Evidence map›Paper›PMID 38280216›Full record

ArticleAngewandte Chemie (International ed. in English)2024

Selective C-H Halogenation of Alkenes and Alkynes Using Flavin-Dependent Halogenases.

Yuhua Jiang, Ahram Kim, Cahmlo Olive, Jared C Lewis

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.

0numbers the graph read from it
0cells of the map it votes in
12citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

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.

2 · The registry

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.

3 · Its place in the literature

Who cites it

12 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Article
  5. Article
  6. Ring-Opening Chlorination and Bromination of Pyrazolopyridines and Isoxazoles.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025
    Article
  7. Article
  8. Unlocking the catalytic precision of ligand-controlled enzymatic halogenation.Proceedings of the National Academy of Sciences of the United States of America · 2025
    Article
  9. Article
  10. Article
  11. Article
  12. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

4 authors.

Yuhua JiangDepartment of Chemistry, Indiana University, Bloomington, IN 47405, USA.
Ahram KimDepartment of Chemistry, Indiana University, Bloomington, IN 47405, USA.
Cahmlo OliveDepartment of Chemistry, Indiana University, Bloomington, IN 47405, USA.
Jared C LewisDepartment of Chemistry, Indiana University, Bloomington, IN 47405, USA.ORCID 0000-0003-2800-8330

Funding

Directed Evolution of Halogenases For Small Molecule FunctionalizationR01GM115665 · NIGMS · UNIVERSITY OF CHICAGO · PI LEWIS, JARED C · 2015 to 2022
$2.5M
Engineering Halogenases for Small Molecule Functionalization and Enantioselective CatalysisR35GM152068 · NIGMS · TRUSTEES OF INDIANA UNIVERSITY · PI JARED C LEWIS · 2024 to 2026
$1.2M
NIGMS NIH HHS R01 GM115665NIGMS NIH HHS R35 GM152068
6 · The paper itself

Abstract

Single component flavin-dependent halogenases (FDHs) possess both flavin reductase and FDH activity in a single enzyme. We recently reported that the single component FDH AetF catalyzes site-selective bromination and iodination of a variety of aromatic substrates and enantioselective bromolactonization and iodoetherification of styrenes bearing pendant carboxylic acid or alcohol substituents. Given this inherent reactivity and selectivity, we explored the utility of AetF as catalyst for alkene and alkyne C-H halogenation. We find that AetF catalyzes halogenation of a range of 1,1-disubstituted styrenes, often with high stereoselectivity. Despite the utility of haloalkenes for cross-coupling and other applications, accessing these compounds in a stereoselective manner typically requires functional group interconversion processes, and selective halogenation of 1,1'-disubstituted olefins remains rare. We also establish that AetF and homologues of this enzyme can halogenate terminal alkynes. Mutagenesis studies and deuterium kinetic isotope effects are used to support a mechanistic proposal involving covalent catalysis for halogenation of unactivated alkynes by AetF homologues. These findings expand the scope of FDH catalysis and continue to show the unique utility of single component FDHs for biocatalysis.

Indexed as

AlkenesHalogenationAlkynesFlavinsStyrenesAlkenesAlkynesFlavinsStyrenes

Identifiers

PMID38280216
PMCPMC10947852

What OpenQuestion holds

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Registered trials

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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.