Synthesis of Novel Polymer/Urea Peptoid Conjugates Using RAFT Polymerization

The synthesis of novel urea peptoids and their conjugation to polymers prepared using reversible addition-fragmentation chain transfer (RAFT) polymerization is reported. Statistical copolymers of poly(styrene-co-3-azidopropyl methacrylate) (poly(styrene-co-AzPMA)) and poly(3-O-methacryloyl-1,2:5,6-di-O-isopropylidene-D-glucofuranose-co-AzPMA) (poly(MAIpGlc-co-AzPMA)) were synthesized with high molecular weight and narrow molecular weight distributions. The polymer conjugates were formed using copper-catalyzed azide/alkyne cycloaddition chemistry and confirmed by FTIR and H-1 NMR spectroscopy. Following conjugate formation with poly(MAIpGlc-co-AzPMA) and the urea peptoid the isopropylidene groups were removed using dilute trifluoroacetic acid. This yielded a sugar functionalized water-soluble, polymer/urea peptoid conjugate. Reactions with fluorescent compounds demonstrated that the peptoids can be further modified after conjugation to the polymar.