Preparation, characterization and antimicrobial activity of 6-amino-6-deoxychitosan

6-Amino-6-deoxychitosans with molecular weights from 0.23 × 10⁴ to 1.41 × 10⁴ and degree of substitution from 0.85 to 0.96 were prepared via N-phthaloylation, tosylation, azidation, hydrazinolysis and reduction of azide groups. Their structures were characterized by FT-IR, ¹H NMR, ¹³C NMR, gel permeation chromatography (GPC) and elemental analysis. The antimicrobial activities of 6-amino-6-deoxychitosans against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, and Aspergillus niger were investigated. The results showed that 6-amino-6-deoxychitosans had a wide spectrum of effective antimicrobial activities. Compared with chitosan, 6-amino-6-deoxychitosans had much better antimicrobial activities. Their minimum inhibitory concentrations (MICs) were between 0.025% and 0.1% (w/v) in acetic/sodium acetate solution with different pH from 5.4 to 7.5. 6-Amino-6-deoxychitosans could also inhibit growth of bacteria tested in distilled water under pH 6.6-8.45. The antimicrobial mechanism was complex and the positive charge on the amino groups was not the sole factor resulting in the antimicrobial activities.