Issue 26, 2016

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

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

  • This article is part of the themed collection: Foldamers

Supplementary files

Article information

Article type
Communication
Submitted
16 feb 2016
Accepted
02 mar 2016
First published
02 mar 2016

Chem. Commun., 2016,52, 4816-4819

Author version available

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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