Fluorogenic Pyrimidyltetrazine-Coumarin, CoumFluor-Tz1, CAS 2594424-82-3
IUPAC Name: 7-(azetidin-1-yl)-4-methyl-3-(5-(6-(pyrimidin-2-yl)-1,2,4,5-tetrazin-3-yl)pyridin-3-yl)-2H-chromen-2-one
Molecular weight: 450.45 g/mol
Molecular formula: C24
The compound reacts rapidly in Diels-Alder reactions with strained dienophiles such as trans-cyclooctene (TCO) and bicyclononyne (BCN) producing a fluorescent click product with fluorescence turn-on values of several hundred-fold (λabs = 405 nm, λEm = 480 nm). This powerful fluorogenic reagent enables no-wash labelling of various dienophile-modified (bio)molecules in living cells.
CoumFluor-Tz1, CAS 2594424-82-3 was synthesized and licensed at the IOCB Prague, lab of Milan Vrábel.
The synthesis and the application of CoumFluor-Tz1, CAS 2594424-82-3 are described in the following articles:
- Galeta, Juraj, et al. “A Systematic Study of Coumarin–Tetrazine Light‐Up Probes for Bioorthogonal Fluorescence Imaging.” Chemistry–A European Journal 26.44 (2020): 9945-9953.
- La–Venia, Agustina, et al. “An Optimized Protocol for the Synthesis of Peptides Containing trans‐Cyclooctene and Bicyclononyne Dienophiles as Useful Multifunctional Bioorthogonal Probes.” Chemistry–A European Journal 27.54 (2021): 13632-13641.
- Carbohydrate derivatives and kits for cell surface labeling, WO2022268239 A1 2022-12-29
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