Synthesis of soluble polymers for medicine that degrade by intramolecular acid catalysis

Aqueous soluble polymers designed to rapidly degrade by an intramolecular assisted acid catalysed mechanism were prepared. Degradation studies at pH 5.5 and 2.0 exhibited a rapid first phase followed by a slower phase and incomplete degradation to macromonomeric species. The fast phase was attributed to repeat units containing a carboxylic acid pendent chain cis to an amide bond in the polymer mainchain and the slow phase by the absence of this free carboxylic acid moiety.