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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 . doi:10.1021/acs.bioconjchem.0c00465 (In Press)

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Official URL: https://doi.org/10.1021/acs.bioconjchem.0c00465

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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
Subjects: Q Science > QD Chemistry
Q Science > QP Physiology
Divisions: Faculty of Science > Chemistry
Faculty of Science > Physics
Faculty of Medicine > Warwick Medical School
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 September 2020
Dates:
DateEvent
21 September 2020Available
11 September 2020Accepted
Date of first compliant deposit: 13 October 2020
DOI: 10.1021/acs.bioconjchem.0c00465
Status: Peer Reviewed
Publication Status: In Press
Publisher Statement: “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
RIOXX Funder/Project Grant:
Project/Grant IDRIOXX Funder NameFunder ID
CRYOMAT 638661European Research Councilhttp://dx.doi.org/10.13039/501100000781
BB/M02878X/1[BBSRC] Biotechnology and Biological Sciences Research Councilhttp://dx.doi.org/10.13039/501100000268
BB/M02878X/1Innovate UKhttp://dx.doi.org/10.13039/501100006041
BB/M01116X/1[BBSRC] Biotechnology and Biological Sciences Research Councilhttp://dx.doi.org/10.13039/501100000268
UNSPECIFIEDIceni Diagnostics Ltd.https://www.icenidiagnostics.com/
NF170965)Royal Societyhttp://dx.doi.org/10.13039/501100000288
814236Horizon 2020 Framework Programmehttp://dx.doi.org/10.13039/100010661

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