A simple preparation of half N-acetylated chitosan highly soluble in water and aqueous organic solvents.
A simple and improved method of preparing highly soluble chitosan (half N-acetylated chitosan) was developed using a series of chitosan samples of low molecular weights, and the solubility of the half N-acetylated chitosan in water and organic solvents was investigated in detail. To reduce the molecular weight, chitosan was treated with NaBO3 under the condition that chitosan was homogeneously dissolved in aqueous acetic acid. Weight-average molecular weights of the obtained chitosan samples were determined using a size-exclusion chromatography system equipped with a low-angle laser light-scattering photometer. Each chitosan sample was then N-acetylated with acetic anhydride under the condition that chitosan was homogeneously dissolved in aqueous acetic acid again. The water solubility of the half N-acetylated chitosan thus prepared increased with decreasing molecular weight. From 1H NMR spectroscopy, it was suggested that the sequence of N-acetylglucosamine and glucosamine residues was random. The solubility of the half N-acetylated chitosan of low molecular weight was rather high even in aqueous dimethylacetamide and dimethylsulfoxide.
Kubota
N
N
General Education Chemistry and Physics, Oita Medical University, Japan. nkubota@oita-med.ac.jp
Tatsumoto
N
N
Sano
T
T
Toya
K
K
D000107:Acetylation; D002240:Carbohydrate Sequence; D002686:Chitin / Q000031:analogs & derivatives* / Q000737:chemistry; D048271:Chitosan; D002850:Chromatography, Gel; D004121:Dimethyl Sulfoxide; D004187:Disaccharides / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D008970:Molecular Weight; D012995:Solubility
D004187:Disaccharides; D002686:Chitin; D048271:Chitosan; D004121:Dimethyl Sulfoxide