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Fluorogenic diazaborine formation of semicarbazide with designed coumarin derivatives.

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.

SUBMITTER: Cambray S

PROVIDER: S-EPMC5698122 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature

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Fluorogenic diazaborine formation of semicarbazide with designed coumarin derivatives.

Cambray Samantha S Bandyopadhyay Anupam A Gao Jianmin J

Chemical communications (Cambridge, England) 20171101 93

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, whic ...[more]

PMID: 29085929

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