Synthesis and conformation of 3′-O,4′-C-methyleneribonucleosides, novel bicyclic nucleoside analogues for 2′,5′-linked oligonucleotide modification

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Satoshi Obika, Ken-ichiro Morio, Daishu Nanbu and Takeshi Imanishi


Abstract

Novel bicyclic nucleoside analogues 3′-O,4′-C-methyleneribonucleosides 1 are conveniently prepared starting from uridine; the sugar puckering of 1 is found to be nearly in the S-conformation by means of PM3 calculations and 1H NMR studies.


References

  1. R. Kierzek, L. He and D. H. Turner, Nucleic Acids Res., 1992, 20, 1685 CrossRef CAS.
  2. J. P. Dougherty, C. J. Rizzo and R. Breslow, J. Am. Chem. Soc., 1992, 114, 6254 CrossRef CAS.
  3. H. Hashimoto and C. Switzer, J. Am. Chem. Soc., 1992, 114, 6255 CrossRef CAS.
  4. H. Robinson, K.-E. Jung, C. Switzer and A. H.-J. Wang, J. Am. Chem. Soc., 1995, 117, 837 CrossRef CAS.
  5. V. Lalitha and N. Yathindra, Curr. Sci., 1995, 68, 68 Search PubMed.
  6. P. A. Giannaris and M. J. Damha, Nucleic Acids Res., 1993, 21, 4742 CrossRef CAS.
  7. J. Seki, K. Kuroda, H. Ozaki and H. Sawai, Nucleic Acids Symp. Ser., 1993, 29, 71 Search PubMed.
  8. A. Maran, R. K. Maitra, A. Kumar, B. Dong, W. Xiao, G. Li, B. R. G. Williams, P. F. Torrence and R. H. Silverman, Science, 1995, 265, 789.
  9. E. R. Kanimalla, A. Manning, Q. Zhao, D. R. Shaw, R. A. Byrn, V. Sasisekharan and S. Agrawal, Nucleic Acids Res., 1997, 25, 370 CrossRef.
  10. H. C. Schröder, R. J. Suhadolnik, W. Pfleiderer, R. Charubala and W. E. G. Muller, Int. J. Biochem., 1992, 24, 55 Search PubMed; G. C. Sen and P. Lengyei, J. Biol. Chem., 1992, 267, 5017 CAS.
  11. C. Horndler and W. Pfleiderer, Helv. Chim. Acta, 1996, 79, 718 CrossRef and references cited therein.
  12. Some other bicyclic nucleoside analogues have appeared in the literature. For example, M. Tarkoy and C. Leumann, Angew. Chem., Int. Ed. Engl., 1996, 35, 1968 Search PubMed; R. Zou and M. D. Matteucci, Tetrahedron Lett., 1996, 37, 941 CrossRef; K.-H. Altmann, R. Imwinkelried, R. Kesselring and G. Rihs, Tetrahedron Lett., 1994, 35, 7625 CrossRef CAS.
  13. S. L. Cook and J. A. Secrist, J. Am. Chem. Soc., 1979, 101, 1554 CrossRef CAS.
  14. G. H. Jones, M. Taniguchi, D. Tegg and J. G. Moffatt, J. Org. Chem., 1979, 44, 1309 CrossRef CAS.
  15. S. Obika, Y. Hari, K.-i. Morio, D. Nanbu and T. Imanishi, unpublished work.
  16. T.-S. Lin, M.-Z. Luo, M.-C. Liu, Y.-L. Zhu, E. Gullen, G. E. Dutschman and Y.-C. Cheng, J. Med. Chem., 1996, 39, 693 CrossRef CAS.
  17. C. Altona and M. Sundaralingam, J. Am. Chem. Soc., 1973, 95, 2333 CrossRef CAS; 1972, 94, 8205.
  18. J. J. P. Stewart, J. Comput. Chem., 1989, 10, 209, 221.
  19. T.-S. Lin, J.-H. Yang, M.-C. Liu, Z.-Y. Shen, Y.-C. Cheng, W. H. Prusoff, G. I. Birnbaum, J. Giziewicz, I. Ghazzouli, V. Brankovan, J.-S. Feng and G.-D. Hsiung, J. Med. Chem., 1991, 34, 693 CrossRef CAS.
  20. T. L. Sheppard, A. T. Rosenblatt and R. Breslow, J. Org. Chem., 1994, 59, 7243 CrossRef CAS.
  21. S. Arnott and W. Hukins, Biochem. J., 1972, 130, 453 CAS.
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