Synthesis and Characterization of Optically Active Macromolecular Prodrugs with Chemo-Enzymatic Protocol
A facile procedure combining enzymatic resolution with chemical polymerization was developed to prepare optically active polymeric prodrug containing glucose. Polymerizable optically active (R)-1-O-vinyladipoyl-chlorphenesin ((R)-OVAC) was obtained in excellent optically purity (ee>99.9%) and high yield (~50%) in short time, and optically active (S)-N-vinyladipoyl-propranolol ((S)-NVAP) was obtained in optically purity (ee=88%) by lipase-catalyzed resolution after optimization of reaction conditions. Then, polymerizable optically active monomer was copolymerized with polymerizable glycolipid 6-O-vinyladipyl-D-glucose (OVADG) using AIBN as the initiator. The obtained optically active polymeric prodrugs poly-(OVAC-co-OVADG) and poly-(NVAP-co-OVADG) were characterized by IR, NMR and GPC.