Crystal and solution structure of 5'-O-(guanosine-2'-O- phosphonomethyl)cytidine, an isopolar nonisosteric phosphonate analog of GpC

Nucleosides and Nucleotides

Volumn 18, Issue 11-12, 1999, Pages 2581-2599

  Zachova J ^a   Cisarova I ^a   Budesinsky M ^b   Liboska, R ^b   Tocik Z ^b   Rosenberg, I ^b  

^a CHARLES UNIVERSITY   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

CYTIDINE DERIVATIVE;

ARTICLE; CONFORMATION; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN ANALYSIS; PROTEIN STRUCTURE; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 1642618187     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319908044628     Document Type: Article

References (46)

1. Vlassov, V.V.; Vlassova, I.E.; Pautova, L.V. in Progress in Nucleic Acid Research and Molecular Biology, vol. 57 (Moldave, K.; ed.), p. 95. Academic Press, San Diego 1997.
2. Hunziker, J.; Leumann, C. in Modern Synthetic Methods 1995 (Ernst, B.; Leumann, C.; eds.), p. 333. VHCA, Basel 1995.
3. Kool, E. T. Chem. Rev., 1997, 97, 1473-1487.
4. Tazawa, I.; Tazawa, S.; Stempel, L.M.; Ts'o, P.O.P. Biochemistry, 1970, 9, 3499-3514.
5. Letsinger, R.L.; Bach, S.A.; Eadie, J.S. Nucleic Acids Res., 1986, 14, 3487-3499.
6. Miller, P.S.; Yano, J.; Yano, E.; Carroll, C.; Jayaraman, K.; Ts'o, P.O.P. Biochemistry, 1979, 18, 5134-5143.
7. Muraoka, M.; Takahashi, S; Uesugi, S. Nucleosides Nucleotides, 1995, 14, 1503-1518.
8. Mojzeš, P.; Štěpánek, J.; Rosenberg, I.; Točík, Z.; Burian, M.; Pavelčíková, M.; Réfrégiers, M.; Videlot, H. J. Mol. Struct., 1995, 348, 45-48.
9. Zajíček, J.; Rosenberg, I.; Liboska, R.; Točík, Z.; Fazakerley, G.V.; Guschlbauer, W.; Holý, A. Collect. Czech. Chem. Commun., 1997, 62, 83-98.
10. Štěpánek, J.; Hanuš, J.; Endová, M.; Dole, J. Točík, Z.; Rosenberg, I., in Spectroscopy of Biological Molecules: Modern Trends (Carmona, P.; ed.), Kluwer Acad. Publ., Dordrecht 1997, pp 239-240.
11. Pressová, M.; Endová, M.; Točík, Z.; Liboska, R.; Rosenberg, I. Bioorg. Med. Chem. Lett., 1998, 8, 1225-1230.
12. Krishnan, R.; Seshadri, T.P.; Viswamitra, M.A. Nucleic Acids Res., 1991, 19, 379-384.
13. Rosenberg, I.; Holý, A. Collect. Czech. Chem. Commun., 1987, 52, 2572-2588.
14. Sheldrick G.M. Acta Crystallogr. A., 1990, 46, 467-473.
15. Sheldrick G.M. SHELXL97. Program for Crystal Structure Refinement from Diffraction Data. University of Gottingen, Gottingen 1997.
16. Castellano, S., Bothner-By, A.A. J. Chem. Phys., 1964, 41, 3863-3869.
17. Bodenhausen, G.; Freeman, R.; Niedermeyer, R.; Turner, D.L. J. Magn. Reson., 1977, 26, 133-164.
18. Bachmann, P.; Aue, W.P.; Muller, L.; Ernst, R.R. J. Magn. Reson., 1977, 28, 29-39.
19. Bax, A.; Davis, D.G. J. Magn. Reson., 1985, 63, 207-213.
20. Kessler, H.; Griesinger, C.; Kerssebaum, R.; Wagner, K.; Ernst, R.R. J. Am. Chem. Soc., 1987, 109, 607-609.
21. Muller, L. J. Am. Chem. Soc., 1979, 101, 4481-4484.
22. Bax, A.; Griffey, R.H.; Hawkins, B.L. J. Magn. Reson., 1983, 55, 301-315.
23. IUPAC/TUB JCBN Recommendations 1982, Eur. J. Biochem., 1983, 131, 9-15.
24. Krishnan, R.; Seshadri, T.P. Biopolymers, 1994, 34, 1637-1646.
25. Taylor, R., Kennard, O. J. Mol. Struct., 1982, 78, 1-25.
26. Saenger, W. in Principles of Nucleic Acid Structure, Springer-Verlag, New York, 1984, p. 56 and 132.
27. Štrajbl, M.; Florián, J. J. Biomol. Struct. Dyn., 1996, 13, 687-694.
28. Barvík, I.; Bok, J.; Štěpánek, J. unpublished results.
29. Altona, C.; Sundaralingam, M. J. Am. Chem. Soc., 1972, 94, 8205-8212.
30. Altona, C.; Sundaralingam, M. J. Am. Chem. Soc., 1973, 95, 2333-2344.
31. Haasnoot, C.A.G.; de Leeuw, F.A.A.M.; de Leeuw, H.P.M.; Altona, C. Org. Magn. Reson., 1981, 15, 43-52.
32. Haasnoot, C.A.G.; de Leeuw, F.A.A.M.; Altona, C. Tetrahedron, 1980, 36, 2783-2792.
33. de Leeuw, F.A.A.M.; Altona, C. J. Chem. Soc., Perkin Trans. 2, 1982, 375-384.
34. de Leeuw, F.A.A.M.; Altona, C. J. Comp. Chem., 1983, 4, 428-437.
35. Raich, I. PhD Thesis, Prague Institute of Technology, Prague 1994.
36. Altona, C. Recl. Trav. Chim. Pays-Bas, 1982, 101, 413-433.
37. Remin, M.; Shugar D. Biochem. Biophys. Res. Commun., 1972, 48, 636-642.
38. Lankhorst, P.P.; Haasnoot, C.A.G.; Erkelens, C.; Altona, C. J. Biomol. Struct. Dyn., 1984, 1, 1387-1405.
39. Mooren, M.M.W.; Wijmenga, S.S.; van der Marel, G.A.; van Boom, J.H.; Hilbers, C.W. Nucleic. Acids Res., 1994, 22, 2658-2666.
40. Thiem, J.; Meyer, B. Org. Magn. Reson., 1978, 11, 50-51.
41. Hamer, G.K.; Balza P.; Cyr, N.; Perlin, A.S. Can. J. Chem., 1978, 56, 3109-3116.
42. Wijmenga, S.S.; Mooren, M.M.W.; Hilbers, C.W. in NMR of Macromolecules, Oxford Univ. Press, Oxford, 1993, p.217-288.
43. Lemieux, R.U.; Nagabushan, T.L.; Paul B. Can. J. Chem., 1972, 50, 773-776.
44. Delbaere, L.T.J.; James, M.N.G.; Lemieux, R.U. J. Am. Chem. Soc., 1973, 95, 7866-7868.
45. Wüthrich, K. in NMR of Proteins and Nucleic Acids, J. Wiley, New York, 1986, p.177.
46. Lane, A.N. Magn. Reson. Chem., 1996, 34, S3-S10.