Preparation of multifunctional glycopolymers using double orthogonal reactions and the effect of electrostatic groups on the glycopolymer–lectin interaction

Takahiro Oh, Kazuki Jono, Yuri Kimoto, Yu Hoshino, Yoshiko Miura

Research output: Contribution to journalArticlepeer-review

Abstract

We investigated synthetic biomacromolecules to control molecular interactions. Multifunctional glycopolymers for molecular recognition were prepared via living radical polymerization and post-click chemistry with orthogonal Huisgen and thiol-epoxy reactions. The synthesis of the polymer backbone and the subsequent side-chain introduction successfully proceeded in high yield. The multifunctional glycopolymers had a tri-block structure: the first and third blocks contained mannose, and the second block contained either a positively or negatively charged group or a neutral hydrophilic group. The molecular recognition of the glycopolymers toward lectin was evaluated via fluorescence quenching measurements. Because of the electrostatic interaction, the binding constant varied in the following order: positively charged glycopolymer (PT110) > negatively charged glycopolymer (NT110). The effect of the electrostatic interactions was modest compared with the effect of the carbohydrate–lectin binding. These results suggested that the carbohydrate–lectin interaction was an important factor in the molecular recognition of glycopolymers. This study provides guidelines for the preparation of multifunctional polymers, such as biomaterials.

Original languageEnglish
Pages (from-to)1299-1308
Number of pages10
JournalPolymer Journal
Volume51
Issue number12
DOIs
Publication statusPublished - Dec 1 2019

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Materials Chemistry

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