Synthesis of bifunctional L-lysine derivatives with phage-inactivating effect.

A new type of lysine derivative connected with dicarboxylic acid was synthesized. The acid was coupled with ε-benzyloxycarbonyl-lysine ethyl ester (Lys(Z)-OEt) by conventional methods of peptide synthesis. The removal of the Z-group from the protected compounds by hydrogenation gave dihydrochlorides of the final products: succinyl-Lys-OEt, glutaryl-Lys-OEt, adipoyl-Lys-OEt, pimeloyl-Lys-OEt, suberoyl-Lys-OEt, azelaoyl-Lys-OEt and sebacoyl-Lys-OEt. Among the eight products, azelaoyl-Lys-OEt dihydrochloride showed the highest inactivating effect on several phages.