Polyesters of lactic acid (PLA), glycolic acid (PGA) and their copolymers (PLGA) are the most commonly used materials for biomedical, and disposable or non-recoverable polymer goods applications because they degrade under biological and environmental conditions, their degradation products occur naturally in the body and the environment, and their monomers are naturally derived.  We recently designed and synthesized acrylate inimers that produced the first truly hyperbranched analogs of linear polyacrylates upon homopolymerization using atom transfer radical polymerization.  The key intermediate of this new class of inimers is a 2-halo-3-hydroxypropionic acid (halo = Cl or Br), which we synthesize regioselectively starting from serine, a natural amino acid that can be isolated from soybean protein.  Since 2-halo-3-hydroxypropionic acids are halogenated isomers of lactic acid, yet have a primary alcohol group like glycolic acid, we believe they are ideal comonomers to copolymerize with glycolic acid and/or lactic acid to provide PLA and PLGA with sites for attaching biologically active or other functional molecules.We will present the synthesis of halogenated PLGA and PLGA by both acid-catalzyed and enzymatic polymerizations, as well as some functionalization reactions based on the bromine substituent, and the ability of the halogenated PLA to blend with high molecular weight PLA.

Synthesis of functionalized PLA and PLGA polyesters

247th National Meeting (2014)

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