| This dissertation details the synthesis and characterization of N-alkyl-N,N-linked urea oligomers and their incorporation into glycosaminoglycan mimicking polymers. N-alkyl- N,N-linked urea oligomers are oligomers that can incorporate a wide variety of functional side chains and are prepared through standard organic chemistry techniques. Polymers in this thesis were synthesized using reversible addition-fragmentation chain transfer (RAFT) polymerization. RAFT polymerization is a controlled/"living" radical polymerization technique that can be used to prepare (co)polymers of controlled molecular weights and narrow polydispersities. The N-alkyl-N,N-linked urea oligomer containing polymers have been designed to mimic the properties of the naturally occurring anticoagulant GAG molecule heparin through incorporation of sulfonated carbohydrates as N-alkyl side groups. Heparin is a naturally occurring heterogeneous, sulfated, anionic sugar macromolecule that is commonly used as a therapeutic anticoagulant. In the second chapter, N-alkyl- N,N-linked urea oligomers containing terminal alkyne units were modified with monomeric saccharides. In third chapter, copper catalyzed azide-alkyne cycloaddition (CuAAC) or "click" chemistry is used to synthesize a universal N-alkyl-N,N-linked urea oligomer that allows for the quick and simple synthesis of several oligomers bearing different monomeric saccharides. In the fourth chapter, more complex saccharide units are incorporated and sequence specificity is built in to the universal N-alkyl- N,N-linked urea oligomer of chapter 3 by utilizing simple protecting group chemistry to allow for the step-wise modification of the N-alkyl urea peptoid oligomer backbone. |
