Work

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

Year: 2016

Type: article

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.

Source: Chemical Communications

DOI: 10.1039/c6cc01428c

Authors: A. J. Metrano, N. C. Abascal, B. Q. Mercado, E. K. Paulson, S. J. Miller

Institution: Yale University

Language: English

Topic: Axial and Atropisomeric Chirality Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: Site-Selective Catalysts for Organic Synthesis, G3238794756, Site-Selective Catalysis for Organic Synthesis