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Issue 24, 2014
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Rigid tetrazine fluorophore conjugates with fluorogenic properties in the inverse electron demand Diels–Alder reaction

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Abstract

1,2,4,5-Tetrazine fluorophore derivatives with structurally rigid molecular designs were synthesized using Sonogashira and Stille cross-coupling as well as copper-catalyzed azide–alkyne cycloaddition. The synthesized bichromophoric systems exhibit low fluorescence quantum yields due to quenching by the tetrazine. The extent of fluorescence quenching observed for those systems was shown to depend on the distance between the fluorophore and the tetrazine. The decreased fluorescence is “turned on” by conversion of the tetrazine in the inverse electron demand Diels–Alder cycloaddition. Time resolved spectroscopy indicated resonance energy transfer between BODIPY and the tetrazine as the underlying quenching mechanism. The synthesized conjugates were successfully applied in protein labeling experiments.

Graphical abstract: Rigid tetrazine fluorophore conjugates with fluorogenic properties in the inverse electron demand Diels–Alder reaction

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Publication details

The article was received on 31 Jan 2014, accepted on 23 Apr 2014 and first published on 23 Apr 2014


Article type: Paper
DOI: 10.1039/C4OB00245H
Citation: Org. Biomol. Chem., 2014,12, 4177-4185
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    Rigid tetrazine fluorophore conjugates with fluorogenic properties in the inverse electron demand Diels–Alder reaction

    A. Wieczorek, T. Buckup and R. Wombacher, Org. Biomol. Chem., 2014, 12, 4177
    DOI: 10.1039/C4OB00245H

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