Synthesis and properties of oligo-2′-deoxyribonucleotides containing internucleotidic phosphoramidate linkages modified with pendant groups ending with either two amino or two hydroxyl functions

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 16, 2003, Pages 3499-3511

  Asseline, Ulysse ^a   Chassignol, Marcel ^a   Draus, Jolanta ^a   Durand, Maurice ^a   Maurizot, Jean Claude ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYRIBONUCLEOTIDE;

ARTICLE; CIRCULAR DICHROISM; DRUG SYNTHESIS; GENE TARGETING; STEREOCHEMISTRY; TRIPLE HELIX;

EID: 0038487839     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00273-6     Document Type: Article

References (52)

1. Christopoulos T. Anal. Chem. 71:1999;425R.
2. Seeman N.C. TIBTECH. 17:1999;437.
3. Praseuth D., Guieysse A.L., Hélène C. Biochem. Biophys. Acta. 1489:1999;181.
4. Ma D.D.F., Rede T., Naqvi N.A., Cook P.D. Biotech. Ann. Rev. 5:2000;155.
5. Fox K.R. Curr. Med. Chem. 7:2000;17.
6. Breaker R.R. Chem. Rev. 97:1997;371.
7. Le Doan T., Perrouault L., Praseuth D., Habhoub N., Decout J.L., Thuong N.T., Lhomme J., Hélène C. Nucleic Acids Res. 15:1987;7749.
8. Moser H.E., Dervan P.B. Science. 238:1987;645.
9. Cooney M., Czernuszewicz G., Postel E.H., Flint S.J., Hogan M.E. Science. 241:1988;546.
10. Pilch D.S., Levensen C., Shafer R.H. Biochemistry. 30:1991;6081.
11. Beal P.A., Dervan P.B. Science. 251:1991;1360.
12. Giovannangeli C., Rougée M., Garestier T., Thuong N.T., Hélène C. Proc. Natl. Acad. Sci. U.S.A. 89:1992;8631.
13. Miller P.S., Yano J., Yano E., Carrol C., Jayaraman K., Ts'o P.O.P. Biochemistry. 18:1979;5134.
14. Asseline U., Thuong N.T., Hélène C. J. Biol. Chem. 260:1985;8936.
15. Lancelot G., Guesnet J.L., Asseline U., Thuong N.T. Biochemistry. 27:1988;1265.
16. Durand M., Maurizot J.C., Asseline U., Barbier C., Thuong N.T., Hélène C. Nucleic Acids Res. 17:1989;1823.
17. Hau J.F., Asseline U., Thuong N.T. Tetrahedron Lett. 32:1991;2497.
18. Froehler B.C., Ng P., Matteucci M.D. Nucleic Acids Res. 16:1988;4831.
19. Ozaki H., Kitamura M., Yamana K., Shimidzu T. Bull. Chem. Soc. J. 63:1990;1929.
20. Fathi R., Huang Q., Coppola G., Delaney W., Teasdale R., Krieg A.M., Cook A.F. Nucl. Acids Res. 22:1994;5416.
21. Letsinger R.L., Singman C.N., Histand G., Salunkhe M. J. Am. Chem. Soc. 110:1988;4470.
22. Jung P.M., Histand G., Letsinger R.L. Nucleosides and Nucleotides. 13:1994;1597.
23. Horn T., Chatuverdi S., Balasubramanian T.N., Letsinger R.L. Tetrahedron Lett. 37:1996;743.
24. Chatuverdi S., Horn T., Letsinger R.L. Nucleic Acids Res. 24:1996;2318.
25. Laurent A., Naval M., Debart F., Vasseur J.J., Rayner B. Nucleic Acids Res. 27:1999;4151.
26. Ehrenmann F., Vasseur J.-J., Debart F. Nucleosides Nucleotides Nucleic Acids. 20:2001;797.
27. Dagle J.M., Weeks D.L. Nucleic Acids Res. 24:1996;2143.
28. De Mesmaeker A., Waldner A., Lebreton J., Hoffmann P., Fritsch V., Wolf R.M., Freier S.M. Angew. Chem. Ed. Engl. 33:1994;226.
29. Waldner A., De Mesmaeker A., Lebreton J., Fritsch V., Wolf R.M. Synlett. 1994;57.
30. Morvan F., Sangvhi Y.S., Perbost M., Vasseur J.-J., Bellon L. J. Am. Chem. Soc. 118:1996;255.
31. Dempcy R.O., Browne K.A., Bruice T.C. J. Am. Chem. Soc. 117:1995;6140.
32. Linkletter B.A., Bruice T.C. Bioorg. Med. Chem. Lett. 8:1998;1285.
33. Linkletter B.A., Szabo I.E., Bruice T.C. Nucl. Acids Res. 29:2001;2370.
34. Linkletter B.A., Bruice T.C. Bioorg. and Med. Chem. 8:2000;1893.
35. Arya D.P., Bruice T.C. J. Am. Chem. Soc. 120:1998;6619.
36. Kojima N., Szabo I.E., Bruice T.C. Tetrahedron. 58:2002;867.
37. Hanvey J.C., Peffer N.C., Bisi J.E., Thomson S.A., Cadilla R., Josey J.A., Ricca D.J., Hassman C.F., Bonham M.A., Au K.G., Carter S.G., Bruckenstein D.A., Boyd A.L., Noble S.A., Babiss L.E. Science. 258:1992;1481.
38. Hickman D.T., King P.M., Slater J.M., Cooper M.A., Micklefield J. Nucleotides, Nucleosides and Nucleic Acids. 20:2001;1169.
39. Rumney IV S., Kool E.T. J. Am. Chem. Soc. 117:1995;5635.
40. Bannwarth W., Dora A., Iaiza P., Pannekouke X. Helv. Chim. Acta. 77:1994;182.
41. O'Sullivan M.C., Dalrymple D. Tetrahedron Lett. 36:1985;3451.
42. Seela F., Kretschmer U. J. Org. Chem. 56:1991;3861.
43. Sinha N.D., Biernat J., McManus J., Köster H. Nucleic Acids Res. 12:1984;4539.
44. Privat E., Asseline U. Bioconjugate Chem. 12:2001;757.
45. Connolly B.A., Potter B.V., Eckstein F., Pingould A., Grotjahn L. Biochemistry. 23:1984;3443.
46. Tömösközi I., Gacs-Baitz E., Ötvös L. Tetrahedron. 51:1995;6797.
47. Miller P.S., Dreon N., Pulford S.M., McFarland C.B. J. Biol. Chem. 255:1980;9659.
48. Nawrot B., Boczkowska M., Wojcik M., Sochacki M., Kazmierski S., Stec W.J. Nucleic Acids Res. 26:1988;2650.
49. Atkinson, T.; Smith, M. In Oligonucleotides Synthesis: A Practical Approach; Gait, M. J., Ed.; IRL: Oxford, 1984.
50. Cantor C.R., Warshaw M.M., Shapiro H. Biopolymers. 9:1970;1059.
51. Shabarova Z.A. Biochimie. 70:1988;1323.
52. Beaucage S.L., Caruthers M.H. Tetrahedron Lett. 22:1981;1859.