Functional characterization of tlmK unveiling unstable carbinolamide intermediates in the tallysomycin biosynthetic pathway

Journal of Biological Chemistry

Volumn 284, Issue 13, 2009, Pages 8256-8264

  Wang, Liyan ^a   Tao, Meifeng ^a   Wendt Pienkoski, Evelyn ^a   Galm, Ute ^a   Coughlin, Jane M ^a   Shen, Ben ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOINFORMATICS ANALYSIS; BIOSYNTHETIC GENE CLUSTER; BIOSYNTHETIC PATHWAY; BLEOMYCIN; BLEOMYCINS; EXPERIMENTAL EVIDENCE; FUNCTIONAL CHARACTERIZATION; GLYCOSYL TRANSFERASE; HYDROXYL GROUPS; OXIDATIVE FRAGMENTATION; SUGAR MOIETY;

ALDEHYDES; AMIDES; AMINES; BIOCHEMICAL ENGINEERING; BIOCHEMISTRY; BIOINFORMATICS; BIOMOLECULES; BIOSYNTHESIS; CARBOXYLIC ACIDS; METABOLISM; METABOLITES; ORGANIC ACIDS; SUGAR (SUCROSE);

SUGARS;

BACTERIAL PROTEIN; PROTEIN TLMK1; PROTEIN TLMK2; PROTEIN TLMK3; PROTEIN TLMK4; PROTEIN TLMK5; TALLYSOMYCIN A; TALLYSOMYCIN B; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GENE; BACTERIUM MUTANT; CONTROLLED STUDY; DRUG SYNTHESIS; GENE INACTIVATION; HYDROLYSIS; NONHUMAN; OXIDATION; PRIORITY JOURNAL; STREPTOALLOTEICHUS HINDUSTANUS; STREPTOMYCETACEAE;

ACTINOMYCETALES; ANTIBIOTICS, ANTINEOPLASTIC; BACTERIAL PROTEINS; BLEOMYCIN; GENE DELETION; GENES, BACTERIAL; GLUCOSYLTRANSFERASES; MULTIGENE FAMILY;

STREPTOALLOTEICHUS HINDUSTANUS;

EID: 67649745810     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M900640200     Document Type: Article

References (39)

1. Kawaguchi, H., Tsukiura, H., Tomita, K., Konishi, M., and Saito, K. (1977) J. Antibiot. (Tokyo) 30, 779-788
2. Konishi, M. S. K., Numata, K., Tsuno, T., and Asama, K. (1977) J. Antibiot. (Tokyo) 30, 789-805
3. Chen, J., and Stubbe, J. (2005) Nat. Rev. Cancer 5, 102-112
4. Hecht, S. M. (2000) J. Nat. Prod. 63, 158-168
5. Boger, D. L., and Cai, H. (1999) Angew. Chem. Int. Ed. 38, 448-476
6. Leitheiser, C. J., Smith, K. L., Rishel, M. J., Hashimoto, S., Konishi, K., Thomas, C. J., Li, C., McCormick, M. M., and Hecht, S. M. (2003) J. Am. Chem. Soc. 125, 8218-8227
7. Shen, B., Du, L., Sanchez, C., Edwards, D. J., Chen, M., and Murrell, J. M. (2002) J. Nat. Prod. 65, 422-431
8. Tao, M., Wang, L., Wendt-Pienkowski, E., George, N. P., Galm, U., Zhang, G., Coughlin, J. M., and Shen, B. (2007) Mol. Biosyst.. 3, 60-74
9. Galm, U., Wendt-Pienkowski, E., Wang, L., Geor-ge, N., Oh, J., Yi, F., Tao, M., Coughlin, J., and Shen, B. (2009) Mol. Biosyst. 5, 77-90
10. Nicaise, C., Ajani, J., Goudeau, P., Rozencweig, M., Levin, B., and Krakoff, I. (1990) Cancer Chemother. Pharmacol. 26, 221-222
11. Nicaise, C., Hong, W. K., Dimery, W., Usakewicz, J., Rozencweig, M., and Krakoff, I. (1990) Investig. New Drugs 8, 325-328
12. MacNeil, J., Gewain, M., Ruby, L., Dezeny, G., Gibbons, H., and MacNeil, T. (1992) Gene (Amst.) 111, 61-68
13. Sambrook, J., and Russell, W. (2001) Molecular Cloning: A Laboratory Manual, 3rd Ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York
14. Gust, B., Challis, L., Fowler, K., Kieser, T., and Chater, F. (2003) Proc. Natl. Acad. Sci. U. S. A. 100, 1541-1546
15. Kieser, T., Bibb, J., Buttner, J., Chater, F., and Hopwood, A. (2000) Practical Streptomyces Genetics, 2nd Ed., John Innes Foundation, Norwich, UK
16. Bibb, M., White, J., Ward, J., and Janssen, J. (1994) Mol. Microbiol. 14, 533-545
17. Greenaway, F. T., Dabrowiak, J. C., Grulich, R., and Crooke, S. T. (1980) Org. Magnet. Res. 13, 270-273
18. Calafat, A., Won, H., and Marzilli, L. (1997) J. Am. Chem. Soc. 119, 3656-3664
19. Miyaki, T., Numata, K., Matsumoto, K., Yamamoto, H., Nishiyama, Y., Ohbayashi, M., Imanishi, H., Konishi, M., and Kawaguchi, H. (1981) J. Antibiot. (Tokyo) 34, 658-664
20. Fujii, A., Takita, T., Shimada, N., and Umezawa, H. (1974) J. Antibiot. (Tokyo) 27, 73-77
21. Oka, S. (1980) Recent Res. Cancer Res. 74, 163-171
22. Mansouri, K., and Piepersberg, W. (1991) Mol. Gen. Genet. 228, 459-469
23. Debono, M., Turner, W. W., LaGrandeur, L., Burkhardt, F. J., Nissen, J. S., Nichols, K. K., Rodriguez, M. J., Zweifel, M. J., Zeckner, D. J., and Gordee, R. S. (1995) J. Med. Chem. 38, 3271-3281
24. Tawara, S., Ikeda, F., Maki, K., Morishita, Y., Otomo, K., Teratani, N., Goto, T., Tomishima, M., Ohki, H., Yamada, A., Kawabata, K., Takasugi, H., Sakane, K., Tanaka, H., Matsumoto, F., and Kuwahara, S. (2000) Antimicrob. Agents Chemother. 44, 57-62
25. Umezawa, H., Kondo, S., Iinuma, H., Kunimoto, S., Ikeda, Y., Iwasawa, H., Ikeda, D., and Takeuchi, T. (1981) J. Antibiot. (Tokyo) 34, 1622-1624
26. Smith, A., Safnov, I., and Corbett, R. (2002) J. Am. Chem. Soc. 124, 11102-11113
27. Kamiya, T., Maeno, S., Hashimoto, M., and Mine, Y. (1972) J. Antibiot. (Tokyo) 25, 576-581
28. Miyoshi, T., Miyairi, N., Aoki, H., Kosaka, M., and Sakai, H. (1972) J. Antibiot. (Tokyo) 25, 569-575
29. Miyamura, S., Ogasawara, N., Otsuka, H., Niwayama, S., and Tanaka, H. (1973) J. Antibiot. (Tokyo) 26, 479-484
30. Kakeya, H., Takahashi, I., Okada, G., Isono, K., and Osada, H. (1995) J. Antibiot. (Tokyo) 48, 733-735
31. Singh, S., Goetz, M., Jones, E., Bills, G., Giacobbe, R., Herranz, L., Miles, S., and Williams, D. (1995) J. Org. Chem. 60, 7040-7042
32. James, D., Martin, S., David, K., Timothy, H., and Irving, W. (2005) J. Clin. Pharmacol. 45, 227-233
33. Dowell, J., Pu, F., LEE, J., Stogniew, M., Krause, D., and Henkel, T. (2003) Interscience Conference of Antimicrobiology Agents and Chemotherapy, Chicago, September 14, 2003, Abstr. A-1576, American Society for Microbiology
34. Troast, D., and Porco, J. (2002) Org. Lett. 4, 991-994
35. Goodwin, K., Lewis, M., Long, C., and Georgiadis, M. (2008) Proc. Natl. Acad. Sci. U. S. A. 105, 5052-5056
36. Boger, D. L., Teramoto, S., Honda, T., and Zhou, J. (1995) J. Am. Chem. Soc. 117, 7338-7343
37. Shipley, B., and Hecht, M. (1998) Chem. Res. Toxicol. 1, 25-27
38. Zuber, G., Quada, J., and Hecht, M. (1998) J. Am. Chem. Soc. 120, 9368-9369
39. Biggins, J. B., Prudent, J. R., Marshall, D. J., Ruppen, M., and Thorson, J. S. (2000) Proc. Natl. Acad. Sci. U. S. A. 97, 13537-13542