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J Am Chem Soc. 2018 Jan 24;140(3):868-871. doi: 10.1021/jacs.7b11303. Epub 2018 Jan 10.

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

Author information

1
Department of Chemistry, University of Utah , 315 South 1400 East, Salt Lake City, Utah 84112, United States.
2
Department of Chemistry, Yale University , P.O. Box 208107, New Haven, Connecticut 06520-8107, United States.

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.

PMID:
29300461
PMCID:
PMC5817992
DOI:
10.1021/jacs.7b11303
[Indexed for MEDLINE]
Free PMC Article

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