Boranophosphate backbone: A mimic of phosphodiesters, phosphorothioates, and methyl phosphonates

Methods in Enzymology

Volumn 313, Issue , 2000, Pages 226-257

  Shaw, Barbara Ramsay ^a   Sergueev, Dmitri ^a   He, Kaizhang ^a   Porter, Ken ^a   Summers, Jack ^a   Sergueeva, Zinaida ^a   Rait, Vladimir ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; OLIGODEOXYNUCLEOTIDE DERIVATIVE; OLIGODEOXYNUCLEOTIDE PHOSPHOROTHIOATE; OLIGODEOXYRIBONUCLEOSIDE METHYLPHOSPHONATE;

ARTICLE; CHEMICAL ANALYSIS; CONTROLLED STUDY; DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ION EXCHANGE CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; THERMOSTABILITY;

EID: 0033990454     PISSN: 00766879     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0076-6879(00)13015-0     Document Type: Article

References (70)

1. A. Sood, B. R. Shaw, and B. Spielvogel, J. Am. Chem. Soc. 112, 9000 (1990).
2. J. Summers and B. R. Shaw, in preparation (1998).
3. B. R. Shaw, J. Madison, A. Sood, and B. F. Spielvogel, Methods Mol. Biol. 20, 225 (1993).
4. F. Eckstein, Annu. Rev. Biochem. 54, 367 (1985).
5. P. S. Miller, in "Antisense RNA and DNA" (J. A. H. Murray, ed.), p. 241. Wiley-Liss, New York, 1992.
6. J. S. Summers, D. Roe, P. D. Boyle, M. Colvin, and B. R. Shaw, Inorg. Chem. 37, 4158 (1998).
7. F. Huang, Ph.D. dissertation, Duke University (1994).
8. J. G. Wilson, Chem. Rev. 98, 2389 (1998).
9. J. Tomasz, B. R. Shaw, K. Porter, B. Spielvogel, and A. Sood, Angew. Chem. Int. Ed. Eng. 31, 1373 (1992).
10. K. W. Porter, J. D. Briley, and B. R. Shaw, Nucleic Acids Res. 25, 1611 (1997).
11. K. He, A. Hasan, B. K. Krzyzanowska, and B. R. Shaw, J. Org. Chem. 63, 5769 (1998).
12. B. K. Krzyzanowska, K. He, A. Hasan, and B. R. Shaw, Tetrahedron 54, 5119 (1998).
13. D. Sergueev and B. R. Shaw, J. Am. Chem. Soc. 120, 9417 (1998).
14. H. Li, K. Porter, F. Huang, and B. R. Shaw, Nucleic Acids Res. 21, 4495 (1995).
15. K. He and B. R. Shaw, in preparation (1999).
16. F. Huang, A. Sood, B. F. Spielvogel, and B. R. Shaw, J. Biol. Struct. Dyn. 10, a078 (1993).
17. V. Rait and B. R. Shaw, Antisense Nucleic Acid Drug Dev., in press.
18. C. A. Stein and Y.-C. Cheng, Science 261, 1004 (1993).
19. L. Cummins, D. Graff, G. Beaton, W. S. Marshall, and M. H. Caruthers, Biochemistry 35, 8734 (1996).
20. M. K. Ghosh, K. Ghosh, O. Dahl, and J. C. Cohen, Nucleic Acids Res. 21, 5761 (1993).
21. A. Kers, I. Kers, A. Kraszewski, M. Sobkowski, T. Szabo, M. Thelin, R. Zain, and J. Stawinski, Nucleosides Nucleotides 15, 361 (1996).
22. D. Sergueev, A. Hasan, M. Raraaswamy, and B. Ramsay Shaw, Nucleosides Nucleotides 16, 1533 (1997).
23. B. C. Froehler, in "Protocols for Oligonucleotides and Analogs" (S. Agrawal, ed.), p. 63. Humana Press, Totowa, 1993.
24. A. Kume, M. Fuju, M. Sekine, and T. Hata, J. Org. Chem. 49, 2139 (1984).
25. C. L. Lane, Chem. Rev. 76, 773 (1976).
26. T. Reetz, J. Am. Chem. Soc. 82, 5039 (1960).
27. C. J. Foret, K. R. Korzekwa, and D. R. Martin, J. Inorg. Nucleic Chem. 42, 1223 (1980).
28. P. J. Garegg, I. Lindh, T. Regberg, J. Stawinski, and R. Stromberg, Tetrahedron Lett. 27, 4051 (1986).
29. Y.-Q. Chen, F.-C. Qu, and Y.-B. Zhang, Tetrahedron Lett. 36, 745 (1995).
30. K. He, D. Sergueev, Z. Sergueev, and B. R. Shaw, Tetrahedron Lett., in press.
31. Y. Jin and G. Just, Tetrahedron Lett. 39, 6433 (1998).
32. Z. A. Sergueeva, D. S. Sergueev, and B. R. Shaw, Tetrahedron Lett. 40, 2041 (1999).
33. J. Zhang, T. Terhorst, and M. D. Matteucci, Tetrahedron Lett. 38, 4957 (1997).
34. A. P. Higson, A. Sierzchala, H. Brummel, Z. Zhao, and M. H. Caruthers, Tetrahedron Lett. 39, 3899 (1998).
35. D. S. Sergueev, Z. A. Sergueeva, and B. R. Shaw, unpublished data (1998).
36. G. E. Ryschkewitsch and E. R. Birnbaum, Inorg. Chem. 4, 575 (1965).
37. S. Matsumura and N. Tokura, Tetrahedron Lett. 9, 4703 (1968).
38. L. E. Benjamin, D. A. Carvalho, S. F. Stafiej, and E. A. Takacs, Inorg. Chem. 9, 1844 (1970).
39. G. E. Ryschkewitsch and V. R. Miller, J. Am. Chem. Soc. 95, 2836 (1973).
40. Y. Jin and G. Just, Tetrahedron Lett. 39, 6429 (1998).
41. S. Sergueev, Z. A. Sergueeva, and B. R. Shaw, unpublished data (1998).
42. A. Hasan, H. Li, J. Tomasz, and B. R. Shaw, Nucleic Acids Res. 24, 2150 (1996).
43. A. Sood, B. R. Shaw, B. F. Spielvogel, E. S. Hall, L. K. Chi, and I. H. Hall, Pharmazie 47, 833 (1992).
44. F. Eckstein, P. J. Romaniuk, and B. A. Connolly, Methods Enzymol. 87, 197 (1982).
45. P. A. Frey, J. P. Richard, H. Ho, R. S. Brody, R. D. Sammons, and K. Sheu, Methods Enzymol. 87, 213 (1982).
46. K. R. Birikh, P. A. Heaton, and F. Eckstein, Eur. J. Biochem. 245, l (1997).
47. P. A. Frey, Adv. Enzymol. 62, 119 (1989).
48. K. He, K. Porter, A. Hasan, D. Briley, and B. R. Shaw, Nucleic Acids Res., in press.
49. J. Ludwig and F. Eckstein, J. Org. Chem. 54, 631 (1989).
50. R. A. Jones, in "Oligonucleotide Synthesis: A Practical Approach" (M. J. Gait, ed.), p. 23. IRL Press, Oxford, 1984.
51. V. Rait and B. R. Shaw, unpublished data (1998).
52. K. Porter and B. R. Shaw, unpublished data (1997).
53. C. A. Stein, C. Subasinghe, K. Shinozuka, and J. S. Cohen, Nucleic Acids Res. 16, 3209 (1988).
54. L. J. Maher III and B. J. Dolnick, Nucleic Acids Res. 16, 3341 (1988).
55. P. J. Furdon, Z. Dominski, and R. Kole, Nucleic Acids Res. 18, 9193 (1989).
56. L. Cummins, D. Graff, G. Beaton, W. S. Marshal, and M. H. Caruthers, Biochemistry 35, 8734 (1996).
57. P. D. Cook, in "Antisense Research and Applications" (S. T. Crooke and B. Lebleu, eds.), p. 149. CRC Press, Boca Raton, FL, 1993.
58. R. Blake and J. Fresco, Biopolymers 12, 775 (1973).
59. C. R. Cantor, M. M. Warshaw, and H. Shapiro, Biopolymers 9, 1059 (1970).
60. J. Li and R. M. Wartell, Biochemistry 37, 5154 (1998).
61. D. M. Tidd, in "Antisense Therapeutics: Progress and Reports" (G. L. Trainor, ed.), p. 51. ESCOM Science Publishers B.V., Leiden, 1996.
62. R. V. Giles and D. M. Tidd, Anti-Cancer Drug Res. 7, 37 (1992).
63. M. K. Ghosh, K. Ghosh, and J. S. Cohen, Anti-Cancer Drug Res. 8, 15 (1993).
64. R. V. Giles, C. J. Rudell, D. G. Spiller, J. A. Green, and D. M. Tidd, Nucleic Acids Res. 23, 954 (1995).
65. R. V. Giles, D. G. Spiller, J. Grzymbowski, R. E. Clark, P. Nicklin, and D. M. Tidd, Nucleic Acids Res. 26, 1567 (1998).
66. R. J. Crouch and M. L. Dirksen, in "Nucleases" (S. M. Linn and R. J. Roberts, eds.), p. 211. Cold Spring Harbor Press, Cold Spring Harbor, NY, 1982.
67. R. F. Borch, M. D. Bernstein, and H. D. Durst, J. Am. Chem. Soc. 93, 2897 (1971).
68. V. K. Rait and B. R. Shaw, in preparation (1999).
69. H. Li, C. Hardin, and B. R. Shaw, J. Am. Chem. Soc. 118, 6606 (1996).
70. H. Li, F. Huang, and B. R. Shaw, Bioorg. Med. Chem. 5, 787 (1997).