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Dolan, Jonathan P., Machin, Darren C., Dedola, Simone, Field, Robert A. 
ORCID: https://orcid.org/0000-0001-8574-0275, Webb, Michael E. and Turnbull, W. Bruce
(2022)
Synthesis of cholera toxin B subunit glycoconjugates using site-specific orthogonal oxime and sortase ligation reactions.
Frontiers in Chemistry, 10.
ISSN 2296-2646
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Abstract
The chemoenzymatic synthesis of a series of dual N- and C-terminal–functionalized cholera toxin B subunit (CTB) glycoconjugates is described. Mucin 1 peptides bearing different levels of Tn antigen glycosylation [MUC1(Tn)] were prepared via solid-phase peptide synthesis. Using sortase-mediated ligation, the MUC1(Tn) epitopes were conjugated to the C-terminus of CTB in a well-defined manner allowing for high-density display of the MUC1(Tn) epitopes. This work explores the challenges of using sortase-mediated ligation in combination with glycopeptides and the practical considerations to obtain high levels of conjugation. Furthermore, we describe methods to combine two orthogonal labeling methodologies, oxime- and sortase-mediated ligation, to expand the biochemical toolkit and produce dual N- and C-terminal–labeled conjugates.
| Item Type: | Article |
|---|---|
| Additional Information: | Data availability statement: The original contributions presented in the study are included in the article/Supplementary Material; the raw data associated with this paper including SDS-PAGE images, NMR and mass spectra are openly available from the University of Leeds data repository. https://doi.org/10.5518/1194. Funding Information: The authors thank the Biotechnology and Biological Research Council (BB/M011151/1) and Iceni Glycoscience for PhD studentship for JD. The authors would like to acknowledge Jeanine Williams, University of Leeds, for technical support with analytical HPLC. |
| Uncontrolled Keywords: | glycoconjugates,glycopeptide,neoglycoproteins,oxime ligation,protein modification,sortase,transpeptidase,chemistry(all),sdg 3 - good health and well-being ,/dk/atira/pure/subjectarea/asjc/1600 |
| Faculty \ School: | Faculty of Science > School of Chemistry, Pharmacy and Pharmacology |
| Related URLs: | |
| Depositing User: | LivePure Connector |
| Date Deposited: | 03 Sep 2024 14:33 |
| Last Modified: | 25 Sep 2024 18:05 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/96471 |
| DOI: | 10.3389/fchem.2022.958272 |
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