Absolute structure of prunustatin A, a novel GRP78 molecular chaperone down-regulator

Organic Letters

Volumn 9, Issue 21, 2007, Pages 4239-4242

  Umeda, Yukiko ^a   Furihata, Kazuo ^a   Sakuda, Shohei ^a   Nagasawa, Hiromichi ^a   Ishigami, Ken ^a   Watanabe, Hidenori ^a   Izumikawa, Miho ^c   Takagi, Motoki ^c   Doi, Takayuki ^b   Nakao, Yoichi ^d   Shin ya, Kazuo ^c  

^a UNIVERSITY OF TOKYO   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^c NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^d WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHAPERONE; CYCLOPEPTIDE; GLUCOSE; HEAT SHOCK PROTEIN; MACROLIDE; MOLECULAR CHAPERONE GRP78; NEOANTIMYCIN; ORGANIC COMPOUND; PRUNUSTATIN A; SW 163A; SW-163A; UNCLASSIFIED DRUG;

ARTICLE; CELL CULTURE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; HUMAN; METABOLISM; STEREOISOMERISM; STREPTOMYCES;

GLUCOSE; HEAT-SHOCK PROTEINS; HUMANS; MACROLIDES; MOLECULAR CHAPERONES; MOLECULAR STRUCTURE; ORGANIC CHEMICALS; PEPTIDES, CYCLIC; STEREOISOMERISM; STREPTOMYCES; TUMOR CELLS, CULTURED;

EID: 35548994250     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7017856     Document Type: Article

References (23)

1. Kaufman, R. J. Genes Dev. 1999, 13, 1211-1233.
2. Katschinski, D. M.; Jacobson, E. L.; Wiedmann, G. J.; Robins, H. I. J. Cancer Res. Clin. Oncol. 2001, 127, 425-435.
3. Umeda, Y.; Chijiwa, S.; Furihata, K.; Furihata, K.; Sakuda, S.; Nagasawa, H.; Watanabe, H.; Shin-ya. K. J. Antibiot. 2005, 58, 206-209.
4. Cagliote, L.; Misiti, D.; Selva, A.; Arcamone, F.; Cassinelli, G. Tetrahedron 1969, 25, 2193-2221.
5. Hayashi, K.; Nozaki, H. J. Antibiot. 1999, 52, 325-328.
6. Choo, S.-J.; Park, H.-R.; Ryoo, I.-J.; Kim, J.-P.; Yun, B.-S.; Kim, C.-J.; Shin-ya, K.; Yoo, I.-D. J. Antibiot. 2005, 58, 210-213.
7. Park, H.-R.; Ryoo, I.-J.; Choo, S.-J.; Hwang, J.-H.; Kim, J.-Y.; Cha, M.-R.; Shin-ya, K.; Yoo, I.-D. Toxicology 2007, 229, 253-261.
8. Park, H.-R.; Furihata, K.; Hayakawa, Y.; Shin-ya, K. Tetrahedron Lett. 2002, 43, 6941-6945.
9. Park, H.-R.; Tomida, A.; Sato, S.; Tsukumo, Y.; Yun, J.; Yamori, T.; Hayakawa, Y.; Tsuruo, T.; Shin-ya, K. J. Natl. Cancer Inst. 2004, 96, 1300-1310.
10. Park, H.-R.; Chijiwa, S.; Furihata, K.; Hayakawa, Y.; Shin-ya, K. Org. Lett. 2007, 9, 1457-1460.
11. Izumikawa, M.; Ueda, J.; Chijiwa, S.; Takagi, M.; Shin-ya, K. J. Antibiot. In press.
12. Kobayashi, H.; Shin-ya, K.; Furihata, K.; Hayakawa, Y.; Seto, H. Tetrahedron Lett. 2001, 42, 4021-4032.
13. Hayakawa, Y.; Kim, J. W.; Adachi, H.; Shin-ya, K.; Fujita, K.; Seto, H. J. Am. Chem. Soc. 1998, 120, 3524-3525.
14. Takahashi, K.; Tsuda, E.; Kurosawa, K. J. Antibiot. 2001, 54, 867-873.
15. Benedetti, E.; Ganis, P.; Bombieri, G.; Caglioti, L.; Germain, G. Acta. Crystallogr. 1975, B31, 1097-1100.
16. Adamson, J. G.; Hoang, T.; Grivici, A.; Lajoie, G. A. Anal. Biochem. 1992, 202, 210-214.
17. Matsunaga, S.; Liu, P. C.; Celatka, A.; Panek, J. S.; Fusetani, N. J. Am. Chem. Soc. 1999, 121, 5605-5606.
18. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
19. Murata, M.; Matsuoka, S.; Matsumori, N.; Paul, G. K.; Tachibana, K. J. Am. Chem. Soc. 1999, 121, 870-871.
20. Murai, A.; Amino, Y.; Ando, T. J. Antibiot. 1985, 38, 1610-1612.
21. Shin, I.; Lee, M.-R.; Lee, J.; Jung, M.; Lee, W.; Jongbok Yoon, J. J. Org. Chem. 2000, 65, 7667-7675.
22. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
23. Takeda, Y.; Masuda, T.; Matsumoto, T.; Takechi, Y.; Shingu, T.; Flos, H. G. J. Nat. Prod. 1998, 61, 978-981.