Fluorogenic Photo‐Crosslinking of Glycan‐Binding Protein Recognition Using a Fluorinated Azido‐Coumarin Fucoside
Abstract: Glycan recognition by glycan‐binding proteins is central to the biology of all living organisms. The efficient capture and characterization of relatively weak non‐covalent interactions remains an important challenge in various fields of research. Photoaffinity labeling strategies can create covalent bonds between interacting partners, and photoactive scaffolds such as benzophenone, diazirines and aryl azides have proved widely useful. Since their first introduction, relatively few improvements have been advanced and products of photoaffinity labeling remain difficult to detect. We report a fluorinated azido‐coumarin scaffold which enables photolabeling under fast and mild activation, and which can leave a fluorescent tag on crosslinked species. Coupling this scaffold to an α‐fucoside, we demonstrate fluorogenic photolabeling of glycan‐protein interactions over a wide range of affinities. We expect this strategy to be broadly applicable to other chromophores and we envision that such “fluoro‐crosslinkers” could become important tools for the traceable capture of non‐covalent binding events.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Fluorogenic Photo‐Crosslinking of Glycan‐Binding Protein Recognition Using a Fluorinated Azido‐Coumarin Fucoside ; day:31 ; month:10 ; year:2023 ; extent:9
Angewandte Chemie / International edition. International edition ; (31.10.2023) (gesamt 9)
- Creator
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Bousch, Cécile
Vreulz, Brandon
Kansal, Kartikey
El‐Husseini, Ali
Cecioni, Samy
- DOI
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10.1002/anie.202314248
- URN
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urn:nbn:de:101:1-2023110114021307831579
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 11:01 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Bousch, Cécile
- Vreulz, Brandon
- Kansal, Kartikey
- El‐Husseini, Ali
- Cecioni, Samy
Other Objects (12)
Fluorogenic Photo‐Crosslinking of Glycan‐Binding Protein Recognition Using a Fluorinated Azido‐Coumarin Fucoside
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Induzierbarkeit der Biotransformation von 7-(2-Methylbenzyloxy)-coumarin, 7-(3-Methylbenzyloxy)-coumarin, 7-(4-Methylbenzyloxy)-coumarin, 7-(3-Phenylpropoxy)-coumarin und 7-(Naphthyl(1)-methoxy)-coumarin durch Phenobarbital, β-Naphhoflavon [Beta-Naphthoflavon] und Dexamethason in der Rattenleber
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Fluorogenic Phenothiazine‐Derivative as Radical Sensors
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Fluorogenic Photo‐Crosslinking of Glycan‐Binding Protein Recognition Using a Fluorinated Azido‐Coumarin Fucoside
Fluorogenic cell surface glycan labelling with fluorescence molecular rotor dyes and nucleic acid stains
Fluorogenic cell surface glycan labelling with fluorescence molecular rotor dyes and nucleic acid stains
Fluorogenic PNA probes
Synthesis of coumarin-containing poly(2-oxazoline)s and light-induced crosslinking for hydrogel formation
Cell-based glycan arrays for probing glycan–glycan binding protein interactions
Organocatalytic Fluorogenic Synthesis of Chromenes
Fluorinated butatrienes
Induzierbarkeit der Biotransformation von 7-(2-Methylbenzyloxy)-coumarin, 7-(3-Methylbenzyloxy)-coumarin, 7-(4-Methylbenzyloxy)-coumarin, 7-(3-Phenylpropoxy)-coumarin und 7-(Naphthyl(1)-methoxy)-coumarin durch Phenobarbital, β-Naphhoflavon [Beta-Naphthoflavon] und Dexamethason in der Rattenleber
Fluorogenic CRISPR for genomic DNA imaging
Fluorogenic Phenothiazine‐Derivative as Radical Sensors
Bioorthogonal Ligation‐Activated Fluorogenic FRET Dyads
Fluorogenic Photo‐Crosslinking of Glycan‐Binding Protein Recognition Using a Fluorinated Azido‐Coumarin Fucoside
Fluorogenic cell surface glycan labelling with fluorescence molecular rotor dyes and nucleic acid stains
Fluorogenic cell surface glycan labelling with fluorescence molecular rotor dyes and nucleic acid stains
Fluorogenic PNA probes
Synthesis of coumarin-containing poly(2-oxazoline)s and light-induced crosslinking for hydrogel formation
Cell-based glycan arrays for probing glycan–glycan binding protein interactions
Organocatalytic Fluorogenic Synthesis of Chromenes
Fluorinated butatrienes
Induzierbarkeit der Biotransformation von 7-(2-Methylbenzyloxy)-coumarin, 7-(3-Methylbenzyloxy)-coumarin, 7-(4-Methylbenzyloxy)-coumarin, 7-(3-Phenylpropoxy)-coumarin und 7-(Naphthyl(1)-methoxy)-coumarin durch Phenobarbital, β-Naphhoflavon [Beta-Naphthoflavon] und Dexamethason in der Rattenleber
Fluorogenic CRISPR for genomic DNA imaging
Fluorogenic Phenothiazine‐Derivative as Radical Sensors