Hydrolysis of 5-methylfuran-2-yl to 2,5-dioxopentanyl allows for stable bio-orthogonal proximity-induced ligation
- Author
- Alex Manicardi (UGent) , Enrico Cadoni (UGent) and Annemieke Madder (UGent)
- Organization
- Project
-
- MEFuran
- SANI: Generation of Stable, Addressable multi-Nanobody Immunoarrays through oriented covalent immobilisation
- MMBio (Molecular Tools for Nucleic Acid Manipulation for Biological Intervention)
- Furan-based Artificial DNA Anchoring Systems
- Design, synthesis and screening of tRNA stabilising and antigenomic compounds for the treatment of mitochondrial diseases.
- MOLECULAR DESIGN OF ‘FROZEN’ APTAMERS: Aptamers with enhanced properties by covalent and non-covalent stabilization using functionalized nucleotides: a combined modelling, NMR and electrochemistry approach
- Abstract
- Proximity-based ligations commonly require an external stimulus such as a catalyst or irradiation, or highly reactive functional groups. Here the reaction of alpha effect nucleophiles and 2,5-dioxopentanyl derivatives allows direct proximity-based ligation while avoiding highly reactive moieties. Ligation methodologies featuring bio-orthogonal units and leading to the formation of a stable adduct are the ideal candidates for being applied in a biological context. However, most of the available strategies rely on highly reactive species that require careful handling, or on the activation of pro-reactive functional groups. We here report on a proximity-induced ligation reaction that relies on a stable 2,5-dione, that can be conveniently generated under acidic conditions from a 2,5-dialkylfuran building block, and hydrazine nucleophiles. This bio-orthogonal ligation, which proceeds under physiological conditions, does not require any stimulus or trigger and leads to the formation of a pyridazinium adduct that demonstrates excellent stability under harsh conditions (24 h at 90 degrees C). The reaction was applied to the formation of PNA-PNA adducts, DNA- and RNA-templated ligations, and for the formation of peptide-peptide adducts in solution. This convenient methodology was further implemented on plastic and glass surfaces to realize self-addressable covalent constructs.
- Keywords
- PICTET-SPENGLER LIGATION, TEMPLATED REACTION, EFFICIENT METHOD, DNA, PYRIDAZINE, SOLVENT
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-8738954
- MLA
- Manicardi, Alex, et al. “Hydrolysis of 5-Methylfuran-2-Yl to 2,5-Dioxopentanyl Allows for Stable Bio-Orthogonal Proximity-Induced Ligation.” COMMUNICATIONS CHEMISTRY, vol. 4, no. 1, 2021, doi:10.1038/s42004-021-00584-1.
- APA
- Manicardi, A., Cadoni, E., & Madder, A. (2021). Hydrolysis of 5-methylfuran-2-yl to 2,5-dioxopentanyl allows for stable bio-orthogonal proximity-induced ligation. COMMUNICATIONS CHEMISTRY, 4(1). https://doi.org/10.1038/s42004-021-00584-1
- Chicago author-date
- Manicardi, Alex, Enrico Cadoni, and Annemieke Madder. 2021. “Hydrolysis of 5-Methylfuran-2-Yl to 2,5-Dioxopentanyl Allows for Stable Bio-Orthogonal Proximity-Induced Ligation.” COMMUNICATIONS CHEMISTRY 4 (1). https://doi.org/10.1038/s42004-021-00584-1.
- Chicago author-date (all authors)
- Manicardi, Alex, Enrico Cadoni, and Annemieke Madder. 2021. “Hydrolysis of 5-Methylfuran-2-Yl to 2,5-Dioxopentanyl Allows for Stable Bio-Orthogonal Proximity-Induced Ligation.” COMMUNICATIONS CHEMISTRY 4 (1). doi:10.1038/s42004-021-00584-1.
- Vancouver
- 1.Manicardi A, Cadoni E, Madder A. Hydrolysis of 5-methylfuran-2-yl to 2,5-dioxopentanyl allows for stable bio-orthogonal proximity-induced ligation. COMMUNICATIONS CHEMISTRY. 2021;4(1).
- IEEE
- [1]A. Manicardi, E. Cadoni, and A. Madder, “Hydrolysis of 5-methylfuran-2-yl to 2,5-dioxopentanyl allows for stable bio-orthogonal proximity-induced ligation,” COMMUNICATIONS CHEMISTRY, vol. 4, no. 1, 2021.
@article{8738954,
abstract = {{Proximity-based ligations commonly require an external stimulus such as a catalyst or irradiation, or highly reactive functional groups. Here the reaction of alpha effect nucleophiles and 2,5-dioxopentanyl derivatives allows direct proximity-based ligation while avoiding highly reactive moieties. Ligation methodologies featuring bio-orthogonal units and leading to the formation of a stable adduct are the ideal candidates for being applied in a biological context. However, most of the available strategies rely on highly reactive species that require careful handling, or on the activation of pro-reactive functional groups. We here report on a proximity-induced ligation reaction that relies on a stable 2,5-dione, that can be conveniently generated under acidic conditions from a 2,5-dialkylfuran building block, and hydrazine nucleophiles. This bio-orthogonal ligation, which proceeds under physiological conditions, does not require any stimulus or trigger and leads to the formation of a pyridazinium adduct that demonstrates excellent stability under harsh conditions (24 h at 90 degrees C). The reaction was applied to the formation of PNA-PNA adducts, DNA- and RNA-templated ligations, and for the formation of peptide-peptide adducts in solution. This convenient methodology was further implemented on plastic and glass surfaces to realize self-addressable covalent constructs.}},
articleno = {{146}},
author = {{Manicardi, Alex and Cadoni, Enrico and Madder, Annemieke}},
issn = {{2399-3669}},
journal = {{COMMUNICATIONS CHEMISTRY}},
keywords = {{PICTET-SPENGLER LIGATION,TEMPLATED REACTION,EFFICIENT METHOD,DNA,PYRIDAZINE,SOLVENT}},
language = {{eng}},
number = {{1}},
pages = {{9}},
title = {{Hydrolysis of 5-methylfuran-2-yl to 2,5-dioxopentanyl allows for stable bio-orthogonal proximity-induced ligation}},
url = {{http://doi.org/10.1038/s42004-021-00584-1}},
volume = {{4}},
year = {{2021}},
}
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