Polymer, Vol.39, No.13, 2751-2757, 1998
Poly(vinyl alcohol) functionalized by monosuccinate groups. Coupling of bioactive amino compounds
Poly (vinyl alcohol) (PVAL) partially functionalized with monosuccinate groups was obtained by reaction of PVAL with succinic anhydride using triethylamine as catalyst and N-Methyl-2-pyrrolidone as solvent. The structure of the resulting polymers was determined by H-1 and C-13 nuclear magnetic resonance (n.m.r.) spectroscopy. The influence of the type of catalyst, solvent composition and temperature was evaluated. The activation energy was found to be 31.8 kJ/mol. C-13 n.m.r. spectroscopy was used for the determination of the sequence distribution of partially modified PVAL [considered as a vinyl alcohol (VAL)-vinyl succinate (VSU) copolymer]. The results obtained show that VSU units have a random distribution with a slight alternating tendency in the copolymer. High degrees of modification were obtained in the coupling of model bioactive amino compounds (benzocaine, phenethylamine and 2-amino-2-deoxy-D-glucose (glucosamine)) to monosuccinylated PVAL activated with ethyl chloroformate. Interaction experiments between glucosamine-carrying PVAL (PVAL-G) and Concanavalin A (Con A) in a phosphate buffer (pH 7.2) at room temperature showed that PVAL-G interacts with Con A.