Synthesis of polymeric N-hydroxysuccinimide esters of N-substituted amino acids and peptides

Abstract

1 A number of macrosieve poly-N-hydroxysuccinimide esters of N-protected amino acids and peptides was synthesized using the following methods for the condensation of the polymer-activator with the carboxyl components: dicyclohexylcarbodiimide, mixed anhydrides, trifluoroacetate, and a method that is based on the use of N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline as the condensing agent. 2. A comparative evaluation was made of the efficiency of the indicated methods for the condensation of N-protected amino acids and peptides with the polymer-activator as regards the yield of polymeric esters, the consumption of the carboxyl component, and the length of the activation process. 3. It was shown that the trifluoroacetate and mixed anhydride methods are the most efficient.