Metabolic engineering of aminocoumarins: Inactivation of the methyltransferase gene cloP and generation of new clorobiocin derivatives in a heterologous host

ChemBioChem

Volumn 6, Issue 8, 2005, Pages 1411-1418

  Freitag, Anja ^a   Rapp, Heike ^a   Heide, Lutz ^a   Li, Shu Ming ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

Antibiotics; Biosynthesis; Heterologous Expression; Methyltransferase; Streptomyces roseochromogenes

Indexed keywords

5 METHYLPYRROLE 2 CARBONYL GROUP; AMINOCOUMARIN DERIVATIVE; ANTIBIOTIC AGENT; CARBONYL DERIVATIVE; CLOROBIOCIN; CLOROBIOCIN DERIVATIVE; COUMARIN DERIVATIVE; DEOXYSUGAR; GYRASE INHIBITOR; HYDROXYL GROUP; ISOCLOROBIOCIN; METHYL GROUP; METHYLTRANSFERASE; NOVCLOBIOCIN; NOVIOSE; NOVOBIOCIN; UNCLASSIFIED DRUG;

ACYLATION; ANTIBACTERIAL ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; CLOP GENE; GENE; GENE CLUSTER; GENE EXPRESSION; GENE INACTIVATION; HETEROLOGOUS EXPRESSION; HOST; METABOLIC ENGINEERING; METABOLITE; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STREPTOMYCES; STREPTOMYCES COELICOLOR; STREPTOMYCES COELICOLOR M512; STREPTOMYCES ROSEOCHROMOGENES; STRUCTURE ACTIVITY RELATION;

ACYLATION; ANTI-BACTERIAL AGENTS; ANTIBIOTICS, ANTINEOPLASTIC; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COSMIDS; COUMARINS; GENE TARGETING; GENE TRANSFER TECHNIQUES; MASS SPECTROMETRY; METHYLTRANSFERASES; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; MONOSACCHARIDES; MUTATION; NOVOBIOCIN; STREPTOMYCES COELICOLOR; STRUCTURE-ACTIVITY RELATIONSHIP;

STREPTOMYCES COELICOLOR; STREPTOMYCES ROSEOCHROMOGENES;

EID: 23644445499     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/cbic.200500019     Document Type: Article

References (32)

1. S. R. Palumbi, Science 2001, 293, 1786-1790.
2. T. Walsh, Nat. Rev. Microb. 2003, 1, 65-70.
3. C. T. Walsh, ChemBioChem 2002, 3, 124-134.
4. S.-M. Li, L. Heide, Curr. Med. Chem. Anti-Infect. Agents 2004, 3, 279-295.
5. S. H. Olson, L. H. Slossberg, Tetrahedron Lett. 2002, 44, 61-63.
6. A. M. Periers, P. Laurin, Y. Benedetti, S. Lachaud, D. Ferroud, A. Iltis, J. L. Haesslein, M. Klich, G. L'Hermite, B. Musicki, Tetrahedron Lett. 2000, 41, 867-871.
7. L. Schio, F. Chatreaux, V. Loyau, M. Murer, A. Ferreira, P. Mauvais, A. Bonnefoy, M. Klich, Bioorg. Med. Chem. Lett. 2001, 11, 1461-1464.
8. A. Maxwell, Biochem. Soc. Trans. 1999, 27, 48-53.
9. I. I. Raad, R. Y. Hachem, D. Abi-Said, K. V. I. Rolston, E. Whimbey, A. C. Buzaid, S. Legha, Cancer 1998, 82, 403-411.
10. M. A. Montecalvo, H. Horowitz, G. P. Wormser, K. Seiter, C. A. Carbonaro, Antimicrob. Agents Chemother. 1995, 39, 794.
11. T. J. Walsh, H. C. Standiford, A. C. Reboli, J. F. John, M. E. Mulligan, B. S. Ribner, J. Z. Montgomerie, M. B. Goetz, C. G. Mayhall, D. Rimland, D. A. Stevens, S. L. Hansen, G. C. Gerard, R. J. Ragual, Antimicrob. Agents Chemother. 1993, 37, 1334-1342.
12. A. Maxwell, D. M. Lawson, Curr. Top. Med. Chem. 2003, 3, 283-303.
13. F. Pojer, S.-M. Li, L. Heide, Microbiology 2002, 148, 3901-3911.
14. L. Westrich, L. Heide, S.-M. Li, ChemBioChem 2003, 4, 768-773.
15. A. S. Eustáquio, B. Gust, U. Galm, S.-M. Li, Chater K. F, L. Heide, Appl. Environ. Microbiol. 2005, 71, 2452-2459.
16. A. S. Eustáquio, B. Gust, S.-M. Li, S. Pelzer, W. Wohlleben, K. F. Chater, L. Heide, Chem. Biol. 2004, 11, 1561-1572.
17. R. Fouces, E. Mellado, B. Diez, J. L. Barredo, Microbiology 1999, 145, 855-868.
18. S.-M. Li, L. Westrich, J. Schmidt, C. Kuhnt, L. Heide, Microbiology 2002, 148, 3317-3326.
19. H. Xu, R. Kahlich, B. Kammerer, L. Heide, S.-M. Li, Microbiology 2003, 149, 2183-2191.
20. F. Pojer, E. Wemakor, B. Kammerer, H. Chen, C. T. Walsh, S.-M. Li, L. Heide, Proc. Natl. Acad. Sci. USA 2003, 100, 2316-2321.
21. F. Pojer, R. Kahlich, B. Kammerer, S.-M. Li, L. Heide, J. Biol. Chem. 2003, 278, 30661-30668.
22. U. Galm, M. A. Dessoy, J. Schmidt, L. A. Wessjohann, L. Heide, Chem. Biol. 2004, 11, 173-183.
23. F. W. Crow, W. K. Duholke, K. A. Parley, C. E. Hadden, D. A. Hahn, B. D. Kaluzny, C. S. Mallory, G. E. Martin, R. F. Smith, T. J. Thamann, J. Heterocycl. Chem. 1999, 36, 365-370.
24. A. Maxwell, Mol. Microbiol. 1993, 9, 681-686.
25. H. Xu, L. Heide, S.-M. Li, Chem. Biol. 2004, 11, 655-662.
26. H. Xu, Z.-X. Wang, J. Schmidt, L. Heide, S.-M. Li, Mol. Genet. Genomics 2002, 268, 387-396.
27. B. Floriano, M. Bibb, Mol. Microbiol. 1996, 21, 385-396.
28. T. Kieser, M. J. Bibb, M. J. Buttner, K. F. Chater, D. A. Hopwood, Practical Streptomyces Genetics, 2nd ed. John Innes Foundation, Norwich, UK, 2000.
29. J. Sambrook, D. W. Russell, Molecular Cloning: A Laboratory Manual, 3rd ed. Cold Spring Harbor Laboratory Press, New York 2001.
30. B. Gust, G. L. Challis, K. Fowler, T. Kieser, K. F. Chater, Proc. Natl. Acad. Sci. USA 2003, 100, 1541-1546.
31. A. S. Eustaquio, B. Gust, T. Luft, S.-M. Li, K. F. Chater, L. Heide, Chem. Biol. 2003, 10, 279-288.
32. H. M. Thorpe, S. E. Wilson, M. C. Smith, Mol. Microbiol. 2000, 38, 232-241.