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 journalArticle

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

Fingerprint

Molecular recognition
Electrostatics
Coulomb interactions
Polymers
Living polymerization
Molecular interactions
Biocompatible Materials
Mannose
Free radical polymerization
Sulfhydryl Compounds
Lectins
Biomaterials
Quenching
Fluorescence

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Materials Chemistry

Cite this

Preparation of multifunctional glycopolymers using double orthogonal reactions and the effect of electrostatic groups on the glycopolymer–lectin interaction. / Oh, Takahiro; Jono, Kazuki; Kimoto, Yuri; Hoshino, Yu; Miura, Yoshiko.

In: Polymer Journal, Vol. 51, No. 12, 01.12.2019, p. 1299-1308.

Research output: Contribution to journalArticle

@article{4a0fff0fae764329937779e540e435e3,
title = "Preparation of multifunctional glycopolymers using double orthogonal reactions and the effect of electrostatic groups on the glycopolymer–lectin interaction",
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.",
author = "Takahiro Oh and Kazuki Jono and Yuri Kimoto and Yu Hoshino and Yoshiko Miura",
year = "2019",
month = "12",
day = "1",
doi = "10.1038/s41428-019-0244-x",
language = "English",
volume = "51",
pages = "1299--1308",
journal = "Polymer Journal",
issn = "0032-3896",
publisher = "Nature Publishing Group",
number = "12",

}

TY - JOUR

T1 - Preparation of multifunctional glycopolymers using double orthogonal reactions and the effect of electrostatic groups on the glycopolymer–lectin interaction

AU - Oh, Takahiro

AU - Jono, Kazuki

AU - Kimoto, Yuri

AU - Hoshino, Yu

AU - Miura, Yoshiko

PY - 2019/12/1

Y1 - 2019/12/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85070791888&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85070791888&partnerID=8YFLogxK

U2 - 10.1038/s41428-019-0244-x

DO - 10.1038/s41428-019-0244-x

M3 - Article

AN - SCOPUS:85070791888

VL - 51

SP - 1299

EP - 1308

JO - Polymer Journal

JF - Polymer Journal

SN - 0032-3896

IS - 12

ER -