The base-pairing properties of 7-deaza-2'-deoxyisoguanosine and 2'- deoxyisoguanosine in oligonucleotide duplexes with parallel and antiparallel chain orientation

Helvetica Chimica Acta

Volumn 82, Issue 5, 1999, Pages 726-745

  Seela, Frank ^a   Wei, Changfu ^a  

^a UNIVERSITY OF OSNABRÜCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2' DEOXYISOGUANOSINE TRIPHOSPHATE; 7 DEAZA 2' DEOXYISOGUANOSINE; OLIGONUCLEOTIDE; PHOSPHONIC ACID DERIVATIVE; SINGLE STRANDED DNA; UNCLASSIFIED DRUG;

ARTICLE; BASE PAIRING; CARBON NUCLEAR MAGNETIC RESONANCE; DNA SEQUENCE; DNA STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYBRIDIZATION; NUCLEOTIDE SEQUENCE; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0032894327     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1522-2675(19990505)82:5<726::AID-HLCA726>3.0.CO;2-K     Document Type: Article

References (35)

1. J. H. van de Sande, N. B. Ramsing, M. W. Germann, W. Elhorst, B. W. Kalisch, E. v. Kitzing, R. T. Pon, R. C. Clegg, T. M. Jovin, Science (Washington, D.C.) 1988, 241, 551; for a review, see T. M. Jovin, in 'Nucleic Acids and Molecular Biology', Ed. F. Eckstein and D. M. J. Lilley, Springer-Verlag, Berlin-Heidelberg, 1991, Vol. 5, p. 25.
2. J. H. van de Sande, N. B. Ramsing, M. W. Germann, W. Elhorst, B. W. Kalisch, E. v. Kitzing, R. T. Pon, R. C. Clegg, T. M. Jovin, Science (Washington, D.C.) 1988, 241, 551; for a review, see T. M. Jovin, in 'Nucleic Acids and Molecular Biology', Ed. F. Eckstein and D. M. J. Lilley, Springer-Verlag, Berlin-Heidelberg, 1991, Vol. 5, p. 25.
3. F. Seela, B. Gabler, Z. Kazimierczuk, Collect. Czech. Chem. Commun. (Special Issue) 1993, 58, 170.
4. H. Sugiyama, S. Ikeda, I. Saito, J. Am. Chem. Soc. 1996, 118, 9994.
5. F. Seela, C. Wei, A. Melenewski, E. Feiling, Nucleosides Nucleotides 1998, 17, 2045.
6. F. Seela, C. Wei, Helv. Chim. Acta 1997, 80, 73.
7. F. Seela, C. Wei, A. Melenewski, Nucleic Acids Res. 1996, 24, 4940.
8. F. Seela, B. Gabler, Helv. Chim. Acta 1994, 77, 622.
9. F. Seela, S. Menkhoff, S. Behrendt, J. Chem. Soc., Perkin Trans. 2 1986, 525.
10. S. Mizusawa, S. Nishimura, F. Seela, Nucleic Acids Res. 1986, 14, 1319.
11. D. M. Williams, D. Loakes, D. M. Brown, J. Chem. Soc., Perkin Trans. 1 1998, 3565.
12. Z. Kazimierczuk, R. Mertens, W. Kawczynski, F. Seela, Helv. Chim. Acta 1991, 74, 1742.
13. F. Seela, A. Kehne, H.-D. Winkeler, Liebigs Ann. Chem. 1983, 137.
14. F. Seela, H. Steker, H. Driller, U. Bindig, Liebigs Ann. Chem. 1987, 15.
15. F. Seela, C. Wei, H. Reuter, G. Kastner, Acta Crystallogr., Sect. C 1999, 55, in press.
16. F. Seela, C. Wei, Z. Kazimierczuk, Helv. Chim. Acta 1995, 78, 1843.
17. G. S. Ti, B. L. Gaffney, R. A. Jones, J. Am. Chem. Soc. 1982, 104, 1316.
18. T. Horn, C.-A. Chang, M. L. Collins, Tetrahedron Lett. 1995, 36, 2033.
19. S. C. Jurczyk, J. T. Kodra, J. D. Rozzell, S. A. Benner, T. R. Battersby, Helv. Chim. Acta 1998, 81, 793.
20. C. Y. Switzer, S. E. Moroney, S. A. Benner, Biochemistry 1993, 32, 10489.
21. F. Seela, C. Wei, A. Melenewski, Nucleosides Nucleotides 1997, 16, 1523.
22. F. Seela, C. Wei, Chem. Commun. 1997, 1869.
23. J. A. McDowell, D. H. Turner, Biochemistry 1996, 35, 14077.
24. Y. Tor, P. B. Dervan, J. Am. Chem. Soc. 1993, 115, 4461.
25. C. Switzer, S. E. Moroney, S. A. Benner, J. Am. Chem. Soc. 1989, 111, 8322.
26. H. Robinson, Y.-G. Gao, C. Bauer, C. Roberts, C. Switzer, A. H.-J. Wang, Biochemistry 1998, 37, 10897.
27. R. Krishnamurthy, S. Pitsch, M. Minton, C. Miculka, N. Windhab, A. Eschenmoser, Angew. Chem. 1996, 108, 1619.
28. C. Roberts, R. Bandaru, C. Switzer, J. Am. Chem. Soc. 1997, 119, 4640.
29. X.-L. Yang, H. Sugiyama, S. Ikeda, I. Saito, A. H.-J. Wang, Biophys. J. 1998, 75, 1163.
30. J. Sepiol, Z. Kazimierczuk, D. Shugar, Z. Naturforsch., C 1976, 31, 361.
31. F. H. Martin, M. M. Castro, F. Aboul-ela, I. Tinoco, Jr, Nucleic Acids Res. 1985, 13, 8927.
32. F. Seela, C. Mittelbach, Nucleosides Nucleotides 1999, in press.
33. S. L. Beaulage, in 'Methods in Molecular Biology', Vol. 20, 'Protocols for Oligonucleotides and Analogs, Synthesis and Properties', Ed. S. Agrawal, Humana Press, Totowa, New Jersey, 1993, p. 33.
34. J. Davoll, J. Chem. Soc. 1960, 131.
35. F. Seela, Y. Chen, 1997, unpublished work.