Multiple oligodeoxyribonucleotide syntheses on a reusable solid-phase CPG support via the hydroquinone-O,O'-diacetic acid (Q-Linker) linker arm

Nucleic Acids Research

Volumn 27, Issue 6, 1999, Pages 1531-1538

  Pon, Richard T ^b   Yu, Shuyuan ^b   Guo, Zhiqiang ^a   Sanghvi, Yogesh S ^a  

^a ISIS PHARMACEUTICALS   (United States)

^b UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXYBENZOTRIAZOLE; ANTISENSE OLIGODEOXYNUCLEOTIDE; BENZOTRIAZOLE DERIVATIVE; ESTER; HYDROQUINONE DERIVATIVE; HYDROQUINONE DIACETIC ACID; HYDROXYL GROUP; O BENZOTRIAZOLYL N,N,N',N' TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE; OLIGODEOXYRIBONUCLEOTIDE; UNCLASSIFIED DRUG; GLASS; HYDROQUINONE O,O' DIACETIC ACID; HYDROQUINONE-O,O'-DIACETIC ACID;

ARTICLE; DRUG SYNTHESIS; NUCLEOTIDE METABOLISM; POLYACRYLAMIDE GEL ELECTROPHORESIS; PRIORITY JOURNAL; CHEMICAL MODEL; CHEMISTRY; SYNTHESIS;

GLASS; HYDROQUINONES; MODELS, CHEMICAL; OLIGODEOXYRIBONUCLEOTIDES;

EID: 0033558372     PISSN: 03051048     EISSN: None     Source Type: Journal    
DOI: 10.1093/nar/27.6.1531     Document Type: Article

References (45)

1. Pon, R.T. and Yu, S. (1997) Nucleic Acids Res., 25, 3629-3635.
2. Pon, R.T. and Yu, S. (1997) Tetrahedron Lett., 38, 3331-3334.
3. Brown, K.D. (1998) Genet. Engng News, 18, 1-30.
4. Sanghvi, Y.S., Andrade, M., Deshmukh, R.R., Holmberg, L., Scozzari, A.N. and Cole, D.L. (1999) In Hartmann, G. and Endres, S. (eds), Manual of Antisense Methodology. Kluwer Academic, Norwell, MA, in press.
5. Lashkari, D.A., Hunickesmith, S.P., Norgren, R.M., Davis, R.W. and Brennan, T. (1995)Proc. Natl Acad. Sci. USA, 92, 7912-7915.
6. Sindelar, L.E. and Jaklevic, J.M. (1995) Nucleic Acids Res., 23, 982-987.
7. Frank, R., Heikens, W., Heisterberg-Moutsis, G. and Blocker, H. (1983) Nucleic Acids Res., 13, 4365-4377.
8. Matthes, H.W.D., Zenke, W.M., Grundström, T., Staub, A., Wintzerith, M and Chambon, P. (1984) EMBO J., 3, 801-805.
9. Ott, J. and Eckstein, F. (1984) Nucleic Acids Res., 12, 9137-9142.
10. Bonora, G.M., Biancotto, G., Maffini, M. and Scremin, C.L. (1993) Nucleic Acids Res., 21, 1213-1217.
11. Greenberg, M.M. (1993) Tetrahedron Lett., 34, 251-254.
12. Lebec, C. and Wickstrom, E. (1996) J. Org. Chem., 61, 510-513.
13. Hovinen, J., Guzaev, A., Azhayev, A. and Lonnberg, H. (1994) Tetrahedron, 50, 7203-7218.
14. Lyttle, M.H., Adams, H., Hudson, D. and Cook, R.M. (1997) Bioconjugate Chem., 8, 193-198.
15. Pon, R.T. (1993) In Agrawal, S. (ed.), Protocols for Oligonucleotides and Analogs. Humana Press, Totowa, NJ, pp. 465-496.
16. Zhang, X.H. and Jones, R.A. (1996) Tetrahedron Lett., 37, 3789-3790.
17. Zhang, X.H., Gaffney, B.L. and Jones, R.A. (1997) Nucleic Acids Res., 25, 3980-3983.
18. Matray, T.J., Yoo, D.J., McMinn, D.L. and Greenberg, M.M. (1997) Bioconjugate Chem., 8, 99-102.
19. Hakala, H., Heinonen, P., Iitia, A. and Lonnberg, H. (1997) Bioconjugate Chem., 8, 378-384.
20. Markiewicz, W.T., Adrych-Rozek, K., Markiewicz, M., Zebrowska, A. and Astriab, A. (1994) In Epton, R. (ed.), Innovation and Perspectives in Solid Phase Synthesis: Peptides, Proteins and Nucleic Acids: Biological and Biomedical Applications. Mayflower Worldwide, Birmingham, UK, pp. 339-346.
21. Waldvogel, S.R. and Pfleiderer, W. (1998) Helv. Chim. Acta, 81, 46-58.
22. Maskos, U. and Southern, E.M. (1992) Nucleic Acids Res., 20, 1679-1684.
23. Debear, J.S., Hayes, J.A., Koleck, M.P. and Gough, G.R. (1987) Nucleosides Nucleotides, 6, 821-830.
24. Scott, S., Hardy, P., Sheppard, R.C. and McLean, M.J. (1994) In Epton, R. (ed.), Innovation and Perspectives in Solid Phase Synthesis: Peptides, Proteins and Nucleic Acids: Biological and Biomedical Applications. Mayflower Worldwide, Birmingham, UK, pp. 115-124.
25. Lyttle, M.H., Hudson, D. and Cook, R.M. (1996) Nucleic Acids Res., 24, 2793-2798.
26. Sylvain, C. Wagner, A. and Mioskowski, C. (1997) Tetrahedron Lett., 38, 1043-1044.
27. Nelson, P.S., Muthini, S., Vierra, M., Acosta, L. and Smith, T.H. (1997) Biotechniques, 22, 752-756.
28. Reese, C.B., Stewart, J.C.M., van Boom, J.H., de Leeuw, H.P.M., Nagel, J. and de Rooy, J.F.M. (1975) J. Chem. Soc. Perkin Trans. I, 934-942.
29. Blumbergs, P. (1994) US patent no. 5296589.
30. Reddy, M.P., Hanna, N.B. and Farooqui, F. (1994) Tetrahedron Lett., 35, 4311-4314.
31. Reddy, M.P. and Voelker, P.J. (1988) Int. J. Peptide Protein Res., 31, 345-348.
32. Palom, Y., Grandas, A. and Pedroso, E. (1998) Nucleosides Nucleotides, 17, 1177-1182.
33. Damha, M.J., Giannaris, P.A. and Zabarylo, S.V. (1990) Nucleic Acids Res., 18, 3813-3821.
34. Cook, A.F. and Maichuk, D.T. (1970) J. Org. Chem., 35, 1940-1943.
35. Matta, K.L. and Barlow, J.J. (1976) Carbohydrate Res., 51, 215-222.
36. Scheuerlarsen, C., Rosenbohm, C., Jorgensen, T.J.D. and Wengel, J. (1997) Nucleosides Nucleotides, 16, 67-80.
37. Sinha, N.D., Davis, P., Usman, N., Pérez, J., Hodge, R., Kremsky, J. and Casale, R. (1993) Biochimie, 75, 13-23.
38. Pon, R.T., Usman, N. and Ogilvie, K.K. (1988) Biotechniques, 6, 768-775.
39. Efimov, V.A., Buryakova, A.A., Reverdatto, S.V., Chakhmakhoheva, O.G. and Ovchinnikov, Y.A. (1983) Nucleic Acids Res., 11, 8369-8387.
40. Stetsenko, D.A., Lubyako, E.N., Potapov, V.K., Azhikina, T.L. and Sverdlov, E.D. (1996) Tetrahedron Lett., 37, 3571-3574.
41. Blankemeyer-Menge, B., Nimtz, M. and Frank, R. (1990) Tetrahedron Lett., 31, 1701-1704.
42. Harth-Fritschy, E. and Cantacuzene, D. (1997) J. Peptide Res., 50, 415-420.
43. Knorr, R., Trzeciak, A., Bannwarth, W. and Gillessen, D. (1989) Tetrahedron Lett., 30, 1927-1930.
44. Bergmann, F., Bannwarth, W. and Tam, S. (1995) Tetrahedron Lett., 36, 6823-6826.
45. Ambrosius, D., Casaretto, M., Gerardy-Schahn, R., Saunders, D., Brandenburg, D. and Zahn, H. (1989) Biol. Chem. Hoppe-Seyler, 370, 217-227.