Skip to main content
Log in

Synthesis of 1-β-D-ribopyranosyl- and ribofuranosyl-6-nitroindole and indoline for the phosphotriester oligonucleotide synthesis

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The glycosylation reaction of 6-nitroindoline with 5-tritylribose led to the synthesis of the 1-Β-D-ribofuranoside and 1-Β-D-ribopyranoside of 6-nitroindoline, the dehydrogenation of which resulted in the isolation of the corresponding 1-Β-D-ribopyranoside and 1-Β-D-ribofuranoside of 6-nitroindole; the last with protecting groups are suitable for utilization in oligonucleotide synthesis.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature Cited

  1. B. L. Gaffney and R. A. Jones, Tetrahedron Lett., 23, 2253 (1982).

    Google Scholar 

  2. R. T. Walker, E. Gloreq, and F. Zekstein, Nucleoside Analogs: Biology, Chemistry, and Molecular Applications, Plenum Press, New York (1979), p. 10.

    Google Scholar 

  3. R. E. Harmon, R. K. Robins, and L. B. Townsend, Chemistry and Biology of Nucleosides and Nucleotides, Academic Press, New York (1978), p. 7.

    Google Scholar 

  4. R. H. Hall, The Modified Nucleosides in Nucleic Acids, Columbia University Press, New York (1971), p. 5.

    Google Scholar 

  5. P. F. Agris, The Modified Nucleosides of Transfer RNA, New York (1980), p. 12.

  6. J. A. McCloskey and S. Nishimura, Acc. Chem. Res., 10, 403 (1977).

    Google Scholar 

  7. R. H. Hall and D. B. Dunn, “Natural occurrence of the modified nucleosides,” in: Handbook of Biochemistry and Molecular Biology, CRC Press, Cleveland (1975), p. 9.

    Google Scholar 

  8. V. I. Mukhanov, T. D. Miniker, and M. N. Preobrazhenskaya, Zh. Org. Khim., 13, 214 (1977).

    Google Scholar 

  9. W. Voelter and E. Breitmaier, Org. Magn. Reson., 5, 311 (1973).

    Google Scholar 

  10. E. Breitmaier, W. Voelter, C. Jung, and C. Tanzer, Chem. Ber., 104, 1147 (1971).

    Google Scholar 

  11. M. N. Preobrazhenskaya, L. A. Savel'eva, and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 4, 692 (1967).

    Google Scholar 

  12. P. R. Whitfield, Biochem. J., 58, 390 (1954).

    Google Scholar 

  13. M. N. Preobrazhenskaya, M. M. Vigdorchik (Vigdorchic), and N. N. Suvorov, Tetrahedron, 23, 4653 (1967).

    Google Scholar 

  14. M. N. Preobrazhenskaya, M. M. Vigdorchik, and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 2, 128 (1968).

    Google Scholar 

  15. J. Stawinski, T. Horumi, S. A. Narang, C. P. Bahl, and R. Wu, Nucleic Acids Res., 4, 353 (1977).

    Google Scholar 

  16. Markiewicz, B. Nowakowska, and K. Adrych, Tetrahdron Lett., 29, 1561 (1988).

    Google Scholar 

  17. J. N. Reeves and J. Munro, Ind. Eng. Chem., Anal. Ed., 12, 551 (1940).

    Google Scholar 

  18. J. M. Webb, J. Biol. Chem., 221, 635 (1956).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1500–1506, November, 1990.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Taktakishvili, M.O., Tsitskishvili, T.K., Kikoladze, V.S. et al. Synthesis of 1-β-D-ribopyranosyl- and ribofuranosyl-6-nitroindole and indoline for the phosphotriester oligonucleotide synthesis. Chem Heterocycl Compd 26, 1249–1254 (1990). https://doi.org/10.1007/BF00476979

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00476979

Keywords

Navigation