Synthesis of chitooligosaccharide derivative with quaternary ammonium group and its antimicrobial activity against Streptococcus mutans.
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 (1)H NMR, of GTMAC to the COS increased up to 116% at 70 degrees C for 24h. The resulting COS-GTMAC exhibited the growth inhibition of above 80% against S. mutans after 5h, 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.
Kim
Ji Young
JY
Department of Polymer Science and Engineering, Kumoh National Institute of Technology, Kumi, Kyungbuk 730-701, South Korea.
Lee
Jong Keun
JK
Lee
Taek Seung
TS
Park
Won Ho
WH
D000890:Anti-Infective Agents / Q000494:pharmacology*; D002686:Chitin / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009844:Oligosaccharides / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D013295:Streptococcus mutans / Q000378:metabolism*; D013997:Time Factors
D000890:Anti-Infective Agents; D004852:Epoxy Compounds; D009844:Oligosaccharides; D000644:Quaternary Ammonium Compounds; D002686:Chitin; C045006:glycidyl trimethylammonium