Journal
COLLOID AND POLYMER SCIENCE
Volume 280, Issue 6, Pages 562-568Publisher
SPRINGER
DOI: 10.1007/s00396-002-0658-3
Keywords
silk fibroin; chitooligosaccharides; conjugates; pH-dependent solubility; bacterial growth retardation
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With the aim of the functionalization of silk fibroin (SF), conjugates of SF and polycationic chitooligosaccharides (COS) were prepared by the chemical modification of SF with cyanuric chloride (CY)-activated COS (COS-CY). The H-1 NMR spectrum of the reaction product between a model compound D-glucosamine and CY suggested that the COS-CY modifier was synthesized by the reaction of the amino group and the terminal anomeric hydroxyl group in COS, with the chlorine atom of CY. The H-1 NMR spectrum and amino acid analysis of the conjugates (COS-CY-SF) clarified that the tyrosine and lysine residues of SF reacted with a second chlorine atom of the triazine ring of the modifier. On the basis of the results of the hexosamine determination and the amino acid analysis of COS-CY-SF it is estimated that COS-CY-SF consists of 38 wt% COS, 8 wt% CY, and 54 wt% SF. The absorbance at 600 nm as a function of pH for COS-CY-SF and SF indicated that the introduction of a large amount of hexosamine made SF amphiphilic and more water-soluble at lower pH values. The COS-CY-SF conjugates retarded the growth of Escherichia coli after incubation for 24 h at a conjugate concentration of 0.6% (w/v), while SF did not retard the growth at a SF concentration of 0.7% (w/v).
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