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 fev 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements