Functional Polylactides for Biomedical Applications

Although there has been considerable progress towards development of bioresorbable biomaterials, additional work is urgently needed to address current demands for polymer therapeutic materials with functional group that allow facile attachment of bioactive moities. To that end, we developed a family of functional carbonate monomers for copolymerization with FDA approved monomers such as L-lactide, e-caprolactone and trimethylene carbonate (Kumar et al, 2002; Chen et al., 1999; Chen et al., 1998; Chen et al., 1997). The general idea of this research was to create a family of carbonate monomers from natural sugars with ketal-protected diols which can be deprotected to liberate hydroxyl functionalities. Furthermore, our group had considerable experience in developing suitable conditions to polymerize substituted cyclic carbonate monomers with medically important monomers such as L-lactide, trimethylene carbonate and e-caprolactone For example, the monomer 1,2-O-isopropylidene-3-benzyloxy-pentofuranose-4,4-cyclic carbonate (IPPTC) was designed and synthesized starting from 1,2-O-isopropylidene-3-benzyloxy-4-(bishydroxymethyl) pentofuranose in 65.0% yield at 0 °C in THF by a one-pot reaction (Scheme 17).

Scheme 17. Synthesis of the monomer 1,2-O-isopropylidene-3-benzyloxy-pentofuranose-4,4-cyclic carbonate (IPPTC).

References

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