Triple hydroxylation of tetracenomycin A2 to tetracenomycin C involving two molecules of o2 and one molecule of H2o

Organic Letters

Volumn 2, Issue 20, 2000, Pages 3225-3227

  Rafanan Jr , Elpidio R ^a   Hutchinson, C Richard ^b   Shen, Ben ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACYCLINE; ANTINEOPLASTIC ANTIBIOTIC; NAPHTHACENE DERIVATIVE; OXYGEN; OXYGENASE; TETRACENOMYCIN A2; TETRACENOMYCIN C; WATER;

ARTICLE; CATALYSIS; CHEMISTRY; FUNGAL GENE; GENETICS; HYDROXYLATION; STREPTOMYCES; SYNTHESIS;

ANTHRACYCLINES; ANTIBIOTICS, ANTINEOPLASTIC; CATALYSIS; GENES, FUNGAL; HYDROXYLATION; NAPHTHACENES; OXYGEN; OXYGENASES; STREPTOMYCES; WATER;

EID: 0034609696     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0002267     Document Type: Article

References (28)

1. (a) Weber, W.; Zahner, H.; Siebers, J.; Schröder, K.; Zeeck, A. Arch. Microbiol. 1979, 121, 111-116.
2. (b) Egert, E.; Noltemeyer, M.; Siebers, J.; Rohr, J.; Zeeck, A. J. Antibiot. 1992, 45, 1190-1192.
3. (a) Drautz, H.; Reuschenbach, P.; Zähner, H.; Rohr, J.; Zeeck, A. J. Antibiot. 1985, 38, 1291-1301.
4. (b) Fiedler, H.-P.; Rohr, J.; Zeeck, A. J. Antibiot. 1986, 39, 856-859.
5. Anderson, M. G.; Khoo, C. L.; Rickards, R. W. J. Antibiot. 1989, 42, 640-643.
6. Udvarnoki, G.; Wagner, C.; Machinek, R.; Rohr, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 565-567.
7. Shen, B.; Hutchinson, C. R. J. Biol. Chem. 1994, 269, 30726-30733.
8. Decker, H.; Motamedi, H.; Hutchinson, C. R. J. Bacteriol. 1993, 175, 3876-3886.
9. (a) Decker, H.; Rohr, J.; Motamedi, H.; Zahner, H.; Hutchinson, C. R. Gene 1995, 166, 121-126.
10. (b) Rafanan, E. R., Jr.; Le, L.; Zhao, L.; Decker, H.; Shen, B. Submitted.
11. (a) Nardini, M.; Ridder, I. S.; Rozeboom, H. J.; Kalk, K. H.; Rink, R.; Janssen, D. B.; Dijkstra, B. W. J. Biol. Chem. 1999, 274, 14579-14566.
12. (b) Argiriadi, M. A.; Morisseau, C.; Hammock, B. D.; Christianson, D. W. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 10637-10642.
13. (c) Leibman, K.; Ortiz, E. Mol. Pharmacol. 1968, 4, 201-207.
14. (d) van der Werf, M. J.; Overkamp, K. M.; de Bont, J. A. M. J. Bacteriol. 1998, 180, 5052-5057.
15. (a) Suzuki, Y.; Imai, K.; Marumo, S. J. Am. Chem. Soc. 1974, 96, 3703-3705.
16. (b) Kolattukudy, P. E.; Brown L. Arch. Biochem. Biophys. 1975, 166, 599-607.
17. (c) Silverman, R. B. J. Am. Chem. Soc. 1981, 103, 5939-5941.
18. (d) Preusch, P. C.; Suttie, J. W. J. Org. Chem. 1983, 48, 3301-3305.
19. (a) Gould, S. J.; Shen, B. J. Am Chem. Soc. 1991, 113, 684-686.
20. (b) Shen, B.; Gould, S. J. Biochemistry 1991, 30, 8936-8944.
21. (c) Gould, S. J.; Kirchmeier, M.; LaFever, R. E. J. Am. Chem. Soc. 1996, 118, 7663-7666.
22. (a) Omura, S.; Minami, S.; Tanaka, H. J. Biochem. 1981, 90, 291-293.
23. (b) Priest, J. W.; Light, R. J. Biochemistry 1989, 28, 9192-9200.
24. (a) Dowd, P.; Ham, S.-W.; Hershline, R. J. Am Chem. Soc. 1992, 114, 7613-7617.
25. (b) Kuliopulos, A.; Hubbard, B. R.; Lam, Z.; Koski, I. J.; Furie, B.; Furie, B. C.; Walsh, C. T. Biochemistry 1992, 31, 7722-7728.
26. (c) Zheng, Y.-J.; Bruice, T. C. J. Am. Chem. Soc. 1998, 120, 1623-1624.
27. (d) Dowd, P.; Hershline, R.; Ham, S. W.; Naganathan, S. Nat. Prod. Rep. 1994, 11, 252-264.
28. Beynon, J. D.; Rafanan, E. R., Jr.; Shen, B.; Fisher, A. J. Acta Crystallogr. D, in press.