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Issue 10, 2017
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Ascorbate as a pro-oxidant: mild N-terminal modification with vinylboronic acids

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Abstract

We describe divergent reactivity of vinylboronic acids for protein modification. In addition to previously reported copper-catalyzed backbone N–H modification, ascorbate in air mediates N-terminal functionalization with the same vinylboronate reagents. This mild and selective aqueous reactivity enables selective single-modification of the B chain of human insulin.

Graphical abstract: Ascorbate as a pro-oxidant: mild N-terminal modification with vinylboronic acids

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Publication details

The article was received on 23 Nov 2016, accepted on 03 Jan 2017 and first published on 03 Jan 2017


Article type: Communication
DOI: 10.1039/C6CC09955F
Citation: Chem. Commun., 2017,53, 1622-1625
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    Ascorbate as a pro-oxidant: mild N-terminal modification with vinylboronic acids

    J. Ohata and Z. T. Ball, Chem. Commun., 2017, 53, 1622
    DOI: 10.1039/C6CC09955F

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