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Synthesis of a glycosaminoglycan polymer mimetic using an N-alkyl-N,N-linked urea oligomer containing glucose pendant groups



The synthesis of a glycosaminoglycan polymer mimetic is reported. An isopropylidene protected glucose methacrylate monomer was copolymerized under reversible addition fragmentation chain transfer polymerization control with an azido-containing comonomer to a molecular weight of 29 000 g mol−1 with polydispersity of 1.21. The comonomer ratio was determined to be 15:1 based on 1H NMR spectroscopy. This copolymer was coupled to sugar-functionalized N-alkyl-N,N-linked urea oligomers using a copper catalyzed alkyne/azide cycloaddition reaction. The reaction efficiency was 100% as monitored by 1H NMR spectroscopy. The isopropylidene protecting groups on the polymer and N-alkyl-N,N-linked urea oligomers were removed using acid hydrolysis to give the final polysaccharide mimetic. It is expected that these polymers will have applications in a variety of future therapeutic applications. © 2013 Society of Chemical Industry