Heterochain polymers based on natural amino acids. Synthesis and enzymatic hydrolysis of regular poly(ester amide)s based on bis(L‐phenylalanine) α,ω‐alkylene diesters and adipic acid

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Abstract
Novel biodegradable regular poly(ester amide)s were synthesized by polycondensation of p‐toluenesulfonic acid salts of bis(phenylalanine) α,ω‐alkylene diesters (1) with bis(p‐nitrophenyl) adipate under mild conditions in organic solvents in the presence of triethyl amine as acid acceptor. Enzymatic hydrolysis (α‐chymotrypsinolysis) of the starting salts 1, the model bis(ester acetamide)s 2 and the obtained poly(ester amide)s 3 was investigated at 37°C and pH 8 using potentiometric titration. It was established that the hydrolysis rate increased with elongation of the α,ω‐alkylene chain. A strong noncovalent immobilization of the enzyme on the polymeric surface was observed.