Cloning, sequencing, heterologous expression, and mechanistic analysis of A-74528 biosynthesis

Journal of the American Chemical Society

Volumn 132, Issue 26, 2010, Pages 9122-9128

  Zaleta Rivera, Kathia ^a   Charkoudian, Louise K ^a   Ridley, Christian P ^a   Khosla, Chaitan ^a,b  

^a STANFORD UNIVERSITY   (United States)

^b Stanford University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AIRCRAFT ENGINES; ANTIBIOTICS; BIOCHEMISTRY; BIOSYNTHESIS; CLONING; PARTIAL DIFFERENTIAL EQUATIONS;

ANTI-VIRAL DRUGS; ANTITUMOR ANTIBIOTICS; BIOLOGICAL ACTIVITIES; FREDERICAMYCIN; FREDERICAMYCIN A; FUNCTIONAL EXPRESSION; GENE CLUSTERS; GENE DISRUPTIONS; HETEROLOGOUS EXPRESSION; MECHANISTIC ANALYSIS; MODE OF ACTION; NATURAL PRODUCTS; OPEN READING FRAME; PHOSPHODIESTERASES; POLYKETIDE SYNTHASES; QUALITATIVE DIFFERENCES; SEQUENCE IDENTITY; STREPTOMYCES GRISEUS; STREPTOMYCES SP; TYPE II; VIRAL REPLICATION;

GENE EXPRESSION;

A 74528; ANTIVIRUS AGENT; FREDERICAMYCIN A; POLYKETIDE SYNTHASE; UNCLASSIFIED DRUG; A-74528; BIOLOGICAL PRODUCT; ENZYME INHIBITOR; POLYCYCLIC HYDROCARBON; PYRONE DERIVATIVE;

ARTICLE; BIOSYNTHESIS; DRUG STRUCTURE; DRUG SYNTHESIS; GENE CLUSTER; GENE DISRUPTION; GENE SEQUENCE; HETEROLOGOUS EXPRESSION; HOST; MOLECULAR CLONING; MUTATIONAL ANALYSIS; NONHUMAN; OPEN READING FRAME; QUALITATIVE ANALYSIS; QUANTITATIVE ANALYSIS; STREPTOMYCES; STREPTOMYCES GRISEUS; CHEMISTRY; GENE DELETION; GENE EXPRESSION; GENETIC ENGINEERING; GENETICS; METABOLISM; STEREOISOMERISM;

BIOLOGICAL PRODUCTS; CLONING, MOLECULAR; ENZYME INHIBITORS; GENE DELETION; GENE EXPRESSION; GENETIC ENGINEERING; POLYCYCLIC COMPOUNDS; PYRONES; STEREOISOMERISM; STREPTOMYCES;

EID: 77954302507     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja102519v     Document Type: Article

References (31)

1. Fujita, Y., Kasuya, A., Matsushita, Y., Suga, M., Kizuka, M., Iijima, Y., and Ogita, T. Bioorg. Med. Chem. Lett. 2005, 15, 4317-21
2. Kubota, K., Nakahara, K., Ohtsuka, T., Yoshida, S., Kawaguchi, J., Fujita, Y., Ozeki, Y., Hara, A., Yoshimura, C., Furukawa, H., Haruyama, H., Ichikawa, K., Yamashita, M., Matsuoka, T., and Iijima, Y. J. Biol. Chem. 2004, 279, 37832-41
3. Player, M. R. and Torrence, P. F. Pharmacol. Ther. 1998, 78, 55-113
4. Schmidt, A., Zilberstein, A., Shulman, L., Federman, P., Berissi, H., and Revel, M. FEBS Lett. 1978, 95, 257-64
5. Johnston, M. I. and Hearl, W. G. J. Biol. Chem. 1987, 262, 8377-82
6. Silverman, R. H. Biochemistry 2003, 42, 1805-12
7. Chadha, K. C., Ambrus, J. L., Jr., Dembinski, W., and Ambrus, J. L., Sr. Exp. Biol. Med. (Maywood, NJ, U.S.) 2004, 229, 285-90
8. Walsh, C. T. Science 2004, 303, 1805-10
9. Khosla, C., Gokhale, R. S., Jacobsen, J. R., and Cane, D. E. Annu. Rev. Biochem. 1999, 68, 219-53
10. Staunton, J. and Weissman, K. J. Nat. Prod. Rep. 2001, 18, 380-416
11. Cane, D. E., Walsh, C. T., and Khosla, C. Science 1998, 282, 63-8
12. Hertweck, C., Luzhetskyy, A., Rebets, Y., and Bechthold, A. Nat. Prod. Rep. 2007, 24, 162-90
13. Marti, T., Hu, Z., Pohl, N. L., Shah, A. N., and Khosla, C. J. Biol. Chem. 2000, 275, 33443-8
14. Ziermann, R. and Betlach, M. C. BioTechniques 1999, 26, 106-10
15. Practical Streptomyces Genetics; Kieser, T., Bibb, M. J., Buttner, M. J., Chater, K. F., and Hopwood, D. A., Eds.; Crowes: Norwich, 2000.
16. Wendt-Pienkowski, E., Huang, Y., Zhang, J., Li, B., Jiang, H., Kwon, H., Hutchinson, C. R., and Shen, B. J. Am. Chem. Soc. 2005, 127, 16442-52
17. Marti, T., Hu, Z., Pohl, N. L., Shah, A. N., and Khosla, C. J. Biol. Chem. 2000, 275, 33443-8
18. Gust, B., Kieser, T., and Chater, K. F. (2002) REDIRECT Technology. PCR Targeting Systems in Streptomyces coelicolor. John Innes Centre, Norwich Research Park: Colney, Norwich NR4 7UH, U.K.
19. Moore, B. S. and Hertweck, C. Nat. Prod. Rep. 2002, 19, 70-99
20. Bililign, T., Hyun, C. G., Williams, J. S., Czisny, A. M., and Thorson, J. S. Chem. Biol. 2004, 11, 959-69
21. Xu, Z., Metsa-Ketela, M., and Hertweck, C. J. Biotechnol. 2009, 140, 107-13
22. Oja, T., Palmu, K., Lehmussola, H., Lepparanta, O., Hannikainen, K., Niemi, J., Mantsala, P., and Metsa-Ketela, M. Chem. Biol. 2008, 15, 1046-57
23. Huang, Y., Wendt-Pienkowski, E., and Shen, B. J. Biol. Chem. 2006, 281, 29660-8
24. Tang, Y., Koppisch, A. T., and Khosla, C. Biochemistry 2004, 43, 9546-55
25. Das, A., Szu, P.-H., Fitzgerald, J. T., and Khosla, C. J. Am. Chem. Soc. 2010, 132, ASAP (DOI: 10.1021/ja102517q).
26. Chen, Y., Wendt-Pienkoski, E., Rajski, S. R., and Shen, B. J. Biol. Chem. 2009, 284, 24735-43
27. Funa, N., Funabashi, M., Yoshimura, E., and Horinouchi, S. J. Biol. Chem. 2005, 280, 14514-23
28. McDaniel, R., Khosla, S. E., Hopwood, D. A., and Khosla, C. J. Am. Chem. Soc. 1994, 116, 10855-9
29. Fu, H., McDaniel, R., Hopwood, D. A., and Khosla, C. Biochemistry 1994, 33, 9321-6
30. Yu, T. W., Shen, Y., McDaniel, R., Floss, H. G., Khosla, C., Hopwood, D. A., and Moore, B. S. J. Am. Chem. Soc. 1998, 120, 7749-59
31. Shen, Y., Yoon, P., Yu, T. W., Floss, H. G., Hopwood, D., and Moore, B. S. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 3622-7