Synthesis of philanthotoxin analogs with bulky heads including porphyrins. Self-assembly monitored by circular dichroism

Heterocycles

Volumn 42, Issue 2, 1996, Pages 723-736

  Huang, Danwen ^a   Matile, Stefan ^a   Berova, Nina ^a   Nakanishi, Koji ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001679024     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s77     Document Type: Article

References (30)

1. A. T. Eldefrawi, M. E. Eldefrawi, K. Konno, N. A. Mansour, K. Nakanishi, E. Oltz, and P. N. R. Usherwood, Proc. Natl. Acad. Sci. USA, 1988, 85, 4910.
2. T. Piek, R. H. Fokkers, H. Karst, C. Kruk, A. Lind, I. Van Marie, T. Nakajima, N. M. N. Nibbering, H. Shinozaki, W. Spanjer, and Y. C. Tong, 'Neurotox'88,' ed. by G. G Lunt, 1988, pp. 61-76.
3. T. Piek, P. Mantel, and E. Engels, Comp. Gen. Pharmacol., 1971, 2, 317.
4. K. Nakanishi, S. K. Choi, D. W. Huang, K. Lerro, M. Orlando, A. G. Kalivretenos, A. Eldefrawi, M. Eldefrawi, and P. N. R. Usherwood, Pure & Appl. Chem., 1994, 66, 671.
5. S. K. Choi, A. Kalivretenos, and K. Nakanishi, Chem. & Bio., 1995, 2, 23.
6. N. Unwin, Nature, 1995, 373, 37.
7. N. Unwin, J. Mol. Biol., 1993, 229, 1101.
8. A. Darszon, 'Methods in Enzymology', 1986, 127, p.486.
9. G. Chang, W. Guida, and W. C. Still, J. Am. Chem. Soc., 1989, 111, 4379.
10. V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, K. J. Rosnack, N. A. Saccomano, J. G. Stroh, and R. A. Volkman, J. Am. Chem. Soc., 1990, 112, 6696.
11. S. Ohta, A. Shimabayashi, M. Aono, and M. Okamoto, Synthesis, 1982, 883.
12. J. A. Anton and P. A. Loach, J. Heterocycl. Chem., 1975, 12, 573. B. Stäubli, H. Fretz, U. Piantini, and W.-D. Woggon, Helv. Chim. Acta, 1987, 70, 1173.
13. J. A. Anton and P. A. Loach, J. Heterocycl. Chem., 1975, 12, 573. B. Stäubli, H. Fretz, U. Piantini, and W.-D. Woggon, Helv. Chim. Acta, 1987, 70, 1173.
14. M. A. Sari, J. P. Battioni, D. Dupre, and D. Mansuy, Biochemistry, 1990, 29, 4205.
15. R. Goodnow, Jr., K.Konno, M. Niwa, T. Kallimopoulos, R.Bukownik, D. Lenares, and K. Nakanishi, Tetrehedron, 1990, 46, 3267.
16. S. Matile, N. Berova, and K. Nakanishi, J. Am. Chem. Soc., 1995, submitted.
17. M. Jodal, A. Kovacs, J. Ott, and G. Snatzke, Chem. Ber., 1989, 122, 1207.
18. T. Goto and T. Kondo, Angew. Chem., Int. Ed. Engl., 1991, 30, 17.
19. H. Sasaki, M. Sisido, and Y. Imanishi, Langmuir, 1990, 6, 1008.
20. H. G. Brittain, Chirality, 1994, 6, 665.
21. T. Kunitake, N. Nakashima, M Shimomura, Y. Okahata, K. Kano, and T. Ogawa, J. Am. Chem. Soc., 1980, 102, 6644; T. Kunitake, N. Nakashima, and K. Morimitsu, Chem. Lett., 1980, 1347; N. Nakashima, K. Morimitsu, and T. Kunitake, Bull. Chem. Soc. Jpn., 1984, 57, 3253.
22. T. Kunitake, N. Nakashima, M Shimomura, Y. Okahata, K. Kano, and T. Ogawa, J. Am. Chem. Soc., 1980, 102, 6644; T. Kunitake, N. Nakashima, and K. Morimitsu, Chem. Lett., 1980, 1347; N. Nakashima, K. Morimitsu, and T. Kunitake, Bull. Chem. Soc. Jpn., 1984, 57, 3253.
23. T. Kunitake, N. Nakashima, M Shimomura, Y. Okahata, K. Kano, and T. Ogawa, J. Am. Chem. Soc., 1980, 102, 6644; T. Kunitake, N. Nakashima, and K. Morimitsu, Chem. Lett., 1980, 1347; N. Nakashima, K. Morimitsu, and T. Kunitake, Bull. Chem. Soc. Jpn., 1984, 57, 3253.
24. T. Kunitake and N. Yamada, J. Chem. Soc., Chem. Commun., 1984, 655.
25. P. N. R. Usherwood et al. unpublished.
26. M. Nappa and J. S. Valentine, J. Am. Chem. Soc., 1978, 100, 5075.
27. a) M. A. Bobrik and F. A. Walker, Inorg. Chem., 1980, 19, 3383.
28. b) F. A. Walker, U. Simonis, H. Zhang, J. M. Walker, T. McDonald Ruscitti, C. Kipp, M. A. Amputch, B. V. Castillo, III, S. H. Cody, D. L. Wilson, R. E. Graul, G. J. Yong, K. Tobin, J. T. West, and B. A. Barichievich, New J. Chem., 1992, 16, 609, and references cited therein.
29. Due to intermolecular pyridine zinc complex formation the assignements of the resulting broad and/or upfield shifted signals is not clear.
30. 1H nmr 2D COSY spectrum. Other polyamine spectra were interpertated based on this assignements.