[Macromol. Biosci.] Neoglycopolymers Based on 4-Vinyl-1,2,3-Triazole Monomers Prepared by Click Chemistry
writer：Hetzer M, Chen GJ, Barner-Kowollik C, Stenzel MH
keywords：click chemistry; glycopolymer; micelles; reversible addition fragmentation chain transfer (RAFT)
source：期刊
specific source：MACROMOLECULAR BIOSCIENCE
Issue time：2010年
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.