Journal
MACROMOLECULAR BIOSCIENCE
Volume 10, Issue 2, Pages 119-126Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/mabi.200900199
Keywords
click chemistry; glycopolymer; micelles; reversible addition fragmentation chain transfer (RAFT)
Funding
- Australian Research Council (ARC)
- University of New South Wales (UNSW)
- Karlsruhe Institute of Technology (KIT)
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The synthesis of a new glycomonomer based on mannose, prepared via CuAAC, is reported. The resulting 1,2,3-triazole linkage between mannose and the polymer backbone ensures the formation of highly stable glycopolymers, which will not undergo hydrolysis. The monomer 2'-(4-vinyl-[1,2,3]-triazol-1-yl)ethyl-O-alpha-D-mannopyranoside was polymerized in the presence of a RAFT agent - 3-benzylsulfanylthiocarbonylsulfanyl propionic acid - to yield well-defined polymers with molecular weights up to 51500 g mol(-1) and a PDI of 1.16. The resulting polymer was employed as a macroRAFT agent in the polymerization of NIPAAm in order to generate thermo-responsive block copolymers, which undergo reversible micelle formation at elevated temperatures. The rapid interaction between the polymers prepared and ConA confirms the high affinity of these structures to proteins. While the linear glycopolymers already undergo a fast complexation with ConA, the reported rates have found to be exceeded by the micellar glycopolymer structure presented in the current contribution.
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