Inulin polysaccharide having pendant amino acids: Synthesis and characterization

Abstract

Inulin polysaccharide was esterified with N-protected α-amino acids (N,N′-di-benzylocarbonyl-L-lysine and N-benzylocarbonyl-glycine) under a mild condition (room temperature) and within short reaction times (6 h). The esterification reactions were conducted in the presence of dicyclohexylcarbodiimide and 4-(dimethylamino)pyridine as a catalyst. The optimal reaction time (6 h) was determined by monitoring the concentration of free carboxylic acid of the N-protected amino acids during the reaction. The degree of substitution per fructose unit was 0.95 for inulin-lysine and 1.01 for inulin-glycine. The resulting biopolymer was deprotected by catalytic transfer hydrogenation method using 1,4-cyclohexadiene as an effective hydrogen donor. The structures, molecular weight, and thermal properties of the amino acid esters of inulin were determined by Fourier transform infrared spectroscopy, 1H and 13C NMR, UV, viscosity, and dicyclohexylcarbodiimide. This new modified inulin polysaccharide would have the potential as a biomaterial for biomedical applications. © 1998 John Wiley & Sons, Inc. J. Appl. Polym. Sci. 70: 953–963, 1998