Issue 11, 2014

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
02 Apr 2014
Accepted
16 May 2014
First published
16 May 2014

Chem. Sci., 2014,5, 4328-4332

Author version available

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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