Efficient synthesis of functionalized oligodeoxyribonucleotides with base-labile groups using a new silyl linker

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 9, 2008, Pages 5345-5351

  Ohkubo, Akihiro ^a   Kasuya, Rintaro ^a   Aoki, Katsufumi ^a   Kobori, Akio ^a   Taguchi, Haruhiko ^a   Seio, Kohji ^a   Sekine, Mitsuo ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

DNA synthesis; N unprotected phosphoramidite approach; Silyl linker; Solid phase synthesis

Indexed keywords

4 AMINOBUTYRIC ACID; DEOXYRIBONUCLEOSIDE; OLIGODEOXYRIBONUCLEOTIDE; OLIGOMER; PHOSPHITE; POLYMER; REAGENT; RESIN; SILANE DERIVATIVE; SPACER DNA;

3' UNTRANSLATED REGION; ARTICLE; SYNTHESIS;

MOLECULAR STRUCTURE; OLIGODEOXYRIBONUCLEOTIDES; SILANES; STEREOISOMERISM;

EID: 43049111042     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.02.076     Document Type: Article

References (38)

1. In: Stein C.A., and Krieg A.M. (Eds). Applied Antisense Oligonucleotide Technology (1998), Wiley-Liss, New York
2. In: Crooke S.T. (Ed). Antisense Drug Technology-Principles, Strategies and Application (2001), Marcel Dekker, New York
3. In: Gewirtz A.M. (Ed). Nucleic Acid Therapeutics in Cancer (2004), Hamana Press, Totowa, NJ
4. Manoharan M. Curr. Opin. Chem. Biol. 8 (2004) 5750
5. Amarzguioui M., Holen T., Babarie E., and Prydz H. Nucleic Acids Res. 31 (2003) 589
6. Schena M., Shalon D., Davis R.W., and Brown P.O. Science 270 (1995) 467
7. Lockhart D.J., Dong H., Byrne M.C., Follettie M.T., Gallo M.V., Chee M.S., Mittmann M., Wang C., Kobayashi M., Norton H., and Brown E.L. Nat. Biotechnol. 14 (1996) 1675
8. Kwiatkowski R.W., Lyamichev V., Arruda M., and Neri B. Mol. Diagn. 4 (1999) 353
9. Yamane A. Nucleic Acids Res. 30 (2002) e97
10. Okamoto A., Tanaka K., Fukuda T., and Saito I. J. Am. Chem. Soc. 125 (2003) 9296
11. Hwang G.T., Seo Y.J., and Kim B.H. J. Am. Chem. Soc. 126 (2004) 6528
12. Nakatani K., Sando S., and Saito I. Nat. Biotechnol. 19 (2001) 51
13. Kerman K., Saito M., Morita Y., Takamura Y., Ozsoz M., and Tamiya E. Anal. Chem. 76 (2004) 1877
14. Liu G., Lee T., and Wang J. J. Am. Chem. Soc. 127 (2005) 38
15. Martin P. Helv. Chim. Acta 78 (1995) 486
16. Grotli M., Douglas M., Eritja R., and Sproat B.S. Tetrahedron 54 (1998) 5899
17. Griffey R.H., Monia B.P., Cummins L.L., Freier S., Greig M.J., Guinosso C.J., Lesnik E., Manalili S.M., Mohan V., Owens S., Ross B.R., Sasmor H., Wancewicz E., Weiler K., Wheeler P.D., and Cook P.D. J. Med. Chem. 39 (1996) 5100
18. Prakash T.P., Manoharan M., Fraser A.S., Kawasaki A.M., Lesnik E.A., and Owens S.R. Tetrahedron Lett. 41 (2000) 4855
19. Prakash T.P., Kawasaki A.M., Lesnik E.A., Owens S.R., and Manoharan M. Org. Lett. 5 (2003) 403
20. Prakash T.P., Puschl A., Lesnik E., Mohan V., Tereshko V., Egli M., and Manoharan M. Org. Lett. 6 (2004) 1971
21. Saneyoshi H., Seio K., and Sekine M. J. Org. Chem. 70 (2005) 10453
22. Shohda K., Okamoto I., Wada T., Seio K., and Sekine M. Bioorg. Med. Chem. Lett. 10 (2000) 1795
23. Lin K., and Matteucci M.D. J. Am. Chem. Soc. 120 (1998) 8531
24. Haaima G., Hansen H.F., Christensen L., Dahl O., and Nielsen P.E. Nucleic Acids Res. 25 (1997) 4639
25. Seio K., Sasami T., Ohkubo A., Ando K., and Sekine M. J. Am. Chem. Soc. 129 (2007) 1026
26. Wada T., Kobori A., Kawahara S., and Sekine M. Tetrahedron Lett. 39 (1998) 6907
27. Wada T., Kobori A., Kawahara S., and Sekine M. Eur. J. Org. Chem. (2001) 4583
28. Parey N., Baraguey C., Vasseur J.-J., and Debart F. Org. Lett. 8 (2006) 3869
29. Beaucage S.L., and Caruthers M.H. Tetrahedron Lett. 22 (1981) 1859
30. Ohkubo A., Seio K., and Sekine M. Tetrahedron Lett. 45 (2004) 979
31. Ohkubo A., Seio K., and Sekine M. J. Am. Chem. Soc. 126 (2004) 10884
32. Kobori A., Miyata K., Ushioda M., Seio K., and Sekine M. Chem. Lett. (2002) 16
33. McCollum C., and Andrus A. Tetrahedron Lett. 32 (1991) 4069
34. Ohkubo A., Sakamoto K., Miyata K., Taguchi H., Seio K., and Sekine M. Org. Lett. 7 (2005) 5389
35. LeProust E., Zhang H., Yu P., Zhou X., and Gao X. Nucleic Acids Res. 29 (2001) 2171
36. Marugg J.E., van der Bargh C., Tromp M., van der Marel G.A., van Zoest W.J., and van Boom J.H. Nucleic Acids Res. 12 (1984) 9095
37. Hayakawa Y., Kataoka M., and Noyori R. J. Org. Chem. 61 (1996) 7996
38. Ohkubo, A.; Kasuya, R.; Sakamoto, K.; Miyata, K.; Nagasawa, H.; Tsukahara, T.; Maki, Y.; Watanobe, T.; Seio, K.; Sekine, M. Nucleic Acids Res. 2008, in press.