Acyl transfer in clorobiocin biosynthesis: Involvement of several proteins in the transfer of the pyrrole-2-carboxyl moiety to the deoxysugar

ChemBioChem

Volumn 6, Issue 12, 2005, Pages 2316-2325

  Freitag, Anja ^a   Wemakor, Emmanuel ^a   Li, Shu Ming ^a   Heide, Lutz ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

Acyl transfer; Biosynthesis; Clorobiocin; Heterologous expression; Pyrrole 2 carboxylic acid; Streptomyces

Indexed keywords

2 PYRROLECARBOXYLIC ACID; AMINOCOUMARIN DERIVATIVE; ANTIBIOTIC AGENT; CARBOXYL GROUP; CARBOXYLIC ACID DERIVATIVE; CLOROBIOCIN; DEOXYSUGAR; PYRROLE 2 CARBOXYL; UNCLASSIFIED DRUG; 2-PYRROLECARBOXYLIC ACID; CARBOHYDRATE; DRUG DERIVATIVE; MULTIENZYME COMPLEX; NOVOBIOCIN; PROLINE;

ARTICLE; CONTROLLED STUDY; COSMID; DRUG STRUCTURE; DRUG SYNTHESIS; GENE CLUSTER; GENE DELETION; GENOME; MASS SPECTROMETER; METABOLITE; MOLECULAR CLONING; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SEQUENCE ANALYSIS; STREPTOMYCES COELICOLOR; ACYLATION; BIOSYNTHESIS; CHEMISTRY; GENETICS; METABOLISM; STREPTOMYCES;

STREPTOMYCES; STREPTOMYCES COELICOLOR; STREPTOMYCES ROSEOCHROMOGENES;

ACYLATION; CARBOHYDRATES; COSMIDS; MULTIENZYME COMPLEXES; NOVOBIOCIN; PROLINE; STREPTOMYCES;

EID: 33746068735     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200500252     Document Type: Article

References (44)

1. A. Maxwell, Biochem. Soc. Trans. 1999, 27, 48-53.
2. R. J. Lewis, O. M. P. Singh, C. V. Smith, T. Skarzynski, A. Maxwell, A. J. Wonacott, D. B. Wigley, EMBO J. 1996, 15, 1412-1420.
3. A. Maxwell, D. M. Lawson, Curr. Top. Med. Chem. 2003, 3, 283-303.
4. M. Steffensky, A. Mühlenweg, Z.-X. Wang, S.-M. Li, L. Heide, Antimicrob. Agents Chemother. 2000, 44, 1214-1222.
5. F. Pojer, S.-M. Li, L. Heide, Microbiology 2002, 148, 3901-3911.
6. Z.-X. Wang, S.-M. Li, L. Heide, Antimicrob. Agents Chemother. 2000, 44, 3040-3048.
7. S.-M. Li, L. Heide, Curr. Med. Chem.: Anti-Infect. Agents 2004, 3, 279-295.
8. A. S. Eustáquio, B. Gust, U. Galm, S.-M. Li, K. F. Chater, L. Heide, Appl. Environ. Microbiol. 2005, 71, 2452-2459.
9. T. T. T. Thuy, H. C. Lee, C. G. Kim, L. Heide, J. K. Sohng, Arch. Biochem. Biophys. 2005, 436, 161-167.
10. H. Chen, C. T. Walsh, Chem. Biol. 2001, 8, 301-312.
11. 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.
12. H. Chen, M. G. Thomas, S. E. O'Connor, B. K. Hubbard, M. D. Burkart, C. T. Walsh, Biochemistry 2001, 40, 11 651-11 659.
13. A. S. Eustáquio, B. Gust, T. Luft, S.-M. Li, K. F. Chater, L. Heide, Chem. Biol. 2003, 10, 279-288.
14. F. Pojer, R. Kahlich, B. Kammerer, S.-M. Li, L. Heide, J. Biol. Chem. 2003, 278, 30 661-30 668.
15. U. Galm, M. A. Dessoy, J. Schmidt, L. A. Wessjohann, L. Heide, Chem. Biol. 2004, 11, 173-183.
16. M. Steffensky, S.-M. Li, L. Heide, J. Biol. Chem. 2000, 275, 21 754-21 760.
17. C. L. Freel Meyers, M. Oberthur, J. W. Anderson, D. Kahne, C. T. Walsh, Biochemistry 2003, 42, 4179-4189.
18. C. Albermann, A. Soriano, J. Jiang, H. Vollmer, J. B. Biggins, W. A. Barton, J. Lesniak, D. B. Nikolov, J. S. Thorson, Org. Lett. 2003, 5, 933-936.
19. H. Xu, Z.-X. Wang, J. Schmidt, L. Heide, S.-M. Li, Mol. Genet. Genomics 2002, 268, 387-396.
20. S. Garneau, P. C. Dorrestein, N. L. Kelleher, C. T. Walsh, Biochemistry 2005, 44, 2770-2780.
21. H. Xu, R. Kahlich, B. Kammerer, L. Heide, S.-M. Li, Microbiology 2003, 149, 2183-2191.
22. L. Westrich, L. Heide, S.-M. Li, ChemBioChem 2003, 4, 768-773.
23. A. Freitag, H. Rapp, L. Heide, S.-M. Li, ChemBioChem 2005, 6, 1411-1418.
24. A. S. Eustáquio, S.-M. Li, L. Heide, Microbiology 2005, 151, 1949-1961.
25. A. S. Eustáquio, T. Luft, Z.-X. Wang, B. Gust, K. F. Chater, S.-M. Li, L. Heide, Arch. Microbiol. 2003, 180, 25-32.
26. E. Schmutz, S. Hennig, S.-M. Li, L. Heide, Microbiology 2004, 150, 641-647.
27. H. C. Wong, G. Liu, Y. M. Zhang, C. O. Rock, J. Zheng, J. Biol. Chem. 2002, 277, 15 874-15 880.
28. T. Stachelhaus, A. Huser, M. A. Marahiel, Chem. Biol. 1996, 3, 913-921.
29. M. G. Thomas, M. D. Burkart, C. T. Walsh, Chem. Biol. 2002, 9, 171-184.
30. M. Holmquist, Curr. Protein Pept. Sci. 2000, 1, 209-235.
31. O. Puk, P. Huber, D. Bischoff, J. Recktenwald, G. Jung, R. D. Süßmuth, K.-H. van Pée, W. Wohlleben, S. Pelzer, Chem. Biol. 2002, 9, 225-235.
32. A. M. van Wageningen, P. N. Kirkpatrick, D. H. Williams, B. R. Harris, J. K. Kershaw, N. J. Lennard, M. Jones, S. J. Jones, P. J. Solenberg, Chem. Biol. 1998, 5, 155-162.
33. O. Puk, D. Bischoff, C. Kittel, S. Pelzer, S. Weist, E. Stegmann, R. Süßmuth, W. Wohlleben, J. Bacteriol. 2004, 186, 6093-6100.
34. A. S. Eustáquio, B. Gust, S.-M. Li, S. Pelzer, W. Wohlleben, K. F. Chater, L. Heide, Chem. Biol. 2004, 11, 1561-1572.
35. 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.
36. D. Mancy, L. Ninet, J. Preud'Homme, Antibiotic 18631 RP. (Rhône-Poulenc S.A.). 189259.[3793147] 1974. U.S., 1974.
37. H. Xu, L. Heide, S.-M. Li, Chem. Biol. 2004, 11, 655-662.
38. S. Shimokawa, H. Fukui, J. Sohma, Mol. Phys. 1970, 19, 695-702.
39. W. Bao, P. J. Sheldon, C. R. Hutchinson, Biochemistry 1999, 38, 9752-9757.
40. B. Floriano, M. Bibb, Mol. Microbiol. 1996, 21, 385-396.
41. D. J. MacNeil, K. M. Gewain, C. L. Ruby, G. Dezeny, P. H. Gibbons, T. MacNeil, Gene 1992, 111, 61-68.
42. J. Sambrook, D. W. Russell, Molecular Cloning: A Laboratory Manual, 3rd ed. Cold Spring Harbor Laboratory Press, New York 2001.
43. B. Gust, G. L. Challis, K. Fowler, T. Kieser, K. F. Chater, Proc. Natl. Acad. Sci. USA 2003, 100, 1541-1546.
44. H. M. Thorpe, S. E. Wilson, M. C. Smith, Mol. Microbiol. 2000, 38, 232-241.