Journal
POLYMER INTERNATIONAL
Volume 63, Issue 1, Pages 127-135Publisher
WILEY
DOI: 10.1002/pi.4567
Keywords
RAFT; biomimetic; carbohydrate; glycosaminoglycan
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Funding
- Division Of Materials Research [1206150] Funding Source: National Science Foundation
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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 29000gmol(-1) with polydispersity of 1.21. The comonomer ratio was determined to be 15:1 based on H-1 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 H-1 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. (c) 2013 Society of Chemical Industry
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