Fluorogenic Strain-Promoted Alkyne-Diazo Cycloadditions

Chemistry : a European Journal
Frédéric FriscourtGeert-Jan Boons

Abstract

Fluorogenic reactions, in which non- or weakly fluorescent reagents produce highly fluorescent products, are attractive for detecting a broad range of compounds in the fields of bioconjugation and material sciences. Herein, we report that a dibenzocyclooctyne derivative modified with a cyclopropenone moiety (Fl-DIBO) can undergo fast strain-promoted cycloaddition reactions under catalyst-free conditions with azides, nitrones, nitrile oxides, as well as mono- and disubstituted diazo-derivatives. Although the reaction with nitrile oxides, nitrones, and disubstituted diazo compounds gave cycloadducts with low quantum yield, monosubstituted diazo reagents produced 1H-pyrazole derivatives that exhibited an approximately 160-fold fluorescence enhancement over Fl-DIBO combined with a greater than 10,000-fold increase in brightness. Concluding from quantum chemical calculations, fluorescence quenching of 3H-pyrazoles, which are formed by reaction with disubstituted diazo-derivatives, is likely due to the presence of energetically low-lying (n,π*) states. The fluorogenic probe Fl-DIBO was successfully employed for the labeling of diazo-tagged proteins without detectable background signal. Diazo-derivatives are emerging as attractive rep...Continue Reading

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Citations

Aug 31, 2016·Topics in Current Chemistry·Thomas Carell, Milan Vrabel
Oct 16, 2016·ACS Chemical Biology·Kalie A MixRonald T Raines
Nov 22, 2016·Chemistry : a European Journal·Josephin M HolsteinAndrea Rentmeister
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Aug 26, 2021·Inorganic Chemistry·Brett M HakeyCarsten Milsmann
Aug 24, 2021·Chemistry : a European Journal·Katie RuffellChristopher J Moody

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