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Fluorogenic Diazaborine Formation of Semicarbazide With Designed Coumarin Derivatives

Samantha Cambray, Anupam Bandyopadhyay, Jianmin Gao

Chem Commun (Camb). 2017 Nov 21;53(93):12532-12535.

PMID: 29085929

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP308103404 2-Acetylphenylboronic acid 2-Acetylphenylboronic acid 308103-40-4 Price
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