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Issue 24, 2016
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Comparison of boron-assisted oxime and hydrazone formations leads to the discovery of a fluorogenic variant

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Abstract

We use kinetic data, photophysical properties, and mechanistic analyses to compare recently developed high-rate constant oxime and hydrazone formations. We show that when Schiff base formation between aldehydes and arylhydrazines is carried out with an appropriately positioned boron atom, then aromatic B–N heterocycles form irreversibly. These consist of an extended aromatic structure amenable to the tailoring of specific properties such as reaction rate and fluorescence. The reactions work best in neutral aqueous buffer and can be designed to be fluorogenic – properties which are particularly interesting in bioconjugation.

Graphical abstract: Comparison of boron-assisted oxime and hydrazone formations leads to the discovery of a fluorogenic variant

  • This article is part of the themed collection: New Talent
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Publication details

The article was received on 20 Jan 2016, accepted on 02 Feb 2016 and first published on 15 Feb 2016


Article type: Communication
DOI: 10.1039/C6OB00168H
Citation: Org. Biomol. Chem., 2016,14, 5529-5533
  • Open access: Creative Commons BY-NC license
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    Comparison of boron-assisted oxime and hydrazone formations leads to the discovery of a fluorogenic variant

    C. J. Stress, P. J. Schmidt and Dennis. G. Gillingham, Org. Biomol. Chem., 2016, 14, 5529
    DOI: 10.1039/C6OB00168H

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