ArticleJournal of the American Chemical Society2023
Asymmetric Carbohydroxylation of Alkenes Using Photoenzymatic Catalysis.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 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
16 citing papers in PubMed, 31 citations in OpenAlex.
- Machine-Learning-Enabled Rapid Evolution of Photoenzymes for the Asymmetric Synthesis of gem-Difluorophosphonates.Angewandte Chemie (International ed. in English) · 2026Article
- Designing and Engineering Enzymes for New-to-Nature Photobiocatalysis.Methods in molecular biology (Clifton, N.J.) · 2026Review
- Photoenzymatic catalysis enables enantioselective radical dearomative spirocyclization.Nature communications · 2025Article
- Aromatic Coupling Reactions Catalyzed by "ene"-Reductase under Visible Light Irradiation.ACS omega · 2025Article
- Biocatalytic Olefin Difunctionalization for Synthesis of Chiral 2-Azidoamines Using Nonheme Iron Enzymes.Angewandte Chemie (International ed. in English) · 2025Article
- Electrochemical Oxidative Radical Polar Crossover Route to 1,4-Keto Carboxylates Mediated by Anchimeric Assistance.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Three-Component Synthesis of γ-Amino Esters with α-Quaternary Carbon Centers via NHC/Photoredox Dual Catalysis.Advanced synthesis & catalysis · 2025Article
- Asymmetric Enantio-complementary Synthesis of Thioethers via Ene-Reductase-Catalyzed C-C Bond Formation.Journal of the American Chemical Society · 2025Article
- Article
- Article
- Threonine Aldolase-Catalyzed Enantioselective α-Alkylation of Amino Acids through Unconventional Photoinduced Radical Initiation.Journal of the American Chemical Society · 2024Article
- Review
- From Ground-State to Excited-State Activation Modes: Flavin-Dependent "Ene"-Reductases Catalyzed Non-natural Radical Reactions.Accounts of chemical research · 2024Review
- Asymmetric Synthesis of α-Chloroamides via Photoenzymatic Hydroalkylation of Olefins.Journal of the American Chemical Society · 2024Article
- Tryptophan to Tryptophan Hole Hopping in an Azurin Construct.The journal of physical chemistry. B · 2024Article
- Novel applications of photobiocatalysts in chemical transformations.RSC advances · 2024Review
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Alkene difunctionalizations enable the synthesis of structurally elaborated products from simple and ubiquitous starting materials in a single chemical step. Carbohydroxylations of olefins represent a family of reactivity that furnish structurally complex alcohols. While examples of this type of three-component coupling have been reported, catalytic asymmetric examples remain elusive. Here, we report an enzyme-catalyzed asymmetric carbohydroxylation of alkenes catalyzed by flavin-dependent "ene"-reductases to produce enantioenriched tertiary alcohols. Seven rounds of protein engineering reshape the enzyme's active site to increase activity and enantioselectivity. Mechanistic studies suggest that C-O bond formation occurs via a 5-endo-trig cyclization with the pendant ketone to afford an α-oxy radical which is oxidized and hydrolyzed to form the product. This work demonstrates photoenzymatic reactions involving "ene"-reductases can terminate radicals via mechanisms other than hydrogen atom transfer, expanding their utility in chemical synthesis.
Indexed as
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.