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Fluorogenic diazaborine formation of semicarbazide with designed coumarin derivatives

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Abstract

Bioorthogonal fluorogenic reactions serve as enabling tools in research and biotechnology. Herein we describe fluorogenic conjugations of semicarbazide with coumarin derivatives that incorporate a 2-acetylphenylboronic acid motif. These designed coumarins rapidly conjugate with semicarbazide to give diazaborine products with significantly enhanced fluorescence. To demonstrate potential applications of this fluorogenic reaction, we synthesized a semicarbazide-presenting amino acid D-Dap-Scz, which readily incorporates into the cell wall of Staphalococcus aureus and serves as a handle for conjugation with the coumarins. The fluorogenic conjugation of the coumarins to cell surface semicarbazide enables facile visualization of D-Dap-Scz treated bacteria.

Graphical abstract: Fluorogenic diazaborine formation of semicarbazide with designed coumarin derivatives

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Publication details

The article was received on 21 Sep 2017, accepted on 24 Oct 2017 and first published on 24 Oct 2017


Article type: Communication
DOI: 10.1039/C7CC07389E
Citation: Chem. Commun., 2017, Advance Article
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    Fluorogenic diazaborine formation of semicarbazide with designed coumarin derivatives

    S. Cambray, A. Bandyopadhyay and J. Gao, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC07389E

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