Aeruginosins, protease inhibitors from the cyanobacterium Microcystis aeruginosa

Tetrahedron

Volumn 55, Issue 36, 1999, Pages 10971-10988

  Ishida, Keishi ^a   Okita, Yuji ^a,b   Matsuda, Hisashi ^a   Okino, Tatsufumi ^a,c   Murakami, Masahiro ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b NIPPON SUISAN KAISHA LTD   (Japan)

^c UTSUNOMIYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AERUGINOSIN; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL; CYANOBACTERIUM; ENZYME INHIBITION; ENZYME ISOLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

MICROCYSTIS AERUGINOSA;

EID: 0033520230     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00621-3     Document Type: Article

References (31)

1. Present address: Central Research Laboratory, Nippon Suisan Kaisha, Ltd. 559-6 Kitano-Machi, Hachioji, 192-8557 Japan.
2. Present address: Department of Applied Biochemistry, Utsunomiya University, 350 Mine-Machi, Utsunomiya, 321-8538 Japan.
3. Namikoshi, M.; Rinehart, K. L. J. Indust. Microbiol. 1996, 17, 373-384.
4. Murakami, M.; Okita, Y.; Matsuda, H.; Okino, H.; Yamaguchi, K. Tetrahedron Lett. 1994, 35, 3129-3132.
5. Murakami, M.; Ishida, K.; Okino, T.; Okita, Y.; Matsuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 2785-2788.
6. Matsuda, H.; Okino, T.; Murakami, M.; Yamaguchi, K. Tetrahedron 1996, 52, 14501-14506.
7. Shin, H. J.; Matsuda, H.; Murakami, M.; Yamaguchi, K. J. Org. Chem. 1997, 62, 1810-1813.
8. Steiner, R. J. L.; Murakami, M.; Tulinsky, A. J. Am. Chem. Soc. 1998, 120, 597-598.
9. Sandler, B.; Murakami, M.; Clardy, J. J. Am. Chem. Soc. 1998, 120, 595-596.
10. Watanabe, M. M.; Hiroki, M. In Nies-collection List of Strains, 5th Ed., Microalgae and Protozoa Microbial Culture Collection; National Institute of Environmental Studies: Tsukuba, Japan, 1997; p79-80.
11. Tarbell, D. S.; Wilson, J. W.; Fanta, P. E. Org. Synth. 1955, 3, 267-270.
12. Nagai, Y.; Kusumi, T. Tetrahedron Lett. 1995, 36, 1853-1856.
13. NOESY correlations of the Choi sulfate moiety of aeruginosin 98-B were observed between H-2/H-3b, H-2/H-3′, H-3′/H-7′, H-3a/H-7a, H-3a/H-5a, H-7′H-7b and H-5a/H-7a.
14. Kosolapoff, G. M. J. Am. Chem. Soc. 1953, 75, 3596.
15. Schlegel, D. C.; Tipton, C. D.; Rinehart, Jr. K. L. J. Org. Chem. 1970, 35, 849.
16. NOESY correlations of the Choi sulfate moiety of aeruginosin 101 were observed between H-2/H-3b, H-2/H-3′, H-3′/H-7′, H-3a/H-7a, H-3a/H-5a, H-7′/H-7b and H-5a/H-7a.
17. NOESY correlations of the Choi moiety of aeruginosin 298-A were observed between H-2 (δ 4.16)/H-3b (δ 2.00), H-2/H-3′ (δ 2.27), H-3′/H-7′ (δ 4.04), H-3a (δ 1.80)/H-7a (δ 1.65), H-3a/H-5a (δ 1.43), H-7′/H-7b (δ 2.02) and H-5a/H-7a.
18. Hamada, Y.; Shioiri, T. Chem. Pharm. Bull. 1982, 30, 1921-1924.
19. NOESY correlations of the Choi moiety of aeruginosin 298-B (major component) were observed between H-2/H-3b, H-2/H-3′, H-3′/H-7′, H-3a/H-7a and H-7′/H-7b.
20. Aoyagi, T.; Takeuchi, T.; Matsuzaki, A.; Kawamura, K.; Kondo, S.; Hamada, M.; Maeda, K.; Umezawa, H. J. Antibiot. 1969, 22, 283-286.
21. NOESY correlations of the Choi moiety of aeruginosin 89-B were observed between H-2/H-3b, H-2/H-3′, H-3a/H-4a and H-3′/H-7′.
22. NOESY correlations of the Choi moiety of aeruginosin 89-A were observed between H-2/H-3b, H-2/H-3′, H-3a/H-7a, H-7′/H-7b and H-3′/H-7′.
23. Souchet, M.; Guilhem, J.; Goffic, F. L. Tetrahedron Lett. 1987, 28, 2371-2374.
24. Bonjoch, J.; Valls, N.; Catena, J.; Isábal, E. Eighth International Symposium on Marine Natural Products VIII (Spain), Symposium Proceedings, 1995, 119-120.
25. Kondo, S.; Kawamura, K.; Iwanaga, J.; Hamada, M.; Aoyagi, T.; Maeda, K.; Takeuchi, T.; Umezawa, H. Chem. Pharm. Bull. 1969, 17, 1896-1901.
26. Kawamura, K.; Kondo, S.; Maeda, K.; Umezawa, H. Chem. Pharm. Bull. 1969, 17, 1902-1909.
27. Maeda, K.; Kawamura, K.; Kondo, S.; Aoyagi, T.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1971, 24, 402-404.
28. Suda, H.; Aoyagi, T.; Hamada, M.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1972, 25, 263-266.
29. Aoyagi, T.; Miyata, S.; Nanbo, M.; Kojima, F.; Matsuzaki, M.; Ishizuka, M.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1969, 22, 558-568.
30. Kupchan, S. M.; Britton, R. W. Ziegler, M. F.; Siegel, C. W. J. Org. Chem. 1973, 38, 178-179.
31. Shin, H. J.; Murakami, M.; Matsuda, H.; Yamaguchi, K. Tetrahedron 1996, 52, 8159-8168.