Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 15, Pages 6196-6200Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201914529
Keywords
chemical biology; cycloaddition; bioconjugation; heterocycles; proteins
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Funding
- Spanish Ministry of Education, Culture and Sport under the FPU program
- Spanish Ministry of Economy and Competitiveness [CTQ2016-77270-R, RTI2018-099592-B-C22, RYC-2013-14706, RTI2018-099592-B-C21]
- EU (Marie-Sklodowska Curie Actions) [701473]
- FCT Portugal [IF/00624/2015]
- European Research Council [676832]
- European Research Council (ERC) [676832] Funding Source: European Research Council (ERC)
- Marie Curie Actions (MSCA) [701473] Funding Source: Marie Curie Actions (MSCA)
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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.
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