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About mechanism of chitosan cross-linking with glutaraldehyde


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.

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Correspondence to S. N. Mikhailov.

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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.

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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).

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Key words

  • chitosan
  • glutaraldehyde
  • cross-linking reagent
  • Shiff bases
  • aldol reaction
  • aldol condensation