Evidence map›Paper›PMID 31909617›Full record

ArticleJournal of the American Chemical Society2020

Inverted Binding of Non-natural Substrates in Strictosidine Synthase Leads to a Switch of Stereochemical Outcome in Enzyme-Catalyzed Pictet-Spengler Reactions.

Elisabeth Eger, Adam Simon, Mahima Sharma, Song Yang, Willem B Breukelaar, Gideon Grogan, K N Houk, Wolfgang Kroutil

Erratum issuedOpen access · hybridAbstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 12 papers.

0numbers the graph read from it
0cells of the map it votes in
12citing papers in PubMed
4.6field-weighted citation impact, top 5% 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

12 citing papers in PubMed, 42 citations in OpenAlex.

  1. Discovery of a Plant Pictet-Spenglerase With R-Stereoselectivity.Angewandte Chemie (International ed. in English) · 2026
    Article
  2. Article
  3. Elucidation of the 1-phenethylisoquinoline pathway from an endemic coniferProceedings of the National Academy of Sciences of the United States of America · 2023
    Article
  4. New Trends and Future Opportunities in the Enzymatic Formation of C-C, C-N, and C-O bonds.Chembiochem : a European journal of chemical biology · 2022
    Review
  5. Article
  6. Review
  7. Enzymatic Late-Stage Modifications: Better Late Than Never.Angewandte Chemie (International ed. in English) · 2021
    Review
  8. Enzymkatalysierte späte Modifizierungen: Besser spät als nie.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2021
    Review
  9. Recent trends in biocatalysis.Chemical Society reviews · 2021
    Review
  10. The AutoDock suite at 30.Protein science : a publication of the Protein Society · 2021
    Article
  11. Article
  12. Article
4 · The record

Corrections and comments

5 · Who and what money

Authors and funding

8 authors at 3 institutions in 3 countries.

Elisabeth EgerDepartment of Chemistry, Organic and Bioorganic Chemistry , University of Graz , Heinrichstrasse 28 , 8010 Graz , Austria.
Adam SimonDepartment of Chemistry and Biochemistry , University of California , Los Angeles , California 90095-1569 , United States.ORCID 0000-0001-6334-3359
Mahima SharmaDepartment of Chemistry , University of York , Heslington , York YO15 5DD , U.K.ORCID 0000-0003-3960-2212
Song YangDepartment of Chemistry and Biochemistry , University of California , Los Angeles , California 90095-1569 , United States.
Willem B BreukelaarDepartment of Chemistry, Organic and Bioorganic Chemistry , University of Graz , Heinrichstrasse 28 , 8010 Graz , Austria.
Gideon GroganDepartment of Chemistry , University of York , Heslington , York YO15 5DD , U.K.ORCID 0000-0003-1383-7056
K N HoukDepartment of Chemistry and Biochemistry , University of California , Los Angeles , California 90095-1569 , United States.ORCID 0000-0002-8387-5261
Wolfgang KroutilDepartment of Chemistry, Organic and Bioorganic Chemistry , University of Graz , Heinrichstrasse 28 , 8010 Graz , Austria.ORCID 0000-0002-2151-6394
University of California, Los Angeles · USUniversity of Graz · ATUniversity of York · GB

Funding

CHEMISTRY BIOLOGY INTERFACE TRAINING PROGRAMT32GM008496 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI MAYNARD, HEATHER D · 1993 to 2019
$6.3M
Steroselectivity of Synthetically Valuable Enzyme CatalystsR01GM124480 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI HOUK, KENDALL N · 2018 to 2021
$1.1M
Austrian Science Fund FWF DOC 46Biotechnology and Biological Sciences Research Council BB/M006832/1NIGMS NIH HHS R01 GM124480NIGMS NIH HHS T32 GM008496
6 · The paper itself

Abstract

The Pictet-Spengler reaction is a valuable route to 1,2,3,4-tetrahydro-β-carboline (THBC) and isoquinoline scaffolds found in many important pharmaceuticals. Strictosidine synthase (STR) catalyzes the Pictet-Spengler condensation of tryptamine and the aldehyde secologanin to give (

Indexed as

Carbon-Nitrogen LyasesCatalysisProtein BindingStereoisomerismSubstrate SpecificityCarbon-Nitrogen Lyasesstrictosidine synthetase

Identifiers

PMID31909617
PMCPMC6966912
OpenAlexW3000296146

What OpenQuestion holds

Textmetadata
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.