Functional Lactide Monomers: Methodology and Polymerization

Side-chain-functionalized lactide analogues have been synthesized from commercially available amino acids and
polymerized using stannous octoate as a catalyst. The synthetic strategy presented allows for the incorporation of
any protected amino acid for the preparation of functionalized diastereomerically pure lactide monomers. The
resulting functionalized cyclic monomers can be homopolymerized and copolymerized with lactides and then
quantitatively deprotected forming new functional poly(lactide)-based materials. This strategy allows for the
introduction of functional groups along a poly(lactide) (PLA) backbone that after deprotection can be viewed as
chemical handles for further functionalization of PLA, yielding improved biomaterials for a variety of applications.