Facile Preparation of a Glycopolymer Library by PET-RAFT Polymerization for Screening the Polymer Structures of GM1 Mimics

Abstract

Commercialized oligosaccharides such as GM1 are useful for biological applications but generally expensive. Thus, facile access to an effective alternative is desired. Glycopolymers displaying both carbohydrate and hydrophobic units are promising materials as alternatives to oligosaccharides. Prediction of the appropriate polymer structure as an oligosaccharide mimic is difficult, and screening of the many candidates (glycopolymer library) is required. However, repeating polymerization manipulation for each polymer sample to prepare the glycopolymer library is time-consuming. Herein, we report a facile preparation of the glycopolymer library of GM1 mimics by photoinduced electron/energy transfer-reversible addition–fragmentation chain-transfer (PET-RAFT) polymerization. Glycopolymers displaying galactose units were synthesized in various ratios of hydrophobic acrylamide derivatives. The synthesized glycopolymers were immobilized on a gold surface, and the interactions with cholera toxin B subunits (CTB) were analyzed using surface plasmon resonance imaging (SPRI). The screening by SPRI revealed the correlation between the log P values of the hydrophobic monomers and the interactions of the glycopolymers with CTB, and the appropriate polymer structure as a GM1 mimic was determined. The combination of the one-time preparation and the fast screening of the glycopolymer library provides a new strategy to access the synthetic materials for critical biomolecular recognition.

Fundamental Investigation on Osmotic Pressure and Phase Behavior of Novel pH-Responsive Draw Solute with Imine-Based Dynamic Covalent Chemistry

“…Table shows the water–octanol partition coefficients (log P ) of the amines, aldehydes, and produced imines calculated using ChemDraw ver. 19.0. , A larger log P value indicates greater hydrophobicity. As shown in Table , the log P values of all amines and 2-pyridinecarboxyaldehyde used in this study were low and formed a homogeneous aqueous solution when these solutes were individually mixed with water.…”

Photocontrolled RAFT polymerization: past, present, and future

“…ZnTPP-catalyzed HTP polymerization has enabled the simple and efficient construction of a library of polymers without prior deoxygenation. [262][263][264][265][266]276,[387][388][389][390] Via preparation and investigation of a large combinatorial library of polymers, researchers efficiently optimized polymerization conditions 262,389 and screened structure-activity relationships of polymers synthesized for antimicrobial applications, 155,263,264 polymer-protein binding interactions, 265,266 conjugation of biomolecules, 276 preparation of a glycopolymer library, 390 and design of single-chain polymer NPs. 388 Other than ZnTPP, EY was also employed for photo-PISA in a 96-well plate, but ascorbic acid was necessary to achieve oxygen tolerance.…”

Unleashing the Power of PET-RAFT Polymerization: Journey from Porphyrin-Based Photocatalysts to Combinatorial Technologies and Advanced Bioapplications

“…The facile preparation of a glycopolymer library as alternatives to expensive oligosaccharides was achieved using PET-RAFT polymerization. 106 Through the incorporation of hydrophobic monomers, the glycopolymers selectively interacted with cholera toxin B subunits and exhibited similar biological function as GM1 mimics. Utilizing surface plasmon resonance imaging for rapid screening and incorporating a one-time preparation approach, a valuable strategy emerges for practical bioapplications, enabling the investigation of synthetic materials involved in biomolecular recognition.…”