Screening of a glycopolymer library for GM1 mimetics synthesized by the “carbohydrate module method”

Abstract

The “carbohydrate module method” is a promising approach for oligosaccharide mimetics using polymeric materials. However, it is difficult to predict the optimal structure for a particular oligosaccharide mimetic, and an...

Glycopolymers based on carbohydrate or vinyl backbones and their biomedical applications

“…94 For example, Miura et al developed a series of glycopolymers from different ratios of acrylamide, galactose arylamine and N -acetylneuraminic acid acrylamide monomers in the presence of 2′,4′,5′,7′-tetrabromofluorescein disodium salt (eosin Y), ascorbic acid (AscA) and water-soluble CTA. 94 The wavelength of the irradiation light of 527 nm was selected based on the absorption peak of the photooxidation–reduction catalyst eosin Y, which did not overlap with the absorption peak of CTA. 94 Tanaka et al combined PET-RAFT and post-polymerization to prepare glycopolymers with pendant mannose, maltose or sialylglycopeptide groups under the irradiation of green light ( λ = 525 nm) in aqueous solution and under an open-air atmosphere.…”

“…94 The wavelength of the irradiation light of 527 nm was selected based on the absorption peak of the photooxidation–reduction catalyst eosin Y, which did not overlap with the absorption peak of CTA. 94 Tanaka et al combined PET-RAFT and post-polymerization to prepare glycopolymers with pendant mannose, maltose or sialylglycopeptide groups under the irradiation of green light ( λ = 525 nm) in aqueous solution and under an open-air atmosphere. 95…”

“…93 Photoinduced electron/energy transfer-reversible additionfragmentation chain-transfer (PET-RAFT) polymerization can be used to prepare glycopolymers in aqueous systems. 94 For example, Miura et al developed a series of glycopolymers from different ratios of acrylamide, galactose arylamine and N-acetylneuraminic acid acrylamide monomers in the presence of 2′,4′,5′,7′-tetrabromofluorescein disodium salt (eosin Y), ascorbic acid (AscA) and water-soluble CTA. 94 The wavelength of the irradiation light of 527 nm was selected based on the absorption peak of the photooxidation-reduction catalyst eosin Y, which did not overlap with the absorption peak of CTA.…”

Design of biointerfaces composed of soft materials using controlled radical polymerizations

“…This high-throughput screening technique would be useful for screening glycomimetics for pathogens of variable or unknown nature, such as the influenza virus and SARS-COV-2. 147 We envision that the new development of CRPs and structure control of biointerfaces can contribute to further future applications in various fields, including biotechnology.…”

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

“…Synthetic glycopolymers have gathered attention as effective alternatives to oligosaccharides. , Glycopolymers, which are macromolecules displaying multiple glycounits, have been developed as glycomimetics for the interaction with carbohydrate recognition proteins (lectins). , To overcome the weakness of the monovalent carbohydrate–protein interaction, glycopolymers multivalently bind to lectins, amplifying the total interaction (the cluster glycoside effect) . Our group has recently demonstrated a synthetic approach for GM1 mimics, the “carbohydrate module method”. − GM1 binds to cholera toxin B subunits (CTB) through the interaction between the nonreducing ends (Gal and Neu5Ac units) and the carbohydrate recognition domain of CTB. In particular, the Gal unit binds to the deep part of the domain and mainly contributes to the interaction with CTB .…”