Efforts toward expansion of the genetic alphabet: Structure and replication of unnatural base pairs

Journal of the American Chemical Society

Volumn 129, Issue 34, 2007, Pages 10466-10473

  Matsuda, Shigeo ^a   Fillo, Jeremiah D ^b,c   Henry, Allison A ^a   Rai, Priyamrada ^d   Wilkens, Steven J ^b   Dwyer, Tammy J ^c   Geierstanger, Bernhard H ^b   Wemmer, David E ^d   Schultz, Peter G ^a,b   Spraggon, Glen ^b   Romesberg, Floyd E ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b GENOMICS INSTITUTE OF THE NOVARTIS RESEARCH FOUNDATION   (United States)

^c UNIVERSITY OF SAN DIEGO   (United States)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC RINGS; AROMATIC SURFACE AREA; GENETIC ALPHABET; NUCLEOBASE ANALOGUES;

AROMATIC COMPOUNDS; GENETIC ENGINEERING; HYDROGEN BONDS; HYDROPHOBICITY; MOLECULAR DYNAMICS;

DNA;

3 FLUOROBENZENE; DNA; DNA POLYMERASE; DOUBLE STRANDED DNA; FLUOROBENZENE; NUCLEIC ACID BASE; NUCLEOSIDE ANALOG; NUCLEOTIDE DERIVATIVE; PHENYL NUCLEOTIDE; UNCLASSIFIED DRUG;

ARTICLE; BASE MISPAIRING; CHEMICAL STRUCTURE; GENE REPLICATION; HYDROGEN BOND; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUBSTITUTION REACTION; SYNTHESIS;

BASE PAIRING; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; DNA; DNA REPLICATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

EID: 34548245052     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja072276d     Document Type: Article

References (46)

1. Piccirilli, J. A.; Krauch, T.; Moroney, S. E.; Benner, S. A. Nature 1990, 343, 33-37.
2. Morales, J. C.; Kool, E. T. Nat. Struct. Biol. 1998, 5, 950-954.
3. Moran, S.; Ren, R. X.-F.; Kool, E. T. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 10506-10511.
4. Moran, S.; Ren, R. X.-F.; Rumney, S. I.; Kool, E. T. J. Am. Chem. Soc. 1997, 119, 2056-2057.
5. Kool, E. T. Biopolymers 1998, 48, 3-17.
6. Kool, E. T. Curr. Opin. Chem. Biol. 2000, 4, 602-608.
7. Tae, E. L.; Wu, Y. Q.; Xia, G.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2001, 123, 7439-7440.
8. Ogawa, A. K.; Wu, Y.; McMinn, D. L.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 3274-3287.
9. Ogawa, A. K.; Wu, Y.; Berger, M.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 8803-8804.
10. McMinn, D. L.; Ogawa, A. K.; Wu, Y.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586.
11. Matsuda, S.; Romesberg, F. E. J. Am. Chem. Soc. 2004, 126, 14419-14427.
12. Matsuda, S.; Henry, A. A.; Romesberg, F. E. J. Am. Chem. Soc. 2006, 128, 6369-6375.
13. Leconte, A. M.; Matsuda, S.; Romesberg, F. E. J. Am. Chem. Soc. 2006, 128, 6780-6781.
14. Leconte, A. M.; Matsuda, S.; Hwang, G. T.; Romesberg, F. E. Angew. Chem., Int. Ed. 2006, 45, 4326-4329.
15. Kim, Y.; Leconte, A. M.; Hari, Y.; Romesberg, F. E. Angew. Chem., Int. Ed. 2006, 45, 7809-7812.
16. Hwang, G. T.; Romesberg, F. E. Nucleic Acids Res. 2006, 34, 2037-2045.
17. Henry, A. A.; Olsen, A. G.; Matsuda, S.; Yu, C.; Geierstanger, B. H.; Romesberg, F. E. J. Am. Chem. Soc. 2004, 126, 6923-6931.
18. Henry, A. A.; Romesberg, F. E. Curr. Opin. Chem. Biol. 2003, 7, 727-733.
19. Ishikawa, M.; Hirao, I.; Yokoyama, S. Tetrahedron Lett. 2000, 41, 3931-3934.
20. Hirao, I.; Harada, Y.; Kimoto, M.; Mitsui, T.; Fujiwara, T.; Yokoyama, S. J. Am. Chem. Soc. 2004, 126, 13298-13305.
21. Mitsui, T.; Kimoto, M.; Harada, Y.; Yokoyama, S.; Hirao, I. J. Am. Chem. Soc. 2005, 127, 8652-8658.
22. Mitsui, T.; Kitamura, A.; Kimoto, M.; To, T.; Sato, A.; Hirao, I.; Yokoyama, S. J. Am. Chem. Soc. 2003, 125, 5298-5307.
23. Hirao, I.; Kimoto, M.; Mitsui, T.; Fujiwara, T.; Kawai, R.; Sato, A.; Harada, Y.; Yokoyama, S. Nat. Methods 2006, 3, 729-735.
24. Kincaid, K.; Beckman, J.; Zivkovic, A.; Halcomb, R. L.; Engels, J. W.; Kuchta, R. D. Nucleic Acids Res. 2005, 33, 2620-2628.
25. Chiaramonte, M.; Moore, C. L.; Kincaid, K.; Kuchta, R. D. Biochemistry 2003, 42, 10472-10481.
26. Hirao, I. Curr. Opin. Chem. Biol. 2006, 10, 622-627.
27. Matray, T. J.; Kool, E. T. Nature 1999, 399, 704-708.
28. Zhang, X.; Lee, I.; Berdis, A. J. Biochemistry 2005, 44, 13101-13110.
29. Zhang, X.; Lee, I.; Zhou, X.; Berdis, A. J. J. Am. Chem. Soc. 2006, 128, 143-149.
30. Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 1999, 121, 2323-2324.
31. Millican, T. A.; Mock, G. A.; Chauncey, M. A.; Patel, T. P.; Eaton, M. A. W.; Gunning, J.; Cutbush, S. D.; Neidle, S.; Mann, J. Nucleic Acids Res. 1984, 12, 7435-7453.
32. Guckian, K. M.; Krugh, T. R.; Kool, E. T. J. Am. Chem. Soc. 2000, 122, 6841-6847.
33. Smirnov, S.; Matray, T. J.; Kool, E. T.; de los Santos, C. Nucleic Acids Res. 2002, 30, 5561-5569.
34. Wu, Y. Q.; Ogawa, A. K.; Berger, M.; McMinn, D. L.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 7621-7632.
35. Saenger, W. Principles of Nucleic Acid Structure; Springer-Verlag: New York, 1984.
36. Lu, X.-J.; Olson, W. K. Nucleic Acids Res. 2003, 31, 5108-5121.
37. Hare, D. R.; Wemmer, D. E.; Chou, S. H.; Drobny, G.; Reid, B. R. J. Mol. Biol. 1983, 171, 319-336.
38. Guckian, K. M.; Krugh, T. R.; Kool, E. T. Nat. Struct. Biol. 1998, 5, 954-959.
39. Reha, D.; Hocek, M.; Hobza, P. Chem. - Eur. J. 2006, 12, 3587-3595.
40. Zahn, A.; Brotschi, C.; Leumann, C. J. Chem. - Eur. J. 2005, 11, 2125-2129.
41. Brotschi, C.; Mathis, G.; Leumann, C. J. Chem. - Eur. J. 2005, 11, 1911-1923.
42. Brotschi, C.; Haberli, A.; Leumann, C. J. Angew. Chem., Int. Ed. 2001, 40, 3012-3014.
43. Brotschi, C.; Leumann, C. J. Angew. Chem., Int. Ed. 2003, 42, 1655-1658.
44. Otwinowski, Z.; Minor, W. Methods Enzvmol. 1997, 276, 307-326.
45. Tickle, I. J.; Laskowski, R. A.; Moss, D. S. Acta Crystallogr. 1998, D54, 243-252.
46. Scott, L. G.; Geierstanger, B. H.; Williamson, J. R.; Hennig, M. J. Am. Chem. Soc. 2004, 126, 11776-11777.