Functional characterization of TtnD and TtnF, unveiling new insights into tautomycetin biosynthesis

Journal of the American Chemical Society

Volumn 132, Issue 19, 2010, Pages 6663-6671

  Luo, Yinggang ^a,c   Li, Wenli ^a   Ju, Jianhua ^a   Yuan, Qiuping ^b   Peters, Noel R ^b   Hoffmann, F Michael ^b   Huang, Sheng Xiong ^a   Bugni, Tim S ^a   Rajski, Scott ^a   Osada, Hiroyuki ^d   Shen, Ben ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b UNIVERSITY OF WISCONSIN   (United States)

^c CHENGDU INSTITUTE OF BIOLOGY   (China)

^d RIKEN   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHETIC GENE CLUSTER; DECARBOXYLASES; FUNCTIONAL CHARACTERIZATION; INHIBITION ASSAYS; MUTANT STRAIN; POLYKETIDE SYNTHASES; PROTEIN PHOSPHATASE; STRUCTURAL DETERMINANTS;

BIOCHEMISTRY; CARBOXYLATION; CARBOXYLIC ACIDS; FUNCTIONAL GROUPS; KETONES; ORGANIC ACIDS;

BIOSYNTHESIS;

CARBOXYLYASE; HYDROLYASE; PHOSPHOPROTEIN PHOSPHATASE INHIBITOR; TAUTOMYCETIN;

ARTICLE; BACTERIAL GENE; BIOSYNTHESIS; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG CYTOTOXICITY; ENZYME INHIBITION; ESCHERICHIA COLI; GENE CLUSTER; GENE INACTIVATION; GENE MUTATION; HUMAN; HUMAN CELL; INFRARED SPECTROSCOPY; MUTANT; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STREPTOMYCES; STREPTOMYCES GRISEOCHROMOGENES; TTND GENE; TTNF GENE;

ALKENES; ANTINEOPLASTIC AGENTS; BACTERIAL PROTEINS; CARBOXY-LYASES; CELL LINE, TUMOR; ENZYME INHIBITORS; FURANS; GENE SILENCING; HUMANS; HYDRO-LYASES; INHIBITORY CONCENTRATION 50; LIPIDS; MULTIGENE FAMILY; MUTATION; PHOSPHOPROTEIN PHOSPHATASES; STREPTOMYCES;

EID: 77952383172     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja9082446     Document Type: Article

References (33)

1. Cheng, X. C., Kihara, T., Ying, X., Uramoto, M., Osada, H., Kusakabe, H., Wang, B. N., Kobayashi, Y., Ko, K., Yamaguchi, I., Shen, Y. C., and Isono, K. J. Antibiot. 1989, 42, 141-144
2. Cheng, X. C., Kihara, T., Kusakabe, H., Magae, J., Kobayashi, Y., Fang, R. P., Ni, Z. F., Shen, Y. C., Ko, K., Yamaguchi, I., and Isono, K. J. Antibiot. 1987, 40, 907-909
3. Mitsuhashi, S., Matsuura, N., Ubukata, M., Oikawa, H., Shima, H., and Kikuchi, K. Biochem. Biophys. Res. Commun. 2001, 287, 328-331
4. Shim, J. H., Lee, H. K., Chang, E. J., Chae, W. J., Han, J. H., Han, D. J., Morio, T., Yang, J. J., Bothwell, A., and Lee, S. K. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 10617-10622
5. Bialojan, C. and Takai, A. Biochem. J. 1988, 256, 283-290
6. Lee, J. H., Lee, J. S., Kim, S. E., Moon, B. S., Kim, Y. C., Lee, S. K., Lee, S. K., and Choi, K. Y. Mol. Cancer Ther. 2006, 5, 3222-3231
7. Li, W., Luo, Y., Ju, J., Rajski, S. R., Osada, H., and Shen, B. J. Nat. Prod. 2009, 72, 450-459
8. Li, W., Ju, J., Rajski, S. R., Osada, H., and Shen, B. J. Biol. Chem. 2008, 283, 28607-28617
9. Oikawa, H. Curr. Med. Chem. 2002, 9, 2033-2054
10. Nishiyama, U., Ubukata, M., Magae, J., Kataoka, T., Erdoedi, F., Hartshorne, D. J., Isono, K., Nagai, K., and Osada, H. Biosci. Biotechnol. Biochem. 1996, 60, 103-107
11. Sheppeck, J. E., II, Liu, W., and Chamberlin, A. R. J. Org. Chem. 1997, 62, 387-398
12. Takai, A., Tsuboi, K., Koyasu, M., and Isobe, M. Biochem. J. 2000, 350, 81-88
13. Kelker, M. S., Page, R., and Peti, W. J. Mol. Biol. 2009, 385, 11-21
14. Cheng, X. C., Ubukata, M., and Isono, K. J. Antibiot. 1990, 43, 890-896
15. Cheng, X. C., Ubukata, M., and Isono, K. J. Antibiot. 1990, 43, 809-819
16. Keatinge-Clay, A. T. Chem. Biol. 2007, 14, 898-908
17. Dale, J. A. H. and Mosher, S. J. Am. Chem. Soc. 1973, 95, 512-519
18. Ohtani, I., Kusumi, T., Kashman, Y., and Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096
19. Uhrín, D., Batta, G., Hruby, V. J., Barlow, P. N., and Kövér, K. E. J. Magn. Reson. 1998, 130, 155
20. Williamson, R. T., Márquez, B. L., Gerwick, W. H., and Kövér, K. E. Magn. Reson. Chem. 2000, 38, 265
21. Ju, J., Li, W., Yuan, Q., Peters, N. R., Hoffmann, F. M., Rajski, S. R., Osada, H., and Shen, B. Org. Lett. 2009, 11, 1639-1642
22. Chang, Z. X., Sitachitta, N., Rossi, J. V., Roberts, M. A., Flatt, P. M., Jia, J. Y., Sherman, D. H., and Gerwick, W. H. J. Nat. Prod. 2004, 67, 1356-1367
23. Gu, L., Wang, B., Kulkarni, A., Gehret, J. J., Lloyd, K. R., Gerwick, L., Gerwick, W. H., Wipf, P., Hakansson, K., Smith, J. L., and Sherman, D. H. J. Am. Chem. Soc. 2009, 131, 16033-16035
24. Zhang, J., Van Lanen, S. G., Ju, J., Liu, W., Dorrestein, P. C., Li, W., Kelleher, N. L., and Shen, B. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 1460-1465
25. Liu, W., Sheppeck, J. E., II, Colby, D. A., Huang, H.-B., Nairin, A. C., and Chamberlin, A. R. Bioorg. Med. Chem. Lett. 2003, 13, 1597-1600
26. Oikawa, H., Yoneta, Y., Ueno, T., Oikawa, M., Wakayama, T., Ichihara, A., Kawamura, T., Matsuzawa, S.-I., and Kikuchi, K. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 1997, 39, 433-438
27. Isobe, M. Yuki, Gosei Kagaku Kyokaishi 1997, 55, 60-71
28. Oikawa, H., Oikawa, M., Ichihara, A., Ubukata, M., and Isono, K. Biosci. Biotechnol. Biochem. 1994, 58, 1933-1935
29. Sambrook, J. E., Fritsch, E. F., and Maniatis, T. Molecular cloning: a Laboratory Manual, 3rd Ed.; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, 2000.
30. Paget, M. S., Chamberlin, L., Atrih, A., Foster, S. J., and Buttner, M. J. J. Bacteriol. 1999, 181, 204-211
31. Gust, B., Challis, G. L., Fowler, K., Kieser, T., and Chater, K. F. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 1541-1546
32. Kieser, T., Bibb, M. J., Buttner, M. J., Chater, K. F., and Hopwood, D. A. Practical Streptomyces Genetics; John Innes Foundation: Norwich, UK, 2000.
33. Liu, W. and Shen, B. Antimicrob. Agents Chemother. 2000, 44, 382-392