The β-(phosphatoxy)alkyl radical rearrangement. Rate constants, arrhenius parameters, and structure activity relationships

Journal of the American Chemical Society

Volumn 118, Issue 28, 1996, Pages 6666-6670

  Crich, David ^a   Jiao, Xian Yun ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOPHOSPHATE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0030004141     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961275a     Document Type: Article

References (63)

1. See: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev., 1987, 87, 1107. (b) Hecht, S. M. Acc. Chem. Res., 1986, 19, 383. (c) Hecht, S. M. Bioconjugate Chem. 1994, 5, 513. (d) Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnam, B. J. Am. Chem. Soc. 1992, 114, 8763. (e) Haggeland, J. J.; De Voss, J. J.; Heath, J. A.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 9200. (f) Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe. J. Biochemistry 1991, 30, 2034. (g) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (h) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (i) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (j) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (k) Dedon, P. C.; Goldberg, I. H. Chem. Res. Toxicol. 1992, 5, 311. (l) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987. (m) Schulte-Frohlinde, D.; Hildenbrand, K. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer, Dordrecht, 1989; p 335. (n) von Sonntag, C.; Schuchmann H-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229. (o) Dizardoglu, M. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: Chichester, 1993; p 19. (p) von Sonntag, C.; Hagen, U.; Schön-Bopp, A.; Schulte-Frohlinde, D In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic: New York, 1981; Vol. 9, p 110. (q) Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. Chem. Biol. 1995, 2, 367. (r) Breen, A. P.; Murphy, J. A. Free Radicals Biol. Med. 1995, 18, 1033.
2. See: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev., 1987, 87, 1107. (b) Hecht, S. M. Acc. Chem. Res., 1986, 19, 383. (c) Hecht, S. M. Bioconjugate Chem. 1994, 5, 513. (d) Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnam, B. J. Am. Chem. Soc. 1992, 114, 8763. (e) Haggeland, J. J.; De Voss, J. J.; Heath, J. A.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 9200. (f) Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe. J. Biochemistry 1991, 30, 2034. (g) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (h) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (i) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (j) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (k) Dedon, P. C.; Goldberg, I. H. Chem. Res. Toxicol. 1992, 5, 311. (l) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987. (m) Schulte-Frohlinde, D.; Hildenbrand, K. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer, Dordrecht, 1989; p 335. (n) von Sonntag, C.; Schuchmann H-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229. (o) Dizardoglu, M. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: Chichester, 1993; p 19. (p) von Sonntag, C.; Hagen, U.; Schön-Bopp, A.; Schulte-Frohlinde, D In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic: New York, 1981; Vol. 9, p 110. (q) Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. Chem. Biol. 1995, 2, 367. (r) Breen, A. P.; Murphy, J. A. Free Radicals Biol. Med. 1995, 18, 1033.
3. See: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev., 1987, 87, 1107. (b) Hecht, S. M. Acc. Chem. Res., 1986, 19, 383. (c) Hecht, S. M. Bioconjugate Chem. 1994, 5, 513. (d) Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnam, B. J. Am. Chem. Soc. 1992, 114, 8763. (e) Haggeland, J. J.; De Voss, J. J.; Heath, J. A.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 9200. (f) Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe. J. Biochemistry 1991, 30, 2034. (g) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (h) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (i) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (j) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (k) Dedon, P. C.; Goldberg, I. H. Chem. Res. Toxicol. 1992, 5, 311. (l) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987. (m) Schulte-Frohlinde, D.; Hildenbrand, K. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer, Dordrecht, 1989; p 335. (n) von Sonntag, C.; Schuchmann H-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229. (o) Dizardoglu, M. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: Chichester, 1993; p 19. (p) von Sonntag, C.; Hagen, U.; Schön-Bopp, A.; Schulte-Frohlinde, D In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic: New York, 1981; Vol. 9, p 110. (q) Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. Chem. Biol. 1995, 2, 367. (r) Breen, A. P.; Murphy, J. A. Free Radicals Biol. Med. 1995, 18, 1033.
4. See: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev., 1987, 87, 1107. (b) Hecht, S. M. Acc. Chem. Res., 1986, 19, 383. (c) Hecht, S. M. Bioconjugate Chem. 1994, 5, 513. (d) Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnam, B. J. Am. Chem. Soc. 1992, 114, 8763. (e) Haggeland, J. J.; De Voss, J. J.; Heath, J. A.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 9200. (f) Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe. J. Biochemistry 1991, 30, 2034. (g) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (h) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (i) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (j) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (k) Dedon, P. C.; Goldberg, I. H. Chem. Res. Toxicol. 1992, 5, 311. (l) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987. (m) Schulte-Frohlinde, D.; Hildenbrand, K. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer, Dordrecht, 1989; p 335. (n) von Sonntag, C.; Schuchmann H-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229. (o) Dizardoglu, M. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: Chichester, 1993; p 19. (p) von Sonntag, C.; Hagen, U.; Schön-Bopp, A.; Schulte-Frohlinde, D In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic: New York, 1981; Vol. 9, p 110. (q) Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. Chem. Biol. 1995, 2, 367. (r) Breen, A. P.; Murphy, J. A. Free Radicals Biol. Med. 1995, 18, 1033.
5. See: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev., 1987, 87, 1107. (b) Hecht, S. M. Acc. Chem. Res., 1986, 19, 383. (c) Hecht, S. M. Bioconjugate Chem. 1994, 5, 513. (d) Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnam, B. J. Am. Chem. Soc. 1992, 114, 8763. (e) Haggeland, J. J.; De Voss, J. J.; Heath, J. A.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 9200. (f) Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe. J. Biochemistry 1991, 30, 2034. (g) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (h) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (i) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (j) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (k) Dedon, P. C.; Goldberg, I. H. Chem. Res. Toxicol. 1992, 5, 311. (l) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987. (m) Schulte-Frohlinde, D.; Hildenbrand, K. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer, Dordrecht, 1989; p 335. (n) von Sonntag, C.; Schuchmann H-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229. (o) Dizardoglu, M. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: Chichester, 1993; p 19. (p) von Sonntag, C.; Hagen, U.; Schön-Bopp, A.; Schulte-Frohlinde, D In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic: New York, 1981; Vol. 9, p 110. (q) Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. Chem. Biol. 1995, 2, 367. (r) Breen, A. P.; Murphy, J. A. Free Radicals Biol. Med. 1995, 18, 1033.
6. See: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev., 1987, 87, 1107. (b) Hecht, S. M. Acc. Chem. Res., 1986, 19, 383. (c) Hecht, S. M. Bioconjugate Chem. 1994, 5, 513. (d) Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnam, B. J. Am. Chem. Soc. 1992, 114, 8763. (e) Haggeland, J. J.; De Voss, J. J.; Heath, J. A.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 9200. (f) Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe. J. Biochemistry 1991, 30, 2034. (g) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (h) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (i) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (j) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (k) Dedon, P. C.; Goldberg, I. H. Chem. Res. Toxicol. 1992, 5, 311. (l) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987. (m) Schulte-Frohlinde, D.; Hildenbrand, K. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer, Dordrecht, 1989; p 335. (n) von Sonntag, C.; Schuchmann H-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229. (o) Dizardoglu, M. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: Chichester, 1993; p 19. (p) von Sonntag, C.; Hagen, U.; Schön-Bopp, A.; Schulte-Frohlinde, D In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic: New York, 1981; Vol. 9, p 110. (q) Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. Chem. Biol. 1995, 2, 367. (r) Breen, A. P.; Murphy, J. A. Free Radicals Biol. Med. 1995, 18, 1033.
7. See: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev., 1987, 87, 1107. (b) Hecht, S. M. Acc. Chem. Res., 1986, 19, 383. (c) Hecht, S. M. Bioconjugate Chem. 1994, 5, 513. (d) Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnam, B. J. Am. Chem. Soc. 1992, 114, 8763. (e) Haggeland, J. J.; De Voss, J. J.; Heath, J. A.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 9200. (f) Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe. J. Biochemistry 1991, 30, 2034. (g) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (h) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (i) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (j) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (k) Dedon, P. C.; Goldberg, I. H. Chem. Res. Toxicol. 1992, 5, 311. (l) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987. (m) Schulte-Frohlinde, D.; Hildenbrand, K. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer, Dordrecht, 1989; p 335. (n) von Sonntag, C.; Schuchmann H-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229. (o) Dizardoglu, M. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: Chichester, 1993; p 19. (p) von Sonntag, C.; Hagen, U.; Schön-Bopp, A.; Schulte-Frohlinde, D In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic: New York, 1981; Vol. 9, p 110. (q) Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. Chem. Biol. 1995, 2, 367. (r) Breen, A. P.; Murphy, J. A. Free Radicals Biol. Med. 1995, 18, 1033.
8. See: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev., 1987, 87, 1107. (b) Hecht, S. M. Acc. Chem. Res., 1986, 19, 383. (c) Hecht, S. M. Bioconjugate Chem. 1994, 5, 513. (d) Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnam, B. J. Am. Chem. Soc. 1992, 114, 8763. (e) Haggeland, J. J.; De Voss, J. J.; Heath, J. A.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 9200. (f) Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe. J. Biochemistry 1991, 30, 2034. (g) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (h) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (i) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (j) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (k) Dedon, P. C.; Goldberg, I. H. Chem. Res. Toxicol. 1992, 5, 311. (l) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987. (m) Schulte-Frohlinde, D.; Hildenbrand, K. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer, Dordrecht, 1989; p 335. (n) von Sonntag, C.; Schuchmann H-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229. (o) Dizardoglu, M. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: Chichester, 1993; p 19. (p) von Sonntag, C.; Hagen, U.; Schön-Bopp, A.; Schulte-Frohlinde, D In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic: New York, 1981; Vol. 9, p 110. (q) Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. Chem. Biol. 1995, 2, 367. (r) Breen, A. P.; Murphy, J. A. Free Radicals Biol. Med. 1995, 18, 1033.
9. See: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev., 1987, 87, 1107. (b) Hecht, S. M. Acc. Chem. Res., 1986, 19, 383. (c) Hecht, S. M. Bioconjugate Chem. 1994, 5, 513. (d) Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnam, B. J. Am. Chem. Soc. 1992, 114, 8763. (e) Haggeland, J. J.; De Voss, J. J.; Heath, J. A.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 9200. (f) Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe. J. Biochemistry 1991, 30, 2034. (g) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (h) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (i) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (j) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (k) Dedon, P. C.; Goldberg, I. H. Chem. Res. Toxicol. 1992, 5, 311. (l) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987. (m) Schulte-Frohlinde, D.; Hildenbrand, K. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer, Dordrecht, 1989; p 335. (n) von Sonntag, C.; Schuchmann H-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229. (o) Dizardoglu, M. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: Chichester, 1993; p 19. (p) von Sonntag, C.; Hagen, U.; Schön-Bopp, A.; Schulte-Frohlinde, D In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic: New York, 1981; Vol. 9, p 110. (q) Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. Chem. Biol. 1995, 2, 367. (r) Breen, A. P.; Murphy, J. A. Free Radicals Biol. Med. 1995, 18, 1033.
10. See: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev., 1987, 87, 1107. (b) Hecht, S. M. Acc. Chem. Res., 1986, 19, 383. (c) Hecht, S. M. Bioconjugate Chem. 1994, 5, 513. (d) Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnam, B. J. Am. Chem. Soc. 1992, 114, 8763. (e) Haggeland, J. J.; De Voss, J. J.; Heath, J. A.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 9200. (f) Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe. J. Biochemistry 1991, 30, 2034. (g) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (h) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (i) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (j) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (k) Dedon, P. C.; Goldberg, I. H. Chem. Res. Toxicol. 1992, 5, 311. (l) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987. (m) Schulte-Frohlinde, D.; Hildenbrand, K. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer, Dordrecht, 1989; p 335. (n) von Sonntag, C.; Schuchmann H-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229. (o) Dizardoglu, M. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: Chichester, 1993; p 19. (p) von Sonntag, C.; Hagen, U.; Schön-Bopp, A.; Schulte-Frohlinde, D In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic: New York, 1981; Vol. 9, p 110. (q) Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. Chem. Biol. 1995, 2, 367. (r) Breen, A. P.; Murphy, J. A. Free Radicals Biol. Med. 1995, 18, 1033.
11. See: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev., 1987, 87, 1107. (b) Hecht, S. M. Acc. Chem. Res., 1986, 19, 383. (c) Hecht, S. M. Bioconjugate Chem. 1994, 5, 513. (d) Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnam, B. J. Am. Chem. Soc. 1992, 114, 8763. (e) Haggeland, J. J.; De Voss, J. J.; Heath, J. A.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 9200. (f) Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe. J. Biochemistry 1991, 30, 2034. (g) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (h) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (i) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (j) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (k) Dedon, P. C.; Goldberg, I. H. Chem. Res. Toxicol. 1992, 5, 311. (l) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987. (m) Schulte-Frohlinde, D.; Hildenbrand, K. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer, Dordrecht, 1989; p 335. (n) von Sonntag, C.; Schuchmann H-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229. (o) Dizardoglu, M. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: Chichester, 1993; p 19. (p) von Sonntag, C.; Hagen, U.; Schön-Bopp, A.; Schulte-Frohlinde, D In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic: New York, 1981; Vol. 9, p 110. (q) Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. Chem. Biol. 1995, 2, 367. (r) Breen, A. P.; Murphy, J. A. Free Radicals Biol. Med. 1995, 18, 1033.
12. See: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev., 1987, 87, 1107. (b) Hecht, S. M. Acc. Chem. Res., 1986, 19, 383. (c) Hecht, S. M. Bioconjugate Chem. 1994, 5, 513. (d) Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnam, B. J. Am. Chem. Soc. 1992, 114, 8763. (e) Haggeland, J. J.; De Voss, J. J.; Heath, J. A.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 9200. (f) Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe. J. Biochemistry 1991, 30, 2034. (g) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (h) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (i) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (j) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (k) Dedon, P. C.; Goldberg, I. H. Chem. Res. Toxicol. 1992, 5, 311. (l) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987. (m) Schulte-Frohlinde, D.; Hildenbrand, K. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer, Dordrecht, 1989; p 335. (n) von Sonntag, C.; Schuchmann H-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229. (o) Dizardoglu, M. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: Chichester, 1993; p 19. (p) von Sonntag, C.; Hagen, U.; Schön-Bopp, A.; Schulte-Frohlinde, D In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic: New York, 1981; Vol. 9, p 110. (q) Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. Chem. Biol. 1995, 2, 367. (r) Breen, A. P.; Murphy, J. A. Free Radicals Biol. Med. 1995, 18, 1033.
13. See: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev., 1987, 87, 1107. (b) Hecht, S. M. Acc. Chem. Res., 1986, 19, 383. (c) Hecht, S. M. Bioconjugate Chem. 1994, 5, 513. (d) Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnam, B. J. Am. Chem. Soc. 1992, 114, 8763. (e) Haggeland, J. J.; De Voss, J. J.; Heath, J. A.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 9200. (f) Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe. J. Biochemistry 1991, 30, 2034. (g) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (h) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (i) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (j) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (k) Dedon, P. C.; Goldberg, I. H. Chem. Res. Toxicol. 1992, 5, 311. (l) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987. (m) Schulte-Frohlinde, D.; Hildenbrand, K. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer, Dordrecht, 1989; p 335. (n) von Sonntag, C.; Schuchmann H-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229. (o) Dizardoglu, M. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: Chichester, 1993; p 19. (p) von Sonntag, C.; Hagen, U.; Schön-Bopp, A.; Schulte-Frohlinde, D In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic: New York, 1981; Vol. 9, p 110. (q) Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. Chem. Biol. 1995, 2, 367. (r) Breen, A. P.; Murphy, J. A. Free Radicals Biol. Med. 1995, 18, 1033.
14. See: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev., 1987, 87, 1107. (b) Hecht, S. M. Acc. Chem. Res., 1986, 19, 383. (c) Hecht, S. M. Bioconjugate Chem. 1994, 5, 513. (d) Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnam, B. J. Am. Chem. Soc. 1992, 114, 8763. (e) Haggeland, J. J.; De Voss, J. J.; Heath, J. A.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 9200. (f) Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe. J. Biochemistry 1991, 30, 2034. (g) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (h) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (i) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (j) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (k) Dedon, P. C.; Goldberg, I. H. Chem. Res. Toxicol. 1992, 5, 311. (l) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987. (m) Schulte-Frohlinde, D.; Hildenbrand, K. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer, Dordrecht, 1989; p 335. (n) von Sonntag, C.; Schuchmann H-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229. (o) Dizardoglu, M. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: Chichester, 1993; p 19. (p) von Sonntag, C.; Hagen, U.; Schön-Bopp, A.; Schulte-Frohlinde, D In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic: New York, 1981; Vol. 9, p 110. (q) Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. Chem. Biol. 1995, 2, 367. (r) Breen, A. P.; Murphy, J. A. Free Radicals Biol. Med. 1995, 18, 1033.
15. See: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev., 1987, 87, 1107. (b) Hecht, S. M. Acc. Chem. Res., 1986, 19, 383. (c) Hecht, S. M. Bioconjugate Chem. 1994, 5, 513. (d) Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnam, B. J. Am. Chem. Soc. 1992, 114, 8763. (e) Haggeland, J. J.; De Voss, J. J.; Heath, J. A.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 9200. (f) Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe. J. Biochemistry 1991, 30, 2034. (g) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (h) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (i) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (j) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (k) Dedon, P. C.; Goldberg, I. H. Chem. Res. Toxicol. 1992, 5, 311. (l) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987. (m) Schulte-Frohlinde, D.; Hildenbrand, K. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer, Dordrecht, 1989; p 335. (n) von Sonntag, C.; Schuchmann H-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229. (o) Dizardoglu, M. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: Chichester, 1993; p 19. (p) von Sonntag, C.; Hagen, U.; Schön-Bopp, A.; Schulte-Frohlinde, D In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic: New York, 1981; Vol. 9, p 110. (q) Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. Chem. Biol. 1995, 2, 367. (r) Breen, A. P.; Murphy, J. A. Free Radicals Biol. Med. 1995, 18, 1033.
16. See: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev., 1987, 87, 1107. (b) Hecht, S. M. Acc. Chem. Res., 1986, 19, 383. (c) Hecht, S. M. Bioconjugate Chem. 1994, 5, 513. (d) Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnam, B. J. Am. Chem. Soc. 1992, 114, 8763. (e) Haggeland, J. J.; De Voss, J. J.; Heath, J. A.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 9200. (f) Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe. J. Biochemistry 1991, 30, 2034. (g) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (h) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (i) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (j) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (k) Dedon, P. C.; Goldberg, I. H. Chem. Res. Toxicol. 1992, 5, 311. (l) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987. (m) Schulte-Frohlinde, D.; Hildenbrand, K. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer, Dordrecht, 1989; p 335. (n) von Sonntag, C.; Schuchmann H-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229. (o) Dizardoglu, M. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: Chichester, 1993; p 19. (p) von Sonntag, C.; Hagen, U.; Schön-Bopp, A.; Schulte-Frohlinde, D In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic: New York, 1981; Vol. 9, p 110. (q) Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. Chem. Biol. 1995, 2, 367. (r) Breen, A. P.; Murphy, J. A. Free Radicals Biol. Med. 1995, 18, 1033.
17. See: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev., 1987, 87, 1107. (b) Hecht, S. M. Acc. Chem. Res., 1986, 19, 383. (c) Hecht, S. M. Bioconjugate Chem. 1994, 5, 513. (d) Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnam, B. J. Am. Chem. Soc. 1992, 114, 8763. (e) Haggeland, J. J.; De Voss, J. J.; Heath, J. A.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 9200. (f) Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe. J. Biochemistry 1991, 30, 2034. (g) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (h) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (i) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (j) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (k) Dedon, P. C.; Goldberg, I. H. Chem. Res. Toxicol. 1992, 5, 311. (l) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987. (m) Schulte-Frohlinde, D.; Hildenbrand, K. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer, Dordrecht, 1989; p 335. (n) von Sonntag, C.; Schuchmann H-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229. (o) Dizardoglu, M. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: Chichester, 1993; p 19. (p) von Sonntag, C.; Hagen, U.; Schön-Bopp, A.; Schulte-Frohlinde, D In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic: New York, 1981; Vol. 9, p 110. (q) Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. Chem. Biol. 1995, 2, 367. (r) Breen, A. P.; Murphy, J. A. Free Radicals Biol. Med. 1995, 18, 1033.
18. See: (a) Stubbe, J.; Kozarich, J. W. Chem. Rev., 1987, 87, 1107. (b) Hecht, S. M. Acc. Chem. Res., 1986, 19, 383. (c) Hecht, S. M. Bioconjugate Chem. 1994, 5, 513. (d) Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnam, B. J. Am. Chem. Soc. 1992, 114, 8763. (e) Haggeland, J. J.; De Voss, J. J.; Heath, J. A.; Townsend, C. A. J. Am. Chem. Soc. 1992, 114, 9200. (f) Kappen, L. S.; Goldberg, I. H.; Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe. J. Biochemistry 1991, 30, 2034. (g) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191. (h) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387. (i) Nicolaou, K. C.; Smith, A. L. Acc. Chem. Res. 1992, 25, 497. (j) Lee, M. D.; Ellestad, G. A.; Borders, D. B. Acc. Chem. Res. 1991, 24, 235. (k) Dedon, P. C.; Goldberg, I. H. Chem. Res. Toxicol. 1992, 5, 311. (l) von Sonntag, C. In The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987. (m) Schulte-Frohlinde, D.; Hildenbrand, K. In Free Radicals in Synthesis and Biology; Minisci, F., Ed.; Kluwer, Dordrecht, 1989; p 335. (n) von Sonntag, C.; Schuchmann H-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229. (o) Dizardoglu, M. In DNA and Free Radicals; Halliwell, B., Aruoma, O. I., Eds.; Ellis Horwood: Chichester, 1993; p 19. (p) von Sonntag, C.; Hagen, U.; Schön-Bopp, A.; Schulte-Frohlinde, D In Advances in Radiation Biology; Lett, J. T., Adler, H., Eds.; Academic: New York, 1981; Vol. 9, p 110. (q) Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. Chem. Biol. 1995, 2, 367. (r) Breen, A. P.; Murphy, J. A. Free Radicals Biol. Med. 1995, 18, 1033.
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