Circinamide, a novel papain inhibitor from the cyanobacterium anabaena circinalis (NIES-41)

Tetrahedron

Volumn 53, Issue 16, 1997, Pages 5747-5754

  Shin, Hee Jae ^a   Matsuda, Hisashi ^a   Murakami, Masahiro ^a   Yamaguchi, Katsumi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; PAPAIN;

ARTICLE; CYANOBACTERIUM; DRUG ISOLATION; DRUG STRUCTURE; ENZYME INHIBITION; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY;

EID: 0030905389     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00285-8     Document Type: Article

References (33)

1. Bode, W.; Huber, R. Eur. J. Biochem. 1992, 204, 433-451.
2. Watanabe, M. M.; Kasai, F.; Hiwatari, T.; Suda, S.; Nei, T. Jpn. J. Freez. Dry. 1984, 30, 23-26.
3. (a) Shin, H. J.; Murakami, M.; Matsuda, H.; Ishida, K.; Yamaguchi, K.Tetrahedron Lett. 1995, 36, 5235-5238.
4. (b) Shin, H. J.; Murakami, M.; Matsuda, H.; Yamaguchi, K. Tetrahedron 1996, 52, 8159-8168.
5. (c) Shin, H. J.; Matsuda, H.; Murakami, M.; Yamaguchi, K. Tetrahedron 1996, 52, 13129-13136.
6. (d) Murakami, M.; Shin, H. J.; Matsuda, H.; Ishida, K.; Yamaguchi, K. Phytochemistry 1997, 44, 449-452.
7. (e) Shin, H. J.; Matsuda, H.; Murakami, M.; Yamaguchi, K. J. Nat. Prod. 1997, in press,
8. (f) Shin, H. J.; Matsuda, H.; Murakami, M.; Yamaguchi, K. J. Org. Chem. 1997, in press.
9. Bax, A.; Subramanian, S. J. J. Magn. Reson. 1986, 67, 565-569.
10. Bax, A.; Sommers, M. F. J. Am. Chem. Soc. 1986, 108, 2093-2094.
11. (a) Bothner-By, A. A.; Stephens, R. L.; Lee, J.; Warren, C. D.; Jeanloz, R. W. J. Am. Chem. Soc. 1984, 106, 811-813.
12. (b) Bax, A. J. Magn. Reson. 1985, 63, 207-213.
13. (a) Davis, D. G.; Bax, A. J. Am. Chem. Soc. 1985, 107, 2820-2821.
14. (b) Edwards, M. W.; Bax, A. J. Am. Chem. Soc. 1986, 108, 918.
15. (a) Kobayashi, H.; Sunaga, R.; Furihata, K.; Morisaki, N.; Iwasaki, S. J. Antibiot. 1995, 48, 42-52.
16. (b) Sugano, M.; Sato, A.; Iijima, Y.; Furuya, K.; Haruyama, H.; Yoda, K.; Hata, T. J. Org. Chem. 1994, 59, 564-569.
17. Kobayashi, J.; Ishibashi, M.; Nakamura, H.; Ohizumi, Y.; Yamasu, T.; Sasaki, T.; Hirata, Y. Tetrahedron Lett. 1986, 27, 5755-5758.
18. Marfey, P. Carlsberg Res. Commun. 1984, 49, 591-596.
19. (a) Aoyagi, T.; Takeuchi, A.; Matsuzaki, A.; Kawamura, K.; Kondo, S.; Hamada, M.; Maeda, K.; Umezawa, H. J. Antibiot. 1969, 22, 283-286.
20. Umezawa, H.; Aoyagi, T.; Morishima, H.; Kunimoto, S.; Matsuzaki, M.; Hamada, M. Takeuchi, T. J. Antibiot. 1970, 23, 425-427.
21. Suda, H.; Aoyagi, T.; Hamada, M.; Takeuchi, H.; Umezawa, H. J. Antibiot. 1972, 25, 263-265.
22. (a) Kashman, Y.; Hirsh, S.; McConnell, O. J.; Ohtani, I.; Kusumi, T.; Kakisawa, H. J. Am. Chem. Soc. 1989, 111, 8925-8926.
23. (b) Ohtani, I.; Kusumi, T.; Kakisawa, H.; Kashman, Y.; Hirsh, S. J. Am. Chem. Soc. 1992, 114, 8472-8479.
24. (c) Ohatani, I.; Kusumi, T.; Kakisawa, H. Tetrahedron Lett. 1992, 33, 2525-2528.
25. Jares-Erijman, E. A.; Sakai, R.; Rinehart, K. L. J. Org. Chem. 1991, 56, 5712-5715.
26. (a)Hamada, K.; Matsuzaki, S.; Niitsu, M.; Samejima, K. Can. J. Bot. 1994, 72, 1114-1120.
27. (b) Ramaswamy, S.; Murthy, M. R. N. Indian J. Biochem. Biophys. 1991, 28, 504-512.
28. (a) Hanada, K.; Tamai, M.; Yamagishi, M.; Ohmura, S.; Sawada, J.; Tanaka, I. Agric. Biol. Chem. 1978, 42, 523-528.
29. (b) Hanada, K.; Tamai, M.; Ohmura, S.; Sawada, J.; Seki, T.; Tanaka, I. Agric. Biol. Chem. 1978, 42, 529-536.
30. Waxman, L. In Methods and Enzymology; Lorand, L., Ed.; Academic Press: New York, 1981, Vol. 80, pp 664-680.
31. Hanada, K.; Tamai, M.; Adachi, T.; Oguma, K.; Kashiwagi, K.; Ohmura, S.; Kominami, E.; Towatari, T.; Katsunuma, N. Medicinal and Biological Aspects. In Proteinase Inhibitors; Katsunuma, N., Umezawa, H., Holzer, H., Eds.; Japan Sci. Soc. Press: Tokyo, 1983, pp 23-36.
32. Sugita, H. Medicina 1985, 22, 282-295.
33. Watanabe, M. M.; Satake, K. N. In NIES-collection. List of Strains; Watanabe, M. M., Nozaki, H., Eds.; Natl. Inst. Environ. Stud., Tsukuba, Japan, 1994, p 30.