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 1 H 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 1 H 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.