Abstract
3-Aminopropyl glycosides of di-, tri-, and tetrasaccharide structurally related to fragments of Streptococcus pneumoniae type 3 bacteria capsular polysaccharide were synthesized.
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S. M. Kharit, in Vaktsini i vactsinatsiya: natsionalnoe rukovodstvo [Vaccines and Vaccination: National Guidelines] Ed. V. V. Zverev, B. F. Semenov, and R. M. Khaitov, GEOTAR-Media, Moscow, 2011, 880 p. (in Russian).
J. P. Kamerling, Pneumococcal polysaccharides: a chemical view, in Streptococcus pneumoniae: molecular biology and mechanism of disease, Eds A. Tomasz, Mary Ann Libert, Inc., Larchmont, New York, 2000, p.81.
E. C. Beuvery, F. Van Rossem, J. Nagel, Infect. Immun., 1982, 37,15.
G. Ada, D. Isaacs, Clin. Microbiol. Infect., 2003, 9,79.
M. B. Rennels, K. M. Edwards, H. L. Keyserling, K. S. Reisinger, D. A. Hogerman, D. V. Madore, I. Chang, P. R. Paradiso, F. J. Malinoski, A. Kimura, Pediatrics, 1998, 101,604.
M. L. Gening, E. A. Kurbatova, Yu. E. Tsvetkov, N. E. Nifantiev, Russ. Chem. Rev., 2015, 84, 1100 (Engl. Transl.), [Uspekhi Khimii, 2015, 84, 1100].
L. Morelli, L. Poletti, L. Lay, Eur. J. Org. Chem., 2011, 5723.
E. V. Sukhova, D. V. Yashunsky, Y. E. Tsvetkov, E. A. Kurbatova, N. E. Nifantiev, Russ. Chem. Bull. (Int. Ed.), 2014, 63, 511 [Izv. Acad. Nauk, Ser. Khim. 2014, 511].
E. A. Kurbatova, D. S. Vorobyov, N. B. Egorova, I. B. Semenova, E. V. Sukhova, D. V. Yashunsky, Yu. E. Tsvetkov, N. E. Nifantiev, Zhurn. Mikrobiol. Epidemiol. Immunobiol., 2012, 36 (in Russian).
E. A. Kurbatova, N. K. Akhmatova, N. B. Egorova, I. B. Semenova, N. E. Yastrebova, Yu. E. Tsvetkov, E. V. Sukhova, D. V. Yashunsky, N. E. Nifantiev, Zhurn. Mikrobiol. Epidemiol. Immunobiol., 2015, 46 (in Russian).
E. A. Kurbatova, D. S. Vorob´ev, E. A. Akhmatov, N. K. Akhmatova, N. B. Egorova, Y. E. Tsvetkov, E. V. Sukhova, D. V. Yashunskii, N. E. Nifant´ev. Bull. Exp. Biol. Med., 2014, 157, 612 [Bull. Experim. Biologii i Meditsini, 2014, 157, 630].
N. K. Akhmatova, E. A. Kurbatova, E. A. Akhmatov, N. B. Egorova, D. Y. Logunov, M. L. Gening, E. V. Sukhova, D. V. Yashunsky, Y. E. Tsvetkov, N. E. Nifantiev, Front. Immunol., 2016, 7,248.
V. P. Ananikov, E. A. Khokhlova, M. P. Egorov, A. M. Sakharov, S. G. Zlotin, A. V. Kucherov, L. M. Kustov, M. L. Gening, N. E. Nifantiev, Mendeleev Commun., 2015, 25,75.
A. Ya. Chernyak, K. V. Antonov, N. K. Kochetkov, Russ. J. Bioorg. Chem. (Engl. Transl.), 1987, 13 [Bioorgan. Khimiya, 987, 13, 958].
D. J. Lefeber, J. P. Kamerling, J. F. G. Vliegenthart, Chem. Eur. J., 2001, 7, 4411.
D. J. Lefeber, E. A. Arévalo, J. P. Kamerling, J. F. G. Vliegenthart, Can. J. Chem., 2002, 80,76.
A.-R. de Jong, B. Hagen, V. van der Ark, H. S. Overkleeft, J. D. C. Codée, G. A. Van der Marel, J. Org. Chem., 2012, 77,108.
D. V. Yashunsky, Y. E. Tsvetkov, A. A. Grachev, A. O. Chizhov, N. E. Nifantiev, Carbohydr. Res., 2016, 419,8.
H. Paulsen, Angew. Chem., Int. Ed., 1982, 21,155.
Y. Wang, Q. Yan, J. Wu, L.-H. Zhang, X.-S. Ye, Tetrahedron, 2005, 61, 4313.
P. J. Garegg, I. Kvarnstrom, A. Niklasson, G. Niklasson, S. C. T. Svensson, J. Carbohydr. Chem., 1993, 12,933.
J. B. Epp, T. S. Widlanski, J. Org. Chem., 1999, 64,293.
H. Tanaka, T. Kawai, Y. Adachi, S. Hanashima, Y. Yamaguchi, N. Ohno, T. Takahashi, Bioorg. Med. Chem., 2012, 20, 3898.
F. M. Ibatullin, K. A. Shabalin, J. V. Jänis, A. G. Shavva, Tetrahedron Lett., 2003, 44, 7961.
V. Jadhav, C. M. Pedersen, M. Bols, Org. Biomol. Chem., 2011, 9, 7525.
G. W. J. Twaddle, D. V. Yashunsky, A. V. Nikolaev, Org. Biomol. Chem., 2003, 1,623.
K. Takeo, T. Fukatsu, T. Yasato, Carbohydr. Res., 1982, 107,71.
M. Alonso-Lopez, J. Barbat, E. Fanton, A. Fernandez-Mayoralas, J. Gelas, D. Horton, M. Martin-Lomas, S. Penades, Tetrahedron, 1987, 43, 1169.
E. A. Kurbatova, E. A. Akhmatov, N. K. Akhmatova, N. B. Egorova, N. E. Yastrebova, E. E. Romanenko, A. Y. Leonova, A. V. Poddubikov, Y. E. Tsvetkov, E. V. Sukhova, M. L. Gening, D. V. Yashunsky, N. E. Nifantiev, Russ. Chem. Bull. (Int. Ed.), 2016, 65, 1608 [Izv. Acad. Nauk, Ser. Khim. 2016, 1608].
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0111—0122, January, 2017.
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Tsvetkov, Y.E., Yashunsky, D.V., Sukhova, E.V. et al. Synthesis of oligosaccharides structurally related to fragments of Streptococcus pneumoniae type 3 capsular polysaccharide. Russ Chem Bull 66, 111–122 (2017). https://doi.org/10.1007/s11172-017-1708-9
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DOI: https://doi.org/10.1007/s11172-017-1708-9