Oligonucleotides containing pyrazolo[3,4-d]pyrimidines: The influence of 7-substituted 8-aza-7-deaza-2'-deoxyguanosines on the duplex structure and stability

Helvetica Chimica Acta

Volumn 82, Issue 10, 1999, Pages 1640-1655

  Seela, Frank ^a   Becher, Georg ^a  

^a UNIVERSITY OF OSNABRÜCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; DEOXYGUANOSINE DERIVATIVE; DOUBLE STRANDED DNA; OLIGONUCLEOTIDE; PYRAZOLO[3,4 D]PYRIMIDINE DERIVATIVE; RNA;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; HALOGENATION; HYDROLYSIS; HYDROPHOBICITY; MOLECULAR STABILITY; SYNTHESIS;

EID: 0032835007     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1522-2675(19991006)82:10<1640::AID-HLCA1640>3.0.CO;2-N     Document Type: Article

References (38)

1. F. Seela, N. Ramzaeva, H. Rosemeyer, in 'Hetarenes', Houben-Weyl, Vol. E 9b, 'Bicyclic 6-Ring Systems Each with One to Two N-Atoms - Purities', Weinheim, 1997, p. 403.
2. A. I. H. Murchie, D. M. J. Lilley, EMBO J. 1994, 13, 993.
3. F. Seela, M. Zulauf, Chem.-Eur. J. 1998, 4, 1781.
4. F. Seela, H. Driller, Helv. Chim. Acta 1988, 71, 1191.
5. F. Seela, K. Kaiser, Helv. Chim. Acta 1988, 71, 1813.
6. F. Seela, M. Zulauf, J. Chem. Soc., Perkin Trans. 1 1999, 479.
7. C. A. Buhr, R. W. Wagner, D. Grant, B. C. Froehler, Nucleic Acids Res. 1996, 24, 2974.
8. G. Balow, V. Mohan, E. A. Lesnik, J. F. Johnston, B. P. Monia, O. L. Acevedo, Nucleic Acids Res. 1998, 26, 3350.
9. D. Graham, J. A. Parkinson, T. Brown, J. Chem. Soc., Perkin Trans. 1 1998, 1131.
10. F. Seela, G. Becher, M. Zulauf, Nucleosides Nucleotides 1999, 18, 1399.
11. F. Seela, G. Becher, Chem. Commun. 1998, 2017.
12. F. Seela, H. Steker, Helv. Chim. Acta 1986, 69, 1602.
13. F. Seela, G. Becher, Synthesis 1998, 207.
14. N. Ramzaeva, G. Becher, F. Seela, Synthesis 1998, 1327.
15. R. F. Heck, J. Am. Chem. Soc. 1968, 90, 5518.
16. F. Seela, G. Becher, H. Rosemeyer, H. Reuter, G. Kastner, I. A. Mikailopulo, Helv. Chim. Acta 1999, 82, 105.
17. J. Plavec, 'Studies on the Stereoelectronic Effects in Nucleosides and Nucleotides', Thesis, Uppsala University, 1995.
18. a) C. Hansch, A. Leo, R. W. Taft, Chem. Rev 1991, 91, 165;
19. b) M. Oivanen, H. Lönnberg, X.-X. Zhon, J. Chattopadyaya, Tetrahedron 1987, 43, 1133.
20. F. Jordan, H. Niv, Nucleic Acids Res. 1977, 4, 697.
21. D. P. C. McGee, J. C. Martin, A. S. Webb, Synthesis 1983, 540.
22. J. Zemlicka, A. Holy, Collect. Czech. Chem. Commun. 1967, 32, 3159.
23. H. Büchi, H. G. Khorana, J. Mol. Biol. 1972, 72, 251.
24. H. Schaller, G. Weimann, B. Lerch, H. G. Khorana, J. Am. Chem. Soc. 1963, 85, 3821.
25. A. D. Barone, J.-Y. Tang, M. H. Caruthers, Nucleic Acids Res. 1984, 12, 4051.
26. N. D. Sinha, J. Biernat, J. McManus, H. Köster, Nucleic Acids Res. 1984, 12, 4539.
27. F. Seela, M. Zulauf, Nucleosides Nucleotides 1999, in press.
28. B. C. Froehler, 'Protocols for Oligonucleotides and Analogs', in 'Methods in Molecular Biology', Ed. E. S. Agrawal, Humana Press, Totowa, N. J., 1994, Vol. 20, p. 63.
29. Oligonucleotide Purification Cartridges, Applied Biosystems, Weiterstadt, Germany.
30. Rainbow™ Universal CPG, Clontech Laboratories Inc., Palo Alto, USA.
31. L. Beigelman, Ribozyme Pharmaceutical Inc., Boulder, CO 80301, USA.
32. C. R. Petrie, A. D. Adams, M. Stamm, J. Van Ness, S. M. Watanabe, R. B. Meyer, Bioconjugate Chem. 1991, 2, 441.
33. F. Seela, H. Driller, Nucleic Acids Res. 1989, 17, 901.
34. F. Seela, N. Ramzaeva, G. Becher, Collect. Czech. Chem. Commun. (Special Issue) 1996, 61, 258.
35. F. Seela, M. Zulauf, J. Chem. Soc., Perkin Trans. 2 1998, 3233.
36. E. A. Lesnik, S. M. Freier, Biochemistry 1995, 34, 10807.
37. N. Ramzaeva, C. Mittelbach, F. Seela, Helv. Chim. Acta 1997, 80, 1809.
38. J. A. McDowell, D. H. Turner, Biochemistry 1996, 35, 14077.