Synthesis of sulfamide linked dinucleotide analogues

Tetrahedron Letters

Volumn 38, Issue 30, 1997, Pages 5387-5390

  Micklefield, Jason ^a   Fettes, Kevin J ^a  

^a UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMINONUCLEOSIDE; CATECHOL; DINUCLEOTIDE; SULFANILAMIDE;

ARTICLE; CHEMICAL REACTION; DRUG CONFORMATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE;

EID: 0030836519     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01179-9     Document Type: Article

References (25)

1. Oligonucleotides as Therapeutic Agents. Proceedings of the Ciba Foundation Symposium No. 209; John Wiley & Sons: Chichester, 1997, in press.
2. Uhlmann, E; Peyman, A. Chem. Rev. 1990, 90, 543.
3. Milligan, J. F.; Matteucci, M. D.; Martin, J. C. J. Med. Chem. 1993, 36, 1923.
4. De Mesmaeker, A.; Häner, R.; Martin, P.; Moser, H. E. Acc. Chem. Res. 1995, 28, 366.
5. Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 6123; Varma, R. S. Synlett 1993, 621; Thuong, N. T.; Hélène, C. Angew. chem. Int. Ed. Engl. 1993, 32, 666
6. Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 6123; Varma, R. S. Synlett 1993, 621; Thuong, N. T.; Hélène, C. Angew. chem. Int. Ed. Engl. 1993, 32, 666
7. Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 6123; Varma, R. S. Synlett 1993, 621; Thuong, N. T.; Hélène, C. Angew. chem. Int. Ed. Engl. 1993, 32, 666
8. Gewirtz, A. M.; Luger, S.; Sokol, D.; Gowdin, B.; Stadtmauer, A.; Reccio, A; Ratajczak, M. Z. In Oligonudeotides as Therapeutic Agents. See ref. 1.
9. Gryaznov, S. M.; Chen, J-K. J. Am. Chem. Soc. 1994, 116, 3143.
10. Gryaznov, S. M.; Lloyd, D. H.; Chen, J-K; Schultz, R. G.; DeDionisio, L. A.; Ratmeyer, L.; Wilson, W. D. Proc. Natl. Acad. Sci. USA 1995, 92, 5798.
11. Chen, J-K.; Schultz, R. G.; Lloyd, D. H.; Gryaznov, S. Nucleic Acids Res. 1995, 23, 2661.
12. Ding, D.; Gryaznov, S. M.; Lloyd, D. H.; Chandrasekaran, S.; Yao. S.; Ratmeyer, L.; Pan, Y.; Wilson, W. D. Nucleic Acids Res. 1996, 24, 354.
13. Barsky, D.; Colvin, M. E.; Zon, G.; Gryaznov, S. M. Nucleic Acids Res. 1997, 25, 830.
14. Marquez, V. E.; Siddiqui, M. A.; Ezzitouni, A.; Russ, P.; Wang, J.; Wagner, R. W.; Matteucci, M. D. J. Med Chem. 1996, 39, 3739; Thibaudeau, C.; Plavec, J.; Garg, N.; Papchikhin, A.; Chattopadhyaya, J. Am. Chem. Soc. 1994, 116, 4038; Saenger, W. Principles of Nucleic Acid Structure; Cantor, C. R., Ed.; Springer-Verlag: New York, 1984.
15. Marquez, V. E.; Siddiqui, M. A.; Ezzitouni, A.; Russ, P.; Wang, J.; Wagner, R. W.; Matteucci, M. D. J. Med Chem. 1996, 39, 3739; Thibaudeau, C.; Plavec, J.; Garg, N.; Papchikhin, A.; Chattopadhyaya, J. Am. Chem. Soc. 1994, 116, 4038; Saenger, W. Principles of Nucleic Acid Structure; Cantor, C. R., Ed.; Springer-Verlag: New York, 1984.
16. Marquez, V. E.; Siddiqui, M. A.; Ezzitouni, A.; Russ, P.; Wang, J.; Wagner, R. W.; Matteucci, M. D. J. Med Chem. 1996, 39, 3739; Thibaudeau, C.; Plavec, J.; Garg, N.; Papchikhin, A.; Chattopadhyaya, J. Am. Chem. Soc. 1994, 116, 4038; Saenger, W. Principles of Nucleic Acid Structure; Cantor, C. R., Ed.; Springer-Verlag: New York, 1984.
17. Yamamoto, I.; Sekine, M.; Hata, T.; J. Chem. Soc. Perkin Trans. 1 1980, 306; Bannwarth, W. Helv. Chim. Acta 1988, 71, 1517.
18. Yamamoto, I.; Sekine, M.; Hata, T.; J. Chem. Soc. Perkin Trans. 1 1980, 306; Bannwarth, W. Helv. Chim. Acta 1988, 71, 1517.
19. Benson G. A; Spillane W. J. In The Chemistry of Sulphonic Acids, Esters and their Derivatives; Patai. S.; Rappoport, Z., Eds.; John Wiley & Sons: Chichester, 1991; pp. 947-1036.
20. DuBois, G. E.; Stephenson, R. A. J. Org. Chem. 1980, 45, 5371; DuBois, G. E. ibid. 1980, 45, 5373.
21. DuBois, G. E.; Stephenson, R. A. J. Org. Chem. 1980, 45, 5371; DuBois, G. E. ibid. 1980, 45, 5373.
22. Atkins, G. M.; Burgess, E. M.; J. Am. Chem. Soc. 1967, 89, 2502; Williams, A; Douglas, K.T. J. Chem. Soc. Perkin Trans. 2 1974, 1727.
23. Atkins, G. M.; Burgess, E. M.; J. Am. Chem. Soc. 1967, 89, 2502; Williams, A; Douglas, K.T. J. Chem. Soc. Perkin Trans. 2 1974, 1727.
24. 18 d(TnsnT) 65%, d(TnsnT) 45 %, d(TnsnA) >95 % and d(TnsnA) 60 %.
25. Rinkel, L. J.; Altona, C.; J. Biomol. Struct. Dyn. 1987, 4, 621.