A Backup Plan for Self-Protection: S-Methylation of Holomycin Biosynthetic Intermediates in Streptomyces clavuligerus

ChemBioChem

Volumn 13, Issue 17, 2012, Pages 2521-2526

  Li, Bo ^a   Forseth, Ry R ^b   Bowers, Albert A ^c,d   Schroeder, Frank C ^b   Walsh, Christopher T ^a  

^a HARVARD MEDICAL SCHOOL   (United States)

^b United States Department of Agriculture   (United States)

^c PURDUE UNIVERSITY   (United States)

^d University of North Carolina at Chapel Hill   (United States)

Author keywords

Antibiotics; Biosynthesis; Comparative metabolomics; Detoxification; Dithiolopyrrolone

Indexed keywords

ANTIBIOTIC AGENT; HOLOMYCIN; MOLECULAR SCAFFOLD; SULFIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; BACTERIAL STRAIN; BIOASSAY; BIOSYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; GENE DELETION; GENE MUTATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLOME; METABOLOMICS; METHYLATION; NONHUMAN; OPEN READING FRAME; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STREPTOMYCES CLAVULIGERUS; UPREGULATION;

ANTI-BACTERIAL AGENTS; DIMERIZATION; LACTAMS; METABOLOMICS; METHYLATION; STREPTOMYCES; SULFUR;

STREPTOMYCES CLAVULIGERUS;

EID: 84869382112     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201200536     Document Type: Article

References (27)

1. A. Jimenez, D. J. Tipper, J. Davies, Antimicrob. Agents Chemother. 1973, 3, 729-738;
2. D. J. Tipper, J. Bacteriol. 1973, 116, 245-256;
3. B. Oliva, A. O'Neill, J. M. Wilson, P. J. O'Hanlon, I. Chopra, Antimicrob. Agents Chemother. 2001, 45, 532-539.
4. D. M. Gardiner, P. Waring, B. J. Howlett, Microbiology 2005, 151, 1021-1032;
5. R. Furumai, A. Matsuyama, N. Kobashi, K. H. Lee, M. Nishiyama, H. Nakajima, A. Tanaka, Y. Komatsu, N. Nishino, M. Yoshida, S. Horinouchi, Cancer Res. 2002, 62, 4916-4921.
6. B. Li, C. T. Walsh, Proc. Natl. Acad. Sci. USA 2010, 107, 19731-19735.
7. M. Schrettl, S. Carberry, K. Kavanagh, H. Haas, G. W. Jones, J. O'Brien, A. Nolan, J. Stephens, O. Fenelon, S. Doyle, PLoS Pathog. 2010, 6, e1000952.
8. P. Waring, A. Sjaarda, Q. H. Lin, Biochem. Pharmacol. 1995, 49, 1195-1201.
9. B. Li, C. T. Walsh, Biochemistry 2011, 50, 4615-4622.
10. A. de La Fuente, L. M. Lorenzana, J. F. Martin, P. Liras, J. Bacteriol. 2002, 184, 6559-6565.
11. W. D. Celmer, I. A. Solomons, J. Am. Chem. Soc. 1955, 77, 2861-2865.
12. K. Okamura, K. Soga, Y. Shimauchi, T. Ishikura, J. Lein, J. Antibiot. 1977, 30, 334-336.
13. R. A. Butcher, F. C. Schroeder, M. A. Fischbach, P. D. Straight, R. Kolter, C. T. Walsh, J. Clardy, Proc. Natl. Acad. Sci. USA 2007, 104, 1506-1509;
14. R. R. Forseth, E. M. Fox, D. Chung, B. J. Howlett, N. P. Keller, F. C. Schroeder, J. Am. Chem. Soc. 2011, 133, 9678-9681.
15. C. Pungaliya, J. Srinivasan, B. W. Fox, R. U. Malik, A. H. Ludewig, P. W. Sternberg, F. C. Schroeder, Proc. Natl. Acad. Sci. USA 2009, 106, 7708-7713.
16. J. Davies, Curr. Opin. Chem. Biol. 2011, 15, 5-10.
17. T. Hjelmgaard, M. Givskov, J. Nielsen, Org. Biomol. Chem. 2007, 5, 344-348.
18. J. E. Schachtner, J. Nienaber, H. D. Stachel, K. Waisser, Pharmazie 1999, 54, 335-340.
19. G. L. Newton, N. Buchmeier, R. C. Fahey, Microbiol. Mol. Biol. Rev. 2008, 72, 471-494.
20. G. W. Kirby, D. J. Robins, M. A. Sefton, R. R. Talekar, J. Chem. Soc. Perkin Trans. 1 1980, 1, 119-121.
21. X. Li, S. K. Kim, K. W. Nam, J. S. Kang, H. D. Choi, B. W. Son, J. Antibiot. 2006, 59, 248-250;
22. H. J. Lee, J. H. Lee, B. Y. Hwang, H. S. Kim, J. J. Lee, Arch. Pharmacal Res. 2001, 24, 397-401.
23. Y. Sun, K. Takada, Y. Takemoto, M. Yoshida, Y. Nogi, S. Okada, S. Matsunaga, J. Nat. Prod. 2012, 75, 111-114.