5-Aza-7-deaza-2'-deoxyguanosine: Oligonucleotide duplexes with novel base pairs, parallel chain orientation and protonation sites in the core of a double helix

European Journal of Organic Chemistry

Volumn , Issue 2, 1999, Pages 485-496

  Seela, Frank ^a   Melenewski, Alexander ^a  

^a UNIVERSITY OF OSNABRÜCK   (Germany)

Author keywords

5 Aza 7 deaza 2' deoxyguanosine; Oligonucleotides; Parallel DNA; Protonated base pairs; T(m) values

Indexed keywords

5 AZA 7 DEAZA 2' DEOXYGUANOSINE; CYTOSINE; DEOXYGUANOSINE DERIVATIVE; GUANINE; OLIGONUCLEOTIDE; PHOSPHONIC ACID DERIVATIVE; PHOSPHORAMIDIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BASE PAIRING; CARBON NUCLEAR MAGNETIC RESONANCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; HYDROGENATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PKA; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032839116     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199902)1999:2<485::AID-EJOC485>3.0.CO;2-J     Document Type: Article

References (45)

1. J. A. Montgomery in Nucleosides, Nucleotides and Their Biological Applications (Eds.: J. L. Rideout, D. W. Henry, L. M. Beacham III) Academic Press, New York, 1983, pp. 19-46.
2. F. Seela, H. Driller, Nucleic Acids Res. 1985, 13, 911-926.
3. C. Y. Switzer, S. E. Moroney, S. A. Banner, Biochemistry 1993, 32, 10489-10496.
4. G. R. Revankar, R. K. Robins, "The Synthesis of Heterocyclic Analogues of Purine Nucleosides and Nucleotides" in Chemistry of Nucleosides and Nucleotides, 2 (Eds.: L. B. Townsend) Plenum Press, New York, London, 1991, pp. 161-398.
5. [5a] F. Seela, A. Kehne, Biochemistry 1987, 26, 2232-2238.
6. [5b] F. Seela, K. Kaiser, Helv. Chim. Acta 1988, 71, 1813-1823.
7. [6a] S. Mizusawa, S. Nishimura, F. Seela, Nucleic Acids Res. 1986, 14, 1319-1324.
8. [6b] F. Seela, S. Menkhoff, Liebigs Ann. Chem. 1985, 1360-1366.
9. [6c] F. Seela, H. Driller, U. Liman, Liebigs Ann. Chem. 1985, 312-320.
10. F. Seela, A. Röling, Nucleic Acids Res. 1992, 20, 55-61.
11. F. Seela, H. Steker, Helv. Chim. Acta 1986, 69, 1602-1613.
12. [9a] N. Ramzaeva, F. Seela, Helv. Chim. Acta 1996, 79, 1549-1558.
13. [9b] F. Seela, H. Thomas, Helv. Chim. Acta 1995, 78, 94-108.
14. [9c] F. Seela, M. Zulauf, Chem. Eur. J. 1998, 4, 1781-1790.
15. J. J. Voegel, S. A. Benner, Helv. Chim. Acta 1996, 79, 1881-1898.
16. H. Rosemeyer, F. Seela, J. Org. Chem. 1987, 52, 5136-5143.
17. G. S. Ti, B. L. Gaffney, R. A. Jones, J. Am. Chem. Soc. 1982, 104, 1316-1319.
18. A. Holy, J. Zemlicka, Collect. Czech. Chem. Commun. 1969, 34, 2449-2458.
19. L. J. McBride, R. Kierzek, S. L. Beaucage, M. H. Caruthers, J. Am. Chem. Soc. 1986, 108, 2040-2048.
20. S. L. Beaucage "Protocols for Oligonucleotides and Analogs" in Methods in Molecular Biology (Ed.: E. S. Agrawal), Humana Press, Totowa, New Jersey, 1994, vol. 20, p. 33.
21. B. C. Froehler, Protocols for Oligonucleotides and Analogs in Methods in Molecular Biology (Ed.: E. S. 0grawal), Humana Press, Totowa, New Jersey, 1994, vol. 20, p. 63.
22. T. Wada, Y. Sato, F. Honda, S. Kawahara, M. Sekine, J. Am. Chem. Soc. 1997, 119, 12710-12721.
23. P. P. Kung, R. A. Jones, Tetrahedron Lett. 1992, 33, 5869-5872.
24. S. M. Gryasnov, R. L. Letsinger, J. Am. Chem. Soc. 1991, 113, 5876-5877.
25. R. P. Panzica, R. J. Rousseau, R. K. Robins, L. B. Townsend, J. Am. Chem. Soc. 1972, 94, 4708-4714.
26. D. J. Cram, Chemtech 1987, 17, 120.
27. A. Eschenmoser, M. Dobler, Helv. Chim. Acta 1992, 75, 218.
28. E. T. Kool, Chem. Rev. 1997, 97, 1473-1487.
29. C. Thibaudeau, J. Plavec, K. A. Watanabe, J. Chattopadhyaya, J. Chem. Soc., Chem. Commun. 1994, 537-540.
30. H. Rosemeyer, F. Seela, J. Chem. Soc., Perkin Trans. 2 1997, 2341-2345.
31. J. van Wijk, C. Altona, PSEUROT 6.2 - A program for the conformational analysis of five-membered rings, University of Leiden, July 1993.
32. E. Westhof, O. Röder, I. Croneiss, H.-D. Lüdemann, Z. Naturforsch., C 1975, 30, 131.
33. F. Seela, I. Münster, U. Löchner, H. Rosemeyer, Helv. Chim. Acta 1998, 81, 1139-1155.
34. F. Seela, A. Melenewski, C. Wei, Bioorg. Med. Chem. Lett. 1997, 7, 2173-2176.
35. F. Seela, Y. Chen, A. Melenewski, H. Rosemeyer, C. Wei, Acta Biochim. Pol. 1996, 43, 45-52.
36. W. Saenger, "Principles of Nucleic Acid Structure" in Springer Advanced Texts in Chemistry (Ed.: C. R. Cantor), Springer Verlag, New York, Berlin, Heidelberg, Tokyo, 1984.
37. K. Rippe, N. B. Ramsing, R. Klement, T. M. Jovin, J. Biomol. Struct. Dyn. 1990, 7, 1199-1209.
38. F. Seela, C. Wei, A. Melenewski, Nucleic. Acids Res. 1996, 24, 4940-4945.
39. F. Seela, C. Wei, Helv. Chim. Acta 1997, 80, 73-85.
40. Y. Tor, P. B. Dervan, J. Am. Chem. Soc. 1993, 115, 4461-4467.
41. K. Groebke, J. Hunziker, W. Fraser, L. Peng, U. Diederichsen, K. Zimmermann, A. Holzner, C. Leumann, A. Eschenmoser, Helv. Chim. Acta 1998, 81, 375-474.
42. F. Seela, T. Wenzel, Helv. Chim. Acta 1992, 75, 1111-1122.
43. T. Teorell, E. Stenhagen, Biochem. Z. 1953, 299, 416-419.
44. F. Seela, K. Kaiser, U. Bindig, Helv. Chim. Acta 1989, 72, 868-881.
45. Applied Biosystems, Oligonucleotide Purification Cartridges.