Synthesis of water soluble N-acyl chitosan derivatives for characterization as antibacterial agents

ORGN 282

Lakia M. Champagne, lchamp2@lsu.edu, Chemistry, Louisiana State University, 744 Choppin Hall, Baton Rouge, LA 70803-1804 and William H. Daly, chdaly@lsu.edu, Department of Chemistry, Louisiana State University, 712 Choppin Hall, Baton Rouge, LA 70803-1804.
Chitosan is an organic natural polysaccharide that has been recognized for its ability to inhibit the growth of E. coli and S. aureus bacterial cells. This research entails the chemical modification of chitosan with aliphatic, cyclic, and novel hydrophilic anhydrides through addition/elimination reactions. The products are given quaternary ammonium functionality by a attaching a cationic substituent to the polysaccharide backbone. These reactions cooperatively work to enhance chitosan's antibacterial properties. It was found that an increase in the N-acyl substitution (% ES) led to a decrease in the cationic substitution (% EQ), which resulted in a decrease in the antibacterial activity. For example, cationic 2-glycerol glutamide chitosan with 5% ES and 61% EQ exhibited an inhibitory concentration of 64 µg/mL against E. coli and 32 µg/mL against S. aureus. At 25% ES and 31% EQ, the derivative exhibited an inhibitory concentration of 128 µg/mL against both E. coli and S. aureus.
 

Biologically Active Molecules
8:00 AM-12:00 PM, Tuesday, April 8, 2008 Morial Convention Center -- Rm. R05, Oral

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008