Guanosine analog with respect to Z-DNA stabilization: Nucleotide with combined C8-bromo and C2′-ethynyl modifications

European Journal of Organic Chemistry

Volumn , Issue 9, 2008, Pages 1544-1549

  Nadler, André ^a   Diederichsen, Ulf ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Circular dichroism; Conformation; Nucleotide modification; Oligonucleotides; Z DNA

Indexed keywords

EID: 53849102218     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700991     Document Type: Article

References (25)

1. N. R. Cozzarelli, J. C. Wang, DNA Topology and Its Biological Effects, Cold Spring Harbor, Laboratory Press, New York, 1990.
2. a) A. Rich, A. Nordheim, A. H.-J. Wang, Annu. Rev. Biochem. 1984, 53, 791-846;
3. b) R. Allemann, M. Egli, Chem. Biol. 1997, 9, 643-650;
4. c) C. Garvie, C. Wolberger, Mol. Cell 2001, 8, 937-946.
5. a) B. Spingler, P. M. Antoni, Chem. Eur. J. 2007, 13, 6617-6622;
6. b) X. Qu, J. O. Trent, I. Fokt, W. Priebe, J. B. Chaires, Proc. Natl. Acad. Sci. USA 2000, 97, 12032-12037;
7. c) Y.-G. Kim, H.-J. Park, K. K. Kim, K. Lowenhaupt, A. Rich, Nucleic Acids Res. 2006, 34, 4937-4942.
8. G. L. Wang, K. M. Vasquez, Front. Biosci. 2007, 12, 4424-4438.
9. a) T. Schwartz, M. A. Rould, K. Lowenhaupt, A. Herbert, A. Rich, Science 1999, 284, 1841-1845;
10. b) T. Schwartz, J. Behlke, K. Lowenhaupt, U. Heinemann, A. Rich, Nat. Struct. Biol. 2001, 8, 761-765;
11. c) Y.-G. Kim, M. Muralinath, T. Brandt, M. Pearcy, K. Hauns, K. Lowenhaupt, B. L. Jacobs, A. Rich, Proc. Natl. Acad. Sci. USA 2003, 100, 6974-6979.
12. A. H.-J. Wang, G. J. Quigley, F. J. Kolpak, J. L. Crawford, J. H. van Boom, G. van der Marel, A. Rich, Nature 1979, 282, 680-686.
13. H. Sugiyama, K. Kawai, A. Matsunaga, K. Fujimoto, I. Saito, H. Robinson, A. H.-J. Wang, Nucleic Acids Res. 1996, 24, 1272-1278.
14. S. Uesugi, T. Shida, M. Ikehara, Biochemistry 1982, 21, 3400-3408.
15. M. Behe, G. Felsenfeld, Proc. Natl. Acad. Sci. USA 1981, 78, 1619-1623.
16. a) R. Buff, J. Hunziker, Bioorg. Med. Chem. Lett. 1998, 8, 521-524;
17. b) R. Buff, J. Hunziker, Nucleosides Nucleotides 1999, 18, 1387-1388;
18. c) R. Buff, J. Hunziker, Helv. Chim. Acta 2002, 85, 224-254.
19. W. Saenger, Principles of Nucleic Acid Structure, Springer, New York, 1984.
20. Y. Xu, R. Ikeda, H. Sugiyama, J. Am. Chem. Soc. 2003, 125, 13519-13524.
21. M. J. Gait, Oligonucleotide Synthesis - A Practical Approach, IRL Oxford University Press, Oxford, 1984.
22. C. Fàbrega, M. J. Marcías, R. Eritja, Nucleosides Nucleotides 2001, 20, 251-260.
23. F a) F. M. Pohl, T. M. Jovin, J. Mol. Biol. 1972, 67, 375-396;
24. b) J. Curtis, CD of Nucleic acids Circular Dichroism, 2nd ed., Wiley-VCH, New York, 2000.
25. J. Šponer, H. A. Gabb, J. Leszczynski, P. Hobza, Biophys. J. 1997, 73, 76-87.