An unnatural hydrophobic base pair with shape complementarity between pyrrole-2-carbaldehyde and 9-methylimidazo[(4,5)-b]pyridine

Journal of the American Chemical Society

Volumn 125, Issue 18, 2003, Pages 5298-5307

  Mitsui, Tsuneo ^a,b,c   Kitamura, Aya ^b,d   Kimoto, Michiko ^b,d   To, Taiko ^b,d   Sato, Akira ^a,d   Hirao, Ichiro ^a,b,c   Yokoyama, Shigeyuki ^a,b,d  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b RIKEN YOKOHAMA INSTITUTE   (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

^d UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; ENZYMES; ESCHERICHIA COLI; HYDROPHOBICITY; NUCLEAR MAGNETIC RESONANCE; VIRUSES;

GENETIC ALPHABETS;

AROMATIC HYDROCARBONS;

2 PYRROLECARBOXALDEHYDE; 2,4 DIFLUOROTOLUENE; 9 METHYLIMIDAZO[4,5 B]PYRIDINE; ALDEHYDE; DNA POLYMERASE; DOUBLE STRANDED DNA; PYRIDINE DERIVATIVE; PYRROLE DERIVATIVE; RNA DIRECTED DNA POLYMERASE; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; AVIAN MYELOBLASTOSIS VIRUS; BASE PAIRING; BINDING AFFINITY; DNA STRUCTURE; ESCHERICHIA COLI; GENE REPLICATION; HYDROPHOBICITY; MOLECULAR INTERACTION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; STRUCTURE ANALYSIS;

BASE PAIRING; DEOXYRIBONUCLEOTIDES; DNA; DNA-DIRECTED DNA POLYMERASE; HYDROPHOBICITY; IMIDAZOLES; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; NUCLEIC ACID CONFORMATION; PYRIDINES; PYRROLES;

EID: 0037955524     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028806h     Document Type: Article

References (38)

1. Benner, S. A.; Burgstaller, P.; Battersby, T. R.; Jurczyk, S. The RNA World, 2nd ed.; Gesteland, R. F., Cech, T. R., Atkins, J. F., Eds.; Cold Spring Harbor Laboratory Press; Cold Spring Harbor, NY, 1999; pp 163-181.
2. Kool, E. T. Curr. Opin. Chem. Biol. 2000, 4, 602-608.
3. Service, R. F. Science 2000. 289, 232-235.
4. Switzer, C.; Moroney, S. E.; Benner, S. A. J. Am. Chem. Soc. 1989, 111. 8322-8323.
5. Piccirilli, J. A.; Krauch, T.; Moroney, S. E.; Benner, S. A. Nature 1990, 343, 33-37.
6. Horlacher, J.; Hottiger, M.; Podust. V. N.; Hübscher, U.; Benner, S. A. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6329-6333.
7. Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 1999, 121, 2323-2324.
8. Kool, E. T.; Morales, J. C.; Guckian, K. M. Angew. Chem., Int. Ed. 2000, 39, 990-1009.
9. Morales, J. C.; Kool, E. T. Nat. Struct. Biol. 1998, 5, 950-954.
10. Matray, T. J.; Kool, E. T. Nature 1999, 399, 704-708.
11. Rappaport, H. P. Biochemistry 1993, 32, 3047-3057.
12. Ishikawa, M.; Hirao, I.; Yokoyama, S. Tetrahedron Lett. 2000, 41, 3931-3934.
13. Ohtsuki, T.; Kimoto, M.; Ishikawa, M.; Mitsui, T.; Hirao, I.; Yokoyama, S. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 4922-4925.
14. Fujiwara, T.; Kimoto, M.; Sugiyama, H.; Hirao, I.; Yokoyama, S. Bioorg. Med. Chem. Lett. 2001, 11, 2221-2223.
15. Hirao, I.; Ohtsuki, T.; Fujiwara, T.; Mitsui, T.; Yokogawa, T.; Okuni, T.; Nakayama, H.; Takio, K.; Yabuki, T.; Kigawa, T.; Kodama, K.; Yokogawa, T.; Nishikawa, K.; Yokoyama, S. Nat. Biotechnol. 2002, 20, 177-182.
16. McMinn, D. L.; Ogawa, A. K.; Wu, Y.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586.
17. Ogawa, A. K.; Wu, Y.; McMinn, D. L.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 3274-3287.
18. Wu, Y.; Ogawa, A. K.; Berger, M.; McMinn, D. L.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 7621-7632.
19. Ogawa, A. K.; Wu, Y.; Berger, M.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 8803-8804.
20. Tae, E. L.; Wu, Y.; Xia, G.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2001, 123, 7439-7440.
21. Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 2000, 122, 1001-1007.
22. Morales, J. C.; Kool, E. T. Biochemistry 2000, 39, 12979-12988.
23. Guckian, K. M.; Krugh, T. R.; Kool, E. T. J. Am. Chem. Soc. 2000, 122, 6841-6847.
24. Kovács, T.; Ötvös, L. Tetrahedron Lett. 1988, 29, 4525-4528.
25. Petruska, J.; Goodman, M. F.; Boosalis, M. S.; Sowers, L. C.; Cheong, C.; Tinoco, I. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 6252-6256.
26. Goodman, M. F.; Creighton, S.; Bloom, L. B.; Petruska, J. Crit. Rev. Biochem. Mol. Biol. 1993, 28, 83-126.
27. Burkard, M. E.; Turner, D. H. Biochemistry 2000, 39, 11748-11762.
28. Clore, G. M.; Oschkinat, H.; McLaughlin, L. W.; Benseler, F.; Happ, C. S.; Happ, E.; Gronenborn, A. M. Biochemistry 1988, 27, 4185-4197.
29. Schmitz, U.; James, T. L. Methods Enzymol. 1995, 261, 3-44.
30. Meade, E. A.; Wotring, L. L.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 1992, 35, 526-533.
31. Ramasamy, K.; Robins, R. K.; Revankar, G. R. Tetrahedron 1986, 42, 5869-5878.
32. Bergstrom, D. E.; Zhang. P.; Toma, P. H.; Andrews, P. C.; Nichols, R. J. Am. Chem. Soc. 1995, 117, 1201-1209.
33. Kazimierczuk, Z.; Cottam, H. B.; Revankar, G. R.; Robins, R. K. J. Am. Chem. Soc. 1984, 106, 6379-6382.
34. Robins, M. J.; Robins, R. K. J. Am. Chem. Soc. 1965, 87, 4934-4940.
35. Kool, E. T., Annu. Rev. Biophys. Biomol. Struct. 2001, 30, 1-22.
36. Berger, M.; Luzzi, S. D.; Henry, A. A.; Romesberg, F. E. J. Am. Chem. Soc. 2002, 124. 1222-1226.
37. Hirao, I.; Mitsui, T.; Fujiwara, T.; Kimoto, M.; To, T.; Okuni, T.; Sato, A.; Harada, Y.; Yokoyama, S. Nucleic Acids Res. Suppl. 2001, 1, 17-18.
38. Jiang, X.-J.; Kalman, T. I. Nucleosides Nucleotides 1994, 13, 379-388.