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Protecting group free synthesis of glyconanoparticles using amino-oxy-terminated polymer ligands
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Laezza, Antonio, Georgiou, Panagiotis G., Richards, Sarah-Jane, Baker, Alexander, Walker, Marc and Gibson, Matthew I. (2020) Protecting group free synthesis of glyconanoparticles using amino-oxy-terminated polymer ligands. Bioconjugate Chemistry, 31 (10). pp. 2392-2403. doi:10.1021/acs.bioconjchem.0c00465 ISSN 1043-1802.
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WRAP-Protecting-group-free-synthesis-glyco-nanoparticle-polymer-ligands-Walton-2020.pdf - Accepted Version - Requires a PDF viewer. Download (2584Kb) | Preview |
Official URL: https://doi.org/10.1021/acs.bioconjchem.0c00465
Abstract
Glycomaterials display enhanced binding affinity to carbohydrate-binding proteins due to the nonlinear enhancement associated with the cluster glycoside effect. Gold nanoparticles bearing glycans have attracted significant interest in particular. This is due to their versatility, their highly tunable gold cores (size and shape), and their application in biosensors and diagnostic tools. However, conjugating glycans onto these materials can be challenging, necessitating either multiple protecting group manipulations or the use of only simple glycans. This results in limited structural diversity compared to glycoarrays which can include hundreds of glycans. Here we report a method to generate glyconanoparticles from unprotected glycans by conjugation to polymer tethers bearing terminal amino-oxy groups, which are then immobilized onto gold nanoparticles. Using an isotope-labeled glycan, the efficiency of this reaction was probed in detail to confirm conjugation, with 25% of end-groups being functionalized, predominantly in the ring-closed form. Facile post-glycosylation purification is achieved by simple centrifugation/washing cycles to remove excess glycan and polymer. This streamlined synthetic approach may be particularly useful for the preparation of glyconanoparticle libraries using automation, to identify hits to be taken forward using more conventional synthetic methods. Exemplar lectin-binding studies were undertaken to confirm the availability of the glycans for binding and show this is a powerful tool for rapid assessment of multivalent glycan binding.
| Item Type: | Journal Article | ||||||||||||||||||||||||
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| Subjects: | Q Science > QD Chemistry Q Science > QP Physiology |
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| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry Faculty of Science, Engineering and Medicine > Science > Physics Faculty of Science, Engineering and Medicine > Medicine > Warwick Medical School |
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| SWORD Depositor: | Library Publications Router | ||||||||||||||||||||||||
| Library of Congress Subject Headings (LCSH): | Glycosides, Ligands (Biochemistry), Glycoconjugates , Protein binding | ||||||||||||||||||||||||
| Journal or Publication Title: | Bioconjugate Chemistry | ||||||||||||||||||||||||
| Publisher: | American Chemical Society | ||||||||||||||||||||||||
| ISSN: | 1043-1802 | ||||||||||||||||||||||||
| Official Date: | 21 October 2020 | ||||||||||||||||||||||||
| Dates: |
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| Volume: | 31 | ||||||||||||||||||||||||
| Number: | 10 | ||||||||||||||||||||||||
| Page Range: | pp. 2392-2403 | ||||||||||||||||||||||||
| DOI: | 10.1021/acs.bioconjchem.0c00465 | ||||||||||||||||||||||||
| Status: | Peer Reviewed | ||||||||||||||||||||||||
| Publication Status: | Published | ||||||||||||||||||||||||
| Reuse Statement (publisher, data, author rights): | “This document is the Accepted Manuscript version of a Published Work that appeared in final form in Bioconjugate Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [insert ACS Articles on Request author-directed link to Published Work, see http://pubs.acs.org/page/policy/articlesonrequest/index.html].” | ||||||||||||||||||||||||
| Access rights to Published version: | Restricted or Subscription Access | ||||||||||||||||||||||||
| Copyright Holders: | © 2020 American Chemical Society | ||||||||||||||||||||||||
| Date of first compliant deposit: | 13 October 2020 | ||||||||||||||||||||||||
| Date of first compliant Open Access: | 21 September 2021 | ||||||||||||||||||||||||
| RIOXX Funder/Project Grant: |
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