Synthesis and transcription studies on 5′-triphosphates derived from 2′-C-branched-uridines: 2′-homouridine-5′-triphosphate is a substrate for T7 RNA polymerase

Organic and Biomolecular Chemistry

Volumn 2, Issue 6, 2004, Pages 869-875

  Pavey, John B J ^a   Lawrence, Anthony J ^a   O'Neil, Ian A ^a   Vortler, Stefan ^b   Cosstick, Richard ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; DEGRADATION; DNA; ELECTROPHORESIS; ENZYMES; EVAPORATION; HYDROLYSIS; POLYMERIZATION; RNA; SYNTHESIS (CHEMICAL);

GEL ELECTROPHORESIS; PHOSPHITYLATION;

PHOSPHATES;

BACTERIOPHAGE T7 RNA POLYMERASE; DNA DIRECTED RNA POLYMERASE; DRUG DERIVATIVE; URIDINE; URIDINE TRIPHOSPHATE; VIRUS PROTEIN;

ARTICLE; CHEMISTRY; GENETIC TRANSCRIPTION; GENETICS; METABOLISM; MUTATION; POLYACRYLAMIDE GEL ELECTROPHORESIS; SYNTHESIS;

DNA-DIRECTED RNA POLYMERASES; ELECTROPHORESIS, POLYACRYLAMIDE GEL; MUTATION; TRANSCRIPTION, GENETIC; URIDINE; URIDINE TRIPHOSPHATE; VIRAL PROTEINS;

EID: 1842586926     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b314348a     Document Type: Article

References (42)

1. For reviews see: (a) J. A. Bittker, K. J. Phillips and D. R. Liu, Curr. Opin. Chem. Biol., 2002, 6, 367; (b) D. S. Wilson and J. W. Szostak, Ann. Rev. Biochem., 1999, 68, 611; (c) R. R. Breaker, Chem. Rev., 1997, 97, 371.
2. For reviews see: (a) J. A. Bittker, K. J. Phillips and D. R. Liu, Curr. Opin. Chem. Biol., 2002, 6, 367; (b) D. S. Wilson and J. W. Szostak, Ann. Rev. Biochem., 1999, 68, 611; (c) R. R. Breaker, Chem. Rev., 1997, 97, 371.
3. For reviews see: (a) J. A. Bittker, K. J. Phillips and D. R. Liu, Curr. Opin. Chem. Biol., 2002, 6, 367; (b) D. S. Wilson and J. W. Szostak, Ann. Rev. Biochem., 1999, 68, 611; (c) R. R. Breaker, Chem. Rev., 1997, 97, 371.
4. P. J. Unrau and D. P. Bartel, Nature, 1998, 395, 260.
5. W. K. Johnston, P. J. Unrau, M. S. Lawrence, M. E. Glasner and D. P. Bartel, Science. 2001, 292, 1319.
6. (a) H. A. Held and S. A. Benner, Nucleic Acids Res., 2002, 30, 3857
7. (b) H. Sawai, A. N. Ozaki, F. Satoh, T. Ohbayashi, M. M. Masud and H. Ozaki, Chem. Commun., 2001, 2604
8. (c) T. Gourlain, A. Sidorov, N. Mignet, S. J. Thorpe, S. E. Lee, J. A. Grasby and D. M. Williams, Nucleic Acids Res., 2001, 29, 1898
9. (d) O. Thum, S. Jager and M. Famulok, Angew. Chem., Int. Ed., 2001, 40, 3990
10. (e) K. Sakthivel and C. F. Barbas, Angew. Chem., Int. Ed., 1998, 37, 2872.
11. N. K. Vaish, A. W. Fraley, J. W. Szostak and L. W. McLaughlin, Nucleic Acids Res., 2000, 28, 3316.
12. L. Lermer, Y. Roupioz, R. Ting and D. M. Perrin, J. Am. Chem. Soc., 2002, 124, 9960; (a) D. M. Perrin, T. Garestier and C. Helene, J. Am. Chem. Soc., 2001, 123, 1556; (b) S. W. Santoro, G. F. Joyce, K. Sakthivel, S. Gramatikova and C. F. Barbas, J. Am. Chem. Soc., 2000, 122, 2433; (c) T. M. Tarasow, S. L. Tarasow and B. E. Eaton, Nature, 1997, 389, 54.
13. L. Lermer, Y. Roupioz, R. Ting and D. M. Perrin, J. Am. Chem. Soc., 2002, 124, 9960; (a) D. M. Perrin, T. Garestier and C. Helene, J. Am. Chem. Soc., 2001, 123, 1556; (b) S. W. Santoro, G. F. Joyce, K. Sakthivel, S. Gramatikova and C. F. Barbas, J. Am. Chem. Soc., 2000, 122, 2433; (c) T. M. Tarasow, S. L. Tarasow and B. E. Eaton, Nature, 1997, 389, 54.
14. L. Lermer, Y. Roupioz, R. Ting and D. M. Perrin, J. Am. Chem. Soc., 2002, 124, 9960; (a) D. M. Perrin, T. Garestier and C. Helene, J. Am. Chem. Soc., 2001, 123, 1556; (b) S. W. Santoro, G. F. Joyce, K. Sakthivel, S. Gramatikova and C. F. Barbas, J. Am. Chem. Soc., 2000, 122, 2433; (c) T. M. Tarasow, S. L. Tarasow and B. E. Eaton, Nature, 1997, 389, 54.
15. L. Lermer, Y. Roupioz, R. Ting and D. M. Perrin, J. Am. Chem. Soc., 2002, 124, 9960; (a) D. M. Perrin, T. Garestier and C. Helene, J. Am. Chem. Soc., 2001, 123, 1556; (b) S. W. Santoro, G. F. Joyce, K. Sakthivel, S. Gramatikova and C. F. Barbas, J. Am. Chem. Soc., 2000, 122, 2433; (c) T. M. Tarasow, S. L. Tarasow and B. E. Eaton, Nature, 1997, 389, 54.
16. (a) S. P. Zinnen, K Domenico, M. Wilson, B. A. Dickinson, A. Beaudry, V. Mokler, A. T. Daniher, A. Burgin and L. Beigelman, RNA, 2002, 8, 214
17. (b) M. Sioud and D. R. Sørensen, Nature Biotech., 1998, 16, 556.
18. (a) A. De Mesmaeker, R. Haner, P. Martin and H. E. Moser, Acc. Chem. Res., 1995, 28, 366
19. (b) B. E. Eaton and W. A. Pieken, Ann. Rev. Biochem., 1995, 64, 837.
20. S. P. Ryder, L. Ortoleva-Donnolly, A. B. Kosek and S. A. Strobel, Methods Enzymol., 2000, 317, 92.
21. C. Raines and P. A. Gottleib, RNA, 1998, 4, 340.
22. R. Sousa and R. Padilla, EMBO J., 1995, 14, 4609.
23. H. Aurup, D. M. Williams and F. Eckstein, Biochemistry, 1992, 31, 9636.
24. R. Padilla and R. Sousa, Nucleic Acids Res., 1999, 27, 1561.
25. 4 R. Padilla and R. Sousa, Nucleic Acids Res., 2002, 30, e138.
26. F. Conrad, A. Hanne, R. K. Gaur and G. Krupp, Nucleic Acids Res., 1995, 23, 1845.
27. A. J. Lawrence, J. B. J. Pavey, I. A. O'Neil and R. Cosstick, Tetrahedron Lett., 1995, 36, 6341.
28. J. B. J. Pavey, A. J. Lawrence, A. J. Potter, R. Cosstick and I. A. O'Neil, Tetrahedron Lett., 1998, 39, 6967.
29. A. J. Lawrence, J. B. J. Pavey, I. A. O'Neil and R. Cosstick, J. Org. Chem., 1996, 61, 9213.
30. J. Ludwig and F. Eckstein, J. Org. Chem., 1989, 54, 631.
31. A. J. Lawrence, J. B. J. Pavey, M.-Y. Chan, R. Fairhurst, S. Collingwood, J. Fisher, Cosstick and I. A. O'Neil, J. Chem. Soc., Perkin Trans. 1, 1997, 2761.
32. J. P. Richard and P. A. Frey, J. Am. Chem. Soc., 1982, 104, 3476.
33. D. M. Brown, M. Fried and A. R. Todd, Chem. Ind. (London), 1953, 352.
34. J. F. Milligan, D. R. Groebe, G. W. Witherell and O. Uhlenbeck, Nucleic Acids Res., 1987, 15, 8783.
35. Y. Huang, A. Beaudry, J. McSwiggen and R. Sousa, Biochemistry, 1997, 36, 13718.
36. S. Tabor and C. Richardson, Proc. Natl. Acad. Sci. USA, 1989, 86, 4076.
37. J. Sambrook, E. F. Fritsch, T. Maniatis, Molecular Cloning: A Laboratory Manual, 2 ed, Cold Spring Harbor Laboratory Press, NY, 1989.
38. G. Gish and F. Eckstein, Science, 1988, 240, 1520.
39. Y. Huang, F. Eckstein, R. Padilla and R. Sousa, Biochemistry, 1997, 36, 8231.
40. C. M. Joyce, Proc. Natl. Acad Sci. USA, 1997, 94, 1619.
41. W. Saenger, in Principles of Nucleic acid Structure, ed. W. Saenger, Springer, New York, 1984.
42. C. Altona and M. Sundaralingam, J. Am. Chem. Soc., 1973, 93, 2333.