Title :
Synthesis and Characterization of Optically Active Macromolecular Prodrugs with Chemo-Enzymatic Protocol
Author :
Quan, Jing ; Zheng, Yan ; Wu, Cheng-Yao ; Zhu, Li-Min ; Lin, Xian-Fu
Author_Institution :
Coll. of Chem., Chem. Eng. & Biotechnol., Donghua Univ., Shanghai, China
Abstract :
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.
Keywords :
chromatography; drugs; enzymes; infrared spectra; molecular biophysics; nuclear magnetic resonance; polymerisation; polymers; spectrochemical analysis; (R)-1-O-vinyladipoyl-chlorphenesin; (R)-OVAC; (S)-N-vinyladipoyl-propranolol; (S)-NVAP; GPC; IR spectra; NMR; chemical polymerization; chemoenzymatic protocol; copolymerization; enzymatic resolution; glycolipid 6-O-vinyladipyl-D-glucose; optically active polymeric prodrug; optically purity; polymerizable optically active monomer; Biochemistry; Biomedical optical imaging; Chemical engineering; Chemistry; Drugs; Nuclear magnetic resonance; Optical polymers; Powders; Protocols; Sugar;
Conference_Titel :
Bioinformatics and Biomedical Engineering , 2009. ICBBE 2009. 3rd International Conference on
Conference_Location :
Beijing
Print_ISBN :
978-1-4244-2901-1
Electronic_ISBN :
978-1-4244-2902-8
DOI :
10.1109/ICBBE.2009.5163552
