Ring-opening polymerization of an O-carboxyanhydride monomer derived from L-malic acid

The synthesis and ring-opening polymerization (ROP) of an O-carboxyanhydride (OCA) monomer derived from L-malic acid (L-malOCA) is reported. Application of 4-dimethylaminopyridine as catalyst led to the observation of a number of undesirable side products. Investigation of different para-substituted pyridines as catalysts identified 4-methoxypyridine to have the ideal balance of activity and selectivity to enable the controlled ROP of L-malOCA. Deprotection of the benzyl ester side groups of the resultant polymers was achieved by hydrogenolysis and the resulting hydrophilic poly(α-malic acid) was observed to fully degrade within 7 days in aqueous solution.

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