CHITOSAN DERIVATIVES BEARING C-10-ALKYL GLYCOSIDE BRANCHES - A TEMPERATURE-INDUCED GELLING POLYSACCHARIDE

Undecenyl beta-D-glycosides of glucose, galactose, and lactose have been ozonolyzed to give formylnonyl glycosides, which were reductively N-alkylated to chitosan. These chitosan derivatives, having mixed hydropobic/hydrophilic branches, were prepared with degree of substitution values as high as 1.5. Solutions of derivatives bearing pendant monosaccharides with ds > 1.0, in 1% aqueous acetic acid, gelled upon heating to 50-degrees-C. Lower ds samples did not exhibit this property, nor did derivatives having a disaccharide pendant residue. Further control over the properties of these derivatives was possible by preparing mixed-branched derivatives having short- and long-chain alkyl glycoside pendant groups.