A-aminopurine derivatives with C6-substituted olefin as novel cross-linking agents and the synthesis of the corresponding β-phosphoramidite precursors

Tetrahedron

Volumn 53, Issue 9, 1997, Pages 3035-3044

  Nagatsugi, Fumi ^a   Uemura, Kengo ^a   Nakashima, Shouji ^a   Maeda, Minoru ^a   Sasaki, Shigeki ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE; OLIGODEOXYNUCLEOTIDE;

ARTICLE; CROSS LINKING; DRUG PURIFICATION; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0031550888     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00069-0     Document Type: Article

References (29)

1. 1) Recent reviews: a) Hélène, C., European Journal of Cancer, 1994, 30A, 1721;
2. b) Beaucage, S. L.; Iyer, R. P., Tetrahedron, 1993, 49, 1925;
3. c) Marshall, W. S.; Caruthers, M. H., Science, 1993, 259, 1564;
4. d) Stein, C. A.; Cheng, Y.-C., ibid, 1993, 261, 1004; Milligan, J. F.; Matteucci, M. D.; Martin, J. C., J. Med. Chem., 1993, 36, 1923.
5. d) Stein, C. A.; Cheng, Y.-C., ibid, 1993, 261, 1004; Milligan, J. F.; Matteucci, M. D.; Martin, J. C., J. Med. Chem., 1993, 36, 1923.
6. 2) Recent reviews: Soyfer, V. N.; Potaman, V. N., Triple-Helical Nucleic Acids; Springer-Verlag: New York, 1996, and references cited therein.
7. 3) Tabone, J. C.; Stamm, M. R.; Gamper, H. B.; Meyer, R. B. Jr., Biochemistry, 1994, 33, 375.
8. 4) Coleman, R. S.; Kesicki, E. A., J. Org. Chem., 1995, 60, 6252.
9. 5) Chatterjee, M.; Rokita, S. E., J. Amer. Chem. Soc., 1994, 116, 1690, and references cited therein.
10. 6) Chang, E. H.; Miller, P. S.; Cushman, C.; Devadas, K.; Pirollo, K. F.; Ts'o P. O. P.; Yu, Z. P., Biochemistry, 1991, 30, 8283.
11. 7) Cowart, M.; Benkovic, S. J., ibid, 1991, 30, 788.
12. 8) a) Young, S. L.; Krawczyk, S. H.; Matteucci, M. D.; Toole, J. J., Proc. Natl. Acad. Sci. U.S.A., 1991, 88, 10023;
13. b) Shaw, J.-P.; Milligan, J. F.; Krawczyk, S. H.; Matteucci, M. D., J. Amer. Chem. Soc., 1991, 113, 7765;
14. c) Baker, B. F.; Dervan, P. B., ibid, 1989, 111, 2700;
15. d) Webb, T. R.; Matteucci, M. D., ibid, 1986, 108, 2764;
16. e) Vlassov, V. V.; Zarytova, V. F.; Kutiavin, I. V.; Mamaev, S. V.; Podyminogin, M. A., Nucleic Acids Res., 1986, 14, 4065.
17. 9) Nagatsugi, F.; Uemura, K.; Nakashima, S.; Maeda, M.; Sasaki, S., Tetrahedron Lett., 1995, 36, 421
18. 10) Nagatsugi, F.; Uemura, K.; Nakashima, S.; Maeda, M.; Sasaki, S., Nucleic Acids Symposium Series, 1995, 34, 171.
19. 11) Sakata, S.; Yonei, S.; Yoshino, H., Chem. Pharm. Bull., 1982, 30, 2583.
20. 12) a) Gundersen, L.-L., Tetrahedron Lett., 1994, 35, 3155,
21. b) Van Aershot, A. A.; Mamos, P.; Weyns, N. J.; Ikeda, S.; De Clercq, E.; Herdewijin, P. A., J. Med. Chem., 1993, 36, 2983.
22. 13) Cross-coupling with vinyl triflates; Scott, W. J.; Peña, M. R.; Swärd, K.; Stoessel, S. J.; Stille, J. K., J. Org. Chem., 1985, 50, 2302.
23. 14) a) Povsic, T. J.; Strobel, S. A.; Dervan, P. B., J. Amer. Chem. Soc., 1992, 114, 5934,
24. b) Meyer, R. B. Jr.; Tabone, J. C.; Hurst, G. D.; Smith, T. M.; Gamper, H., ibid, 1989, 111, 8517.
25. 15) The calculations were performed with CAChe system on Macintosh.
26. 16) The pKa values were determined spectrophotometrically, see experimental.
27. 17) Nagai, H.; Fujiwara, T.; Fujii, M.; Sekine, T.; Hata, T., Nucleic Acids Res., 1987, 17, 8581.
28. 18) Synthesis and evaluation of cross-linking reaction of the oligonucleotides incorporating 10 and 11 will be reported elsewhere.
29. 19) Lamm, G.; Pack, G. R., Proc. Natl. Acad. Sci. U.S.A., 1990, 87, 9033.