Evidence map›Paper›PMID 34297552›Full record

ArticleJournal of the American Chemical Society2021

Mechanisms and Dynamics of Synthetic and Biosynthetic Formation of Delitschiapyrones: Solvent Control of Ambimodal Periselectivity.

Yike Zou, K N Houk

Open access · greenAbstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing papers in PubMed
2.9field-weighted citation impact, top 10% 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

2 citing papers in PubMed, 24 citations in OpenAlex.

  1. Article
  2. 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

2 authors at 1 institution in 1 country.

Yike ZouDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.ORCID 0000-0003-4380-7827
K N HoukDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.ORCID 0000-0002-8387-5261
University of California, Los Angeles · US

Funding

Steroselectivity of Synthetically Valuable Enzyme CatalystsR01GM124480 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI HOUK, KENDALL N · 2018 to 2021
$1.1M
NIGMS NIH HHS R01 GM124480
6 · The paper itself

Abstract

The mechanism and dynamics for the formation of the delitschiapyrone family of natural products are studied by density functional theory (DFT) calculations and quasiclassical molecular dynamics simulations with DFT and xTB. In the uncatalyzed reaction, delitschiapyrones A and B are formed by Diels-Alder reactions through a single transition state and a post-transition state bifurcation that favors formation of delitschiapyrone B. In water and most likely in the enzyme, the acidic hydroxyquinone ionizes, and the resulting conjugate base undergoes cycloaddition preferentially to delitschiapyrone A. We demonstrate a new type of biosynthetic transformation and variable selectivity from a (4 + 2)/(4 + 3) ambimodal transition state.

Indexed as

Biological ProductsNaphthalenesPyronesTolueneWaterCycloaddition ReactionDensity Functional TheoryMolecular Dynamics SimulationMolecular StructureSolventsBiological Productsdelitschiapyrone ANaphthalenesPyronesSolventsTolueneWater

Identifiers

PMID34297552
PMCPMC9307257
OpenAlexW3183738503

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.