Evidence map›Paper›PMID 38752612›Full record

ArticleAngewandte Chemie (International ed. in English)2024

Biocatalytic Strategy for the Highly Stereoselective Synthesis of Fluorinated Cyclopropanes.

Juan D Villada, Jadab Majhi, Valentin Lehuédé, Michelle E Hendricks, Katharina Neufeld, Veronica Tona, Rudi Fasan

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 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing 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

3 citing papers in PubMed.

  1. Article
  2. Article
  3. 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

7 authors.

Juan D VilladaDepartment of Chemistry and Biochemistry, University of Texas at Dallas, 800 W. Campbell Road, Richardson, TX 75080, United States.ORCID https://orcid.org/0000-0002-9424-9194
Jadab MajhiDepartment of Chemistry and Biochemistry, University of Texas at Dallas, 800 W. Campbell Road, Richardson, TX 75080, United States.ORCID https://orcid.org/0000-0002-0736-6422
Valentin LehuédéJohnson & Johnson Innovative Medicine, Chemical Process R&D, Turnhoutseweg 30, 2340, Beerse, Belgium.
Michelle E HendricksDepartment of Chemistry and Biochemistry, University of Texas at Dallas, 800 W. Campbell Road, Richardson, TX 75080, United States.ORCID https://orcid.org/0000-0001-8600-304X
Katharina NeufeldJohnson & Johnson Innovative Medicine, Chemical Process R&D, Turnhoutseweg 30, 2340, Beerse, Belgium.
Veronica TonaJohnson & Johnson Innovative Medicine, Chemical Process R&D, Cilag AG, Hochstrasse 201, 8200, Schaffhausen, Switzerland.ORCID https://orcid.org/0009-0002-7715-2689
Rudi FasanDepartment of Chemistry and Biochemistry, University of Texas at Dallas, 800 W. Campbell Road, Richardson, TX 75080, United States.ORCID https://orcid.org/0000-0003-4636-9578

Funding

Research Training in Complementary and Integrative MedicineT32AT000051 · NCCIH · HARVARD UNIVERSITY (MEDICAL SCHOOL) · PI GLORIA Y YEH · 1999 to 2026
$10.2M
Selective P450 Oxidation Catalysts for Synthesis of Bioactive MoleculesR01GM098628 · NIGMS · UNIVERSITY OF TEXAS DALLAS · PI FASAN, RUDI · 2012 to 2024
$4.7M
NIH Training Grant in Chemistry-Biology InterfaceT32GM145461 · NIGMS · UNIVERSITY OF ROCHESTER · PI KARA L. BREN, Bradley L. Nilsson · 2022 to 2026
$988k
GINSENG'S EFFECTS ON MRNA PROFILES IN A DIABETES-2 MODELF32AT000051 · NCCIH · UNIVERSITY OF TEXAS AUSTIN · PI PAN, SHUJIA J · 1999 to 2001
$96k
NCCIH NIH HHS F32 AT000051NCCIH NIH HHS T32 AT000051NIGMS NIH HHS GM098628NIGMS NIH HHS R01 GM098628NIGMS NIH HHS T32 GM145461Welch Foundation AT-0051
6 · The paper itself

Abstract

Fluorinated cyclopropanes are highly desired pharmacophores in drug discovery owing to the rigid nature of the cyclopropane ring and the beneficial effects of C-F bonds on the pharmacokinetic properties, cell permeability, and metabolic stability of drug molecules. Herein a biocatalytic strategy for the stereoselective synthesis of mono-fluorinated and gem-difluoro cyclopropanes is reported though the use of engineered myoglobin-based catalysts. In particular, this system allows for a broad range of gem-difluoro alkenes to be cyclopropanated in the presence of diazoacetonitrile with excellent diastereo and enantiocontrol (up to 99 : 1 d.r. and 99 % e.e.), thereby enabling a transformation not currently accessible with chemocatalytic methods. The synthetic utility of the present approach is further exemplified through the gram-scale synthesis of a key gem-difluorinated cyclopropane intermediate useful for the preparation of fluorinated bioactive molecules.

Indexed as

Asymmetric cyclopropanationBiocatalysisCarbene TransferFluorinated cyclopropanesMyoglobin

Identifiers

PMID38752612
PMCPMC13439834

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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.