Synthesis and chemistry of chromoprotein antitumor antibiotics: Nine-membered enediynes are equilibrated with p-benzyne type biradicals

Pure and Applied Chemistry

Volumn 69, Issue 3, 1997, Pages 525-530

  Hirama, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000049521     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199769030525     Document Type: Article

References (51)

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37. (b) For other studies on p-benzyne: Hoffmann, R.; Imamura, A.; Hehre, W. J. Am. Chem. Soc. 1968, 90, 1499; Lockhart, T. P.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4091; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 5367; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1991, 113, 1907; Nicolaides, A.; Borden, W. T. J. Am. Chem. Soc. 1993, 115, 11951; Wierschke, S. G.; Nash, J. J.; Squires, R. R. J. Am. Chem. Soc. 1993, 115, 11958; Kraka, E.; Cremer, D. J. Am. Chem. Soc. 1994, 116, 4929; Lindh, R.; Persson, B. J. J. Am. Chem. Soc. 1994, 116, 4963; Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590.
38. (b) For other studies on p-benzyne: Hoffmann, R.; Imamura, A.; Hehre, W. J. Am. Chem. Soc. 1968, 90, 1499; Lockhart, T. P.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4091; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 5367; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1991, 113, 1907; Nicolaides, A.; Borden, W. T. J. Am. Chem. Soc. 1993, 115, 11951; Wierschke, S. G.; Nash, J. J.; Squires, R. R. J. Am. Chem. Soc. 1993, 115, 11958; Kraka, E.; Cremer, D. J. Am. Chem. Soc. 1994, 116, 4929; Lindh, R.; Persson, B. J. J. Am. Chem. Soc. 1994, 116, 4963; Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590.
39. (b) For other studies on p-benzyne: Hoffmann, R.; Imamura, A.; Hehre, W. J. Am. Chem. Soc. 1968, 90, 1499; Lockhart, T. P.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4091; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 5367; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1991, 113, 1907; Nicolaides, A.; Borden, W. T. J. Am. Chem. Soc. 1993, 115, 11951; Wierschke, S. G.; Nash, J. J.; Squires, R. R. J. Am. Chem. Soc. 1993, 115, 11958; Kraka, E.; Cremer, D. J. Am. Chem. Soc. 1994, 116, 4929; Lindh, R.; Persson, B. J. J. Am. Chem. Soc. 1994, 116, 4963; Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590.
40. (b) For other studies on p-benzyne: Hoffmann, R.; Imamura, A.; Hehre, W. J. Am. Chem. Soc. 1968, 90, 1499; Lockhart, T. P.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4091; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 5367; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1991, 113, 1907; Nicolaides, A.; Borden, W. T. J. Am. Chem. Soc. 1993, 115, 11951; Wierschke, S. G.; Nash, J. J.; Squires, R. R. J. Am. Chem. Soc. 1993, 115, 11958; Kraka, E.; Cremer, D. J. Am. Chem. Soc. 1994, 116, 4929; Lindh, R.; Persson, B. J. J. Am. Chem. Soc. 1994, 116, 4963; Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590.
41. (b) For other studies on p-benzyne: Hoffmann, R.; Imamura, A.; Hehre, W. J. Am. Chem. Soc. 1968, 90, 1499; Lockhart, T. P.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4091; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 5367; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1991, 113, 1907; Nicolaides, A.; Borden, W. T. J. Am. Chem. Soc. 1993, 115, 11951; Wierschke, S. G.; Nash, J. J.; Squires, R. R. J. Am. Chem. Soc. 1993, 115, 11958; Kraka, E.; Cremer, D. J. Am. Chem. Soc. 1994, 116, 4929; Lindh, R.; Persson, B. J. J. Am. Chem. Soc. 1994, 116, 4963; Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590.
42. (b) For other studies on p-benzyne: Hoffmann, R.; Imamura, A.; Hehre, W. J. Am. Chem. Soc. 1968, 90, 1499; Lockhart, T. P.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4091; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 5367; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1991, 113, 1907; Nicolaides, A.; Borden, W. T. J. Am. Chem. Soc. 1993, 115, 11951; Wierschke, S. G.; Nash, J. J.; Squires, R. R. J. Am. Chem. Soc. 1993, 115, 11958; Kraka, E.; Cremer, D. J. Am. Chem. Soc. 1994, 116, 4929; Lindh, R.; Persson, B. J. J. Am. Chem. Soc. 1994, 116, 4963; Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590.
43. (b) For other studies on p-benzyne: Hoffmann, R.; Imamura, A.; Hehre, W. J. Am. Chem. Soc. 1968, 90, 1499; Lockhart, T. P.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4091; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 5367; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1991, 113, 1907; Nicolaides, A.; Borden, W. T. J. Am. Chem. Soc. 1993, 115, 11951; Wierschke, S. G.; Nash, J. J.; Squires, R. R. J. Am. Chem. Soc. 1993, 115, 11958; Kraka, E.; Cremer, D. J. Am. Chem. Soc. 1994, 116, 4929; Lindh, R.; Persson, B. J. J. Am. Chem. Soc. 1994, 116, 4963; Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590.
44. (b) For other studies on p-benzyne: Hoffmann, R.; Imamura, A.; Hehre, W. J. Am. Chem. Soc. 1968, 90, 1499; Lockhart, T. P.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4091; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 5367; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1991, 113, 1907; Nicolaides, A.; Borden, W. T. J. Am. Chem. Soc. 1993, 115, 11951; Wierschke, S. G.; Nash, J. J.; Squires, R. R. J. Am. Chem. Soc. 1993, 115, 11958; Kraka, E.; Cremer, D. J. Am. Chem. Soc. 1994, 116, 4929; Lindh, R.; Persson, B. J. J. Am. Chem. Soc. 1994, 116, 4963; Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590.
45. Grissom, J. W.; Calkins, T. L.; McMillen, H. A.; Jiang, Y. J. Org. Chem. 1994, 59, 5833.
46. Logan, C.F.; Chen, P. J. Am. Chem. Soc. 1996, 118, 2113; Schottelius, M. J.; Chen, P. J. Am. Chem. Soc. 1996, 118, 4896.
47. Logan, C.F.; Chen, P. J. Am. Chem. Soc. 1996, 118, 2113; Schottelius, M. J.; Chen, P. J. Am. Chem. Soc. 1996, 118, 4896.
48. Our NMR and computer modeling studies indicated that Tyr32 is proximate to the nine-membered core of 1 (Iida, K.; Fukuda, S.; Tanaka, T.; Hirama, M.; Imajo, S.; Ishiguro, M.; Yoshida, K.; Otani, T. Tetrahedron Lett, in press). For another modeling study, see: Okuno, Y.; Otsuka, M.; Sugiura, Y. J. Med. Chem. 1994, 37, 2266, and also see ref 4.
49. Our NMR and computer modeling studies indicated that Tyr32 is proximate to the nine-membered core of 1 (Iida, K.; Fukuda, S.; Tanaka, T.; Hirama, M.; Imajo, S.; Ishiguro, M.; Yoshida, K.; Otani, T. Tetrahedron Lett, in press). For another modeling study, see: Okuno, Y.; Otsuka, M.; Sugiura, Y. J. Med. Chem. 1994, 37, 2266, and also see ref 4.
50. Our NMR and computer modeling studies indicated that Tyr32 is proximate to the nine-membered core of 1 (Iida, K.; Fukuda, S.; Tanaka, T.; Hirama, M.; Imajo, S.; Ishiguro, M.; Yoshida, K.; Otani, T. Tetrahedron Lett, in press). For another modeling study, see: Okuno, Y.; Otsuka, M.; Sugiura, Y. J. Med. Chem. 1994, 37, 2266, and also see ref 4.
51. 3CN) solution of 14 and the powder C-1027 holoprotein exhibited broad spectra whose intensity varied reversibly with temperature. Identification and analysis of these spectra will be reported in due course.