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Fluorogenic Pyrimidyltetrazine-Coumarin, CoumFluor-Tz1, CAS 2594424-82-3

Characterisation

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: C₂₄H₁₈N₈O₂

SMILES: O=C1OC=2C=C(C=CC2C(=C1C=3C=NC=C(C3)C=4N=NC(=NN4)C=5N=CC=CN5)C)N6CCC6

Description

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 (λ_abs = 405 nm, λ_Em = 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:

1. 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.
2. 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.
3. Carbohydrate derivatives and kits for cell surface labeling, WO2022268239 A1 2022-12-29

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