Article
Stable Pyrrole-Linked Bioconjugates through Tetrazine-Triggered Azanorbornadiene Fragmentation
Author/s | 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. |
Department | Universidad de Sevilla. Departamento de Química orgánica |
Publication Date | 2020 |
Deposit Date | 2022-11-30 |
Published in |
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Abstract | 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. |
Funding agencies | Ministerio de Economía y Competitividad (MINECO). España Union Europea Fundación para la Ciencia y la Tecnología. Portugal Consejo Europeo de Investigación |
Project ID. | CTQ2016-77270-R
![]() RTI2018-099592-B-C22 ![]() RYC-2013-14706 ![]() RTI2018-099592-B-C21 ![]() IF/00624/2015 ![]() 676832 ![]() |
Citation | 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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