Stereostructure of a novel cytotoxic 18-membered macrolactone antibiotic FD-891

Organic Letters

Volumn 4, Issue 20, 2002, Pages 3383-3386

  Eguchi, Tadashi ^a   Kobayashi, Kayako ^a   Uekusa, Hidehiro ^a   Ohashi, Yuji ^a   Mizoue, Kazutoshi ^b   Matsushima, Yoshitaka ^a   Kakinuma, Katsumi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b TAISHO PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; CONCANAMYCIN A; FD 891; MACROLIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; X RAY DIFFRACTION;

ANTI-BACTERIAL AGENTS; MACROLIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM; X-RAY DIFFRACTION;

EID: 0037015426     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026518k     Document Type: Article

References (27)

1. Seki-Asano, M.; Okazaki, T.; Yamagishi, M.; Sakai, N.; Hanada, K.; Mizoue, K. J. Antibiot. 1994, 47, 1226.
2. Seki-Asano, M.; Tsuchida, Y.; Hanada, K.; Mizoue, K. J. Antibiot. 1994, 47, 1234.
3. (a) Muroi, M.; Shiragami, N.; Nagao, K.; Yamasaki, M.; Takatsuki, A. Cell Struct. Funct. 1993, 18, 139.
4. (b) Drose, S.; Bindseil, K. U.; Bowman, E. J.; Siebers, A., Zeeck, A.; Altendorf, K. Biochemistry 1993, 32, 3902.
5. Kataoka, T.; Shinohara, N.; Takayama, H.; Takaku, K.; Kondo, S.; Yonehara, S.; Nagai, K. J. Immunol. 1996, 156, 3678.
6. Kataoka, T.; Yamada, A.; Bando, M.; Honma, T.; Mizoue, K. Nagai, K. Immunology 2000, 100, 170.
7. 3) δ 14.4, 32.8, 36.0, 36.4, 60.7, 62.7, 71.4, 128.4, 129.6, 133.0, 167.1.
8. (a) Arai, H.; Matsushima, Y.; Eguchi, T.; Shindo, K.; Kakinuma, K. Tetrahedron Lett. 1998, 39, 3181.
9. (b) Ireland, R. E.; Thaisrivongs, S.; Dussault, P. H. J. Am. Chem. Soc. 1988, 110, 5768.
10. 12 For each search, 20 000 starting structures were generated and minimized to an energy convergence of 0.05 (kJ/mol)/(Å/mol) using the full matrix Newton-Raphson method implemented in Macromodel. Duplicated structures and those greater than 50 kJ/mol above the global minimum were discarded.
11. (a) Halgren, T. A. J. Comput. Chem. 1996, 17, 490.
12. (b) Halgren, T. A. J. Comput. Chem. 1996, 17, 520.
13. (c) Halgren, T. A. J. Comput. Chem. 1996, 17, 553.
14. (d) Halgren, T. A. J. Comput. Chem. 1996, 17, 587.
15. Macromodel Version 6.5; Department of Chemistry, Columbia University: New York.
16. (a) Hasel, W.; Hendrickson, T. F.; Still, W. C. Tetrahedron Comput. Methodol. 1988, 1, 103.
17. (b) Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127.
18. (a) Chang, G.; Guida, W. C.; Still, W. C. J. Am. Chem. Soc. 1989, 111, 5239.
19. (b) Goodman, J. M.; Still, W. C. J. Comput. Chem. 1991, 12, 1110.
20. (c) Guida, W. C.; Bohacek, R. S.; Erion, M. D. J. Comput. Chem. 1992, 13, 214.
21. (d) Kolossvary, I.; Guida, W. C. J. Chem. Inf. Comput. Sci. 1992, 32, 191.
22. (e) Kolossvary, I.; Guida, W. C. J. Comput. Chem. 1993, 14, 691.
23. (f) Kolossvary, I.; Guida, W. C. J. Am. Chem. Soc. 1993, 115, 2107.
24. Haasnoot, C. A. G.; De Leeuw, F. A. M.; Altona, C. Tetrahedron 1980, 36, 2783.
25. Nakai, H.; Matsuhashi, S. Acta Crystallogr. 1992, C48, 1519.
26. (a) Droese, S.; Boddien, C.; Gassel, M.; Ingenhorst, G.; Zeeck, A.; Altendorf, K. Biochemistry 2001, 40, 2816.
27. (b) Woo, J. T.; Shinohara, C.; Sakai, K.; Hasumi, K.; Endo, A. J. Antibiot. 1992, 45, 1108.