SYNTHESIS OF POLYAMIDES CONTAINING DIPEPTIDE LINKAGES

A synthetic approach to polyamides containing the tyrosine-leucine linkage is presented. The DPPA coupling technique was utilized to synthesize the monomers. A chloroform solution of tyrosylleucyliminohexamethyleneiminoleucyltyrosine, monomer I, and triethylamine was reacted with chloroform solutions of adipoyl and sebacoyl chlorides, to give polymers with molecular weight, M(w)/M(n) of 14200/7200 and 20800/8100, respectively. Interfacial polymerization of monomer I yielded a fibrous cross-linked material. This was found to be a poly(amide ester) as indicated by IR analysis. In another reaction, the monomer, beta-alanyltyrosylleucyl-beta-alanine (monomer II) in DMF was polymerized using DPPA and triethylamine to give a polyamide with M(w)/M(n) of 16500/5700.