Stable Pyrrole‐Linked Bioconjugates through Tetrazine‐Triggered Azanorbornadiene Fragmentation
| Autor: | Emily A. Hoyt, Gonzalo Jiménez-Osés, Claudio D. Navo, Ester Jiménez-Moreno, Antonio J. Moreno-Vargas, Alena Istrate, Inmaculada Robina, Enrique Gil de Montes, Gonçalo J. L. Bernardes, Francisco Corzana |
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| Rok vydání: | 2020 |
| Předmět: |
Aza Compounds
Bioconjugation Cycloaddition Reaction 010405 organic chemistry Chemistry General Chemistry 010402 general chemistry Norbornanes 01 natural sciences Combinatorial chemistry Catalysis Cycloaddition 0104 chemical sciences Sulfone chemistry.chemical_compound Tetrazine Reagent Pyrroles Cysteine Bioorthogonal chemistry Bond cleavage Pyrrole |
| Zdroj: | Angewandte Chemie International Edition. 59:6196-6200 |
| ISSN: | 1521-3773 1433-7851 |
| Popis: | An azanorbornadiene bromovinyl sulfone reagent for cysteine-selective bioconjugation has been developed. Subsequent reaction with dipyridyl tetrazine leads to bond cleavage and formation of a pyrrole-linked conjugate. The latter involves ligation of the tetrazine to the azanorbornadiene-tagged protein through inverse electron demand Diels-Alder cycloaddition with subsequent double retro-Diels-Alder reactions to form a stable pyrrole linkage. The sequence of site-selective bioconjugation followed by bioorthogonal bond cleavage was efficiently employed for the labelling of three different proteins. This method benefits from easy preparation of these reagents, selectivity for cysteine, and stability after reaction with a commercial tetrazine, which has potential for the routine preparation of protein conjugates for chemical biology studies. |
| Databáze: | OpenAIRE |
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