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

ABSTRACT: We report the development of a method to parameterize and predict the performance of structurally flexible ?-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 ?-turn types, type I' pre-helical and type II' ?-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.

SUBMITTER: Crawford JM

PROVIDER: S-EPMC5817992 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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

Crawford Jennifer M JM Stone Elizabeth A EA Metrano Anthony J AJ Miller Scott J SJ Sigman Matthew S MS

Journal of the American Chemical Society 20180110 3

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 mul ...[more]

PMID: 29300461

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