Work

Parameterization and Analysis of Peptide-Based Catalysts for the Atroposelective Bromination of 3-Arylquinazolin-4(3H)-ones

Year: 2018

Type: article

Abstract: We report the development of a method to parameterize and predict the performance of structurally flexible β-turn-containing peptide catalysts, using the atroposelective bromination of 3-arylquinazolin-4(3H)-ones as a case study. The multivariate correlations obtained for tetrapeptides of two β-turn types, type I' pre-helical and type II' β-hairpin, indicate that although one conformer may be associated with a more dominant contribution to the observed enantioselectivity, it is possible that multiple conformers contribute to a complex transition state ensemble.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.7b11303

Authors: Jennifer M. Crawford, Elizabeth A. Stone, Anthony J. Metrano, Scott J. Miller, Matthew S. Sigman

Institutions: University of Utah, Yale University

Language: English

Topic: Axial and Atropisomeric Chirality Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, National Institute of General Medical Sciences, National Institute of Environmental Health Sciences

Awards: Predoctoral Program in Biophysics, Using Numerical Analysis Tools to Design and Study Chiral Catalysts, Environmental Health Sciences Research Center, Methods for Selective Organic Synthesis based on Ionic Catalysts