Precise recognition of nucleic acid bases by polymeric receptors in methanol. Predominance of hydrogen bonding over apolar interactions

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 9, 1998, Pages 1915-1918

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

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001261339     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a803278e     Document Type: Article

References (34)

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18. On the molecular recognition by natural receptors, see (a) K. A. Watson, E. P. Mitchell, J. N. Johnson, J. C. Son, C. J. F. Bichard, M. G. Orchard, G. W. J. Fleet, N. G. Oikonomakos, D. D. Leonidas, M. Kontou and A. Papageorgioui, Biochemistry, 1994, 33, 5745; (b) H.-J. Böhm and G. Klebe, Angew. Chem., Int. Ed. Engl., 1996, 35, 2588.
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26. Direct evidence of hydrogen bond formation in methanol was obtained by FTIR measurement: the carbonyl stretching band of uracil shifted to lower frequency on the adduct formation with PVDAT. A similar IR shift was also observed on the hydrogen bond formation between PVDAT and uracil in water, as previously reported in reference 8. This argument was further confirmed by the fact that 3-methyluracil, whose hydrogen bonding site is blocked by a methyl group, was hardly adsorbed by PVDAT.
27. 3b. In contrast, VDAT (monomer of PVDAT) hardly bound uracil in homogeneous DMSO-water mixture. See ref. 8.
28. The slight decrease in the activity with increasing molecular size of the substituent is probably associated with the steric hindrance at the binding sites.
29. T. Itahara, J. Chem. Soc., Perkin Trans. 2, 1996, 2695.
30. Homopolymer of styrene or 4-vinylbiphenyl showed no adsorption activity towards all the guests used in this study.
31. The great binding-activity of PVB-VDAT on adenine in water is ascribed to enhanced hydrophobic interactions.
32. PAAm-VDAT was water-soluble when the VDAT/acrylamide ratio in the polymerization mixture was 1/5.
33. For more hydrophobic copolymers (PST-VDAT and PVB-VDAT), it took about 1 h to attain the equilibrium.
34. D. M. Ruthven, Principles of Adsorption and Adsorption Processes, Wiley Interscience, New York, 1984, p. 49.