Molecular Cloning: a Laboratory Manual, 3rd edn. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory.
28. Sofia, H. J., Chen, G., Hetzler, B. G., Reyes-Spindola, J. F. & Miller, N. E. (2001). Radical SAM, a novel protein superfamily linking unresolved steps in familiar biosynthetic pathways with radical mechanisms: functional characterization using new analysis and information visualization methods. Nucleic Acids Res 29, 1097-1106.
29. Steffensky, M., Li, S.-M., Vogler, B. & Heide, L. (1998). Novobiocin biosynthesis in Streptomyces spheroides: identification of a dimethylallyl diphosphate:4-hydroxyphenylpyruvate dimethylallyl transferase. FEMS Microbiol Lett 169, 69-74.
30. Steffensky, M., Mühlenweg, A., Wang, Z. X., Li, S.-M. & Heide, L. (2000a). Identification of the novobiocin biosynthetic gene cluster of Streptomyces spheroides NCIB 11891. Antimicrob Agents Chemother 44, 1214-1222.
31. Steffensky, M., Li, S.-M. & Heide, L. (2000b). Cloning, overexpression, and purification of novobiocic acid synthetase from Streptomyces spheroides NCIMB 11891. J Biol Chem 275, 21754-21760.
32. Thiara, A. S. & Cundliffe, E. (1988). Cloning and characterization of a DNA gyrase B gene from Streptomyces sphaeroides that confers resistance to novobiocin. EMBO J 7, 2255-2259.
33. Thomas, M. G., Burkart, M. D. & Walsh, C. T. (2002). Conversion of L-proline to pyrrolyl-2-carboxyl-S-PCP during undecylprodigiosin and pyoluteorin biosynthesis. Chem Biol 9, 171-184.
34. Trefzer, A., Pelzer, S., Schimana, J., Stockert, S., Bihlmaier, C., Fiedler, H. P., Welzel, K., Vente, A. & Bechthold, A. (2002). Biosynthetic gene cluster of simocyclinone, a natural multihybrid antibiotic. Antimicrob Agents Chemother 46, 1174-1182.
35. Tsai, F. T., Singh, O. M., Skarzynski, T. & 9 other authors (1997). 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, 41-52.
36. Wang, Z. X., Li, S.-M. & Heide, L. (2000). Identification of the coumermycin A(1) biosynthetic gene cluster of Streptomyces rishiriensis DSM 40489. Antimicrob Agents Chemother 44, 3040-3048.