ArticleOrganic letters2016
Solution Structures and Molecular Associations of a Peptide-Based Catalyst for the Stereoselective Baeyer-Villiger Oxidation.
Article in Organic letters, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Selective Oxidation of Disparate Functional Groups Mediated by a Common Aspartic Acid-Based Peptide Catalyst Platform.Accounts of chemical research · 2025Article
- Organocatalytic activation of hydrogen peroxide: towards green and sustainable oxidations.Chemical science · 2024Review
- Cu(ii)/SPDO complex catalyzed asymmetric Baeyer-Villiger oxidation of 2-arylcyclobutanones and its application for the total synthesis of eupomatilones 5 and 6.Chemical science · 2022Article
- Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.Chemical reviews · 2020Review
- Catalysis-Enabled Access to Cryptic Geldanamycin Oxides.ACS central science · 2020Article
- Asymmetric Baeyer-Villiger oxidation: classical and parallel kinetic resolution of 3-substituted cyclohexanones and desymmetrization ofChemical science · 2019Article
- Conformational Dynamics in Asymmetric Catalysis: Is Catalyst Flexibility a Design Element?Synthesis · 2019Article
- Molecular Dynamics Simulations of a Conformationally Mobile Peptide-Based Catalyst for Atroposelective Bromination.ACS catalysis · 2018Article
- Overriding Traditional Electronic Effects in Biocatalytic Baeyer-Villiger Reactions by Directed Evolution.Journal of the American Chemical Society · 2018Article
- Parameterization and Analysis of Peptide-Based Catalysts for the Atroposelective Bromination of 3-Arylquinazolin-4(3H)-ones.Journal of the American Chemical Society · 2018Article
- Diversity of Secondary Structure in Catalytic Peptides with β-Turn-Biased Sequences.Journal of the American Chemical Society · 2017Article
- Aspartyl Oxidation Catalysts That Dial In Functional Group Selectivity, along with Regio- and Stereoselectivity.ACS central science · 2016Article
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
The structural analysis of a peptide-based catalyst for the Baeyer-Villiger oxidation (BVO) is reported. This unique structure is then analyzed in the context of its previously documented facility to control selectivity (both enantioselectivity and migratory aptitude) in catalytic reactions. The effects of additives on the solution conformation of the peptide are found to be dramatic, revealing substrate-specific interactions and a possible "induced fit" model. The experimental observation of dynamic behavior supports the notion that flexibility in stereoselective catalysts can be an advantageous feature.
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Registered trials
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