AMINO ACID BASED BIOANALOGOUS POLYMERS. SYNTHESIS AND STUDY OF NEW POLY(ESTER AMIDE)S COMPOSED OF HYDROPHOBIC α-AMINO ACIDS AND DIANHYDROHEXITOLES

A new class of biodegradable poly(ester-amide)s was prepared by a two step method. At first isosorbide or isomannide were esterified with α-amino acids in the presence of p-toluenesulfonic acid, and the resulting esters bisammonium tosylates were isolated. Second, the amino groups were liberated and polycondensed with p-nitrophenyl esters of aliphatic dicarboxylic acids. The resulting poly(ester-amide)s were characterized by elemental analyses, viscosity and GPC measurements, by NMR spectroscopy and DSC measurements. They proved to be materials having glass-transition temperatures in the range of 60-120°C. Using chymotrypsin or lipase, preliminary studies of the enzymatic degradation were performed.