Synthesis and biodegradation of poly(ester amide)s containing amino acid residues: The effect of the stereoisomeric composition of L- and D-phenylalanines on the enzymatic degradation of the polymers

Biodegradable poly(ester amide)s that contained phenylalanine residues in the main chains were synthesized by the polycondensation of di-p-nitrophenyl sebacate and phenylalanine 2-aminoethyl ester. The stereoisomeric composition (L/D ratio) of the phenylalanine residue in the monomer did not affect the yield and molecular weight of the polymer much. From the optical rotations of the polymers, it was found that the L/D ratio of the phonylalanine residue in the polymer was almost equal to the L/D ratio of the phenylalanine residue in the monomer. The biodegradability of the poly(ester amide)s was studied in aqueous solutions with proteases as catalysts. The polymer with 100% L-phenylalanine residue was effectively degraded by a-chymotrypsin or subtilisins. However, the replacement of 10% L-phenylalanine with D-isomer resulted in a dramatic decrease in degradability. The polymers with less than 30% L-isomer were hardly degraded by the enzymes. Gel permeation chromatography studies suggested that the solubility of the degradation products in water greatly affected the rate and extent of biodegradation. (C) 2001 John Wiley Sons, Inc.