Synthesis of chitooligosaccharide derivative with quaternary ammonium group and its antimicrobial activity against Streptococcus mutans

Abstract

A derivative of chitooligosaccharide (COS) with quaternary ammonium functionality was synthesized and characterized by means of FT-IR and NMR spectroscopy. Its amtimicrobial activity was evaluated against Streptococcus mutans, which is a principal etiological agent of dental caries in humans. Introduction of quaternary ammonium group to COS has been easily accomplished by coupling of glycidyl trimethylammonium chloride (GTMAC) to COS in aqueous solution without an additional catalyst. The degree of substitution (%), as determined by 1H NMR, of GTMAC to the COS increased up to 116% at 70 °C for 24 h. The resulting COS-GTMAC exhibited the growth inhibition of above 80% against S. mutans after 5 h, whereas the COS showed the growth inhibition of about 10%. It was found that antimicrobial activity of the COS could be considerably enhanced by the introduction of quaternary ammonium functionality.