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Issue 6, 2015
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Boronic acids facilitate rapid oxime condensations at neutral pH

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Abstract

We report here the discovery and development of boron-assisted oxime formation as a powerful connective reaction for chemical biology. Oximes proximal to boronic acids form in neutral aqueous buffer with rate constants of more than 104 M−1 s−1, the largest to date for any oxime condensation. Boron's dynamic coordination chemistry confers an adaptability that seems to aid a number of elementary steps in the oxime condensation. In addition to applications in bioconjugation, the emerging importance of boronic acids in chemical biology as carbohydrate receptors or peroxide probes, and the growing list of drugs and drug candidates containing boronic acids suggest many potential applications.

Graphical abstract: Boronic acids facilitate rapid oxime condensations at neutral pH

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Publication details

The article was received on 13 Mar 2015, accepted on 07 Apr 2015 and first published on 13 Apr 2015


Article type: Edge Article
DOI: 10.1039/C5SC00921A
Citation: Chem. Sci., 2015,6, 3329-3333
  • Open access: Creative Commons BY license
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    Boronic acids facilitate rapid oxime condensations at neutral pH

    P. Schmidt, C. Stress and D. Gillingham, Chem. Sci., 2015, 6, 3329
    DOI: 10.1039/C5SC00921A

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