Hydrogen bonding in water by poly(vinyldiaminotriazine) for the molecular recognition of nucleic acid bases and their derivatives

Macromolecules

Volumn 31, Issue 2, 1998, Pages 371-377

  Asanuma, Hiroyuki ^a   Ban, Takeshi ^a   Gotoh, Sumie ^a   Hishiya, Takayuki ^a   Komiyama, Makoto ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; DERIVATIVES; HYDROGEN BONDS; MOLECULAR STRUCTURE; NUCLEIC ACIDS; SOLUTIONS; WATER;

POLYVINYLDIAMINOTRIAZINE; PURINE; PYRIMIDINE;

VINYL RESINS;

EID: 0031674541     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma970892w     Document Type: Article

References (31)

1. A preliminary communication: Asanuma, H.; Gotoh, S.; Ban, T.; Komiyama, M. J. Inclusion Phenom. Mol. Recognit. Chem. 1997, 27, 259.
2. (a) Conn, M. M.; Deslongchamps, G.; de Mendoza, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1993,115, 3548.
3. (b) Kato, Y.; Conn, M. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1994, 116, 3279.
4. (c) Kato, Y.; Conn, M. M.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 1208, and references cited therein.
5. (a) Hamilton, A. D.; Van Engen, D. J. Am. Chem. Soc. 1987, 109, 5035.
6. (b) Fan, E.; Arman, S. A. V.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369, and references cited therein.
7. (a) Perreault, D. M.; Chen, X.; Anslyn, E. V. Tetrahedron 1995,51, 353.
8. (b) Bonar-Law, R. P.; Sanders, J. K. M. J. Am. Chem. Soc. 1995, 117, 259.
9. (c) Yoon, S. S.; Still, W. C. J. Am. Chem. Soc. 1993, 115, 823.
10. (d) Newkome, G. R.; Woosley, B. D.; He, E.; Moorefield, C. N.; Güther, R.; Baker, G. R.; Escamilla, G. H.; Merrill, J.; Luftmann, H. J. Chem. Soc., Chem. Commun. 1996, 2737.
11. (e) Mammen, M.; Simanek, E. E.; Whitesides, G. M. J. Am. Chem. Soc. 1996, 118, 12614.
12. (f) Marchi-Artzner, V.; Jullien, L.; Gulik-Krzywicki, T.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1997, 777, and references cited therein.
13. Molecular imprinting techniques have been also used for the preparation of artificial receptors: (a) Beach, J. V.; Shea, K. J. J. Am. Chem. Soc. 1994, 776, 379. (b) Matsui, J.; Kato, T.; Takeuchi, T.; Suzuki, M.; Yokoyama, K.; Tamiya, E.; Karube, I. Anal. Chem. 1993, 65, 2223. (c) Whitcombe, M. J.; Rodriguez, M. E.; Villar, P.; Vulfson, E. N. J. Am. Chem. Soc. 1995, 777, 7105. (d) Wulff, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1812, and references cited therein.
14. Molecular imprinting techniques have been also used for the preparation of artificial receptors: (a) Beach, J. V.; Shea, K. J. J. Am. Chem. Soc. 1994, 776, 379. (b) Matsui, J.; Kato, T.; Takeuchi, T.; Suzuki, M.; Yokoyama, K.; Tamiya, E.; Karube, I. Anal. Chem. 1993, 65, 2223. (c) Whitcombe, M. J.; Rodriguez, M. E.; Villar, P.; Vulfson, E. N. J. Am. Chem. Soc. 1995, 777, 7105. (d) Wulff, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1812, and references cited therein.
15. Molecular imprinting techniques have been also used for the preparation of artificial receptors: (a) Beach, J. V.; Shea, K. J. J. Am. Chem. Soc. 1994, 776, 379. (b) Matsui, J.; Kato, T.; Takeuchi, T.; Suzuki, M.; Yokoyama, K.; Tamiya, E.; Karube, I. Anal. Chem. 1993, 65, 2223. (c) Whitcombe, M. J.; Rodriguez, M. E.; Villar, P.; Vulfson, E. N. J. Am. Chem. Soc. 1995, 777, 7105. (d) Wulff, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1812, and references cited therein.
16. Molecular imprinting techniques have been also used for the preparation of artificial receptors: (a) Beach, J. V.; Shea, K. J. J. Am. Chem. Soc. 1994, 776, 379. (b) Matsui, J.; Kato, T.; Takeuchi, T.; Suzuki, M.; Yokoyama, K.; Tamiya, E.; Karube, I. Anal. Chem. 1993, 65, 2223. (c) Whitcombe, M. J.; Rodriguez, M. E.; Villar, P.; Vulfson, E. N. J. Am. Chem. Soc. 1995, 777, 7105. (d) Wulff, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1812, and references cited therein.
17. On the molecular recognition by natural receptors, see: (a) Watson, K. A.; Mitchell, E. P.; Johnson, J. N.; Son, J. C.; Bichard, C. J. F.; Orchard, M. G.; Fleet, G. W. J.; Oikonomakos, N. G.; Leonidas, D. D.; Kontou, M.; Papageorgioui, A. Biochemistry 1994, 33, 5745. (b) Böhm, H.-J.; Klebe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2588.
18. On the molecular recognition by natural receptors, see: (a) Watson, K. A.; Mitchell, E. P.; Johnson, J. N.; Son, J. C.; Bichard, C. J. F.; Orchard, M. G.; Fleet, G. W. J.; Oikonomakos, N. G.; Leonidas, D. D.; Kontou, M.; Papageorgioui, A. Biochemistry 1994, 33, 5745. (b) Böhm, H.-J.; Klebe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2588.
19. Fersht, A. R. Trends Biochem. Sci. 1987, 12, 301.
20. Constant, J. F.; Fahy, J.; Lhomme, J. Tetrahedron Lett. 1987, 28, 1777.
21. Kurihara, K.; Ohto, K.; Honda, Y.; Kunitake, T. J. Am. Chem. Soc. 1991, 773, 5077.
22. Nowick, J. S.; Chen, J. S. J. Am. Chem. Soc. 1992,114, 1107.
23. -3 and a = 0.51 (Overberger, C. G.; Michelotti, F. W. J. Am. Chem. Soc. 1958, 80, 988).
24. Nomura, Y.; Yoshida, T.; Kakurai, T.; Noguchi, T. J. Synth, Org. Chem., Jpn. 1966, 24, 125.
25. Ruthven, D. M. Principles of Adsorption and Adsorption Processes; Wiley-Interscience Publication: New York, 1984; p 49.
26. -1: (a) Adcock, J. L.; Zhang, H. J. Org. Chem. 1995, 60, 1999. (b) Rao, C. N. R. Chemical Applications of Infrared Spectroscopy; Academic Press: New York and London, 1963; p 28. The spectrum of PVDAT was little affected by the hydrogen bonding, since only 5% of DAT residues bound uracil.
27. -1: (a) Adcock, J. L.; Zhang, H. J. Org. Chem. 1995, 60, 1999. (b) Rao, C. N. R. Chemical Applications of Infrared Spectroscopy; Academic Press: New York and London, 1963; p 28. The spectrum of PVDAT was little affected by the hydrogen bonding, since only 5% of DAT residues bound uracil.
28. 2O mixture was not successful, since uracil has only limited solubility in the mixture.
29. The dimer model (73 μmol), which was insoluble in water, was incubated with 1 mL of aqueous solutions of the pyrimidine derivatives (1 mM) at 25 °C for 24 h.
30. The size of the type-I binding sites would fit the pyrimidine derivatives but would be too small for the purine derivatives.
31. The structure of type-II binding sites would be sterically less favorable for hydrogen bonding.