α-Oligodeoxyribonucleotide N3'→P5' phosphoramidates: Synthesis and duplex formation

Nucleic Acids Research

Volumn 26, Issue 4, 1998, Pages 1099-1106

  Pongracz, Krisztina ^a   Gryaznov, Sergei M ^a  

^a ILLUMINA INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3' AZIDO 2',3' DIDEOXYURIDINE; AMINONUCLEOSIDE; COMPLEMENTARY DNA; COMPLEMENTARY RNA; OLIGODEOXYRIBONUCLEOTIDE; PHOSPHORAMIDIC ACID DERIVATIVE; ZIDOVUDINE;

ARTICLE; DENATURATION; GLYCOSYLATION; NUCLEIC ACID SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

BASE SEQUENCE; DIMERIZATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NUCLEIC ACID CONFORMATION; NUCLEIC ACID DENATURATION; NUCLEIC ACID HETERODUPLEXES; OLIGODEOXYRIBONUCLEOTIDES; ORGANOPHOSPHORUS COMPOUNDS; OXIDATIVE PHOSPHORYLATION; THERMODYNAMICS;

EID: 0032519308     PISSN: 03051048     EISSN: None     Source Type: Journal    
DOI: 10.1093/nar/26.4.1099     Document Type: Article

References (40)

1. Zamecnik, P.C. and Stephenson, M.L. (1978) Proc. Natl. Acad. Sci. USA, 75, 280-284.
2. Helene, C. and Toulme, J.-J. (1990) Biochim. Biophys. Acta, 1049, 99-125.
3. Bielinska, A., Shivdasami, R.A., Zhang, L. and Nabel, G.J. (1990) Science 250, 997-1001.
4. Bock, L.C., Griffin, L.C., Latham, J.A., Vermaas, E.H. and Toole, J.J. (1992) Nature (Lond.), 255, 564-566.
5. Milligan, J.F., Matteucci, M.D. and Martin, J.C. (1993) J. Med. Chem., 36, 1923-1937.
6. De Mesmacker, A., Altman, K.-H., Waldner, A. and Wendeborn, S. (1995) Curr. Opin. Struct. Biol., 5, 343-355.
7. Matteucci, M. (1996) Perspect. Drug Discovery Design, 4, 1-16.
8. Bayever, E., Iversen, P.L., Bishop, M.R., Sharp, J.G. and Teasary, H.K., Arneson, M.A., Pirruccelo, S.J., Ruddon, R.W., Kessinger, A., Zon, G. and Armitage, J.O. (1993) Antisense Res. Dev., 3, 383-390.
9. Zhang, R., Yan, J., Shahinian, H., Amin, G., Lu, Z., Liu, T., Saag, M.S., Jiang, Z., Temsamani, S., Martin, R.R., et al. (1995) Clin. Pharm. Ther., 58, 44-53.
10. Crooke, S.T., Grillone, L.R., Tendolkar, A., Garrett, A., Fraktin, M.J., Leeds, S. and Barr, W.H., (1995) Clin. Pharm. Ther., 56, 641-646.
11. Kiebler-Herzog, L., Zon, G., Uzanski, B., Whitter, G. and Wilson, W.D. (1991) Nucleic Acids Res., 19, 2979-2986.
12. Wilson, W.D., Mizan, S., Tanious, F.A., Yao, S. and Zon, G. (1994) J. Mol. Recognit., 7, 89-98.
13. Gryaznov, S.M. and Chen, J.-K. (1994) J. Am. Chem. Soc., 116, 3143-3144.
14. Chen, J.-K., Schultz, R.G., Lloyd, D.H. and Gryaznov, S.M. (1994) Nucleic Acids Res., 23, 2661-2668.
15. Gryaznov, S.M., Lloyd, D.H., Chen, J.-K., Schultz, R.G., DeDionisio, L.A., Ratmeyer, L. and Wilson, W.D. (1995) Proc. Natl. Acad. Sci. USA, 92, 5798-5802.
16. Escude, C., Giovannageli, C., Sun, J.-S., Lloyd, D.-H., Chen, J.-K., Gryaznov, S.M., Garestier, T. and Helene, C. (1996) Proc. Natl. Acad. Sci. USA, 93, 4365-1369.
17. Gryaznov, S.M., Skorski, T., Cucco, C., Nieborowska-Skorska, M, Chiu, C.Y., Lloyd, D.H., Chen, J.-K., Koziolkiewicz, M. and Calabretta, B. (1996) Nucleic Acids Res., 24, 1508-1514.
18. Giovannangeli, C., Diviacco, S., Labrousse, V., Gryaznov, S.M., Charneau, P. and Helene, C. (1997) Proc. Natl. Acad. Sci. USA, 94, 79-84.
19. Skorski, T., Perrotti, D., Nieborowska-Skorska, M., Gryaznov, S.M. and Calabretta, B. (1997) Proc. Natl. Acad. Sci. USA, 94, 3966-3971.
20. Morvan, F. Rayner, B., Imbach, J.-L., Thenet, S., Bertrand, J.R., Paoletti, J., Malvy, C. and Paoletti, C. (1987) Nucleic Acids Res., 15, 3421-3437.
21. Thenet, S., Morvan, F., Bertrand, J.-R., Gautie, C. and Malvy, C. (1988) Biochimie, 70, 1729-1732.
22. Gagnor, C., Rayner, B., Leonetti, J.-P., Imbach, J.-L. and Lebleu, B. (1989) Nucleic Acids Res., 17, 5107-5114.
23. Morvan, F., Porumb, H., Degols, G., Lefebre, I., Pompon, A., Sproat, B.S., Rayner, B., Malvy, C., Lebleu, B. and Imbach, J.-L. (1993) J. Med. Chem., 36, 280-287.
24. Lavignon, M., Bertrand, J.-R., Rayner, B., Imbach, J.-L., Malvy, C. and Paoletti, C. (1989) Biochem. Biophys. Res. Commun., 161, 1184-1190.
25. Lavignon, M., Tounekti, N., Rayner, B., Imbach, J.-L., Keith, G., Paoletti, J. and Malvy, C. (1992) Antisense Res. Dev., 2, 315-324.
26. Boiziau, C., Debart, F., Rayner, B., Imbach, J.-L. and Toulme, J.-J. (1995) FEBS Lett., 361, 41-45.
27. Liquier, J., Letellier, R., Dagneaux, C., Ouali, M., Morvan, F., Raynier, B., Imbach, J.L. and Taillandier, E. (1993) Biochemistry, 32, 10591-10598.
28. Debart, F., Rayner, B., Degols, G. and Imbach, J.-L. (1992) Nucleic Acids Res., 6, 1193-1200.
29. Czernecki, S. and Valery, J.-M. (1991) Synthesis, 239-240.
30. Ward, D.I., Jeffs, S.M., Coe, P.L. and Walker, R.T. (1993) Tetrahedron Lett., 34, 6779-6782.
31. Gryaznov, S.M. and Lloyd, D.H. (1993) Nucleic Acids Res., 21, 5909-5915.
32. Imazawa, M. and Eckstein, F. (1978) J. Org. Chem., 43, 3044-3048.
33. Yamaguchi, T. and Saneyoshi, M. (1984) Chem. Pharm. Bull., 32, 1441-1450.
34. Koga, M., Wilk, A., Moore, M.F., Screamin, C.L., Zhou, L. and Beaucage, S.L. (1995) J. Org. Chem., 60, 1520-1530.
35. Rizance, J.H., Baase, W.A., Johnson, W.C., Hall, K., Cruz, P. and Tinoco, I., Jr (1985) Nucleic Acids Res., 13, 4983-4989.
36. Divacar, K.J. and Reese, C.B. (1982) J. Chem. Soc. Perkin Trans., I., 1171-1176.
37. Schultz, R.G. and Gryaznov, S.M. (1996) Nucleic Acids Res., 24, 2966-2973.
38. Ding, D., Gryaznov, S.M., Lloyd, D.H., Chandrasekaran, S., Yao, S., Ratmeyer, L., Li Pan, Y. and Wilson, W.D. (1996) Nucleic Acids Res., 24, 354-360.
39. Rentzeperis, D., Rippe, K., Jovin, T.M. and Marky, L.A. (1992) J. Am. Chem. Soc., 114, 5926-5928.
40. Tunis-Schneider, M.J.B. and Meastre, M.F. (1970) J. Mol. Biol., 52, 521.