Role of the [4.2.2] bicyclic unit in bicyclomycin: Synthesis, structure, chemical, biochemical, and biological properties

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7756-7763

  Santillán Jr , Alejandro ^a   Park, Hyeung Geun ^a   Zhang, Xiangdong ^a   Lee, Oh Seuk ^a   Widger, William R ^b   Kohn, Harold ^a  

^a University of Houston   (United States)

^b UNIVERSITY OF HOUSTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

10 METHYLBICYCLOMYCIN; ADENOSINE TRIPHOSPHATASE; ANTIBIOTIC AGENT; BICOZAMYCIN; BICOZAMYCIN DERIVATIVE; TRANSCRIPTION FACTOR; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; ESCHERICHIA COLI; MINIMUM INHIBITORY CONCENTRATION; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; TRANSCRIPTION TERMINATION;

EID: 16144365995     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961003q     Document Type: Article

References (26)

1. (a) Tokuma, Y.; Koda, S.; Miyoshi, T.; Morimoto, Y. Bull. Chem. Soc. Jpn. 1974, 47, 18-23.
2. (b) Kohn, H.; Abuzar, S.; Korp, J. D.; Zektzer, A. S.; Martin, G. E. J. Heterocycl. Chem. 1988, 25, 1511-1517.
3. (c) Zhang, Z.; Kohn, H. J. Am. Chem. Soc. 1994, 116, 9815-9826.
4. Müller, B. W., Zak, O.; Kump, W.; Tosch, W.; Wacker, O. J. Antibiot. 1979, 32, 689-705.
5. Kamiya, T.; Maeno, S.; Kitaura, Y. Belgium Patent 847 475.
6. Zhang, Z.; Kohn, H. J. Am. Chem. Soc. 1994, 116, 9815-9826.
7. Park, H. Ph.D. Thesis, University of Houston, 1995.
8. (a) Park. H.-g.; Vela, M. A.; Kohn, H. J. Am. Chem. Soc. 1994, 116, 471-478.
9. (b) Kohn, H.; Abuzar, S. J. Am. Chem. Soc. 1988, 110, 3661-3663.
10. Stothers, J. B. Carbon-13 NMR Spectroscopy; Academic Press: New York; 1972.
11. Someya, S.; Iseki, M.; Tanaka, N. J. Antibiot. 1979, 32, 402-407.
12. Williams, R. M.; Armstrong, R. W.; Dung, J.-S. J. Med. Chem. 1985, 28, 733-740.
13. Pisabarro, A. G.; Canada, F. J.; Vasquez, D.; Arriaga, P.; Rodriguez-Tebar, A. J. Antibiot. 1986, 34, 914-921.
14. Abuzar, S.; Kohn, H. J. Am. Chem. Soc. 1988, 110, 4089-4090.
15. Abuzar, S.; Kohn, H. J. Org. Chem. 1989, 54, 4000-4003.
16. Abuzar, S.; Kohn, H. J. Am. Chem. Soc. 1989, 111, 4895-4903.
17. Abuzar, S.; Kohn, H. J. Am. Chem. Soc. 1990, 112, 3114-3121.
18. Maag, H.; Blount, J. F.; Coffen, D. L.; Steppe, T. V.; Wong, F. J. Am. Chem. Soc. 1978, 100, 6786-6788.
19. Kohn, H.; Abuzar, S. J. Org. Chem. 1988, 53, 2769-2773.
20. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper & Row: New York, 1987; pp 297-298.
21. Sharp, J. A.; Galloway, J. L.; Platt, T. J. Biol. Chem. 1983, 258, 3482-3486.
22. Park, H.-g.; Zhang, X.; Moon, H.-s.; Zwiefka, A.; Cox, K.; Gaskell, S. J.; Widger, W. R.; Kohn, H. Arch. Biochem. Biophys. 1995, 323, 447-454.
23. Wu, A. M.; Christie, G. E.; Platt, T. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 2913-2917.
24. Magyar, A.; Zhang, X.; Kohn, H.; Widger, W. R. J. Biol. Chem. 1996, 271, 25369-25374.
25. Park, H.-g.; Zhang, X.; Widger, W. R.; Kohn, H. J. Org. Chem. 1996, 61, 7750.
26. Ericsson, H. M.; Sherris, J. C. Acta Pathol. Microbiol. Scand. 1971, Suppl. 217, 1-90.