Evidence map›Paper›PMID 33369395›Full record

ArticleJournal of the American Chemical Society2021

Quaternary Charge-Transfer Complex Enables Photoenzymatic Intermolecular Hydroalkylation of Olefins.

Claire G Page, Simon J Cooper, Jacob S DeHovitz, Daniel G Oblinsky, Kyle F Biegasiewicz, Alyssa H Antropow, Kurt W Armbrust, J Michael Ellis, Lawrence G Hamann, Evan J Horn and 3 more

Open access · greenAbstract read
In one paragraph

Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 52 papers.

0numbers the graph read from it
0cells of the map it votes in
52citing papers in PubMed
9.6field-weighted citation impact, top 1% of its field
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

52 citing papers in PubMed, 150 citations in OpenAlex.

  1. Article
  2. Article
  3. Article
  4. Review
  5. Designing and Engineering Enzymes for New-to-Nature Photobiocatalysis.Methods in molecular biology (Clifton, N.J.) · 2026
    Review
  6. Article
  7. Article
  8. Article
  9. Emergent Mechanisms in Biocatalysis.ACS central science · 2025
    Review
  10. Article
  11. Article
  12. Transitioning enzyme catalysis towards photocatalysis.Philosophical transactions. Series A, Mathematical, physical, and engineering sciences · 2025
    Review
  13. Article
  14. Article
  15. Article
  16. Article
  17. Article
  18. Article
  19. Review
  20. Review
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

13 authors at 3 institutions in 1 country.

Claire G PageDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.
Simon J CooperDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0003-1465-5879
Jacob S DeHovitzDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0001-9994-6311
Daniel G OblinskyDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0001-7460-8260
Kyle F BiegasiewiczDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0003-1905-1919
Alyssa H AntropowBristol Myers Squibb, 200 Cambridge Park Drive, Suite 3000, Cambridge, Massachusetts 02140, United States.
Kurt W ArmbrustBristol Myers Squibb, 200 Cambridge Park Drive, Suite 3000, Cambridge, Massachusetts 02140, United States.
J Michael EllisBristol Myers Squibb, 200 Cambridge Park Drive, Suite 3000, Cambridge, Massachusetts 02140, United States.
Lawrence G HamannTakeda Pharmaceuticals, 30 Landsdowne Street, Cambridge, Massachusetts 02139, United States.
Evan J HornBristol Myers Squibb, 10300 Campus Point Drive, Suite 100, San Diego, California 92121, United States.
Kevin M ObergBristol Myers Squibb, 10300 Campus Point Drive, Suite 100, San Diego, California 92121, United States.
Gregory D ScholesDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0003-3336-7960
Todd K HysterDepartment of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.ORCID 0000-0003-3560-355X
Princeton University · USBristol-Myers Squibb (United States) · USTakeda (United States) · US

Funding

Hyster (Rivas-Souchet) Diversity SupplementR01GM127703 · NIGMS · PRINCETON UNIVERSITY · PI Todd Kurt Hyster · 2018 to 2026
$2.9M
NIGMS NIH HHS R01 GM127703
6 · The paper itself

Abstract

Intermolecular C-C bond-forming reactions are underdeveloped transformations in the field of biocatalysis. Here we report a photoenzymatic intermolecular hydroalkylation of olefins catalyzed by flavin-dependent 'ene'-reductases. Radical initiation occurs via photoexcitation of a rare high-order enzyme-templated charge-transfer complex that forms between an alkene, α-chloroamide, and flavin hydroquinone. This unique mechanism ensures that radical formation only occurs when both substrates are present within the protein active site. This active site can control the radical terminating hydrogen atom transfer, enabling the synthesis of enantioenriched γ-stereogenic amides. This work highlights the potential for photoenzymatic catalysis to enable new biocatalytic transformations via previously unknown electron transfer mechanisms.

Indexed as

AlkenesAlkylationAmidesBiocatalysisCatalytic DomainDinitrocresolsFlavoproteinsLightModels, ChemicalOxidoreductases4,6-dinitro-o-cresolAlkenesAmidesDinitrocresolsFlavoproteinsOxidoreductases

Identifiers

PMID33369395
PMCPMC7832516
OpenAlexW3116028859

What OpenQuestion holds

Textmetadata
LicenceTDM
Read underepoch 390

Registered trials

None linked

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.