Abstract
Hexyl, octyl, and cyclohexyl β-glycosides and heptyl and cyclohexyl α-glycosides of muramyl dipeptide (MDP) were synthesized. Tests in vitro and in vivo revealed lower immunostimulating activities of MDP α-glycosides in comparison with the corresponding β-glycosides and MDP itself. In the case of alkyl β-glycosides, differences in hydrocarbon chain lengths (C4–C8) and in aglycone (aliphatic chain and aliphatic or aromatic ring) exerted no substantial effect on the immunostimulating activity.
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Lefrancier, P., Derrien, M., Lederman, I., Nief, F., Choay, J., and Lederer, E., Int. J. Peptide Protein Res., 1978, vol. 11, pp. 289–296.
Durette, P.L., Dorn, C.P., Friedman, A., and Schlabach, A., J. Med. Chem., 1982, vol. 25, pp. 1028–1033.
Zemlyakov, A.E. and Chirva, V.Ya., Khim. Prir. Soedin., 1987, no. 5, pp. 714–718.
Kur'yanov, V.O., Zemlyakov, A.E., and Chirva, V.Ya., Ukr. Khim. Zh., 1994, vol. 60, pp. 858–861.
Kur'yanov, V.O., Zemlyakov, A.E., and Chirva, V.Ya., Bioorg. Khim., 1994, vol. 20, pp. 439–447.
Kur'yanov, V.O., Zemlyakov, A.E., and Chirva, V.Ya., Bioorg. Khim., 1996, vol. 22, pp. 287–290.
Zemlyakov, A.E., Tsikalov, V.V., Kur'yanov, V.O., Chirva, V.Ya., and Bovin, N.V., Bioorg. Khim., 2001, vol. 27, pp. 390–394.
Kalyuzhin, O.V., Zemlyakov, A.E., and Fuchs, B.B., Int. J. Immunopharmacol., 1996, vol. 18, pp. 651–659.
Krivorutchenko, Yu.L., Andronovskaja, I.B., Hinkula, J., Krivoshein, Yu.S., Ljungdahl-Ståhle, E., Pertel, S.S., Grishkovets, V.I., Zemlyakov, A.E., and Wahren, B., Vaccine, 1997, vol. 15, pp. 1479–1486.
Kalyuzhin, O.V., Kalyuzhin, V.V., Zemlyakov, A.E., Elkina, S.I., Shkalev, M.V., and Sergeev, V.V., Byull. Eksp. Biol., 1999, no. 5, pp. 543–545.
Kalyuzhin, O.V., Nelyubov, M.V., Kuzovlev, F.N., Kalyuzhina, M.I., Zemlyakov, A.E., Shkalev, M.V., Mulik, E.L., and Karaulov, A.V., Vopr. Biol. Med. Farm. Khim., 2001, no. 1, pp. 45–46.
Zemlyakov, A.E., Kur'yanov, V.O., Sidorova, E.A., and Chirva, V.Ya., Bioorg. Khim., 1998, vol. 24, pp. 623–630.
Nagai, Y., Akiyama, K., Kotani, S., Watanabe, Y., Shimono, T., Shiba, T., and Kusumoto, S., Cell. Immunol., 1978, vol. 35, pp. 168–172.
Azuma, I., Okumura, H., Saiki, I., Kiso, M., Hasegawa, A., Tanio, Y., and Yamamura, Y., Infect. Immun., 1981, vol. 33, pp. 834–839.
Hasegawa, A., Kigawa, K., Kiso, M., and Azuma, I., Agric. Biol. Chem., 1986, vol. 50, pp. 2091–2094.
Hasegawa, A., Hioki, Y., Kiso, M., and Azuma, I., Carbohydr. Res., 1983, vol. 123, pp. 63–67.
Rostovtseva, L.I., Andronova, T.M., Mal'kova, V.P., Sorokina, I.B., and Ivanov, V.T., Bioorg. Khim., 1981, vol. 7, pp. 1843–1858.
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Zemlyakov, A.E., Tsikalov, V.V., Kalyuzhin, O.V. et al. N-Acetylmuramyl-L-Alanyl-D-Isoglutamine Glycosides: Effect of Glycoside Bond Configuration and Aglycone on Biological Activity. Russian Journal of Bioorganic Chemistry 29, 286–292 (2003). https://doi.org/10.1023/A:1023944818406
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DOI: https://doi.org/10.1023/A:1023944818406