NCAs are prone to hydrolysis to the parent amino acid:
:RCHNHC(O)OC(O) + HO → HNCH(R)COH + CO
Some derivatives however tolerate water briefly.
NCAs convert to homopolypeptides ( [N(H)CH(R)CO)]) through ring-opening polymerization:
:nRCHNHC(O)OC(O) → [N(H)CH(R)CO)] + nCO
Poly--lysine has been prepared from N-carbobenzyloxy-α-N-carboxy--lysine anhydride, followed by deprotection with phosphonium iodide. Peptide synthesis from NCAs does not require protection of the amino acid functional groups. N-Substituted NCAs, such as sulfenamide derivatives have also been examined. The ring-opening polymerization of NCAs is catalyzed by metal catalysts.
The polymerization of NCA’s have been considered as a prebiotic route to polypeptides.