Structure and absolute stereochemistry of 21-hydroxyoligomycin A

Journal of Natural Products

Volumn 70, Issue 3, 2007, Pages 367-371

  Wagenaar, Melissa M ^a   Williamson, R Thomas ^a,c   Ho, Douglas M ^b   Carter, Guy T ^a  

^a WYETH RESEARCH   (United States)

^b PRINCETON UNIVERSITY   (United States)

^c Roche Carolina   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

21 HYDROXYOLIGOMYCIN A; ANTIPARASITIC AGENT; LL F28249OMEGA; OLIGOMYCIN; PROBIOTIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DRUG ISOLATION; DRUG STRUCTURE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STREPTOMYCES; STREPTOMYCES CYANEOGRISEUS; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

CRYSTALLOGRAPHY, X-RAY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OLIGOMYCINS; STEREOISOMERISM; STREPTOMYCES;

STREPTOMYCES CYANEOGRISEUS;

EID: 34247140170     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np060519u     Document Type: Article

References (30)

1. Smith, R. M.; Peterson, W. H.; McCoy, E. Antibiot. Chemother. 1954, 4, 962-970.
2. Yamazaki, M.; Yamashita, T.; Harada, T.; Nishikiori, T.; Saito, S.; Shimada, N.; Fujii, A. J. Antibiot. 1992, 45, 171-179.
3. Masamune, S.; Sehgal, J. M.; van Tamelen, E. E.; Strong, F. M.; Peterson, W. H. J. Am. Chem. Soc. 1958, 80, 6092-6095.
4. Enomoto, Y.; Shiomi, K.; Matsumoto, A.; Takahashi, Y.; Iwai, Y.; Harder, A.; Kölbl, H.; Woodruff, H. B.; Omura, S. J. Antibiot. 2001, 54, 308-313.
5. (a) Laatsch, H.; Kellner, M.; Wolf, G.; Lee, Y.; Hansske, F.; Konetschny-Rapp, S.; Pessara, U.; Scheuer, W.; Stockinger, H. J. Antibiot. 1993, 46, 1334-1341.
6. (b) Kim, H. S.; Han, S. B.; Kim, H. M.; Kim, Y. H.; Lee, J. J. J. Antibiot. 1996, 49, 1275-1277.
7. Kobayashi, K.; Nishino, C.; Ohya, J.; Sato, S.; Mikawa, T.; Shiobara, Y.; Kodama, M.; Nishimoto, N. J. Antibiot. 1987, 40, 1053-1057.
8. (a) Lardy, H. A.; Johnson, D.; McMurray, W. C. Arch. Biochem. Biophys. 1958, 78, 587-597.
9. (b) Lardy, H. A.; Witoncky, P.; Johnson, D. Biochemistry 1965, 4, 552-554.
10. (c) Tzagoloff, A.; Meagher, P. J. Biol. Chem. 1972, 274, 594-603.
11. Li, Y. C.; Fung, K. P.; Kwok, T. T.; Lee, C. Y.; Suen, Y. K.; Kong, S. K. Chemotherapy 2004, 50, 55-62.
12. Kihara, T.; Kusakabe, H.; Nakamura, G.; Sakurai, T.; Isono, K. J. Antibiot. 1981, 34, 1073-1074.
13. Thompson, R. Q.; Hoehn, M. M.; Higgens, C. E. Antimicrob. Agents Chemother. 1961, 474-480.
14. Kirst, H. A.; Larsen, S. H.; Paschal, J. W.; Occolowitz, J. L.; Creemer, L. C.; Steiner, J. L.; Lobkovsky, E.; Clardy, J. J. Antibiot. 1995, 48, 990-996.
15. Nakagawa, A.; Miura, S.; Imai, H.; Imamura, N.; Ōmura, S. J. Antibiot. 1989, 42, 919-925.
16. Hirota, A.; Okada, H.; Kanza, T.; Nakayma, M.; Hirota, H.; Isogai, A. Agric. Biol. Chem. 1989, 53, 2831-2833.
17. Hochlowski, J. E.; Mullally, M. M.; Brill, G. M.; Whittern, D. N.; Buko, A. M.; Hill, P.; McAlpine, J. B. J. Antibiot. 1991, 44, 1318-1330.
18. Kihara, T.; Isono, K. J. Antibiot. 1983, 36, 1236.
19. Evans, D. A.; Rieger, D. L.; Jones, T. K.; Kaldor, S. W. J. Org. Chem. 1990, 55, 6260-6268.
20. Nakata, M.; Ishiyama, T.; Hirose, Y.; Maruoka, H.; Tatsuta, K. Tetrahedron Lett. 1993, 34, 8439-8442.
21. Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001-7031.
22. Panek, J. S.; Jain, N. F. J. Org. Chem. 2001, 66, 2747-2756.
23. Matsumori, N.; Kaneno, D.; Murata, M.; Nakamura, H.; Tachibana, K. J. Org. Chem. 1999, 64, 866-876.
24. Carter, G. T. J. Org. Chem. 1986, 51, 4264-4271.
25. Bu'Lock, J. D.; Morris, G. A.; Richards, M. K. Tetrahedron Lett. 1986, 27, 2917-2920.
26. Iitaka, Y.; Yamazaki, M.; Yamashita, T.; Harada, T.; Nishikiori, T.; Saito, S.; Shimada, N.; Fujii, A.; Takita, T. Anal. Sci. 1991, 7, 983-985.
27. Arnoux, B.; Garcia-Alvarez, M. C.; Marazano, C.; Das, B. C.; Pascard, C.; Merienne, C.; Staron, T. J. Chem. Soc., Chem. Commun. 1978, 318-319.
28. Von Glehn, M.; Norrestam, R.; Kierkegaard, P.; Maron, L.; Ernster, L. FEBS Lett. 1972, 20, 267-269.
29. Carter, G. T.; Torrey, M. J.; Greenstein, M. U.S. Patent, 5, 169,956, 1992.
30. Crystallographic data for the 21-hydroxyoligomycin A bis(chloroform) tris(methanol) solvate reported in this paper have been deposited with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained, free of charge, on application to the Director, CCDC, 12 Union Road, Cambridge CB2 1 EZ, UK (fax: +44-(0)1223-33603.3 or e-mail: deposit@ccdc.cam.ac.uk).