Base-modified phosphoramidite analogs of pyrimidine ribonucleosides for RNA structure-activity studies

Methods in Enzymology

Volumn 317, Issue , 2000, Pages 39-65

  Beigelman, Leonid ^a   Matulic Adamic, Jasenka ^a   Karpeisky, Alexander ^a   Haeberli, Peter ^a   Sweedler, David ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHORAMIDIC ACID DERIVATIVE; PYRIMIDINE DERIVATIVE; RIBONUCLEOSIDE DERIVATIVE;

ARTICLE; LIGAND BINDING; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PRIORITY JOURNAL; REACTION ANALYSIS; RNA BINDING; RNA STRUCTURE; STRUCTURE ACTIVITY RELATION;

EID: 0034131473     PISSN: 00766879     EISSN: None     Source Type: Book Series    
DOI: 10.1016/s0076-6879(00)17005-3     Document Type: Article

References (55)

1. D. D. Perrin and W. L. Armarego, "Purification of Laboratory Chemicals," 3rd Ed. Pergamon, New York, 1988.
2. N. Usman, K. K. Ogilvie, M.-Y. Jiang, and R. J. Cedergren, J. Am. Chem. Soc. 109, 7845 (1987).
3. M. Smith, D. H. Rammler, I. H. Goldberg, and H. G. Khorana, J. Am. Chem. Soc. 84, 430 (1962).
4. K. K. Ogilve, K. L. Sadana, E. A. Thompson, M. A. Quilliam, and B. Westmore, Tetrahedron Lett. 15, 2861 (1974).
5. N. Sinha, J. Biernat, and H. Koster, Tetrahedran Lett 24, 5843 (1983).
6. S. L. Beaucage and R. P. Iyer, Tetrahedron Lett. 48, 2251 (1992).
7. L. Beigelman, A. Karpeisky, and N. Usman, Bioorg. Med. Chem. Lett. 4, 1715 (1994).
8. R. I. Ferrier and R. H. Furnaux, Carbohydr. Res. 52, 63 (1976).
9. G. H. Hakimelahi, Z. A. Proba, and K. K. Ogilvie, Can. J. Chem. 60, 1106 (1982).
10. T. Tuschl, M. M. P. Ng, W. Pieken, F. Benseler, and F. Eckstein, Biochemistry 32, 658 (1993).
11. S. A. Scaringe, C. Franclyn, and N. Usman, Nucleic Acids Res. 18, 5433 (1990).
12. J. Matulic-Adamic, L. Beigelman, S. Portmann, M. Egli, and N. Usman, J. Org. Chem. 61, (11), 3909 (1996).
13. S. Czernecki and G. Ville, J. Org. Chem. 54, 610 (1989).
14. H. S. Jensen, G. Limberg, and C. Pedersen, Carbohydr. Res. 302, 109 (1997).
15. K. K. Ogilvie in "Nucleosides and Nucleotides and Their Biological Applications," p. 209. Academic Press, San Diego, 1983.
16. J. A. Piccirilli, T. Krauch, L. J. MacPherson, and S. A. Benner, Helv. Chem. Acta. 74, 397 (1991).
17. N. C. Chaudhuri and E. T. Kool, Tetrahedron Lett. 36, 1795 (1995).
18. H. Vorbrüggen and B. Bennua, Tetrahedron Lett. 19, 1339 (1978).
19. E. Lukevics and A. Zablocka, "Nucleoside Synthesis, Organosilicon Methods." Ellis Horwood, 1991.
20. H. Pischel and G. Wagner, Arch. Pharm. (Weinheim) 300, 602 (1967).
21. U. Niedballa and H. Vorbrüggen, J. Org. Chem. 39, 3668 (1974).
22. H. Vorbrüggen, K. Krolikiewicz, and B. Bennua, Chem. Ber. 114, 1234 (1981).
23. L. W. Dudycz and G. E. Wright, Nucleosides and Nucleotides 3, 34 (1984).
24. L. Birkofer, A. Ritter, and H.-P. Kühlthau, Chem. Ber. 97, 934 (1964).
25. U. Niedballa and H. Vorbrüggen, "Nucleic Acid Chemistry" (L. B. Townsend and R. S. Tipson, eds.), Part 1, pp. 481-484. J. Wiley & Sons, New York, 1978.
26. M. P. Schweizer, E. B. Benta, J. T. Witkowski, and R. K. Robins, J. Am. Chem. Soc. 95, 3370 (1987).
27. U. Niedballa and H. Vorbrüggen, J. Org. Chem. 39, 3660 (1974).
28. H. Vorbrüggen and K. Krolikiewitcz, Angew. Chem. Int. Ed. Ingl. 14, 421 (1975).
29. W. L. Sung, J. Org. Chem. 47, 3623 (1982).
30. K. J. Divakar and C. B. Reese, J. Chem. Soc. Perkin Trans. 1, 1171 (1982).
31. R. Kierzek, Nucleosides & Nucleotides 14, 255 (1995).
32. F. Wincott, A. DiRenzo, C. Shaffer, S. Grimm, D. Tracz, C. Workman, D. Sweedler, C. Gonzalez, S. Scaringe, and N. Usman, Nucleic Acids Res. 23, 2677 (1995).
33. B. Sproat, F. Colonna, B. Mullah, D. Tsou, A. Andrus, and A. Hampel, Nudeosides & Nucleotides 14, 255 (1995).
34. M. Lyttle, P. Wright, N. Sinha, I. Bain, and A. Chamberlin, J. Org Chem. 56, 4608 (1991).
35. J. T. Goodwin, W. A. Stanick, and G. D. Glick, J. Org Chem. 59, 7941 (1994).
36. M. P. Reddy, N. B. Hanna, and F. Farooqui, Tetrahedron Lett. 35, 4311 (1994).
37. F. Wincott and N. Usman, in "Methods in Molecular Biology" (P. C. Turner, ed.), Vol. 74, p. 59. Humana Press, 1997.
38. H. J. Fritz, R. Belagaje, E. L. Brown, R. H. Fritz, R. A. Jones, R. F. Lees, and H. G. Khorana, Biochemistry 17, 1225 (1978).
39. R. Vinayak, in "Methods in Molecular Biology" (P. C. Turner, ed.), Vol. 74, p. 51. Humana Press, 1997.
40. J. S. Eadie, J. McBride, J. Lincoln, W. Efscavitch, L. B. Hoff, and R Cathcart, Anal. Biochem. 165, 442 (1987).
41. S. A. Strobel, T. R. Cech, N. Usman, and L. Beigelman, Biochemistry 33, 13824 (1994).
42. P. A. Limbach, Mass Spectrom. Rev. 15, 297 (1996).
43. R. W. Ball and L. C. Packman, Anal. Biochem. 246, 185 (1997).
44. T. A. Millican, G. A. Mock, M. A. Chauncey, T. P. Patel, M. A. Eaton, J. Cunning, S. D. Cutbush, S. Neidle, and J. Mann, Nucleic Acids Res. 12, 7435 (1984).
45. N. Usman, L. Beigelman, and J. A. McSwiggen, Curr. Opin. Struct. Biol. 1, 527 (1996).
46. L. Beigelman A. Karpeisky, J. Matulic-Adamic, C. Gonzalez, and N. Usman, Nucleosides & Nucleotides 14, 907 (1995).
47. A. Peracchi, A. Karpeisky, L. Maloney, L Beigelman, and D. Herschlag, Biochemistry 37, 14765 (1998).
48. S. Schmidt, L. Beigelman, A. Karpeisky, N. Usman, U. S. Sorensen, and M. J. Gait, Nucleic Acids Res. 24, 573 (1996).
49. Q. Lin, J. B. Green, A. Khodadadi, P. Haeberli, L. Beigelman, and A. M. Pyle, J. Mol. Biol. 267, 163 (1997).
50. N. Baidya, G. E. Ammons, J. Matulic-Adamic, A. Karpeisky, L. Beigelman, and O. C. Uhlenbeck, RNA 3, 1135 (1997).
51. A. Peracchi, L. Beigelman, N. Usman, and D. Herschlag, PNAS 93, 11522 (1996).
52. A. Peracchi, J. Matulic-Adamic, S. Wang, L. Beigelman, and D. Herschlag, RNA 4, 1332 (1998).
53. A. B. Burgin, Jr., C. Gonzalez, J. Matulic-Adamic, A. M. Karpeisky, N. Usman, J. A. McSwiggen, and L. Beigelman, Biochemistry 35, 14090 (1996).
54. L. Beigelman, A. Karpeisky, and N. Usman, Nucleosides & Nucleotides 14, 895 (1995).
55. Li Deng, L. Beigelman, J. Matulic-Adamic, A. Karpeisky, and P. D. Gershon, J. Biol. Chem. 272, 31542 (1997).