Introducing structural diversity in oligonycleotides via photolabile, convertible C5-substituted nucleotides

Journal of the American Chemical Society

Volumn 121, Issue 4, 1999, Pages 597-604

  Kahl, Jeffrey D ^a   Greenberg, Marc M ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOTIDE; OLIGONUCLEOTIDE;

ARTICLE; CHEMICAL BOND; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IRRADIATION; OXIDATION REDUCTION REACTION; PHOTOLYSIS; PHOTOREACTIVITY; REACTION ANALYSIS; SOLID PHASE EXTRACTION; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033518570     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983273r     Document Type: Article

References (39)

1. Zuckerman, R. N.; Corey, D. R.; Schultz, P. G. J. Am. Chem. Soc. 1988, 110, 1614.
2. Truffert, J.-C.; Asseline, U.; Brack, A.; Thuong, N. T. Tetrahedron 1996, 52, 3005.
3. Prober, J. M.; Trainor, G. L.; Dam, R. J.; Hobbs, F. W.; Robertson, C. W.; Zagursky, R. J.; Cocuzza, A. J.; Jensen, M. A.; Baumeister, K. Science 1987, 238, 336.
4. Carmi, N.; Shultz, L. A.; Breaker, R. R. Chem. Biol. 1996, 3, 1039.
5. Osborne, S. E.; Ellington, A. D. Chem. Rev. 1997, 97, 349.
6. Santoro, S. W.; Joyce, G. F. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 4262.
7. Eaton, B. E.; Pieken, W. A. Annu. Rev. Biochem. 1995, 64, 837.
8. Tarasow, T. M.; Tarasow, S. L.; Eaton, B. E. Nature 1997, 389, 54.
9. Dewey, T. M.; Mundt, A. A.; Crouch, G. J.; Zyzniewski, M. C.; Eaton, B. E. J. Am. Chem. Soc. 1995, 117, 8474.
10. (a) Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconj. Chem. 1997, 8, 271.
11. (b) Kohgo, S.; Shinozuka, K.; Ozaki, H.; Sawai, H. Tetrahedron Lett. 1998, 39, 4067.
12. Colocci, N.; Dervan, P. B. J. Am. Chem. Soc. 1994, 116, 785.
13. (a) Moser, H. E.; Dervan, P. B. Science 1987, 238, 645.
14. (b) Dreyer, G. B.; Dervan, P. B. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 968.
15. Hurley, D. J.; Tor, Y. J. Am. Chem. Soc. 1998, 120, 2194.
16. (a) Bashkin, J. K.; Xie, J.; Daniher, A. T.; Sampath, U.; Kao, L.-F. J. Org. Chem. 1996, 61, 2314.
17. (b) Bashkin, J. K.; McBeath, R. J.; Modak, A. S.; Sample, K. R.; Wise, W. B. J. Org. Chem. 1991, 56, 3168.
18. Pomerantz, S. C.; McCloskey, J. A.; Tarasow, T. M.; Eaton, B. E. J. Am. Chem. Soc. 1997, 119, 3861.
19. Allerson, C. R.; Chen, S. L.; Verdine, G. L. J. Am. Chem. Soc. 1997, 119, 7423.
20. Harris, C. M.; Zhou, L.; Strand, E. A.; Harris, T. M. J. Am. Chem. Soc. 1991, 113, 4328.
21. (a) Xu, Y.-Z.; Zheng, Q.; Swann, P. F. J. Org. Chem. 1992, 57, 3839.
22. (b) Xu, Y.-Z. Tetrahedron 1996, 52, 10737.
23. (a) McMinn, D. L.; Matray, T. J.; Greenberg, M. M. J. Org. Chem. 1997, 62, 7074.
24. (b) McMinn, D. L.; Greenberg, M. M. J. Am. Chem. Soc. 1998, 120, 3289.
25. Kahl, J. D.; McMinn, D. L.; Greenberg, M. M. J. Org. Chem. 1998, 63, 4870.
26. Kahl, J. D.; Greenberg, M. M. J. Org. Chem. In press.
27. (a) Haralambidis, J.; Angus, K.; Pownall, S.; Duncan, L.; Chai, M.; Tregear, G. W. Nucleic Acids Res. 1990, 18, 501.
28. (b) Kremsky, J. N.; Pluskal, M.; Casey, S.; Perry-O'Keefe, H.; Kates, S. A.; Sinha, N. D. Tetrahedron Lett. 1996, 37, 4313.
29. McMinn, D. L.; Greenberg, M. M. Tetrahedron 1996, 52, 3827.
30. (a) Hobbs, F. W. J. Org. Chem. 1989, 54, 3420.
31. (b) Casalnuovo, A. L.; Calabrese, J. C. J. Am. Chem. Soc. 1990, 112, 4324.
32. (c) Osborne, S. E.; Cain, R. J.; Glick, G. D. J. Am. Chem. Soc. 1997, 119, 1172.
33. McMinn, D. L.; Greenberg, M. M. Tetrahedron Lett. 1997, 38, 3123.
34. Venkatesan, H.; Greenberg, M. M. J. Org. Chem. 1996, 61, 525.
35. McGall, G. H.; Barone, A. D.; Diggelmann, M.; Fodor, S. P. A.; Gentalen, E.; Ngo, N. J. Am. Chem. Soc. 1997, 119, 5081.
36. See Supporting Information.
37. The yields were determined as described in the footnote to Table 1 and in refs 19a and 19b.
38. Eaton, B. E.; Gold, L.; Hicke, B. J.; Janji'c, N.; Jucker, F. M.; Sebesta, D. P.; Tarasow, T. M.; Willis, M. C.; Zichi, D. A. Bioorganic Med. Chem. 1997, 5, 1087.
39. Majetich, G.; Casares, A.; Chapman, D.; Behnke, M. J. Org. Chem. 1986, 51, 1745.