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Fluorogenic Bifunctional trans ‐Cyclooctenes as Efficient Tools for Investigating Click‐to‐Release Kinetics
Author(s) -
Geus Mark A. R.,
Maurits Elmer,
Sarris Alexi J. C.,
Hansen Thomas,
Kloet Max S.,
Kamphorst Kiki,
Hoeve Wolter,
Robillard Marc S.,
Pannwitz Andrea,
Bonnet Sylvestre A.,
Codée Jeroen D. C.,
Filippov Dmitri V.,
Overkleeft Herman S.,
Kasteren Sander I.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201905446
Subject(s) - tetrazine , bioorthogonal chemistry , chemistry , click chemistry , bifunctional , kinetics , combinatorial chemistry , chloramine t , reaction rate constant , fluorophore , organic chemistry , fluorescence , catalysis , physics , quantum mechanics
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.