Abstract
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.
Original language | English |
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Pages (from-to) | 9900-9904 |
Number of pages | 5 |
Journal | Chemistry - A European Journal |
Volume | 26 |
Issue number | 44 |
DOIs | |
Publication status | Published - 6 Aug 2020 |
Funding
S.I.V.K. was the recipient of an ERC Starting Grant from the European Research Council (ERC-2014-StG-639005). A.J.C.S., D.V.F., H.S.O., and S.I.V.K. were funded by the Institute of Chemical Immunology (NWO Zwaartekracht). The authors thank SURFsara for use of the Lisa supercomputer and kindly acknowledge Mark Somers for technical support.
Funders | Funder number |
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Institute of Chemical Immunology | |
Horizon 2020 Framework Programme | 639005 |
European Research Council | |
Nederlandse Organisatie voor Wetenschappelijk Onderzoek |
Keywords
- bioorthogonal chemistry
- Diels–Alder reactions
- fluorescent probes
- kinetics
- nitrogen heterocycles