Evidence map›Paper›PMID 38584987›Full record

ArticleNature catalysis2024

Stereoselective Construction of β-, γ-, and δ-Lactam Rings via Enzymatic C-H Amidation.

Satyajit Roy, David A Vargas, Pengchen Ma, Arkajyoti Sengupta, Ledong Zhu, K N Houk, Rudi Fasan

Open access · greenAbstract read
In one paragraph

Article in Nature catalysis, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.

0numbers the graph read from it
0cells of the map it votes in
27citing papers in PubMed
10.0field-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

27 citing papers in PubMed, 67 citations in OpenAlex.

  1. Article
  2. Article
  3. Article
  4. Article
  5. Protein engineering: status report.Protein engineering, design & selection : PEDS · 2026
    Review
  6. Article
  7. Article
  8. Article
  9. Article
  10. Enantioconvergent benzylic C(spScience (New York, N.Y.) · 2025
    Article
  11. Review
  12. Article
  13. Article
  14. Enzyme-catalyzed C(spRSC advances · 2025
    Article
  15. Designing Enzymatic Reactivity with an Expanded Palette.Chembiochem : a European journal of chemical biology · 2025
    Review
  16. Photobiocatalytic Enantioselective Benzylic C(spJournal of the American Chemical Society · 2025
    Article
  17. Article
  18. Article
  19. Article
  20. Article
4 · The record

Corrections and comments

5 · Who and what money

Authors and funding

7 authors at 4 institutions in 2 countries.

Satyajit RoyDepartment of Chemistry, University of Rochester, 120 Trustee Road, Rochester, New York, 14627, United States.
David A VargasDepartment of Chemistry, University of Rochester, 120 Trustee Road, Rochester, New York, 14627, United States.
Pengchen MaDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California, 90095, United States.
Arkajyoti SenguptaDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California, 90095, United States.
Ledong ZhuEnvironment Research Institute, Shandong University, Qingdao 266237, PR China.
K N HoukDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California, 90095, United States.
Rudi FasanDepartment of Chemistry, University of Rochester, 120 Trustee Road, Rochester, New York, 14627, United States.
University of California, Los Angeles · USThe University of Texas at Dallas · USMerck & Co., Inc., Rahway, NJ, USA (United States) · USShandong University · CN

Funding

Selective P450 Oxidation Catalysts for Synthesis of Bioactive MoleculesR01GM098628 · NIGMS · UNIVERSITY OF TEXAS DALLAS · PI FASAN, RUDI · 2012 to 2024
$4.7M
Matrix-Assisted Laser Desorption Ionization Time-of-Flight (MALDI-TOF/TOF) Mass SpectrometerS10OD030302 · OD · UNIVERSITY OF ROCHESTER · PI NILSSON, BRADLEY L. · 2021 to 2021
$304k
NIGMS NIH HHS R01 GM098628NIH HHS S10 OD030302
6 · The paper itself

Abstract

Lactam rings are found in many biologically active natural products and pharmaceuticals, including important classes of antibiotics. Methods for the asymmetric synthesis of these molecules are therefore highly desirable, particularly through the selective functionalization of unreactive aliphatic C-H bonds. Here we show the development of a strategy for the asymmetric synthesis of β-, γ-, and δ-lactams via hemoprotein-catalysed intramolecular C-H amidation reaction with readily available dioxazolone reagents. Engineered myoglobin variants serve as excellent biocatalysts for this transformation yielding the desired lactam products in high yields, high enantioselectivity, and on preparative scale. Mechanistic and computational studies elucidate the nature of the C-H amination and enantiodetermining steps and provide insights into protein-mediated control of regioselectivity and stereoselectivity. Additionally, an alkaloid natural product and a drug molecule were synthesized chemoenzymatically in much fewer steps (7-8 vs. 11-12) than previously reported, further demonstrating the power of biosynthetic strategy for the preparation of complex bioactive molecules.

Identifiers

PMID38584987
PMCPMC10997382
OpenAlexW4389388998

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.