Enhancing Hoogsteen interactions: A pyrrole-containing purine nucleoside that competes with guanosine self-assembly

Journal of the American Chemical Society

Volumn 126, Issue 37, 2004, Pages 11460-11461

  Sessler, Jonathan L ^a   Jayawickramarajah, Janarthanan ^a   Sherman, Courtney L ^a   Brodbelt, Jennifer S ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; CHLOROFORM; GUANOSINE; INOSINE DERIVATIVE; NUCLEOSIDE; PROPANE; PURINE; PYRROLE;

ARTICLE; BINDING AFFINITY; CHEMICAL REACTION; DIMERIZATION; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN ASSEMBLY; PROTEIN BINDING; PROTEIN INTERACTION; PROTEIN MOTIF; STOICHIOMETRY; SYNTHESIS; TITRIMETRY;

BINDING, COMPETITIVE; DIMERIZATION; GUANOSINE; HYDROGEN BONDING; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PURINE NUCLEOSIDES; PYRROLES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 4544344212     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046773v     Document Type: Article

References (34)

1. (a) Hoogsteen, K. Acta Crystallogr. 1963, 16, 907-916.
2. (b) Hoogsteen, K. Acta Crystallogr. 1959, 12, 822-823.
3. (a) Zimmerman, S. C.; Schmitt, P. J. Am. Chem. Soc. 1995, 117, 10769-10770.
4. (b) Castellano, R. K.; Gramlich, V.; Diederich, F. Chem. Eur. J. 2002, 8, 118-129.
5. (c) Sessler, J. L.; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303.
6. (d) Manet, I.; Francini, L.; Masiero, S.; Pieraccini, S.; Spada, G. P.; Gottarelli, G. Helv. Chim. Acta 2001, 84, 2096-2107.
7. (e) Gottarelli, G.; Masiero, S.; Mezzina, E.; Spada, G. P.; Mariani, P.; Recanatini, M. Helv. Chim. Acta 1998, 81, 2078-2092.
8. (f) Shi, X.; Mullaugh, K. M.; Fettinger, J. C.; Jiang, Y.; Hofstadler, S. A.; Davis, J. T. J. Am. Chem. Soc. 2003, 125, 10830-10841.
9. (g) Hunziker, J.; Priestley, E. S.; Brunar, H.; Dervan, P. B. J. Am. Chem. Soc. 1995, 117, 2661-2662.
10. (h) Conn, M. M.; Deslongchamps, G.; Mendoza, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1993, 115, 3548-3557.
11. (i) Janke, E. M. B.; Limbach, H.-H.; Weisz, K. J. Am. Chem. Soc. 2004, 126, 2135-2141.
12. (j) Schall, O. F.; Gokel, G. W. J. Am. Chem. Soc. 1994, 116, 6089-6100.
13. For examples of DNA triplexes, see: (a) Felsenfeld, G.; Davies, D. R.; Rich, A. J. Am. Chem. Soc. 1957, 79, 2023-2024.
14. (b) Moser, H. E.; Dervan, P. B. Science 1987, 238, 645-650.
15. For examples of guanine quadruplex formation, see: (c) Davis, J. T. Angew. Chem., Int. Ed. 2004, 43, 668-698 and references therein,
16. (d) Guschlbauer, W.; Chantot, J. F.; Thiele, D. J. Biomol. Struct. Dyn. 1990, 8, 491-511.
17. (a) Zahler, A. M.; Williamson, J. R.; Cech, T. R.; Prescott, D. M. Nature 1991, 350, 718-720.
18. (b) Sen, D.; Gilbert, W. Nature 1988, 334, 364-366.
19. (a) Lyonnais, S.; Hounsou, C.; Teulade-Fichou, M.-P.; Jeusset, J.; Le Cam, E.; Mirambeau, G. Nucleic Acids Res. 2002, 30, 5276-5283.
20. (b) Sundquist, W. I.; Heaphy, S. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 3393-3397.
21. In the strictest definition the interaction in question is actually a three-point reverse Hoogsteen-type interaction, due to the anti relationship of the ribose moieties (see Figure 1A).
22. Hayakawa, H.; Haraguchi, K.; Tanaka, H.; Miyasaka, T. Chem. Pharm. Bull. 1987, 35, 72-79.
23. Fürstner A.; Grabowski, J.; Lehmann, C. W.; Kataoka, T.; Nagai, K. ChemBioChem 2001, 2, 60-68.
24. Sessler, J. L.; Andrievsky, A.; Gale, P. A.; Lynch, V. M. Angew. Chem., Int. Ed. Engl. 1996, 2782-2785.
25. 2 at 30 °C by this method.
26. 2 at 30 °C by this method.
27. 2 at 30 °C by this method.
28. See Supporting Information for details
29. (a) Zimmerman, S. C.; Corbin, P. S. Struct. Bond. 2000, 96, 63-94 and references therein,
30. -1 This value is likely a lower limit due to this method being unable to account for the GG dimerization equilibrium.
31. 2 shift of 10 becomes too broad to allow for an accurate peak pick. However, the estimated peak ,does not shift much from 5.75 ppm, even after 6 equiv of 5 was added.
32. (a) Sakamoto, S.; Nakatani, K.; Saito, L; Yamaguchi, K. Chem. Commun. 2003, 788-789.
33. (b) David, W. M.; Brodbelt, J.; Kerwin, S. M.; Thomas, P. W. Anal. Chem. 2002, 74, 2029-2033.
34. Iosotope spacing confirms that this ion is consistent with a doubly charged guanine octamer. Similar ions have been observed previously with the use of ESI-MS; see ref 2d.