Synthesis of the analogue nucleoside 3-deaza-2'-deoxycytidine and its template activity with DNA polymerase

Tetrahedron

Volumn 55, Issue 41, 1999, Pages 11985-11996

  Searls, Tim ^a   McLaughlin, Larry W ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

Hydrogen bonding; Nucleic acid analogues; Polymerization; Pyridones

Indexed keywords

DEOXYCYTIDINE; DNA DIRECTED DNA POLYMERASE; NITROGEN DERIVATIVE; NUCLEOSIDE ANALOG; PYRIMIDINE DERIVATIVE;

ARTICLE; BASE PAIRING; DNA TEMPLATE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME STABILITY; HYDROGEN BOND; NONHUMAN; POLYMERIZATION; PRIORITY JOURNAL;

EID: 0033536648     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00703-6     Document Type: Article

References (27)

1. Bloch, A.; Gutschman, G.; Currie, G. L.; Robins, R. K.; Robins, M. J. J. Med. Chem. 1973, 16, 294.
2. Khare, G. P.; Sidwell, R. W.; Huffman, J. H.; Tolman, R. L.; Robins, R. K. Proc. Soc. Exp. Biol. Med. 1972, 40, 990.
3. Devadas, B.; Rogers, T. E.; Gray, S. H. Synthetic Communications 1995, 25, 3199.
4. Momparler, R. L.; Momparler, L. F. Antiviral Research 1989, 12, 259.
5. Currie, B. L.; Robins, R. K.; Robins, M. J. J. Heterocyclic Chem. 1970, 7, 323.
6. Cook, D.; Day, R. T.; Robins, R. K. J. Heterocyclic Chem. 1977, 14, 1295.
7. Morales, J. C.; Kool, E. T. Nat. Struct. Biol. 1995, 5, 950.
8. Niedballa, U.; Vorbruggen, H. J. J. Org. Chem. 1974, 39, 2654.
9. Matteucci, M. D.; Caruthers, M. H. J. Am. Chem. Soc. 1981, 103, 3185.
10. Watkins, B. E.; Kiely, J. S.; Rapoport, H. J. Am. Chem. Soc. 1982, 104, 5702.
11. Watkins, B. E.; Rapoport, H. J. Org. Chem. 1982, 47, 4471.
12. McLaughlin, L. W.; Benseler, F. Synthesis 1986, 45.
13. Stryer, L. Biochemistry, 4th Ed., W.H. Freeman, New York 1995, 89.
14. Watson, J. D.; Hopkins, N. H.; Robertson, W.; Steitz, J. A.; Weiner, A. M. Molecular Biology of the Gene Benjamin Cummings, Menlo Park 1987.
15. Loeb, L. A.; Kunkel, T. A. Annu. Rev. Biochem. 1982, 52, 429.
16. Carroll, S. S.; Benkovic, S. J. Chem. Rev. 1990, 90, 1291.
17. Echols, H.; Goodman, M. F. Annu. Rev. Biochem. 1991, 60, 477.
18. El Deiry, W. S.; So, A. G.; Downey, K. M. Biochemistry 1988, 27, 546.
19. Joyce, C. M.; Sun, X. C.; Grindley, N. D. J. Biol Chem. 1992, 267, 24485.
20. Goodman, M. F. Proc. Natl. Acad. Sci. USA 1997, 94, 10493.
21. Kornberg, A.; Baker, A., DNA Replication, 2nd Ed. W.H. Freeman, New York 1992.
22. Brutlag, D.; Komberg, A. J. Biol. Chem. 1972, 247, 241.
23. Kunkel, T. A.; Eckstein, F.; Mildvan, A. S.; Koplitz, R. M.; Loeb, L. A. Proc. Natl. Acad. Sci. USA 1981, 78, 6734.
24. Schwietzer, B. A.; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 1864.
25. Guckian, K. M.; Kool, E. T. Agnew. Chem. Int. Ed. 1998, 36, 2825.
26. Evans, T. A.; Seddon, K. R. Chem. Commun. 1997, 2023.
27. Moran, S.; Ren, R.X.-F.; Kool, E.T. Proc. Natl. Acad. Sci. USA 1997, 94, 10506.