Artículo
Stable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene Fragmentation
Autor/es | Gil de Montes, Enrique
Istrate, Alena Navo, Claudio D. Jiménez Moreno, Ester Hoyt, Emily A. Corzana, Francisco Robina Ramírez, Inmaculada Jiménez Osés, Gonzalo Moreno Vargas, Antonio José Bernardes, Gonçalo J.L. |
Departamento | Universidad de Sevilla. Departamento de Química orgánica |
Fecha de publicación | 2020 |
Fecha de depósito | 2022-11-30 |
Publicado en |
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Resumen | 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 ... 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. |
Agencias financiadoras | Ministerio de Economía y Competitividad (MINECO). España Union Europea Fundación para la Ciencia y la Tecnología. Portugal Consejo Europeo de Investigación |
Identificador del proyecto | CTQ2016-77270-R
RTI2018-099592-B-C22 RYC-2013-14706 RTI2018-099592-B-C21 IF/00624/2015 676832 |
Cita | Gil de Montes, E., Istrate, A., Navo, C.D., Jiménez Moreno, E., Hoyt, E.A., Corzana, F.,...,Bernardes, G.J.L. (2020). Stable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene Fragmentation. Angewandte Chemie - International Edition, 59 (15), 6196-6200. https://doi.org/10.1002/anie.201914529. |
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