The preparation and antioxidant activities of four 2-aminoacyl-chitooligosaccharides

Chitooligosaccharides (COS) with two different molecular weights are acylated with four nonpolar amino acids: glycine (Gly), alanine (Ala), valine (Val) and leucine (Leu) to obtain 2-aminoacetyl-chitooligosaccharide (2-GlyCOS), 2-aminopropionyl-chitooligosaccharide (2-AlaCOS), 2-amino-3-methylbutyryl-chitooligosaccharide (2-ValCOS), and 2-amino-4-methylpentanoyl-chitooligosaccharide (2-LeuCOS). The structure of the derivatives was characterized by FT-IR spectroscopy, 13C NMR spectroscopy, and elemental analysis. The antioxidant activities of the derivatives, such as hydroxyl radical (·OH) scavenging ability, superoxide anion (O2·-) scavenging ability, reducing ability, and DPPH radical scavenging ability, were investigated using various established systems. Compared with chitooligosaccharide and nonpolar amino acids, all derivatives have strong scavenging ability toward hydroxyl radicals and superoxide anions, and the clearance rate was 19.05% and 67.70% separately. The reducing ability and DPPH free radical scavenging ability of the derivatives are only 0.021Abs and 32.97%. Among them, only 2-AlaLCOS has significant reducing ability, and the value can reach 0.143Abs. The above results showed that the antioxidant activity of some derivatives was higher than that of chitooligosaccharide. The water solubility of the new derivatives was also greatly improved compared to that of nonpolar amino acids. Therefore, the application of 2-aminoacyl-chitooligosaccharides (2-AACOS) in antioxidants has laid a foundation and has certain potential application value in the fields of medicine, agriculture, and animal husbandry.