Synthesis of 4-thiothymine based photolabels as new tools for nucleic acids structural studies in solution: Formation of long-range photo-cross- links within a hammerhead ribozyme domain

Tetrahedron

Volumn 56, Issue 9, 2000, Pages 1197-1206

  Saintomé, Carole ^a   Clivio, Pascale ^a   Fourrey, Jean Louis ^a   Woisard, Anne ^a   Laugâa, Philippe ^a   Favre, Alain ^a  

^a CNRS   (France)

Author keywords

Hammerhead ribozyme; Nucleic acids; Photolabels

Indexed keywords

ASPARTIC ACID; DEOXYURIDINE; GLUTAMINE; NUCLEIC ACID; RIBOZYME; THYMINE DERIVATIVE;

ARTICLE; BASE MISPAIRING; CONFORMATION; CROSS LINKING; IRRADIATION; PHOTOAFFINITY LABELING; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN DOMAIN; PROTEIN FOLDING; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034712240     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00024-7     Document Type: Article

References (34)

1. (a) Vaish, N. K.; Kore, A. R.; Eckstein, F. Nucleic Acids Res. 1998, 26, 5237-5242.
2. (b) Eckstein, F., Lilley, D. M. J., Eds. 1997, Catalytic RNA; Springer: Berlin.
3. (c) Burlina, F.; Favre, A.; Fourrey, J.-L. Bioorg. Med. Chem. 1997, 5, 1999-2010.
4. (a) Wedekind, J. E.; McKay, D. B. Annu. Rev. Biomol. Struct. 1998, 27, 475-502.
5. (b) Scott, W. G.; Finch, J. T.; Klug, A. Cell 1995, 81, 991-1002.
6. (c) Pley, H. W.; Flaherly, K. M.; McKay, D. B. Nature 1994, 372, 68-74.
7. (a) Bassi, G. S.; Mollegaard, N. E.; Murchie, A. I. H.; Lilley, D. M. J. Biochem. 1999, 38, 3345-3354.
8. (b) Bassi, G. S.; Mollegaard, N. E.; Murchie, A. I. H.; Kitzing, E.; Lilley, D. M. J. Nature Struct. Biol. 1995, 2, 45-55.
9. Amiri K.M.A., Hagerman P.J. Biochemistry. 33:1994;13172-13177.
10. Tuschl T., Gohlke C., Jovin T.M., Westhof E., Eckstein F. Science. 266:1994;785-789.
11. (a) Zhou, D.-M.; He, Q.-C.; Zhou, J.-M.; Taira, K. FEBS Lett. 1998, 431, 154-160.
12. (b) van Tol, H.; Buzayan, J. M.; Felstein, F.; Eckstein, F.; Bruening, G. Nucleic Acids Res. 1990, 18, 1971-1975.
13. Woisard A., Fourrey J.-L., Favre A. J. Mol. Biol. 239:1994;366-370.
14. Woisard A., Favre A., Clivio P., Fourrey J.-L. J. Am. Chem. Soc. 114:1992;10072-10073.
15. Laugâa P., Woisard A., Fourrey J.-L., Favre A. C. R. Acad. Sci., Life Sci. 318:1995;307-313.
16. Bravo C., Woisard A., Fourrey J.-L., Laugâa P., Favre A. Biochimie. 81:1999;201-212.
17. Scott W.G., Murray J.B., Arnold J., Stoddard B.L., Klug A. Science. 274:1996;2065-2069.
18. (a) Murray, J. B.; Terwey, D. P.; Maloney, L.; Karpeisky, A.; Usman, N.; Beigelman, L.; Scott, W. G. Cell 1998, 92, 665-673.
19. (b) Peracchi, A.; Beigelman, L.; Scott, E. C.; Uhlenbeck, O. C.; Herschlag, D. J. Biol. Chem. 1997, 272, 26822-26826.
20. Saintomé C., Clivio P., Fourrey J.-L., Woisard A., Favre A. Tetrahedron Lett. 35:1994;873-876.
21. Saintomé C., Clivio P., Favre A., Fourrey J.-L., Laugâa P. J. Chem. Soc., Chem. Commun. 1997;167-168.
22. Dreyer G.B., Dervan P.B. Proc. Natl. Acad. Sci. U.S.A. 82:1985;968-972.
23. Crouch G.J., Eaton B.E. Nucleosides Nucleotides. 13:1994;939-944.
24. Hobbs F.W. J. Org. Chem. 54:1989;3420-3422.
25. Tong G., Lawlor J.M., Tregear G.W., Haralambidis J. J. Org. Chem. 58:1993;2223-2231.
26. Dos Santos D.V., Vianna A.-L., Fourrey J.-L., Favre A. Nucleic Acids Res. 21:1993;201-207.
27. 4T moiety of 2-5 was explored via systematic search, performed along the torsional angles of the linker.
28. Favre A., Fourrey J.-L. Acc. Chem. Res. 28:1995;375-382.
29. (a) Saintomé, C.; Clivio, P.; Favre, A.; Fourrey, J.-L. J. Org. Chem. 1997, 62, 8125-8130.
30. (b) Saintomé, C.; Clivio, P.; Fourrey, J.-L.; Favre, A.; Riche, C. J. Am. Chem. Soc. 1996, 118, 8142-8143.
31. Egholm M., Buchardt O., Nielsen P.E., Berg R.H. J. Am. Chem. Soc. 114:1992;1895-1897.
32. Beaucage S., Iyer R.P. Tetrahedron. 48:1993;2223-2311.
33. (a) Lemaigre-Debreuil, Y.; Expert-Bezançon, A.; Favre, A. Nucleic Acids Res. 1991, 19, 3653-3660.
34. (b) Igloï, G. L. Biochemistry 1988, 27, 3842-3849.