| Abstract: | 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 phenylalanine 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 α‐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. © 2001 John Wiley & Sons, Inc. J Polym Sci Part A: Polym Chem 40: 385–392, 2002 |
