Structural effects on the stability of some hydrogen-bonded complexes with nucleobases

European Journal of Organic Chemistry

Volumn , Issue 7, 1999, Pages 1619-1625

  Yu, Lianhe ^a   Schneider, Hans Jörg ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

Amides; C H Aryl interactions; Host guest complexations; Hydrogen bonds; Nucleobases; Supramolecular chemistry

Indexed keywords

ADENINE DERIVATIVE; NUCLEIC ACID BASE; THYMINE DERIVATIVE;

ARTICLE; COMPLEX FORMATION; COMPUTER SIMULATION; HYDROGEN BOND; MOLECULAR INTERACTION; MOLECULAR STABILITY;

EID: 0032775292     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199907)1999:7<1619::aid-ejoc1619>3.0.co;2-%23     Document Type: Article

References (35)

1. G. A. Jeffrey, W. Saenger, Hydrogen Bonding in Biological Structures, Springer, Heidelberg, 1994.
2. [2a] J. Rebek, Jr., Acc. Chem. Res. 1990, 23, 399.
3. [2b] A. D. Hamilton, Bioorg. Chem. Frontiers (Ed.: H. Dugas), Springer, Berlin, Heidelberg, 1991, vol. 2, p. 115.
4. [3a] S. Goswami, D. V. Engen, A. D. Hamilton, J. Am. Chem. Soc. 1989, 111, 3425 (adenine).
5. [3b] A. D. Hamilton, D. Little, J. Chem. Soc., Chem. Commun. 1990, 297 (thymine).
6. [3c] A. V. Muehldorf, D. V. Engen, I. C. Warner, A. D. Hamilton, J. Am. Chem. Soc. 1988, 110, 6561 (thymine).
7. [3d] A. D. Hamilton, D. V. Engen, J. Am. Chem. Soc. 1987, 109, 5035 (thymine).
8. [e] A. V. Muehldorf, O. V. Engen, J. C. Warner, A. D. Hamilton, J. Am. Chem. Soc. 1988, 110, 6561 (thymine).
9. [3f] M. M. Conn, G. Deslongchamps, J. de. Mendoza, J. Rebek, Jr., J. Am. Chem. Soc. 1993, 115, 3548 (adenine).
10. [3g] K. S. Jeong, T. Tjivikua, A. Muehldorf, G. Deslongchamps, M. Famulok, J. Rebek, Jr., J. Am. Chem. Soc. 1991, 113, 201 (adenine).
11. [3h] K. Williams, B. Askew, P. Ballester, C. Buhr, K. S. Jeong, J. Rebek, Jr., J. Am. Chem. Soc. 1989, 111, 1082, 1090 (adenine).
12. [3i] V. M. Rotello, E. A. Viani, G. Deslongchamps, B. A. Murray, J. Rebek, Jr., J. Am. Chem. Soc. 1993, 115, 797 (adenine).
13. [3j] J. Rebek, Jr., B. Askew, P. Ballester, C. Buhr, S. Jones, D. Nemeth, K. Williams, J. Am. Chem. Soc. 1987, 109, 5033 (adenine).
14. [k] J. Rebek, Jr. B. Askew, P. Ballester, C. Buhr, A. Costero, S. Jones, K. Williams, J. Am. Chem. Soc. 1987, 109, 6866 (adenine).
15. [l] K. S. Jeong, J. Rebek, Jr., J. Am. Chem. Soc. 1988, 110, 3327 (cytosine).
16. [4a] H. J. Schneider, Chem. Soc. Rev. 1994, 22, 227.
17. [b] H. J. Schneider, R. K. Juneja, S. Simova, Chem. Ber. 1989, 112, 1211-13.
18. W. Jorgensen, J. Pranata, J. Am. Chem. Soc. 1990, 112, 2208.
19. J. Sartorius, H.-J. Schneider, Chem. Eur. J. 1996, 2, 1446.
20. [7a] S. C. Zimmerman Top. Curr. Chem., 1993, 165.
21. [7b] S. C. Zimmerman, in Bioorganic Chemistry Frontiers, vol. 2 (Ed.: H. D. Dugas), Springer-Verlag, Berlin, Heidelberg, 1991, p. 35-71.
22. U. Lüning, C. Kühl, Tetrahedron Lett. 1998, 39, 5735.
23. H.-J. Schneider, R. Kramer, S. Simova, U. Schneider, J. Am. Chem. Soc. 1988, 110, 6442.
24. K. A. Connors, Binding Constants, John Wiley & Sons, New York, 1987, p. 24.
25. [11a] B. R. Brooks, R. E. Bruccoleri, B. D. Olafson, D. J. States, S. Swaminathan, M. Karplus, J. Comp. Chem. 1983, 4, 187.
26. [b] C. L. Brooks, M. Karplus, Methods Enzymol. 1986, 127, 369.
27. [c] A. T. Brünger, M. Karplus, Acc. Chem. Res. 1991, 24, 54.
28. M. Nishio, M. Hirota, Y. Umezawa, The CH-π Interaction, Wiley, New York, 1998.
29. Y. Kyogoku, R. C. Lord, A. Rich, Proc. Natl. Acad. Sci. U.S.A. 1967, 57, 250.
30. [14a] D. T. Browne, in Synthetic procedures in Nucleic Acid Chemistry (Eds.: W W. Zorbach, R. S. Tipson), John Wiley & Sons, New York, 1968, p. 98.
31. [14b] D. T. Browne, J. Eisinger, N. J. Leonard, J. Am. Chem. Soc. 1968, 70, 7302.
32. A. Castellan, J. P. Desvergne, R. Arnaud, J. P. Bideau, G. Bravic, J. Chem. Soc., Perkin Trans. 2 1983, 1807.
33. E. E. Fenlon, T. J. Murray, M. H. Baloga, S. C. Zimmerman, J. Org. Chem. 1993, 58, 6625.
34. H. Quast, U. Nahr, Chem. Ber. 1984, 117, 2761.
35. O. Meth-Cohn, Z. Yan, J. Chem. Soc., Perkin Trans. 1 1998, 423.