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Modification of hyaluronic acid with aromatic amino acids

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Abstract

Hyaluronic acid was modified with aromatic amino acids (5-aminosalicylic, 4-aminosalicylic, anthranilic, and p-aminobenzoic) in the presence of 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide. The modified glycans contained 9–43% of arylamide groups and 10–33% of isoureidocarbonyl groups depending on the nature of the amino acid. Reduction with sodium borohydride allowed the conversion of isoureidocarbonyl groups into hydroxymethyl groups.

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Abbreviations

DEAE-cellulose:

diethylaminoethylcellulose

EDC:

1-ethyl-3-[3-dimethylamino)propyl]carbodiimide

HA:

hyaluronic acid

TCA:

trichloroacetic acid

TBAH:

tetrabutylammonium hydroxide

REFERENCES

  1. Vercruysse, K.P. and Prestwich, G.D., Ther. Drug Carrier Systems, 1998, vol. 15, no. 5, pp. 513–555.

    Google Scholar 

  2. Cera, C., Terbojevich, M., Cosani, A., and Palumbo, M., Int. J. Biol. Macromol., 1988, vol. 10, p. 66.

    Google Scholar 

  3. Danishefsky, I. and Siscovic, E., Carbohydr. Res., 1971, vol. 16, pp. 199–205.

    Google Scholar 

  4. Pouyani, T. and Prestwich, G.D., Bioconjugate Chem., 1994, vol. 5, pp. 339–347.

    Google Scholar 

  5. Vercruysse, K.P., Marecak, D.M., Marecak, J.F., and Prestwich, G.D., Bioconjugate Chem., 1997, vol. 8, pp. 686–694.

    Google Scholar 

  6. Kuo, J., Swann, D.A., and Prestwich, G.D., Bioconjugate Chem., 1991, vol. 2, pp. 232–241.

    Google Scholar 

  7. Luo, Yi. and Prestwich, G.D., Bioconjugate Chem., 1999, vol. 10, pp. 755–763.

    Google Scholar 

  8. Williams, A. and Ibrahim, T.I., J. Am. Chem. Soc., 1981, vol. 103, pp. 7090–7095.

    Google Scholar 

  9. Scott, J.E. and Heatley, F., Biomacromolecules, 2002, vol. 3, pp. 547–553.

    Google Scholar 

  10. Ionin, B.I., Ershov, B.A., and Kol’tsov, A.I., YaMR-spektroskopiya v organicheskoi khimii (NMR Spectroscopy in Organic Chemistry), Leningrad: Khimiya, 1983.

    Google Scholar 

  11. Nakajima, N. and Ikada, Y., Bioconjugate Chem., 1995, vol. 6, pp. 123–130.

    Google Scholar 

  12. Inoe, Y. and Nagasawa, K., Carbohydr. Res., 1982, vol. 111, pp. 113–125.

    Google Scholar 

  13. Jermyn, M.A., Anal. Biochem., 1975, vol. 68, pp. 332–335.

    Google Scholar 

  14. Siggia, S. and Hanna, J.G., Quantitative Organic Analysis via Functional Groups, New York: Wiley, 1979. Translated under the title Kolichestvennyi analiz po funktsional’nym gruppam, Moscow: Khimiya, 1983.

    Google Scholar 

  15. Methods in Carbohydrate Chemistry, Whistler, R.L. and Wolfrom, M.L., Eds., New York: Academic, 1962–1965. Translated under the title Metody khimii uglevodov, Kochetov, G.A., Ed., Moscow: Mir, 1967.

    Google Scholar 

  16. Kochetov, G.A., Prakticheskoe rukovodstvo po enzimologii (Handbook on Enzymology), Moscow: Vysshaya Shkola, 1980.

    Google Scholar 

  17. Welti, D., Rees, D.A., and Welsh, E.J., Eur. J. Biochem., 1979, vol. 94, pp. 505–514.

    Google Scholar 

  18. Cavalieri, F., Chiessi, E., Paci, M., Paradossi, G., Flabiani, A., and Cesaro, A., Macromolecules, 2001, vol. 34, pp. 99–109.

    Google Scholar 

  19. Jacobson, B.S. and Fairman, K.R., Anal. Biochem., 1980, vol. 106, pp. 114–117.

    Google Scholar 

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Correspondence to I. Yu. Ponedel’kina.

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Translated from Bioorganicheskaya Khimiya, Vol. 31, No. 1, 2005, pp. 90–95.

Original Russian Text Copyright © 2005 by Ponedel’kina, Odinokov, Vakhrusheva, Golikova, Khalilov, Dzhemilev.

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Ponedel’kina, I.Y., Odinokov, V.N., Vakhrusheva, E.S. et al. Modification of hyaluronic acid with aromatic amino acids. Russ J Bioorg Chem 31, 82–86 (2005). https://doi.org/10.1007/s11171-005-0011-y

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  • DOI: https://doi.org/10.1007/s11171-005-0011-y

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