Abstract
A partially protected phosphatidylinositol with a free hydroxyl group in the cyclitol moiety was synthesized by phosphorylation of a tetrasubstituted myo-inositol using the H-phosphonate and phosphoamidite methods. The H-phosphonate method was advantageous for the synthesis of selectively protected monophosphoinositide due to a lesser number of stages. Two schemes for the conjugation of 2',3'-didehydro-3'-de oxythymidine with phosphatidylinositol using succinic acid as a linker were tested in the synthesis of the target nucleoside phospholipid.
Similar content being viewed by others
References
Shastina, N.S., Einisman, L.I., Stepanov, A.E., and Shvets, V.I., Bioorg. Khim., 1996, vol. 22, pp. 446–450.
De Clercq, E., Clin. Microbiol. Rev., 1997, vol. 10, pp. 674–693.
Siddiqui, A.Q., McGuigan, Ch., Ballatore, C., Zuccotto, F., Gilbert, I.H., De Clercq, E., and Balzarini, J., J. Med. Chem., 1999, vol. 42, pp. 4122–4128.
Dessolin, J., Galea, P., Vlieghe, P., Chermann, J.-C., and Kraus, J.-L., J. Med. Chem., 1999, vol. 42, pp. 229–241.
Vodovozova, E.L., Pavlova, Yu.B., Polushkina, M.A., Rzhaninova, A.A., Garaev, M.M., and Molotkovsky, Yul.G., Bioorg. Khim., 1996, vol. 22, pp. 451–457.
Ryakhovskii, V.V., Malekin, S.I., Nosova, V.M., Kisin, A.V., Kruglyak, Yu.L., and Kurochkin, V.K., Bioorg. Khim., 1999, vol. 25, pp. 499–504.
Schott, H., Ludwig, P.S., Immelmann, A., and Schwendener, R.A., Eur. J. Med. Chem., 1999, vol. 34, pp. 343–352.
Jan, S.T., Shin, M.J., Venkatachalam, T.K., Dcruz, O.J., Chen, C.L., and Uckun, F.M., Antivir. Chem. Chemother., 1999, vol. 10, pp. 39–46.
Kucera, G.L., Goff, C.L., Iyer, N., Morrisnatschke, S., Ishaq, K.S., Wyrick, S.D., Fleming, R.A., and Kucera, L.S., Antivir. Res., 2001, vol. 50, pp. 129–137.
Mavromoustakos, T., Calogeropoulou, T., Koufaki, M., Kolocouris, A., Daliani, I., Demetzos, C., Meng, Z.X., Makriyannis, A., Balzarini, J., and De Clercq, E., J. Med. Chem., 2001, vol. 44, pp. 1702–1709.
Mitsuya, H. and Broder, S., Nature, 1987, vol. 325, p. 773.
Hostetler, K.Y., Stuhmiller, L.M., Lenting, H.B.M., van den Bosch, H., and Richman, D.D., J. Biol. Chem., 1990, vol. 265, pp. 6112–6117.
McGuigan, C., Pathirana, R.N., Mahmood, N., Devine, K.G., and Hay, A.J., Antivir. Res., 1992, vol. 17, pp. 311–321.
Siddiqui, A.Q., McGuigan, C., Ballatore, C., De Clercq, E., and Balzarini, J., J. Med. Chem., 1999, vol. 42, pp. 393–399.
Berezovskaya, Yu., Chudinov, M., Kirillova, Yu., Shastina, N., Shvets, V., and Yurkevich, A., Nucleosides Nucleotides, 1998, vol. 17, pp. 3777–3783.
Berrige, M.J., Annu. Rev. Biochem., 1987, vol. 56, pp.-59–193.
Shvets, V.I., Stepanov, A.E., Krylova, V.N., and Gulak, P.V., mio-Inozit i fosfoinozitidy (myo-Inositol and Phosphoinositides), Moscow: Nauka, 1987.
Stepanov, A.E. and Shvets, V.I., Bioorg. Khim., 1998, vol. 24, pp. 731–746.
Ceolotto, C., Flekt, W., and Schorsch, F.J., Biochim. Biophys. Acta, Bio-Membr., 1996, vol. 1285, pp. 71–78.
Tremblay, J.M., Helmkamp, G.M., and Yarbrough, L.R., J. Biol. Chem., 1996, vol. 271, pp. 21 075–21 080.
Klyashchitskii, B.A., Shvets, V.I., and Preobrazhenskii, N.A., Chem. Phys. Lipids, 1969, vol. 3, pp. 394–400.
IUPAC-IUB Comission on Biochemical Nomenclature (CBN), Eur. J. Biochem., 1967, vol. 2, p. 127.
Zamyatina, A.Yu., Bushnev, A.S., and Shvets, V.I., Bioorg. Khim., 1994, vol. 20, pp. 1253–1295.
Shastina, N.S., Einisman, L.I., Kashiricheva, I.I., Stepanov, A.E., and Shvets, V.I., Bioorg. Khim., 1995, vol. 21, pp. 641–650.
Falck, J.R., Krishna, U.M., Katipally, K.R., Capdevila, J.H., and Ulug, E.T., Tetrahedron Lett., 2000, vol. 41, pp. 4271–4275.
De Almedia, M.V., Cleophax, J., Gateau-Olesker, A., Prestat, G., Dubreuil, D., and Gero, S.D., Tetrahedron, 1999, vol. 55, pp. 12 997–13 010.
Lindh, I. and Stawinski, J., J. Org. Chem., 1989, vol. 54, pp. 1338–1342.
Shvets, V.I., Klyashchitskii, B.A., Stepanov, A.E., and Evstigneeva, R.P., Tetrahedron, 1973, vol. 29, p. 331.
Bruzik, K.S., Salamonczyk, G., and Stec, W.J., J. Org. Chem., 1986, vol. 52, pp. 2368–2370.
Gigg, J., Gigg, R., and Conant, R., Carbohydr. Res., 1985, vol. 142, pp. 132–134
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Shastina, N.S., Tuchnaya, O.A., Einisman, L.I. et al. Asymmetrically Substituted myo-Inositols. XXXIX. The Synthesis of Conjugate of 2',3'-Didehydro-3'-deoxythymidine with Phosphatidylinositol: A New Nucleoside Phospholipid with Potential Anti-HIV Activity. Russian Journal of Bioorganic Chemistry 29, 267–273 (2003). https://doi.org/10.1023/A:1023988500659
Issue Date:
DOI: https://doi.org/10.1023/A:1023988500659