A new and unusual pathway for the reaction of neocarzinostatin chromophore with thiols. Revised structure of the protein-directed thiol adduct

Journal of the American Chemical Society

Volumn 118, Issue 19, 1996, Pages 4725-4726

  Myers, Andrew G ^a   Arvedson, Stephen P ^a   Lee, Robert W ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ZINOSTATIN CHROMOPHORE;

ARTICLE; DNA CLEAVAGE; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029898829     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960335+     Document Type: Article

References (24)

1. Isolation: (a) Shoji, J. J. Antibiot. 1961, 14, 27. (b) Ishida, N.; Miyazaki, K.; Kumagai, K.; Rikimaru. M J. Antibiot. 1965, 18, 68,
2. Isolation: (a) Shoji, J. J. Antibiot. 1961, 14, 27. (b) Ishida, N.; Miyazaki, K.; Kumagai, K.; Rikimaru. M J. Antibiot. 1965, 18, 68,
3. Characterization: (c) Napier, M A.: Holmquist, B.; Strydom, D. J.; Goldberg, I. H. Biochem. Biophys. Res. Commun. 1979, 89, 635. (d) Koide, Y.; Ishi, F.; Hasuda, K.; Koyama, Y.; Edo, K., Katamine, S.; Kitame. F.; Ishida. N J Antibiot. 1980, 33, 342.
4. Characterization: (c) Napier, M A.: Holmquist, B.; Strydom, D. J.; Goldberg, I. H. Biochem. Biophys. Res. Commun. 1979, 89, 635. (d) Koide, Y.; Ishi, F.; Hasuda, K.; Koyama, Y.; Edo, K., Katamine, S.; Kitame. F.; Ishida. N J Antibiot. 1980, 33, 342.
5. Chromophore structure: (e) Edo, K.; Mizugaki, M.; Koide, Y.; Seto, H.; Funhata, K.; Otake. N.; Ishida, N. Tetrahedron Lett. 1985, 26, 331.
6. Chromophore stereochemistry: (f) Myers, A G., Proteau, P. J.; Handel, T. M J. Am. Chem.Soc. 1988, 110, 7212.
7. X-ray crystal structure of holo-NCS: (g) Kim, K -H.; Kwon, B.-M., Myers, A G.; Rees, D. C. Science 1993, 262, 1042.
8. (2)(a) Poon, R.; Beerman, T. A.; Goldbera, I. H., Biochemistry 1977, 16, 486.
9. (b) Hatayama, T.; Goldberg, I. H., Takeshita, M.; Grollman, A. P. Proc. Natl. Acad. Sci. USA 1978, 75, 3603.
10. (c) D'Andrea, A. D : Haseltine, W A. Proc. Natl. Acad. Sci. USA 1978, 75, 3608.
11. Myers, A. G. Tetrahedron Lett 1987, 28, 4493
12. Myers, A. G.; Cohen, S. B.; Kwon, B-M J. Am. Chem Soc. 1994, 116 1670 and references therein.
13. (5)(a) Sugiyama, H.; Yamashita, K.; Nishi, M.; Saito, I. Tetrahedron Lett 1992, 33, 515.
14. (b) Sugiyama, H.; Yamashita. K.; Fujiwara, T : Saito, I. Tetrahedron 1994, 50, 1311.
15. o).
16. Chin, D.-H.: Goldberg, I. H. J. Am. Chem. Soc. 1993, 115, 9341.
17. (a) Padwa, A.; Au, A. J. Am. Chem. Soc. 1976, 98, 5581.
18. (b) Baer, H H.; Kienzle, F. J. Org. Chem. 1968, 33, 1823.
19. (c) Parisot, D; Devys, M., Barbier, M. J. Antibiot. 1989, 42, 1189.
20. Myers, A. G.; Dragovich, P. S : Kuo, E. Y. J. Am. Chem. Soc. 1992, 114, 9369 and references therein.
21. (a) Closs, G. L.; Kaplan, L. R : Bendall, V. I J. Am. Chem. Soc. 1967, 89, 3376.
22. (b) Wenthold, P. G., Wierschke, S. G.; Nash, J. J : Squires, R. R J Am. Chem. Soc. 1994, 116, 7378.
23. 9 Presumably, the alkoxy-substituted α.2-dehydrotoluene biradical of Scheme 3 can react in the same capacity.
24. Newton, G. L.: Fahey, R C. Glutathione In Prokaryotes In Glutathione. Metabolism and Physiological Functions: Vina. J. Ed.; CRC Press: Boca Raton, FL. 1990; pp 69-77.