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Literature DB >> 29300461

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

Jennifer M Crawford¹, Elizabeth A Stone², Anthony J Metrano², Scott J Miller², Matthew S Sigman¹.

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.

Entities: Chemical

Mesh：

Substances：
Peptides
Quinazolinones

Year: 2018 PMID： 29300461 PMCID： PMC5817992 DOI： 10.1021/jacs.7b11303

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

28 in total

10. A Case Study in Catalyst Generality: Simultaneous, Highly-Enantioselective Brønsted- and Lewis-Acid Mechanisms in Hydrogen-Bond-Donor Catalyzed Oxetane Openings.

Authors: Daniel A Strassfeld; Russell F Algera; Zachary K Wickens; Eric N Jacobsen
Journal: J Am Chem Soc Date: 2021-06-21 Impact factor: 16.383

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

1. Peptide-plane flipping in proteins.

2. In search of peptide-based catalysts for asymmetric organic synthesis.

3. Lewis base catalysis of bromo- and iodolactonization, and cycloetherification.

4. Calculation of vibrational infrared intensities and Raman activities using explicit anharmonic wave functions.

Review 5. Asymmetric catalysis mediated by synthetic peptides.

Review 6. Asymmetric catalysis with short-chain peptides.

7. Pursuit of Noncovalent Interactions for Strategic Site-Selective Catalysis.

Review 8. The anatomy and taxonomy of protein structure.

9. Influence of the Trans/Cis Conformer Ratio on the Stereoselectivity of Peptidic Catalysts.

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

1. Disparate Catalytic Scaffolds for Atroposelective Cyclodehydration.

2. Interrogation of 2,2'-Bipyrimidines as Low-Potential Two-Electron Electrolytes.

3. Terahertz Spectroscopy of Tetrameric Peptides.

4. Isolating Conformers to Assess Dynamics of Peptidic Catalysts Using Computationally Designed Macrocyclic Peptides.

Review 5. Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

6. Molecular Dynamics Simulations of a Conformationally Mobile Peptide-Based Catalyst for Atroposelective Bromination.

Review 7. Quantitative Structure-Selectivity Relationships in Enantioselective Catalysis: Past, Present, and Future.

8. Enantioselective fluorination of homoallylic alcohols enabled by the tuning of non-covalent interactions.

9. Peptide-Based Catalysts Reach the Outer Sphere through Remote Desymmetrization and Atroposelectivity.

10. A Case Study in Catalyst Generality: Simultaneous, Highly-Enantioselective Brønsted- and Lewis-Acid Mechanisms in Hydrogen-Bond-Donor Catalyzed Oxetane Openings.