Oligonucleotide synthesis by the use of a 2-(levulinyloxymethyl)-5-nitrobenzoyl group as the novel base-labile protecting group for the 5'-hydroxyl groups of ribonucleoside and 2'-deoxyribonucleoside 3'-phosphoramidites

Tetrahedron Letters

Volumn 38, Issue 39, 1997, Pages 6857-6860

  Kamaike, Kazuo ^a   Takahashi, Hiroaki ^a   Kakinuma, Takashi ^a   Morohoshi, Kimio ^a   Ishido, Yoshiharu ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGODEOXYNUCLEOTIDE DERIVATIVE; RIBONUCLEOSIDE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 0030747030     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01617-1     Document Type: Article

References (27)

1. a) Matteucci, M. D.; Caruthers, M. H. J. Am. Chem. Soc. 1981, 103, 3135 - 3191;
2. b) Tanaka, T.; Letsinger, R. L. Nucleic Acids Res. 1982, 10, 3249 - 3260.
3. a) Barone, A. D.; Tang, J. -Y.; Caruthers, M. H. Nucleic Acids Res. 1984, 12, 4051 - 4061;
4. b) Kierzek, R.; Rozek, M.; Markiewiecz, W. T. Nucleic Acids Res. Symp. Ser. 1987, 18, 201-204.
5. a) Reese, C. B.; Skone, P. A. Nucleic Acids Res. 1985, 13, 5215-5231;
6. b) Hirao, I.; Ishikawa, M.; Miura, K. Nuclei Acids Res. Symp. Ser. 1985, 16, 173-176;
7. c) Christodoulou, C.; Agrawal, S.; Gait, M. J. Tetrahedron Lett. 1986, 13, 1521-1522.
8. a) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1992, 48, 2223-2311;
9. b) Bergmann, F.; Pfleiderer, W. Helv. Chim. Acta 1994, 77, 203-215;
10. c) idem., ibid. 1994, 77,481-501;
11. d) idem., ibid. 1994, 77, 988-998.
12. a) van Boom, J. H.; Burgers, P. M. J. Tetrahedron Lett. 1976, 4875-4878;
13. b) van Boom, J. H.; Burgers, P. M. J., Verdegaal, C. H. M.; Wille, S. Tetrahedron 1978, 34, 1999-2007;
14. c) Iwai, S.; Ohtsuka, E. Nucleic Acids Res. 1988, 16, 9443-9456;
15. d) Iwai, S.; Sasaki, T.; Ohtsuka, E. Tetrahedron 1990, 46, 6673-6688.
16. a) van Boom, J. H.; Christodoulou, C.; Reese, C. B.; Sindona, G. J. Chem. Soc., Perkin Trans, I 1984, 1785-1790;
17. b) Reese, C. B. Nucleosides Nucleotides 1987, 6, 121-129;
18. c) Christodoulou, C.; Agrawal, S.; Gait, M. ibid. 1987, 6, 341-344.
19. Cain, B. F. J. Org. Chem. 1976, 41, 2029-2031.
20. Kamaike, K.; Uemura, F.; Yamakage, S.; Nishino, S.; Ishido, Y. Nucleosides Nucleotides 1987, 6, 699-736.
21. Sinha, N. D.; Biernat, J.; McManus, J.; Köster, H. Nucleic Acids Res. 1984, 12, 4539-4557.
22. a) Miyoshi, K.; Huang, H.; Itakura, K. Nucleic Acid Res. 1980, 8, 5491-5505;
23. b) Marugg, J. E.; Piel, N.; McLaughlin, L. M.; Tromp, M.; Veeneman, G. H.; van der Marel, G. A.; van Boom, J. H. Nucleic Acids Res. 1984, 12, 8639-8651.
24. Seliger, H.; Scalfi, C.; Eisenbeiss, F. Tetrahedron Lett. 1983, 24, 4963-4966.
25. Belke, C. J.; Su, C. K.; Shafer, J. A. J. Am. Chem. Soc. 1971, 93, 4552-4560.
26. It was demonstrated by Reese and his co-workers [a) Griffin, B. E.; Reese, C. B. Tetrahedron Lett. 1964, 2925-2931;
27. b) Griffin, B. E.; Jarman, M.; Reese, C. B. Tetrahedron 1968, 24, 639-662.] that the Thp protecting group can be removed by treating with 0.01 M hydrochloric acid for 3-4 h at room temperature, and only 1 % of the 3'-5' phosphodiester linkage rearranged into the corresponding 2'-5' phosphodiester linkage after 216 h at 20°C.