Base pair recognition of the stereochemically α-substituted γ-turn of pyrrole/imidazole hairpin polyamides

Journal of the American Chemical Society

Volumn 128, Issue 46, 2006, Pages 14905-14912

  Zhang, Wen ^a   Minoshima, Masafumi ^a   Sugiyama, Hiroshi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR STRUCTURE; ORGANIC ACIDS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SURFACE PLASMON RESONANCE;

BINDING AFFINITY; BINDING PREFERENCE; MOLECULAR MODELING; THYMINE;

POLYAMIDES;

2 AMINOBUTYRIC ACID; 2,4 DIAMINOBUTYRIC ACID; ALPHA HYDROXYL GAMMA AMINOBUTYRIC ACID; IMIDAZOLE; POLYAMIDE; PYRROLE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BASE PAIRING; BINDING AFFINITY; COMPUTER MODEL; HYDROGEN BOND; MOLECULAR MODEL; MOLECULAR RECOGNITION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SURFACE PLASMON RESONANCE; SYNTHESIS;

BASE PAIRING; BASE SEQUENCE; IMIDAZOLES; MODELS, MOLECULAR; NYLONS; PYRROLES; STEREOISOMERISM; SURFACE PLASMON RESONANCE;

EID: 33845205540     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja064369l     Document Type: Article

References (27)

1. (a) Dervan, P. B. Bioorg. Med. Chem. 2001, 9, 2215-2235.
2. (b) Bando, T.; Sugiyama, H. Acc. Chem. Res., published online August 22, 2006 10.1021/ar030287f.
3. Dervan, P. B.; Edelson, B. S. Curr. Opin. Struct. Biol. 1999, 13, 284-299.
4. (a) Pelton, J. G.; Wemmer, D. E. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 5723-5727.
5. (b) Wade, W. S.; Mrksich, M.; Dervan, P. B. J. Am. Chem. Soc. 1992, 114, 8783-8794.
6. (c) White, S.; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B. Nature 1998, 391, 468-471.
7. (a) Pelton, J. G.; Wemmer, D. E. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 5723-5727.
8. (b) Wade, W. S.; Mrksich, M.; Dervan, P. B. J. Am. Chem. Soc. 1992, 114, 8783-8794.
9. (c) White, S.; Szewczyk, J. W.; Turner, J. M.; Baird, E. E.; Dervan, P. B. Nature 1998, 391, 468-471.
10. (a) Marques, M. A.; Doss, R. M.; Urbach, A. R.; Dervan, P. B. Helv. Chim. Acta. 2002, 85, 4485-4517.
11. (b) Walker, W. L.; Kopka, M. L.; Goodsell, D. S. Biopolymers 1997, 44, 323-334.
12. Kielkopf, C. L.; Baird, E. E.; Dervan, P. B.; Rees, D. C. Nat. Struct. Biol. 1998, 5, 104-109.
13. Kelly, J. J.; Baird, E. E.; Dervan, P. B. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 6981-6985.
14. (a) Lamamie de Clairac, R. P.; Geierstanger, B. H.; Mrksich, M.; Dervan, P. B.; Wemmer, D. E. J. Am. Chem. Soc. 1997, 119, 7909-7916.
15. (b) Herman, D. M.; Baird, E. E.; Dervan, P. B. J. Am. Chem. Soc. 1998, 120, 1382-1391.
16. Trauger, J. W.; Baird, E. E.; Mrksich, M.; Dervan, P. B. J. Am. Chem. Soc. 1996, 118, 6160-6166.
17. Floreancig, P. E.; Swalley, S. E.; Trauger, J. W.; Dervan, P. B. J. Am. Chem. Soc. 2000, 122, 6342-6350.
18. Zhang, W.; Bando, T.; Sugiyama, H. J. Am. Chem. Soc. 2006, 128, 8766-8776.
19. Wurtz, N. R.; Turner, J. M.; Baird, E. E.; Dervan, P. B. Org. Lett. 2001, 3, 1201-1203.
20. Beyerman, H. C.; Bontekoe, J. S. Recl. Trav. Chim. Pays-Bas 1962, 81, 691-697.
21. Davis, T. M.; Wilson, W. D. Anal. Biochem. 2000, 284, 348-353.
22. Tanious, F. A.; Hamelberg, D.; Bailly, C.; Czarny, A.; Boykin, D. W.; Wilson, W. D. J. Am. Chem. Soc. 2004, 126, 143-153.
23. Biacore AB. In BIAapplicatums Handbook; Biacore AB: Uppsala, Sweden, 1998; p 3-2.
24. (a) White, S.; Baird, E. E.; Dervan, P. B. Chem. Biol. 1997, 4, 569-578.
25. (b) Swalley, S. E.; Baird, E. E.; Dervan, P. B. J. Am. Chem. Soc. 1999, 121, 1113-1120.
26. Woods, C. R.; Ishii, T.; Wu, B.; Bair, K. W.; Boger, D. L. J. Am. Chem. Soc. 2002, 124, 2148-2152.
27. Bando, T.; Narita, A.; Sasaki, S.; Sugiyama, H. J. Am. Chem. Soc. 2005, 127, 13890-13895.