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Scope and Limitations of Boron Fluorescent Complexes from Stable Nitrile Oxides in ABPP Assays.

ABSTRACT: Anthracenenitrile oxide undergoes 1,3-dipolar cycloaddition reactions with 1-substituted-4-(prop-2-yn-1-yloxy)benzene affording the expected isoxazoles in good yields and as single regioisomers. N-O Bond cleavage and boron complexation afforded the corresponding boron complexes, derivatized with either a triple bond for click-chemistry applications or an oxime group for nitrile oxide 1,3-dipolar cycloaddition. The optical properties of these compounds show potential for employment as fluorescent tags in imaging techniques. The activity-based protein profiling assays showed good reactivity for the synthesized probes even with short peptide chains (epoxomicin). Scope and limitations are discussed in the light of the obtained results.

SUBMITTER: Moiola M

PROVIDER: S-EPMC6648418 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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Scope and Limitations of Boron Fluorescent Complexes from Stable Nitrile Oxides in ABPP Assays.

Moiola Mattia M Crespi Stefano S Memeo Misal M Collina Simona S Overkleeft Herman H Florea Bogdan B Quadrelli Paolo P

ACS omega 20190429 4

Anthracenenitrile oxide undergoes 1,3-dipolar cycloaddition reactions with 1-substituted-4-(prop-2-yn-1-yloxy)benzene affording the expected isoxazoles in good yields and as single regioisomers. N-O Bond cleavage and boron complexation afforded the corresponding boron complexes, derivatized with either a triple bond for click-chemistry applications or an oxime group for nitrile oxide 1,3-dipolar cycloaddition. The optical properties of these compounds show potential for employment as fluorescent ...[more]

PMID: 31459866

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