Synthetic replacement of the methylamino group of neocarzinostatin chromophore with hydroxyl prohibits thiol activation in organic solvents and diminishes the rate and efficiency of thiol-promoted DNA cleavage in water

Tetrahedron Letters

Volumn 40, Issue 28, 1999, Pages 5129-5133

  Myers, Andrew G ^a,b   Liang, Jun ^a   Hammond, Marlys ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^b HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; DNA; HYDROXYL GROUP; METHYLAMINE; ORGANIC SOLVENT; THIOL; WATER; ZINOSTATIN CHROMOPHORE;

AQUEOUS SOLUTION; ARTICLE; DNA CLEAVAGE; DRUG SYNTHESIS;

EID: 0033538608     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00880-1     Document Type: Article

References (27)

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4. (d) Koide, Y; Ishii, F.; Hasuda, K.; Koyama, Y; Edo, K.; Katamine, F; Ishida, N. J. Antibiot. 1980, 33, 342.
5. Chromophore structure: (a) Edo, K.; Mizugaki, M.; Koide, Y; Seto, H.; Furihata, K.; Otake, N.; Ishida, N. Tetrahedron Lett. 1985, 26, 331. Carbohydrate stereochemistry:
6. (b) Edo, K.; Akiyama, Y; Saito, K.; Mizugaki, M.; Koide, Y; Ishida, N. J. Antibiot. 1986, 39, 1615.
7. Chromophore stereochemistry: (c) Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212.
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17. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: New York, 1983; Chapter 2.
18. (a) Myers, A. G.; Hammond, M.; Wu, Y.; Xiang, J.-N.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1996, 118, 10006.
19. (b) Myers, A. G.; Liang, J.; Hammond, M.; Harrington, P. M.; Wu, Y; Kuo, E. Y. J. Am. Chem. Soc. 1998, 120, 5319.
20. Reviews: (a) Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1982, 21, 781.
21. (b) Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21.
22. (c) Schmidt, R. R.; Jung, K.-H. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker: New York, 1997; Chapter 12.
23. Ireland, R. E.; Anderson, R. C.; Badoud, R.; Fitzsimmons, B. J.; McGarvey, G.; Thaisrivongs, S.; Wilcox, C. S. J. Am. Chem. Soc. 1983, 705, 1988.
24. For other examples of desilylation during hydrogenolysis, see (a) Smith III, A. B.; Rivero, R. A.; Hale, K. J.; Vaccaro, H. A. J. Am. Chem. Soc. 1991, 113, 2092.
25. (b) Carreira, E. M.; Du Bois, J. J Am. Chem. Soc. 1995, 117, 8106.
26. Hatayama, T.; Goldberg, I. H.; Takeshita, M.; Grollman, A. P. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 3603. See also Ref. 5b.
27. Similar results are observed with neocarzinostatin chromophore 1; cleavage in the presence of apo-NCS requires extended reaction (≥12 h) at 37°C due to tight binding to apo-NCS.