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Synthesis of bi- and tervalent ligands of galectins, derivatives of β-lactosylamine, with the amino group in the terminal position of the spacer

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Abstract

A method for the synthesis of glycoclusters by N-alkylation of N-glycyl-β-lactosylamine with N-chloroacetyl derivatives of β-lactosylamine and N,N’-iminodiacetyldilactosylamine has been developed. The glycoclusters obtained with two and three lactosylamine residues with the amino group in the spacer were found to be suitable for further conjugation with carboxy-containing physiologically active compounds.

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References

  1. M. Monsigny, A.-C. Roche, P. Midoux, R. Mayer, Adv. Drug Deliv. Rev., 1994, 14, 1.

    Article  CAS  Google Scholar 

  2. M. Monsigny, C. Quetard, S. Bourgerie, D. Delay, C. Pichon, P. Midoux, R. Mayer, A.-C. Roche, Biochimie, 1998, 80, 99.

    Article  CAS  Google Scholar 

  3. W. Wang, in Carbohydrate Drug Design, Eds A. A. Klyosov, Z. J. Witczak, D. Platt, Am. Chem. Soc., Washington, 2006, p. 149–155.

    Google Scholar 

  4. L. M. Likhosherstov, O. S. Novikova, A. O. Zheltova, V. N. Shibaev, Izv. Akad. Nauk, Ser. Khim., 2000, 1461 [Russ. Chem. Bull., 2000, 49, 1454 (Engl. Transl.)].

    Google Scholar 

  5. I. D. Manger, T. W. Rademacher, R. A. Dwek, Biochemistry, 1992, 31, 10724

    Google Scholar 

  6. I. D. Manger, S. Y. C. Wong, T. W. Rademacher, R. A. Dwek, Biochemistry, 1992, 31, 10733.

    Google Scholar 

  7. A. B. Tuzikov, A. S. Gambaryan, l. R. Juneja, N. V. Bovin, J. Carbohydr. Chem., 2000, 19, 1191

    Article  CAS  Google Scholar 

  8. N. V. Shilova, O. E. Galanina, T. V. Pochechueva, A. A. Chinarev, V. A. Kadykov, A. B. Tuzikov, N. V. Bovin, Glycocon. J., 2005, 22, 43.

    Article  CAS  Google Scholar 

  9. U. K. Saha, R. Roy, Tetrahedron Lett., 1995, 36, 3635

    Article  CAS  Google Scholar 

  10. U. K. Saha, R. Roy, J. Chem. Soc., Chem. Commun., 1995, 2571.

  11. U. K. Saha, R. Roy, Tetrahedron Lett., 1997, 38, 7697.

    Article  CAS  Google Scholar 

  12. A. V. Orlova, N. N. Kondakov, A. I. Zinin, B. G. Kimel’, L. O. Kononov, I. B. Sivaev, V. I. Bregadze, Bioorg. Khim., 2006, 32, 632 [Russ. J. Bioorg. Chem., 2006, 32, 568].

    CAS  Google Scholar 

  13. L. M. Likhosherstov, O. S. Novikova, L. O. Kononov, V. N. Shibaev, Izv. Akad. Nauk, Ser. Khim., 2006, 1214 [Russ. Chem. Bull., Int. Ed., 2006, 55, 1262].

    Google Scholar 

  14. L. M. Likhosherstov, O. S. Novikova, L. O. Kononov, A. V. Orlova, I. B. Sivaev, V. I. Bregadze, Izv. Akad. Nauk, Ser. Khim., 2007, 2033 [Russ. Chem. Bull., Int. Ed., 2007, 56, 2105].

    Google Scholar 

  15. S. D. Abbott, L. Gagnon, M. Lagraoui, S. Kadhim, G. Attardo, B. Zacharie, C. L. Penney, J. Med. Chem., 1998, 41, 1909.

    Article  CAS  Google Scholar 

  16. S. Svedhem, L. Ohberg, S. Borrelli, R. Valiokas, M. Andersson, S. Oscarson, S. C. T. Svensson, B. Liedberg, P. Konradsson, Langmuir, 2002, 18, 2848.

    Article  CAS  Google Scholar 

  17. R. S. Bresalier, P.-S. Yan, J. C. Byrd, R. Lotan, A. Raz, Cancer, 1997, 80, 776.

    Article  CAS  Google Scholar 

  18. L. M. Likhosherstov, O. S. Novikova, V. N. Shibaev, N. K. Kochetkov, Izv. Akad. Nauk, Ser. Khim., 1996, 1848 [Russ. Chem. Bull., 1996, 45, 1760 (Engl. Transl.)].

    Google Scholar 

  19. L. M. Likhosherstov, O. S. Novikova, V. N. Shibaev, Dokl. Akad. Nauk, 2002, 383, 500 [Dokl. Chem., 2002, 383, 89 (Engl. Transl.)].

    Google Scholar 

  20. A. I. Usov, M. A. Rekhter, Zh. Obshch. Khim., 1969, 39, 912 [J. Gen. Chem. USSR, 1969, 39 (Engl. Transl.)].

    CAS  Google Scholar 

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    L. M. Likhosherstov & O. S. Novikova

  2. Higher Chemical College, Russian Academy of Sciences, 9 Miusskaya pl., 125047, Moscow, Russian Federation

    G. V. Mokrov

Authors
  1. L. M. Likhosherstov
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  2. O. S. Novikova
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  3. G. V. Mokrov
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Corresponding author

Correspondence to L. M. Likhosherstov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 647–651, March, 2008.

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Likhosherstov, L.M., Novikova, O.S. & Mokrov, G.V. Synthesis of bi- and tervalent ligands of galectins, derivatives of β-lactosylamine, with the amino group in the terminal position of the spacer. Russ Chem Bull 57, 660–664 (2008). https://doi.org/10.1007/s11172-008-0104-x

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  • DOI: https://doi.org/10.1007/s11172-008-0104-x

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