Evidence map›Paper›PMID 24009388›Full record

ArticleScience (New York, N.Y.)2013

Expanding the fluorine chemistry of living systems using engineered polyketide synthase pathways.

Mark C Walker, B W Thuronyi, Louise K Charkoudian, Brian Lowry, Chaitan Khosla, Michelle C Y Chang

Abstract read
In one paragraph

Article in Science (New York, N.Y.), 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 73 papers.

0numbers the graph read from it
0cells of the map it votes in
73citing papers in PubMed
19.7field-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

73 citing papers in PubMed, 197 citations in OpenAlex.

  1. Article
  2. Article
  3. Article
  4. Article
  5. Article
  6. Article
  7. Harnessing Photoenzymatic Systems for Intermolecular C-H Fluorination.Angewandte Chemie (International ed. in English) · 2026
    Article
  8. Review
  9. Review
  10. Article
  11. Article
  12. Article
  13. Biocatalytic enantioselective C(spNature synthesis · 2024
    Article
  14. Review
  15. Current State-of-the-Art Toward Chemoenzymatic Synthesis of Polyketide Natural Products.Chembiochem : a European journal of chemical biology · 2023
    Review
  16. Article
  17. Article
  18. Article
  19. Article
  20. Article

13 more citing papers are in PubMed but not listed here.

4 · The record

Corrections and comments

5 · Who and what money

Authors and funding

6 authors at 2 institutions in 1 country.

Mark C WalkerDepartment of Molecular and Cell Biology, University of California, Berkeley, Berkeley, CA 94720-1460, USA.
B W Thuronyi
Louise K Charkoudian
Brian Lowry
Chaitan Khosla
Michelle C Y Chang
Stanford University · USUniversity of California, Berkeley · US

Funding

Univ of Calif Berkeley Chemistry-Biology Interface ProgramT32GM066698 · NIGMS · UNIVERSITY OF CALIFORNIA BERKELEY · PI CHANG, CHRISTOPHER J., FRANCIS, MATTHEW B · 2004 to 2023
$7.5M
Structure, Mechanism, and Engineering of Assembly Line Polyketide SynthasesR01GM087934 · NIGMS · STANFORD UNIVERSITY · PI KHOSLA, CHAITAN · 2009 to 2021
$4.9M
Discovery and mechanistic study of fluorine biochemistryDP2OD008696 · OD · UNIVERSITY OF CALIFORNIA BERKELEY · PI CHANG, MICHELLE C · 2011 to 2011
$2.3M
500 MHz NMR SPECTROMETERS10RR016634 · NCRR · UNIVERSITY OF CALIFORNIA BERKELEY · PI ELLMAN, JONATHAN A. · 2002 to 2002
$500k
600 MHz NMR Spectrometer for Solution-state NMRS10RR023679 · NCRR · UNIVERSITY OF CALIFORNIA BERKELEY · PI ELLMAN, JONATHAN A · 2007 to 2007
$500k
Mechanistic analysis of 6-deoxyerythronolide B synthaseF32CA137994 · NCI · STANFORD UNIVERSITY · PI CHARKOUDIAN, LOUISE KARINE · 2009 to 2011
$151k
NCI NIH HHS F32 CA137994NCRR NIH HHS 1S10RR023679-01NCRR NIH HHS S10 RR023679NCRR NIH HHS S10 RR16634-01NIGMS NIH HHS R01 GM087934NIGMS NIH HHS T32 GM066698NIH HHS 1 DP2 OD008696NIH HHS DP2 OD008696PHS HHS 1 T32 GMO66698
6 · The paper itself

Abstract

Organofluorines represent a rapidly expanding proportion of molecules that are used in pharmaceuticals, diagnostics, agrochemicals, and materials. Despite the prevalence of fluorine in synthetic compounds, the known biological scope is limited to a single pathway that produces fluoroacetate. Here, we demonstrate that this pathway can be exploited as a source of fluorinated building blocks for introduction of fluorine into natural-product scaffolds. Specifically, we have constructed pathways involving two polyketide synthase systems, and we show that fluoroacetate can be used to incorporate fluorine into the polyketide backbone in vitro. We further show that fluorine can be inserted site-selectively and introduced into polyketide products in vivo. These results highlight the prospects for the production of complex fluorinated natural products using synthetic biology.

Indexed as

Bacterial ProteinsBase SequenceBiological ProductsBurkholderiaCoenzyme A LigasesEscherichia coliFluoroacetatesMetabolic Networks and PathwaysMolecular Sequence DataPolyketidesPolyketide SynthasesProtein EngineeringProtein Structure, TertiaryStreptomyces coelicoloracetoacetyl-CoA synthase, StreptomycesBacterial ProteinsBiological ProductsCoenzyme A LigasesFluoroacetatesPolyketidesPolyketide Synthases

Identifiers

PMID24009388
PMCPMC4057101
OpenAlexW2094478741

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.