ArticleACS central science2016
Aspartyl Oxidation Catalysts That Dial In Functional Group Selectivity, along with Regio- and Stereoselectivity.
Article in ACS central science, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
23 citing papers in PubMed, 40 citations in OpenAlex.
- Harnessing Random Polymers as Chemoselective Catalysts With Structural Adaptability: Epoxidation of Olefinic Quaternary Ammonium Salts via Charge Recognition.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Selective Noncovalent Catalysis with Small Molecules.Chemical reviews · 2025Review
- Selective Oxidation of Disparate Functional Groups Mediated by a Common Aspartic Acid-Based Peptide Catalyst Platform.Accounts of chemical research · 2025Article
- Late-stage modification of bioactive compounds: Improving druggability through efficient molecular editing.Acta pharmaceutica Sinica. B · 2024Review
- Organocatalytic activation of hydrogen peroxide: towards green and sustainable oxidations.Chemical science · 2024Review
- Aspartyl β-Turn-Based Dirhodium(II) Metallopeptides for Benzylic C(spJournal of the American Chemical Society · 2023Article
- Catalytic Enantioselective Synthesis of Pyridyl Sulfoximines.Journal of the American Chemical Society · 2021Article
- Syntheses and structures of two benzoyl amides: 2-chloro-4-eth-oxy-3,5-dimeth-oxy-Acta crystallographica. Section E, Crystallographic communications · 2021Article
- Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.Chemical reviews · 2020Review
- Asymmetric Catalysis upon Helically Chiral Loratadine Analogues Unveils Enantiomer-Dependent Antihistamine Activity.Journal of the American Chemical Society · 2020Article
- Catalysis-Enabled Access to Cryptic Geldanamycin Oxides.ACS central science · 2020Article
- Catalytic Enantioselective PyridineJournal of the American Chemical Society · 2019Article
- Outer-Sphere Control for Divergent Multicatalysis with Common Catalytic Moieties.The Journal of organic chemistry · 2019Article
- Peptide-Based Catalysts Reach the Outer Sphere through Remote Desymmetrization and Atroposelectivity.Accounts of chemical research · 2019Article
- Molecular Dynamics Simulations of a Conformationally Mobile Peptide-Based Catalyst for Atroposelective Bromination.ACS catalysis · 2018Article
- Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3-Amidocyclohexanones.The Journal of organic chemistry · 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
- Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.Chemical reviews · 2017Review
- Design of peptide-containingChemical science · 2017Article
- Second-Order Biomimicry: In Situ Oxidative Self-Processing Converts Copper(I)/Diamine Precursor into a Highly Active Aerobic Oxidation Catalyst.ACS central science · 2017Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
A remarkable aspect of enzyme evolution is the portability of catalytic mechanisms for fundamentally different chemical reactions. For example, aspartyl proteases, which contain two active site carboxylic acid groups, catalyze the hydrolysis of amide bonds, while glycosyltransferases (and glycosyl hydrolases), which often also contain two active site carboxylates, have evolved to form (or break) glycosidic bonds. However, neither catalyst exhibits cross-reactivity in the intracellular environment. The large, macromolecular architectures of these biocatalysts tailor their active sites to their precise, divergent functions. The analogous portability of a small-molecule catalyst for truly orthogonal chemical reactivity is rare. Herein, we report aspartic acid containing peptides that can be directed to different sectors of a substrate for which the danger of cross-reactivity looms large. A transiently formed aspartyl peracid catalyst can participate either as an electrophilic oxidant to catalyze alkene epoxidation or as a nucleophilic oxidant to mediate the Baeyer-Villiger oxidation (BVO) of ketones. We show in this study that an appended peptide sequence can dictate the mode of reactivity for this conserved catalytic functional group within a substrate that has the potential to undergo both alkene epoxidation and BVO; in both cases the additional aspects of chemical selectivity (regio- and stereoselectivity) are high. This sequence-dependent tuning of a common catalytic moiety for functional group selective reactions constitutes a biomimetic strategy that may impact late-stage diversification of complex polyfunctional molecules.
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.