Protection of the guanine residue during synthesis of 2′-O-alkyl-guanosine derivatives

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 18, 1997, Pages 2779-2788

  Grøtli, Morten ^a   Douglas, Mark ^a   Beijer, Barbro ^b   García, Ramon Güimil ^a   Eritja, Ramon ^a   Sproat, Brian ^b  

^a EUROPEAN MOLECULAR BIOLOGY LABORATORY   (Germany)

^b VPI GmbH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748631069     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a700813i     Document Type: Article

References (33)

1. E. Uhlmann and A. Peyman, Chem. Rev., 1990, 90, 543.
2. P. D. Cook, Anticancer Drug Res., 1991, 6, 585.
3. B. S. Sproat and A. I. Lamond, 2′-O-Alkyloligoribonucleotides, in Antisense Research and Applications, ed. S. T. Crooke and B. Lebleu, CRC Press Inc., Florida, 1993, pp. 351-362.
4. M. Cotten, B. Oberhauser, H. Bruner, A. Holzner, G. Issakides, C. Noe, G. Schaffner, E. Wagner and M. Birnstiel, Nucleic Acids Res., 1993, 19, 2629.
5. G. Paolella, B. S. Sproat and A. I. Lamond, EMBO J., 1992, 11, 1913.
6. L. Beigelman, J. L. McSwiggen, K. C. Draper, C. Gonzalez, K. Jensen, A. M. Karpeisky, A. S. Modak, J. Matulic-Adamic, A. B. DiRenzo, P. Haeberli, D. Sweedler, D. Tracz, S. Grimm, F. E. Wincott, V. G. Thackray and N. Usman, J. Biol. Chem., 1995, 270, 25 702.
7. M. Grøtli, M. Douglas, B. Beijer, R. Eritja and B. Sproat, BioMed. Chem. Lett., 1997, 7, 425.
8. M. Robins, S. Naik and S. Lee, J. Org. Chem., 1974, 39, 1891;
9. T. Pathak and J. Chattopadhyaya, Chem. Scri., 1986, 26, 135.
10. E. Wagner, B. Oberhauser, A. Holzner, H. Bruner, G. Issakides, G. Schaffner, M. Cotten, M. Knollmuller and C. Noe, Nucleic Acids Res., 1991, 19, 5965.
11. R. P. Hodge and N. D. Sinha, Tetrahedron Lett., 1995, 36, 2933.
12. B. S. Sproat, B. Beijer and A. Iribarren, Nucleic Acids Res., 1990, 18, 41.
13. B. S. Sproat, A. Iribarren, B. Beijer, U. Pieles and A. Lamond, Nucleosides, Nucleotides, 1991, 10, 25.
14. B. S. Sproat, A. Iribarren, R. Garcia and B. Beijer, Nucleic Acids Res., 1991, 19, 733.
15. B. Beijer, M. Grøtli, M. E. Douglas and B. S. Sproat, Nucleosides, Nucleotides, 1994, 13, 1905.
16. A. Nyilas and J. Chattopadhyaya, Acta Chem. Scand., Ser. B, 1986, 40, 826.
17. H. Inoue, Y. Hayase, A. Imura, S. Iwai, K. Miura and A. Ohtsuka, Nucleic Acids Res., 1987, 15, 6131.
18. L. Chanteloup and N. T. Thuong, Tetrahedron Lett., 1994, 35, 877.
19. T. Kamimura, M. Tsuchiya, K. Koura, M. Sekine and T. Hata, Tetrahedron Lett., 1983, 24, 2775.
20. T. Kamimura, M. Tsuchiya, K. Urakami, K. Koura, M. Sekine, K. Shinozaki, K. Miura and T. Hata, J. Am. Chem. Soc., 1984, 106, 4552.
21. W. T. Markiewicz, J. Chem. Res. (S), 1979, 24.
22. L. H. McBride, R. Kierzek, S. L. Beaucage and M. H. Caruthers, J. Am. Chem. Soc., 1986, 108, 2040.
23. C. B. Reese and P. A. Skone, J. Chem. Soc., Perkin Trans. 1, 1984, 1226.
24. G. S. Ti, B. L. Gaffney and R. A. Jones, J. Am. Chem. Soc., 1982, 104, 1316.
25. C. Malet and O. Hindsgaul, J. Org. Chem., 1996, 61, 4649.
26. T. H. Keller and R. Häner, Helv. Chim. Acta, 1993, 76, 884.
27. M. E. Douglas, B. Beijer and B. S. Sproat, Bioorg. Med. Chem. Lett., 1994, 4, 995.
28. B. A. Connolly, Oligodeoxynucleotides containing modified bases, in Oligonucleotides and Analogues, ed. F. Eckstein, Oxford University Press, Oxford, 1991, pp. 155-183.
29. L. W. McLaughlin, T. Leong, F. Benseler and N. Piel, Nucleic Acids Res., 1988, 16, 5631.
30. H. P. Daskalov, M. Sekine and T. Hata, Tetrahedron Lett., 1980, 21, 3899.
31. S. Hanessian and P. Lavallee, Can. J. Chem., 1975, 53, 2975.
32. T. H. Fife and B. M. Benjamin, J. Am. Chem. Soc., 1973, 95, 2959.
33. M. Grøtli and K. Undheim, Acta Chem. Scand., 1995, 49, 217.