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Issue 26, 2016
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Structural studies of β-turn-containing peptide catalysts for atroposelective quinazolinone bromination

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Abstract

We describe herein a crystallographic and NMR study of the secondary structural attributes of a β-turn-containing tetra-peptide, Boc-Dmaa-D-Pro-Acpc-Leu-NMe2, which was recently reported as a highly effective catalyst in the atroposelective bromination of 3-arylquinazolin-4(3H)-ones. Inquiries pertaining to the functional consequences of residue substitutions led to the discovery of a more selective catalyst, Boc-Dmaa-D-Pro-Acpc-Leu-OMe, the structure of which was also explored. This new lead catalyst was found to exhibit a type I′ β-turn secondary structure both in the solid state and in solution, a structure that was shown to be an accessible conformation of the previously reported catalyst, as well.

Graphical abstract: Structural studies of β-turn-containing peptide catalysts for atroposelective quinazolinone bromination

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Publication details

The article was received on 16 Feb 2016, accepted on 02 Mar 2016 and first published on 02 Mar 2016


Article type: Communication
DOI: 10.1039/C6CC01428C
Citation: Chem. Commun., 2016,52, 4816-4819
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    Structural studies of β-turn-containing peptide catalysts for atroposelective quinazolinone bromination

    A. J. Metrano, N. C. Abascal, B. Q. Mercado, E. K. Paulson and S. J. Miller, Chem. Commun., 2016, 52, 4816
    DOI: 10.1039/C6CC01428C

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