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Issue 11, 2014
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Synthesis and chemoselective ligations of MIDA acylboronates with O-Me hydroxylamines

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Abstract

N-Methyliminodiacetyl (MIDA) acylboronates undergo chemoselective amide-bond forming ligations in water with O-Me hydroxylamines, including unprotected peptide substrates. These bench-stable boronates were easily prepared from potassium acyltrifluoroborates (KATs) in one step. The reactivity of MIDA acylboronates with O-alkylhydroxylamines – which are unreactive with KATs – was attributed to the nature of the neutral MIDA boronates versus the ionic KATs, leading to differences in the stability of likely intermediates and propensity for elimination.

Graphical abstract: Synthesis and chemoselective ligations of MIDA acylboronates with O-Me hydroxylamines

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Publication details

The article was received on 02 Apr 2014, accepted on 16 May 2014 and first published on 16 May 2014


Article type: Edge Article
DOI: 10.1039/C4SC00971A
Author version available: Download Author version (PDF)
Citation: Chem. Sci., 2014,5, 4328-4332
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    Synthesis and chemoselective ligations of MIDA acylboronates with O-Me hydroxylamines

    H. Noda and J. W. Bode, Chem. Sci., 2014, 5, 4328
    DOI: 10.1039/C4SC00971A

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