Protecting-group-free synthesis of glycopolymers bearing thioglycosides via one-pot monomer synthesis from free saccharides

Tomonari Tanaka, Genri Inoue, Shin Ichiro Shoda, Yoshiharu Kimura

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Polyacrylamides having pendant thioglycosides were successfully synthesized from thioglycosidic monomers that were readily prepared by one-pot method without any protection of the hydroxy groups on the starting free saccharides. The glycomonomers were synthesized by the direct synthesis of thioglycosides using 2-chloro-1,3-dimethylimidazolinium chloride and 4-aminobenzentiol, and the following acrylamidation. They were co-polymerized with acrylamide into glycopolymers by reversible addition-fragmentation chain transfer polymerization using a trithiocarbonate derivative as a chain transfer agent. The gold nanoparticles and gold-coated quartz crystal microbalance sensor immobilized with the thiol-terminated glycopolymers exhibited high affinity for the corresponding lectins due to multivalent interaction between saccharides and protein in aqueous solution.

Original languageEnglish
Pages (from-to)3513-3520
Number of pages8
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume52
Issue number24
DOIs
Publication statusPublished - 2014 Dec 15

Keywords

  • RAFT polymerization
  • cluster effect
  • glycomonomer
  • glycopolymer
  • gold nanoparticle
  • lectin
  • one-pot synthesis
  • quartz crystal microbalance

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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