Abstract
The regularities of the reaction of aminopolysaccharide chitosan with glutaraldehyde (GA) have been considered. The equilibrium forms of GA in water have been thoroughly studied by NMR spectroscopy. It has been established that at pH 5.6, the exchange of the protons of O=CHCH2 groups for deuterium occurs, indicating the presence of an anion, a product of the first stage of the aldol reaction; at pH > 7.2, the formation of the products of an aldol reaction and aldol condensation takes place. The kinetics of the reaction between the amino groups of chitosan and GA, the kinetics of gel formation in chitosan solutions in the presence of GA, and the kinetics of changes in the rigidity of gels formed have been studied by UV spectroscopy. IR spectra of cross-linked chitosan have been obtained. It has been shown that chitosan catalyzes the polymerization of GA to form irregular products; in this process, the length of oligomeric chains in modified or cross-linked chitosan and the concentration of conjugated bonds increase with the GA concentration and pH of the reaction medium.
Similar content being viewed by others
References
DeSantis, G. and Jones, J.B., Curr. Opin. Biotechnol., 1999, vol. 10, pp. 324–330.
Jayakrishnan, A. and Jameela, S.R., Biomaterials, 1996, vol. 17, pp. 471–484.
Migneault, I., Dartiguenave, C., Bertrand, M.J., and Waldron, K.C., Biotechniques, 2004, vol. 37, pp. 790–802.
Kumar, M.N.V.R., React. Funct. Polym., 2000, vol. 46, pp. 1–27.
Muzzarelli, R.A.A. and Muzzarelli, C., Adv. Polym. Sci., 2005, vol. 186, pp. 151–209.
Berger, J., Reist, M., Mayer, J.M., Felt, O., Peppas, N.A., and Gurny, R., Eur. J. Pharm. Biopharm., 2004, vol. 57, pp. 19–34.
Kurita, K., Marine Biotech., 2006, vol. 8, pp. 203–226.
Wipple, E.B. and Ruta, M., J. Org. Chem., 1974, vol. 39, pp. 1666–1668.
Kawahara, J., Ohmori, T., Ohkubo, T., Hattori, S., and Kawamura, M., Anal. Biochem., 1992, vol. 201, pp. 94–98.
Hardy, P.M., Nicholls, A.C., and Rydon, H.N., Chem. Commun., 1969, pp. 565–566.
Margel, S. and Rembaum, A., Macromolecules, 1980, vol. 13, pp. 19–24.
Sorlier, P., Denuziere, A., Viton, C., and Domard, A., Biomacromolecules, 2001, vol. 2, pp. 765–772.
Perminov, P.A., Kildeeva, N.R., Timofeeva, L.M., Abronin, I.A., Babak, V.G., and Nikonorov, V.V., Izv. vuzov (Khimiya Khim. Tekhnol.), 2007, vol. 50, pp. 53–56.
Pretsch, E., Bullman, F., and Affolter, L., Structure Determination of Organic Compounds, Heidelberg: Springer, 2000.
Monteiro, O.A.C. and Airoldi, C., Int. J. Biol. Macromol., 1999, vol. 26, pp. 119–128.
Crescenzi, V., Francescangeli, A., Taglienti, A., Capitani, D., and Mannina, L., Biomacromolecules, 2003, vol. 4, pp. 1045–1054.
Bellamy, L.J., The Infrared Spectra of Complex Molecules, vol. 2, London: Chapman, 1980.
Amedjkouh, M., Tetrahedr. Asymm., 2005, vol. 16, pp. 1411–1414.
Zheng, B.-L., Liu, Q.-Z., Guo, C.-S., Wang, X.-L., and He, L., Org. Biomol. Chem, 2007, vol. 5, pp. 2913–2915.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © N.R. Kildeeva, P.A. Perminov, L.V. Vladimirov, V.V. Novikov, S.N. Mikhailov, 2009, published in Bioorganicheskaya Khimiya, 2009, vol. 35, No. 3, pp. 397–407.
Rights and permissions
About this article
Cite this article
Kildeeva, N.R., Perminov, P.A., Vladimirov, L.V. et al. About mechanism of chitosan cross-linking with glutaraldehyde. Russ J Bioorg Chem 35, 360–369 (2009). https://doi.org/10.1134/S106816200903011X
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S106816200903011X