Tautomerism in 5,8-diaza-7,9-dicarbaguanine ('alloguanine')

Helvetica Chimica Acta

Volumn 88, Issue 7, 2005, Pages 1960-1968

  Wagner, Trixie ^a   Han, Bo ^b   Koch, Guido ^a   Krishnamurthy, Ramanarayanan ^c   Eschenmoser, Albert ^b,c  

^a NOVARTIS PHARMA AG   (Switzerland)

^b ETH ZURICH   (Switzerland)

^c SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; X RAY ANALYSIS;

PURINOID; TAUTOMERS;

STEREOCHEMISTRY;

5,8 DIAZA 7,9 DICARBAGUANINE; GUANINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BASE PAIRING; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ISOMERISM; MOLECULAR INTERACTION; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 23044453112     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200590150     Document Type: Article

References (28)

1. K. Groebke, J. Hunziker, W. Fraser, L. Peng, U. Diederichsen, K. Zimmermann, A. Holzner, C. Leumann, A. Eschenmoser, Helv. Chim. Acta 1998, 81, 375.
2. S. H. Kim, D. G. Bartholomew, L. B. Allen, R. K. Robins, G. R. Revankar, P. Dea, J. Med. Chem. 1978, 21, 883.
3. a) Z. Wang, H. K. Huynh, B. Han, R. Krishnamurthy, A. Eschenmoser, Org. Lett. 2003, 5, 2067;
4. b) B. Han, Z. Wang, R. Krishnamurthy, B. Jaun, A. Eschenmoser, Org. Lett. 2003, 5, 2071;
5. B. Han, B. Jaun, R. Krishnamurthy, A. Eschenmoser, Org. Lett. 2004, 6, 3691
6. B. Han, V. Rajwanshi, J. Nandy, R. Krishnamurthy, A. Eschenmoser, Synlett 2005, 744.
7. K. Groebke, 'Über Purin-Purin-Paarungen bei Hexopyranose- Nukleinsäuren', Dissertation No. 10149, ETH Zürich, 1993.
8. R. Krishnamurthy, S. Pitsch, M. Minton, C. Miculka, N. Windhab, A. Eschenmoser, Angew. Chem. 1996, 108, 1619;
9. Angew. Chem., Int. Ed. 1996, 35, 1537.
10. S. Pitsch, S. Wendeborn, R. Krishnamurthy, A. Holzner, M. Minton, M. Bolli, C. Miculka, N. Windhab, R. Micura, M. Stanek, B. Jaun, A. Eschenmoser, Helv. Chim. Acta 2003, 86, 4270.
11. A. Rich, D. R. Davies, F. H. C. Crick, J. D. Watson, J. Mol. Biol. 1961, 3, 71;
12. D. B. Lerner, D. R. Kearns, Biopolymers 1981, 20, 803;
13. K. A. Hartman Jr., A. Rich, J. Am. Chem. Soc. 1965, 87, 2033;
14. K. Gehring, J-L. Leroy, M. Guéron, Nature 1993, 363, 561.
15. S. Arnott, R. Chandrasekaran, C. M. Marttila, Biochem. J. 1974, 141, 537;
16. S. B. Zimmerman, G. H. Cohen, D. R. Davis, J. Mol. Biol. 1975, 92, 181.
17. J. Sepiol, Z. Kazimierczuk, D. Shugar, Z. Naturforsch. C 1976, 31, 361.
18. B. D. Sharma, J. F. McConnell, Acta Crystallogr. 1965, 19, 797.
19. L. M. Toledo, K. Musa, J. W. Lauher, F. W. Fowler, Chem. Mater. 1995, 7, 1639.
20. A. L. Spek, PLATON, Utrecht University, Utrecht, The Netherlands, 2000.
21. E. Keller, SCHAKAL, University of Freiburg, Freiburg, Germany, 1999.
22. E. Hoffmann, D. Diller, Can. J. Chem. 1965, 43, 3103.
23. P. K. Martin, H. R. Matthews, H. Rapoport, G. Thyagarajan, J. Org. Chem. 1968, 33, 3758.
24. V. I. Kelarev, Ammar Dibi, A. F. Lunin, Chem. Heterocycl. Compd. (New York), 1985, 21, 1284
25. (engl. transl. from Khim. Geterotsikl. Soedin. (Russian) 1985, 21, 1557).
26. S. H. Kim, D. G. Bartholomew, L. B. Allen, R. K. Robins, G. R. Revankar, P. Dea, J. Med. Chem. 1978, 21, 883.
27. G. M. Sheldrick, SADABS, version 2004/1, University of Göttingen, Göttingen, Germany.
28. G. M. Sheldrick, SHELXTL, version 6.10, Bruker AXS, Inc., Madison, WI, USA, 2000.