- Author
- Marvin Nicque (UGent) , Jan H. Meffert (UGent) , Diederick Maes (UGent) , Kevin Bevernaege, Mehwish Iftikhar (UGent) , Olivier Zwaenepoel (UGent) , Jan Gettemans (UGent) , Annemieke Madder (UGent) and Johan Winne (UGent)
- Organization
- Project
-
- Cut-and-paste chemistry: from circular plastics to immunotherapeutics
- Magnetische resonantieapparatuur voor gevorderd materiaalonderzoek: moleculaire karakterisering van vaste, zachte, homogene en heterogene materie in de ontwikkeling van geavanceerde functionele materialen en chemische katalyse
- High resolution NMR Centre – a centre of expertise for structure characterization and molecular analysis in chemical, biochemical, biomedical and materials sciences at Ghent University)
- Cofunding core facility - NMR Expertise Centre
- Oligonucleotides for Medical Applications
- Dynamic and controlled double Michael acceptor based bioconjugation tools.
- Nanobody-assisted precision delivery of the moonlighting host defense protein lactoferrin to combat infections with pathogenic bacteria.
- Perturbation of extracellular matrix (ECM)-degrading cellulair devices by means of photoporation-directed nanobody delivery in immune cells and cancer cells.
- Abstract
- Thiols are used in many click reactions, and are also excellent platforms for biomolecular click or bioconjugation reactions. The direct cross-coupling of two thiols is an attractive biomimetic concept for click chemistry, but leads to statistical mixtures of homo- and heterodimers. Here, we introduce a novel class of thiol-click reagents, bromo-ynones, where the kinetic differentiation between the first and second thiol addition onto these reagents facilitates a stepwise one-pot cross-clicking of two distinct thiols in aqueous media, without the need for intermediate isolation or purification. The two thiols are linked through a single carbon atom, mimicking a disulfide bridge. We demonstrate the use of bromo-ynones in the synthesis of various cross-coupled thiols, including small molecule drugs, fluorophores, carbohydrates, peptides and proteins, including an example of a protein-protein heterodimer. The resulting adducts are robust under physiological conditions and by judicious choice of the bromo-ynone reagent, the adducts can be stable even in the presence of excess free thiols.
- Keywords
- BIOCONJUGATION, CHEMISTRY, CYCLOADDITION, STABILIZATION, PEPTIDES, LINKERS, ALKYNES, PHASE, ACID
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-01K21RNYNQ0TRRVAH8NWWBCTFV
- MLA
- Nicque, Marvin, et al. “Thiol-Thiol Cross-Clicking Using Bromo-Ynone Reagents.” NATURE COMMUNICATIONS, vol. 16, no. 1, 2025, doi:10.1038/s41467-025-61682-5.
- APA
- Nicque, M., Meffert, J. H., Maes, D., Bevernaege, K., Iftikhar, M., Zwaenepoel, O., … Winne, J. (2025). Thiol-thiol cross-clicking using bromo-ynone reagents. NATURE COMMUNICATIONS, 16(1). https://doi.org/10.1038/s41467-025-61682-5
- Chicago author-date
- Nicque, Marvin, Jan H. Meffert, Diederick Maes, Kevin Bevernaege, Mehwish Iftikhar, Olivier Zwaenepoel, Jan Gettemans, Annemieke Madder, and Johan Winne. 2025. “Thiol-Thiol Cross-Clicking Using Bromo-Ynone Reagents.” NATURE COMMUNICATIONS 16 (1). https://doi.org/10.1038/s41467-025-61682-5.
- Chicago author-date (all authors)
- Nicque, Marvin, Jan H. Meffert, Diederick Maes, Kevin Bevernaege, Mehwish Iftikhar, Olivier Zwaenepoel, Jan Gettemans, Annemieke Madder, and Johan Winne. 2025. “Thiol-Thiol Cross-Clicking Using Bromo-Ynone Reagents.” NATURE COMMUNICATIONS 16 (1). doi:10.1038/s41467-025-61682-5.
- Vancouver
- 1.Nicque M, Meffert JH, Maes D, Bevernaege K, Iftikhar M, Zwaenepoel O, et al. Thiol-thiol cross-clicking using bromo-ynone reagents. NATURE COMMUNICATIONS. 2025;16(1).
- IEEE
- [1]M. Nicque et al., “Thiol-thiol cross-clicking using bromo-ynone reagents,” NATURE COMMUNICATIONS, vol. 16, no. 1, 2025.
@article{01K21RNYNQ0TRRVAH8NWWBCTFV,
abstract = {{Thiols are used in many click reactions, and are also excellent platforms for biomolecular click or bioconjugation reactions. The direct cross-coupling of two thiols is an attractive biomimetic concept for click chemistry, but leads to statistical mixtures of homo- and heterodimers. Here, we introduce a novel class of thiol-click reagents, bromo-ynones, where the kinetic differentiation between the first and second thiol addition onto these reagents facilitates a stepwise one-pot cross-clicking of two distinct thiols in aqueous media, without the need for intermediate isolation or purification. The two thiols are linked through a single carbon atom, mimicking a disulfide bridge. We demonstrate the use of bromo-ynones in the synthesis of various cross-coupled thiols, including small molecule drugs, fluorophores, carbohydrates, peptides and proteins, including an example of a protein-protein heterodimer. The resulting adducts are robust under physiological conditions and by judicious choice of the bromo-ynone reagent, the adducts can be stable even in the presence of excess free thiols.}},
articleno = {{6386}},
author = {{Nicque, Marvin and Meffert, Jan H. and Maes, Diederick and Bevernaege, Kevin and Iftikhar, Mehwish and Zwaenepoel, Olivier and Gettemans, Jan and Madder, Annemieke and Winne, Johan}},
issn = {{2041-1723}},
journal = {{NATURE COMMUNICATIONS}},
keywords = {{BIOCONJUGATION,CHEMISTRY,CYCLOADDITION,STABILIZATION,PEPTIDES,LINKERS,ALKYNES,PHASE,ACID}},
language = {{eng}},
number = {{1}},
pages = {{9}},
title = {{Thiol-thiol cross-clicking using bromo-ynone reagents}},
url = {{http://doi.org/10.1038/s41467-025-61682-5}},
volume = {{16}},
year = {{2025}},
}
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