Clicked peptide polymer

Clicked peptide polymers are prepared by the azide-alkyne Huisgen cycloaddition also called the click reaction; which is commonly used in bioconjugation reactions to link molecules together with a stable triazole bridge.

Peptide based polymers are produced from a cycloaddition variant of step-growth polymerization.

The addition of the azide occurs by Cu(II)-catalyzed diazo transfer.

Degradation of the polymer occurs at the peptide bonds linking individual amino acids.

The amide bonds can be attacked non-specifically by acid or base catalyzed hydrolysis.

Synthetic scheme for a cycloaddition ("click reaction") based step-polymerization of a tripeptide.
Amidation of an tripeptide's C-terminus by propargyl amine. The group, X at the C-terminus can be a normal or activated carboxylate such as an anhydride, acid-chloride, or NHS-ester.
Addition of an azide to the N-terminal amino acid by Cu(II) catalyzed diazo transfer
Enzymatic degradation sites of a clicked peptide polymer.