Abstract
A new uridine derivative, 2"-O-(2,3-dihydroxypropyl)uridine, and its 3"-phosphoramidite were obtained for direct introduction into oligonucleotides during automated chemical synthesis. Oligonucleotides 10 to 15 nt long harboring 2"-O-(2,3-dihydroxypropyl)uridine residues were synthesized; periodate oxidation of these oligomers gave oligonucleotides containing 2"-O-(2-oxoethyl)uridine residues. The presence of a reactive aldehyde group in 2" position of the carbohydrate moiety was confirmed by the interaction withp-nitrophenylhydrazine and methionine methyl ester. The thermostability of DNA duplexes containing modified units does not practically differ from that of the natural analogues.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Mikhailov, S.N., De Bryun, A., and Herdewijn, P., Nucleosides Nucleotides, 1995, vol. 14, pp. 481-485.
Mikhailov, S.N., Efimtseva, E.V., Gurskaya, G.V., Fomitcheva, M.V., and Meshkov, S.V., J. Carbohydr. Chem., 1997, vol. 16, pp. 75-80.
Lowrence, A.J., Pavey, J.B., Cosstick, R., and O'Neil, I.A., J. Org. Chem., 1996, vol. 61, pp. 9213-9222.
Brevnov, M.G., Gritsenko, O.M., Mikhailov, S.N., Efimtseva, E.V., Ermolinsky, B.S., van Aerschot, A., Herdewijn, P., Repyk, A.V., and Gromova, E.S., Nucleic Acids Res., 1997, vol. 25, pp. 3302-3309.
Tinitskaya, V.L., Rusakova, E.E., Memelova, L.V., Kochetkov, S.N., van Aershot, A., Herdewijn, P., Efimtseva, E.V., Ermolinsky, B.S., and Mikhailov, S.N., FEBS Lett., 2000, vol. 442, pp. 20-24.
Sproat, B.S., Iribarren, A.M., Beijer, B., Piels, U., and Lamond, A.I., Nucleosides Nucleotides, 1991, vol. 10, pp. 25-36.
Oretskaya, T.S., Ibragim, Kh.K.Kh., Volkov, E.M., Romanova, E.A., Tashlitskii, V.N., and Shabarova, Z.A., Bioorg. Khim., 1994, vol. 20, pp. 967-973.
Inoue, H., Hayase, Y., Iwai, S., and Ohtsuka, E., FEBS Lett., 1987, vol. 215, pp. 327-330.
Holy, A. and Soucek, M, Tetrahedron Lett., 1971, vol. 12, pp. 185-188.
Matsuda, A., Yasuoka, J., Sasaki, T., and Ueda, T., J. Med. Chem., 1991, vol. 34, pp. 999-1002.
Jones, R.F., Oligonucleotide Synthesis: A Practical Approach, Gait, M.J., Ed., Oxford: IRL, 1984, pp. 23-24.
Beaucage, S.L., Protocols for Oligonucleotides and Analogs: Synthesis and Properties, Agrawal, S., Ed., Totowa, NJ: Humana, 1993, pp. 33-63.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Zatsepin, T.S., Kachalova, A.V., Romanova, E.A. et al. Synthesis and Properties of Modified Oligodeoxyribonucleotides Containing 2"-O-(2,3-Dihydroxypropyl)uridine and 2"-O-(2-Oxoethyl)uridine. Russian Journal of Bioorganic Chemistry 27, 39–44 (2001). https://doi.org/10.1023/A:1009579002330
Issue Date:
DOI: https://doi.org/10.1023/A:1009579002330