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Synthesis of aryl azide chain-end functionalized N-linked glycan polymers and their photo-labelling of specific protein.

ABSTRACT: We report a straightforward synthesis of aryl azide chain-end functionalized N-linked glycan polymers and its application for affinity-assisted photo-labelling of specific protein. The aryl azide chain-end functionalized N-glycan polymers, including N-galactosyl, N-glucosyl, and N-lactosyl polymer, were synthesized from free glycan via glycosylamine intermediates followed by acrylation and polymerization via cyanoxyl-mediated free radical polymerization (CMFRP) in a one-pot fashion. The aryl azide chain-end functionalized N-glycan polymers were characterized by ¹H NMR and IR spectroscopy. The affinity-assisted photo-labeling capabilities of the aryl azide N-glycan polymers were demonstrated with aryl azide N-lactosyl polymer as a ligand for β-galactose-specific lectin from Arachis hypogaea (PNA) after UV irradiation and confirmed by SDS-PAGE with silver staining. Overall, the aryl azide chain-end functionalized N-linked glycan polymers will be useful multivalent ligands for specific protein labelling and functionality studies.

SUBMITTER: Chan KK

PROVIDER: S-EPMC9057295 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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Synthesis of aryl azide chain-end functionalized N-linked glycan polymers and their photo-labelling of specific protein.

Chan Ka Keung KK Lei Qiaoshi Q Tang Jinshan J Sun Xue-Long XL

RSC advances 20201019 63

We report a straightforward synthesis of aryl azide chain-end functionalized N-linked glycan polymers and its application for affinity-assisted photo-labelling of specific protein. The aryl azide chain-end functionalized N-glycan polymers, including N-galactosyl, N-glucosyl, and N-lactosyl polymer, were synthesized from free glycan via glycosylamine intermediates followed by acrylation and polymerization via cyanoxyl-mediated free radical polymeri ...[more]

PMID: 35517525

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Project description:In this work we present a fundamental analysis based on small-angle scattering, linear rheology and differential scanning calorimetry (DSC) experiments of the role of different hydrogen bonding (H-bonding) types on the structure and dynamics of chain-end modified poly(ethylene glycol) (PEG) in bulk. As such bifunctional PEG with a molar mass below the entanglement mass Me is symmetrically end-functionalized with three different hydrogen bonding (H-bonding) groups: thymine-1-acetic acid (thy), diamino-triazine (dat) and 2-ureido-4[1H]-pyrimidinone (upy). A linear block copolymer structure and a Newtonian-like dynamics is observed for PEG-thy/dat while results for PEG-upy structure and dynamics reveal a sphere and a network-like behavior, respectively. These observations are concomitant with an increase of the Flory-Huggins interaction parameter from PEG-thy/dat to PEG-upy that is used to quantify the difference between the H-bonding types. The upy association into spherical clusters is established by the Percus-Yevick approximation that models the inter-particle structure factor for PEG-upy. Moreover, the viscosity study reveals for PEG-upy a shear thickening behavior interpreted in terms of the free path model and related to the time for PEG-upy to dissociate from the upy clusters, seen as virtual crosslinks of the formed network. Moreover, a second relaxation time of different nature is also obtained from the complex shear modulus measurements of PEG-upy by the inverse of the angular frequency where G' and G'' crosses from the network-like to glass-like transition relaxation time, which is related to the segmental friction of PEG-upy polymeric network strands. In fact, not only do PEG-thy/dat and PEG-upy have different viscoelastic properties, but the relaxation times found for PEG-upy are much slower than the ones for PEG-thy/dat. However, the activation energy related to the association dynamics is very similar for both PEG-thy/dat and PEG-upy. Concerning the segmental dynamics, the glass transition temperature obtained from both rheological and calorimetric analysis is similar and increases for PEG-upy while for PEG-thy/dat is almost independent of association behavior. Our results show how supramolecular PEG properties vary by modifying the H-bonding association type and changing the molecular Flory-Huggins interaction parameter, which can be further explored for possible applications.

Dataset Information

Synthesis of aryl azide chain-end functionalized N-linked glycan polymers and their photo-labelling of specific protein.

Publications

Synthesis of aryl azide chain-end functionalized <i>N</i>-linked glycan polymers and their photo-labelling of specific protein.

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