Evidence map›Paper›PMID 26360642›Full record

ArticleChembiochem : a European journal of chemical biology2015

Involvement of Lipocalin-like CghA in Decalin-Forming Stereoselective Intramolecular [4+2] Cycloaddition.

Michio Sato, Fumitoshi Yagishita, Takashi Mino, Nahoko Uchiyama, Ashay Patel, Yit-Heng Chooi, Yukihiro Goda, Wei Xu, Hiroshi Noguchi, Tsuyoshi Yamamoto and 4 more

Abstract read
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In one paragraph

Article in Chembiochem : a European journal of chemical biology, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.

0numbers the graph read from it
0cells of the map it votes in
37citing 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

37 citing papers in PubMed.

  1. Review
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  7. EnzymaticJournal of the American Chemical Society · 2023
    Article
  8. Review
  9. Article
  10. Review
  11. Article
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  13. Article
  14. 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
  15. Review
  16. Article
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  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

14 authors.

Michio SatoDepartment of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan.
Fumitoshi YagishitaDepartment of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan.
Takashi MinoDepartment of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan.
Nahoko UchiyamaNational Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo, 158-8501, Japan.
Ashay PatelDepartment of Chemistry and Biochemistry, University of California, 607 Charles E. Young Drive East, Box 951569, Los Angeles, CA, 90095, USA.
Yit-Heng ChooiDepartment of Chemical and Biomolecular Engineering and, Department of Chemistry and Biochemistry, University of California, 420 Westwood Plaza, Los Angeles, CA, 90095, USA.
Yukihiro GodaNational Institute of Health Sciences, 1-18-1 Kamiyoga, Setagaya-ku, Tokyo, 158-8501, Japan.
Wei XuDepartment of Chemical and Biomolecular Engineering and, Department of Chemistry and Biochemistry, University of California, 420 Westwood Plaza, Los Angeles, CA, 90095, USA.
Hiroshi NoguchiDepartment of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan.
Tsuyoshi YamamotoDepartment of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan.
Kinya HottaSchool of Biosciences, The University of Nottingham Malaysia Campus, Jalan Broga, Selangor, 43500, Malaysia.
Kendall N HoukDepartment of Chemistry and Biochemistry, University of California, 607 Charles E. Young Drive East, Box 951569, Los Angeles, CA, 90095, USA.
Yi TangDepartment of Chemical and Biomolecular Engineering and, Department of Chemistry and Biochemistry, University of California, 420 Westwood Plaza, Los Angeles, CA, 90095, USA.
Kenji WatanabeDepartment of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka, 422-8526, Japan. kenji55@u-shizuoka-ken.ac.jp.

Funding

CHEMISTRY BIOLOGY INTERFACE TRAINING PROGRAMT32GM008496 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI MAYNARD, HEATHER D · 1993 to 2019
$6.3M
Rediscovering Natural Chemical Diversity -1DP1GM106413DP1GM106413 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI TANG, YI · 2012 to 2016
$3.9M
Characterization and Engineering of Fungal Megasynthases in Escherichia coliR01GM085128 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI TANG, YI · 2008 to 2016
$2.1M
Mapping the Evolution of a Novel Enzyme by Experiment and ComputationR01GM097200 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI HOUK, KENDALL N, TANG, YI · 2012 to 2015
$1.3M
NCCDPHP CDC HHS 1DP1M106413NIGMS NIH HHS DP1 GM106413NIGMS NIH HHS R01 GM085128NIGMS NIH HHS R01 GM097200NIGMS NIH HHS T32 GM008496NIGMS NIH HHS T32GM008496PHS HHS 1R01M097200
6 · The paper itself

Abstract

Understanding enzymatic Diels-Alder (DA) reactions that can form complex natural product scaffolds is of considerable interest. Sch 210972 1, a potential anti-HIV fungal natural product, contains a decalin core that is proposed to form through a DA reaction. We identified the gene cluster responsible for the biosynthesis of 1 and heterologously reconstituted the biosynthetic pathway in Aspergillus nidulans to characterize the enzymes involved. Most notably, deletion of cghA resulted in a loss of stereoselective decalin core formation, yielding both an endo (1) and a diastereomeric exo adduct of the proposed DA reaction. Complementation with cghA restored the sole formation of 1. Density functional theory computation of the proposed DA reaction provided a plausible explanation of the observed pattern of product formation. Based on our study, we propose that lipocalin-like CghA is responsible for the stereoselective intramolecular [4+2] cycloaddition that forms the decalin core of 1.

Indexed as

Aspergillus nidulansCycloaddition ReactionFungal ProteinsLipocalinsMolecular ConformationNaphthalenesStereoisomerismThermodynamicsdecalinFungal ProteinsLipocalinsNaphthalenescycloadditiondecalindensity functional calculationsfungal metabolitetetramic acid

Identifiers

PMID26360642
PMCPMC4915928

What OpenQuestion holds

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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.