ArticleChembiochem : a European journal of chemical biology2013
Development of a hypersensitive periodate-cleavable amino acid that is methionine- and disulfide-compatible and its application in MHC exchange reagents for T cell characterisation.
Article in Chembiochem : a European journal of chemical biology, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed, 23 citations in OpenAlex.
- Biocompatible Lysine Protecting Groups for the Chemoenzymatic Synthesis of K48/K63 Heterotypic and Branched Ubiquitin Chains.ACS central science · 2023Article
- Guidelines for the use of flow cytometry and cell sorting in immunological studies (third edition).European journal of immunology · 2021Review
- Engineering of fluorescent or photoactive Trojan probes for detection and eradication of β-Amyloids.Drug delivery · 2020Article
- Secondary Amino Alcohols: Traceless Cleavable Linkers for Use in Affinity Capture and Release.Angewandte Chemie (International ed. in English) · 2020Article
- Guidelines for the use of flow cytometry and cell sorting in immunological studies (second edition).European journal of immunology · 2019Article
- Production and Thermal Exchange of Conditional Peptide-MHC I Multimers.Current protocols in immunology · 2019Article
- A flexible MHC class I multimer loading system for large-scale detection of antigen-specific T cells.The Journal of experimental medicine · 2018Article
- Oximes and Hydrazones in Bioconjugation: Mechanism and Catalysis.Chemical reviews · 2017Review
- Biotin-transfer from a trifunctional crosslinker for identification of cell surface receptors of soluble protein ligands.Scientific reports · 2017Article
- Chemical Modification of Influenza CD8+ T-Cell Epitopes Enhances Their Immunogenicity Regardless of Immunodominance.PloS one · 2016Article
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8 authors at 1 institution in 1 country.
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Abstract
Incorporation of cleavable linkers into peptides and proteins is of particular value in the study of biological processes. Here we describe the synthesis of a cleavable linker that is hypersensitive to oxidative cleavage as the result of the periodate reactivity of a vicinal amino alcohol moiety. Two strategies directed towards the synthesis of a building block suitable for solid-phase peptide synthesis were developed: a chemoenzymatic route, involving L-threonine aldolase, and an enantioselective chemical route; these led to α,γ-diamino-β-hydroxybutanoic acids in diastereoisomerically mixed and enantiopure forms, respectively. Incorporation of the 1,2-amino alcohol linker into the backbone of a peptide generated a conditional peptide that was rapidly cleaved at very low concentrations of sodium periodate. This cleavable peptide ligand was applied in the generation of MHC exchange reagents for the detection of antigen-specific T cells in peripheral blood cells. The extremely low concentration of periodate required to trigger MHC peptide exchange allowed the co-oxidation of methionine and disulfide residues to be avoided. Conditional MHC reagents hypersensitive to periodate can now be applied without limitations when UV irradiation is undesired or less practical.
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