Synthesis and properties of 2′-deoxy-2′-α-C-branched nucleosides and nucleotides

Journal of Organic Chemistry

Volumn 61, Issue 26, 1996, Pages 9213-9222

  Lawrence, Anthony J ^a   Pavey, John B J ^a   Cosstick, Richard ^a   O'Neil, Ian A ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE; NUCLEOTIDE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030463558     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9614607     Document Type: Article

References (41)

1. Joyce, G. J.; Orgel, L. E. In The RNA World; Gesteland, R., Atkins, J., Eds.; Cold Spring Harbor Press: Cold Spring Harbor, NY, 1993; pp 1-25.
2. Robertson, M. P.; Miller, S. L. Science 1995, 268, 702.
3. Wilson, C.; Szostak, J. W. Curr. Opin. Struct. Biol. 1992, 2, 749.
4. De Mesmaeker, A.; Häner, R.; Martin, P.; Moser, H. E. Acc. Chem. Res. 1995, 28, 366.
5. Rammo, J.; Hettich, R.; Roigk, A.; Schneider, H.-J. J. Chem. Soc., Chem. Commun. 1996, 105.
6. Pyle, A. M. Science 1993, 261, 709.
7. Lawrence, A. J.; Pavey, J. B. J.; O'Neil, I. A.; Cosstick, R. Tetrahedron Lett. 1995, 36, 6341.
8. Aurup, H.; Tuschl, T.; Benseler, F.; Ludwig, J.; Eckstein, F. Nucleic Acids Res. 1994, 22, 701.
9. Reese, C. B.; Simons, C.; Zhang, P. Z. J. Chem. Soc., Chem. Commun. 1994, 1809.
10. Schmit, C.; Bévierre, M.-O.; De Mesmaeker, A.; Altman, K.-H. Bioorg. Med. Chem. Lett. 1994, 4, 1969.
11. De Mesmaeker, A.; Lebreton, J.; Hoffman, P.; Freir, S. M. Synlett 1993, 677.
12. (a) Wakabyashi, S.; Kato, H.; Noyori, R. J. Am. Chem. Soc. 1990, 112, 1691.
13. (b) Kuyl-Yeheskiely, E.; Tromp, C. M.; Lefeber, A. W. M.; van der Marel, G. A.; van Boom, J. H. Tetrahedron 1988, 44, 6515.
14. Stelakatos, G. C.; Paganou, A.; Zervas, L. J. Chem. Soc. C 1966, 1373.
15. Galaverna, G.; Corrandini, R.; Dossena, A.; Marchelli, R. Int. J. Peptide Protein Res. 1993, 42, 53.
16. (a) Capaldi, D. C.; Reese, C. B. Nucleic Acid Res. 1994, 22, 2209.
17. (b) Rao, M. V.; Reese, C. B.; Schehlman, V.; Yu, P. K. J. Chem. Soc., Perkin Trans. 1 1993, 43.
18. Sharpless, K. B.; Hartung, J.; Jeong, K. S.; Kwong, H. L.; Morikawa, K.; Wang, Z. M.; Xu, D.; Zhang, X. L. J. Org. Chem. 1992, 57, 2768.
19. Crispino, G. A.; Jeong, K. S.; Kolb, H. C.; Wang, Z. M.; Xu, D.; Sharpless, K. B. J. Org. Chem. 1993, 58, 3785.
20. The chronological order in which the work described in this paper was performed was such that studies on the base-catalyzed hydrolysis of the closely related hydroxyethyl-containing dimer (24a) had already established that conditions necessary for the removal of the acetyl groups would not be deleterious to the phosphodiester linkage.
21. Chauhary, S. K.; Hernandez, O. Tetrahedron Lett. 1979, 20, 95.
22. (a) Nielsen, J.; Taagaard, Marugg, J. E.; van Boom, J. H.; Dahl, O. Nucleic Acids Res. 1986, 14, 7391.
23. (b) Kierzek, R.; Caruthers, M. H.; Longfellow, C. E.; Swinton, D.; Turner, D. H.; Frier, S. M. Biochemistry 1986, 25, 7840.
24. Sinha, N. D.; Biernat, J.; McManus, J.; Köster, H. Nucleic Acids Res. 1984, 12, 4539.
25. Campagna, F.; Carotti, A.; Casini, G. Tetrahedron Lett. 1977, 21, 1813.
26. Yamato, E.; Sugasawa, S. Tetrahedron Lett. 1970, 4383.
27. Hayakawa, Y.; Uchiyama, M.; Noyori, R. Tetrahedron Lett. 1986, 27, 4191.
28. Cosstick, R.; Vyle, J. S. Nucleic Acids Res. 1990, 18, 829.
29. Fourrey, J.-L.; Varenne, J. Tetrahedron Lett. 1985, 26, 1217.
30. While the pH optimum for snake venom phosphodiesterases is normally reported as 9.0, it is dependent on the nature of the substrate (Bernardi, A.; Bernardi, G. The Enzymes; Boyer, P. D., Ed; Academic Press: New York, 1971; Vol. IV, p 329). In general, the enzyme is active over the pH range 6-9, and some substrates are more rapidly hydrolyzed at pH 6.
31. Culp, J. S.; Butler, L. G. Arch. Biochem. Biophys. 1986, 246, 245.
32. Iribarren, A. M.; Sproat, B. S.; Neuner, P.; Sulston, I.; Lamond, A. I. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 7747.
33. The pH optimum for this enzyme is dependent on the substrate, but it is generally used within the pH range 4.0-7.2 (Shishido, K; Ando, T. Nucleases; Lin, S. M., Roberts, R. J., Eds.; Cold Spring Harbor: New York, 1983; p 155).
34. Westheimer, F. H. Acc. Chem. Res. 1968, 1, 70.
35. Dugas, H. Bioorganic Chemistry, 2nd Ed.; Springer-Verlag: New York, 1989; Chapter 3.
36. Christensen, J. J.; Rytting, J. H. J. Phys. Chem. 1967, 71, 2700.
37. Bromilow, R. H.; Kirby, A. J. J. Chem. Soc., Perkin Trans. 2 1972, 149.
38. (a) Lorsch, J. R.; Szostak, J. W. Acc. Chem. Res. 1996, 29, 103.
39. (b) Tuerk, C.; Gold, L. Science 1990, 249, 505.
40. Li, X.; Scott; G. K.; Baxter; A. D.; Taylor, R. J.; Vyle, J. S.; Cosstick, R. J. Chem. Soc., Perkin Trans, 1 1994, 2123.
41. Reese, C. B.; Thompson, E. A. J. Chem. Soc., Perkin Trans. 1 1988, 2881.