Determinants of unnatural nucleobase stability and polymerase recognition

Journal of the American Chemical Society

Volumn 125, Issue 32, 2003, Pages 9638-9646

  Henry, Allison A ^a   Yu, Chengzhi ^a   Romesberg, Floyd E ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOBASE STABILITY;

DNA; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); THERMODYNAMICS;

ENZYMES;

DNA POLYMERASE; NUCLEIC ACID BASE; OXYGEN; SULFUR;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ARTICLE; ATOM; DERIVATIZATION; DNA REPLICATION; HYDROGEN BOND; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; PRODUCTIVITY; PROTEIN CROSS LINKING; PROTEIN FOLDING; PROTEIN STABILITY; STEREOCHEMISTRY; THERMOSTABILITY;

BASE PAIRING; DNA; DNA REPLICATION; DNA-DIRECTED DNA POLYMERASE; KINETICS; NUCLEOSIDES;

EID: 0043127158     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035398o     Document Type: Article

References (30)

1. Bain, J. D.; Switzer, C.; Chamberlin, A. R.; Benner, S. A. Nature 1992, 356, 537-539.
2. Horlacher, J.; Hottiger, M.; Podust, V. N.; Hübscher U.; Benner. S. A. Proc. Natl. Acad. Sci. U.S.A., 1995, 92, 6329-6333.
3. Lutz, M. J.; Held, H. A.; Hottiger, M.; Hübscher, U.; Benner, S. A. Nucleic Acids Res. 1996, 24, 1308-1313.
4. Lutz, M. J.; Horlacher, J.; Benner, S. A. Bioorg. Med. Chem. Lett. 1998, 8, 1149-1152.
5. Lutz, S.; Burgstaller, P.; Benner, S. A. Nucleic Acids Res. 1999, 27, 2792-2798.
6. Moran, S.; Ren, R. X.-F.; Rumney, S. I.; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057.
7. Moran, S.; Ren, R. X.-F.; Kool, E. T. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 10506-10511
8. Morales, J. C.; Kool, E. T. Nat. Struct. Biol. 1998, 5, 950-954.
9. Kool, E. T. Biopolymers 1998, 48, 3-17.
10. Kool, E. T.; Morales, J. C.; Guckian, K. M. Angew. Chem., Int. Ed. 2000, 39, 990-1009.
11. McMinn, D. L.; Ogawa, A. K.; Wu, Y.: Liu, J.; Schultz, P. G.,; Romesberg F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586.
12. Ogawa, A. K.; Wu, Y.; McMinn, D. L.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 3274-3287.
13. Wu, Y.; Ogawa, A. K.; Berger, M.; McMinn, D. L.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 7621-7632.
14. Ogawa, A. K.; Wu, Y.; Berger, M.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 8803-8804.
15. Tae, E. L.; Wu, Y. Q.; Xia, G.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2001, 123, 7439-7440.
16. Berger, M.; Luzzi, S. D.; Henry, A. A.; Romesberg, F. E. J. Am. Chem. Soc. 2002, 124, 1222-1226.
17. Yu, C.; Henry, A. A.; Romesberg, F. E.; Schultz, P. G. Angew. Chem., Int. Ed. 2002, 41, 3841-3844.
18. Bergman, E. D.; Weiler-Feilchenfeld. In The Dipole Moments of Purines; Bergman, E. D., Pullman, B., Eds.; The Israel Academy of Sciences and Humanities: Jerusalem, 1971; pp 21-28.
19. Lister, J. H. The Purines. Supplement 1; John Wiley and Sons: New York, 1996: Vol. 54.
20. Hurst, D. T. An Introduction to the Chemistry and Biochemistry of Pyrimidines, Purines and Pteridines; Page Bros.: Norwich, U. K., 1980.
21. Gilchrist, T. L. Heterocyclic Chemistry; Longman Scientific & Technical: Essex, 1985.
22. Bugg, C. E. In Solid-state packing patterns of purine bases; Bergmann, E. D., Pullman, B., Eds.; The Israel Academy of Sciences and Humanities: Jerusalem, 1971; pp 178-204.
23. Guo, M.-J.; Hildbrand, S.; Leumann, C. J.; McLaughlin, L. W.; Waring, M. J. Nucleic Acids Res. 1998, 26, 1863-1869.
24. Shiotani, S.; Morita, H. J. Heterocyclic Chem. 1982, 19, 1207-1209.
25. Niedballa, U.; Vorbruggen, H. J. Org. Chem. 1974, 39, 3654-3660.
26. Chen, A.; Zheng, Y.; Zhou, X. Synth. Commun. 1999. 29, 3421-3423.
27. Berger, M.; Ogawa, A. K.; McMinn, D. L.; Wu, Y.; Schultz, P. G.; Romesberg, F. E. Angew. Chem., Int. Ed. 2000, 39, 2940-2942.
28. Petruska, J.; Goodman, M. F.; Boosalis, M. S.; Sowers, L. C.; Cheong, C. ; Ignacio Tinoco, J. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 6252-6256.
29. Kiefer, J. R.; Mao, C.; Braman, J. C.; Beese, L. S. Nature 1998, 391, 304-307.
30. Kim, Y.; Eom, S. H.; Wang, J.; Lee, D.-S.; Suh, S. W.; Steitz, T. A. Nature 1995, 376, 612-616.