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Fluorogenic Strain‐Promoted Alkyne–Diazo Cycloadditions
| Content Provider | Scilit |
|---|---|
| Author | Friscourt, Frédéric Fahrni, Christoph J. Boons, Geert‐Jan |
| Copyright Year | 2015 |
| Description | Journal: Chemistry – A European Journal 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 reporters for the labeling of biomolecules, and the studies presented herein demonstrate that Fl-DIBO can be employed for visualizing such biomolecules without the need for probe washout. |
| Related Links | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4712747/pdf |
| Ending Page | 14001 |
| Page Count | 6 |
| Starting Page | 13996 |
| e-ISSN | 15213765 |
| DOI | 10.1002/chem.201502242 |
| Journal | Chemistry – A European Journal |
| Issue Number | 40 |
| Volume Number | 21 |
| Language | English |
| Publisher | Wiley-Blackwell |
| Publisher Date | 2015-08-18 |
| Access Restriction | Open |
| Subject Keyword | Journal: Chemistry – A European Journal Organic Chemistry Fluorogenic Probes |
| Content Type | Text |
| Resource Type | Article |
