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Synthesis and Characterization of Amino Acid Modified Chitooligosaccharides
Author(s) -
Ngamviriyavong Patcharee,
Uppanan Paweena,
Janvikul Wanida
Publication year - 2008
Publication title -
macromolecular symposia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.257
H-Index - 76
eISSN - 1521-3900
pISSN - 1022-1360
DOI - 10.1002/masy.200850421
Subject(s) - chloroacetic acid , chemistry , amino acid , proton nmr , alanine , glycine , serine , organic chemistry , nuclear chemistry , stereochemistry , biochemistry , enzyme
Amino acid modified chitooligosaccharides were synthesized by the new synthetic route. The chloroacetyl‐chitooliogosaccharide intermediates were prepared under a mild condition via a reaction between chitooligosaccharide (COS) and chloroacetic anhydride. The intermediates were subsequently reacted with a variety of amino acids, e.g., glycine, aspartic acid, alanine, arginine, and serine, under a basic condition, yielding amino acid modified COS products. The degree of chloroacetylation was calculated based on new 1 H NMR absorption peaks at 3.80 and 3.94 ppm, corresponding to NHCOC H 2 Cl and OCOC H 2 Cl, respectively. The degrees of chloroacetylation determined were 0.40, 0.44, 0.62, and 0.93 when the mole ratios of chloroacetic anhydride to COS were 0.5, 1, 2, and 4, respectively. The chemical structures of the COS derivatives were also determined using 1 H NMR spectroscopy. The biological properties of the derivatives were evaluated. Cytotoxicity of the derivatives was assessed by a direct contact, using L929 cells. An MTT assay was a method of choice to evaluate the efficacy of the derivatives to enhance the proliferation of L929 cells.