Fluorogenic Bifunctional trans‐Cyclooctenes as Efficient Tools for Investigating Click‐to‐Release Kinetics

The inverse electron demand Diels–Alder pyridazine elimination reaction between tetrazines and allylic substituted trans‐cyclooctenes (TCOs) is a key player in bioorthogonal bond cleavage reactions. Determining the rate of elimination of alkylamine substrates has so far proven difficult. Here, we re...

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Detalles Bibliográficos
Autores principales: de Geus, Mark A. R., Maurits, Elmer, Sarris, Alexi J. C., Hansen, Thomas, Kloet, Max S., Kamphorst, Kiki, ten Hoeve, Wolter, Robillard, Marc S., Pannwitz, Andrea, Bonnet, Sylvestre A., Codée, Jeroen D. C., Filippov, Dmitri V., Overkleeft, Herman S., van Kasteren, Sander I.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7496853/
https://www.ncbi.nlm.nih.gov/pubmed/32154603
http://dx.doi.org/10.1002/chem.201905446
Descripción
Sumario:The inverse electron demand Diels–Alder pyridazine elimination reaction between tetrazines and allylic substituted trans‐cyclooctenes (TCOs) is a key player in bioorthogonal bond cleavage reactions. Determining the rate of elimination of alkylamine substrates has so far proven difficult. Here, we report a fluorogenic tool consisting of a TCO‐linked EDANS fluorophore and a DABCYL quencher for accurate determination of both the click and release rate constants for any tetrazine at physiologically relevant concentrations.

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