Cyanurate mimics of hydrogen-bonding patterns of nucleic bases: Crystal structure of a 1:1 molecular complex of 9-ethyladenine and n-methylcyanuric acid

Organic Letters

Volumn 3, Issue 1, 2001, Pages 99-101

  Pedireddi, V R ^a   Ranganathan, Anupama ^b   Ganesh, Krishna N ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENTIFIC RESEARCH   (India)

Author keywords

[No Author keywords available]

Indexed keywords

9 ETHYLADENINE; 9-ETHYLADENINE; ADENINE; DRUG DERIVATIVE; N METHYLCYANURIC ACID; N-METHYLCYANURIC ACID; NUCLEIC ACID; TRIAZINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; CRYSTALLOGRAPHY; HYDROGEN BOND; STRUCTURE ACTIVITY RELATION;

ADENINE; CRYSTALLOGRAPHY; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NUCLEIC ACIDS; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZINES;

EID: 0035843280     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006811p     Document Type: Article

References (34)

1. (a) Watson, J. D.; Crick, F. H. Nature 1953, 171, 737.
2. (b) Saenger, W. In Principles of Nucleic Acid Structure; Springer-Verlag: New York, 1984.
3. (a) Jeffrey, G. A.; Saenger, W. In Hydrogen Bonding in Biological Structures; Springer-Verlag: Berlin, 1991.
4. (b) Lehn, J. M. Supramolecular Chemistry; VCH: Weinheim, 1995.
5. (c) Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, 1989.
6. (a) Gangamani, B. P.; Kumar V. A.; Ganesh, K. N. Chem. Commun. 1997, 1913.
7. (b) Haaima, G.; Hansen, H. F.; Christensen, L.; Dahl, O.; Nielsen, P. E. Nucleic Acids Res. 1997, 25, 4639.
8. (c) Eldrup, A. B.; Dahl, O.; Nielsen, P. E. J. Am. Chem. Soc. 1997, 119, 1116.
9. MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383.
10. (a) Pedireddi, V. R.; Chatterjee, S.; Ranganathan A.; Rao, C. N. R. J. Am. Chem. Soc. 1997, 119, 10867.
11. (b) Coppens, P.; Vos, A. Acta Crystallogr. 1971, B27, 146.
12. (c) Chang-Zhang, C.; Jian-Qiu, S.; Zhou-Bin, L.; Dong-Shou, G.; Ding, H. X. L. J. Struct. Chem. 1995, 14, 241.
13. (d) Ranganathan, A.; Pediredi, V. R.; Sanjayan, G.; Ganesh, K. N.; Rao, C. N. R. J. Mol. Struct. 2000, 522, 87.
14. Ranganathan, A.; Pedireddi, V. R.; Rao, C. N. R. J. Am. Chem. Soc. 1999, 121, 1752.
15. Sanjayan, G. J.; Pedireddi, V. R.; Ganesh, K. N. Org. Lett. 2000, 2, 2825.
16. (a) Shieh, H.; Voet, D. Acta Crystallogr. 1975, B31, 2192.
17. (b) Shieh, H.; Voet, D. Acta Crystallogr. 1976, B32, 2361.
18. (c) Voet, D.; Rich, A. J. Am. Chem. Soc. 1972, 94, 5888.
19. (d) Voet, D. J. Am. Chem. Soc. 1972, 94, 8213.
20. (e) Shieh, H.; Voet, D. Acta Crystallogr. 1976, B32, 2361.
21. (f) Matsui, J.; Higashi, M.; Takeuchi, T. J. Am. Chem. Soc. 2000, 122, 5218.
22. (a) Shea, K. J.; Spivak, D. A.; Sellergren, B. J. Am. Chem. Soc. 1993, 115, 3368.
23. (b) Spivak, D. A.; Gilmore, M. A.; Shea, K. J. J. Am. Chem. Soc. 1997, 119, 4388.
24. (c) Mathew-Krotz, J.; Shea, K. J. J. Am. Chem. Soc. 1996, 118, 8154.
25. (d) Zimmerman, S. C.; Wu, W. J. Am. Chem. Soc. 1989, 111, 8054.
26. (e) Zimmerman, S. C.; Zeng, Z. J. Org. Chem. 1990, 55, 4789.
27. 2 = 0.138. H atoms were obtained from Fourier differential maps. Data collection, SMART; refinement, SHELX-TL (Bruker-axis. Madison, WI, 1995).
28. Katz, L.; Tomita; K. Rich; A. J. Mol. Biol. 1965, 13, 340.
29. CA and EA did not yield a complex perhaps due to the fact that CA forms an infinite chain of molecular network rather than simple dimers to yield a molecular strip.
30. (a) Leonard, G. A.; McAuley-Hecht, K.; Brown, T.; Hunter, W. N. Acta Crystallogr. 1995, D51, 136.
31. (b) Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford: New York, 1999.
32. Allen, F. H.; Kennard, O. Chem. Des. Automat. News 1993, 8, 31.
33. 2 = 0.142. H atoms were obtained from Fourier differential maps. Data collection, SMART; refinement, SHELX-TL (Bruker-axis, Madison, WI, 1995).
34. Landschulz, W. H.; Johnson, P. F.; McKnight, S. L. Science 1988, 240, 1759.