Synthesis of biodegradable chiral polyesters and microspheres by asymmetric enzymatic polymerization

• Main Authors: Xiao, Y Yan, Cummins, DM David, Palmans, ARA Anja, Koning, CE Cor, Heise, A Andreas
• Format: Article in Journal/Newspaper
• Language: English
• Published: 2008
• Subjects: Antarc*; Antarctica
• Online Access: http://repository.tue.nl/649533

Materials with selective bio-responsiveness could have potential in medical applications. Here we report the synthesis of chiral microspheres obtained from non-crystalline aliphatic polyesters, with the aim to use chirality to program polymer microsphere degradation. By enzymatic enantioselective kinetic resolution polymerization from racemic monomers, hydroxyl-terminated (R)-, (S)- and racemic poly-(4-methylcaprolatone) (PMCL) were successfully synthesized. Preliminary degradation experiments with Candida Antarctica Lipase B show that the degradation rate can be tuned by the polymer chirality. Chiral microspheres around 40 microns were obtained after acrylation of the polymers and subsequent in situ cross-linking in an oil-in-water (O–W) emulsion evaporation approach.