Evidence map›Paper›PMID 38559303›Full record

ArticleACS central science2024

Substrate-Selective Catalysis Enabled Synthesis of Azaphilone Natural Products.

Ye Wang, Katherine J Torma, Joshua B Pyser, Paul M Zimmerman, Alison R H Narayan

Open access · diamondAbstract read
In one paragraph

Article in ACS central science, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.

0numbers the graph read from it
0cells of the map it votes in
5citing papers in PubMed
2.0field-weighted citation impact, top 15% 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

5 citing papers in PubMed, 8 citations in OpenAlex.

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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

5 authors at 1 institution in 1 country.

Ye WangLife Sciences Institute, Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.ORCID https://orcid.org/0000-0001-8285-8657
Katherine J TormaLife Sciences Institute, Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.
Joshua B PyserLife Sciences Institute, Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.ORCID https://orcid.org/0000-0003-2884-5112
Paul M ZimmermanLife Sciences Institute, Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.ORCID https://orcid.org/0000-0002-7444-1314
Alison R H NarayanLife Sciences Institute, Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, United States.ORCID https://orcid.org/0000-0001-8290-0077
University of Michigan · US

Funding

Undergrad Supplement: Expanding the synthetic utility of natural product biosynthetic enzymesR35GM124880 · NIGMS · UNIVERSITY OF MICHIGAN AT ANN ARBOR · PI Alison Narayan · 2017 to 2026
$4.5M
NIGMS NIH HHS R35 GM124880
6 · The paper itself

Abstract

Achieving substrate-selectivity is a central element of nature's approach to synthesis. By relying on the ability of a catalyst to discriminate between components in a mixture, control can be exerted over which molecules will move forward in a synthesis. This approach can be powerful when realized but can be challenging to duplicate in the laboratory. In this work, substrate-selective catalysis is leveraged to discriminate between two intermediates that exist in equilibrium, subsequently directing the final cyclization to arrive at either the linear or angular tricyclic core common to subsets of azaphilone natural products. By using a flavin-dependent monooxygenase (FDMO) in sequence with an acyl transferase (AT), the conversion of several orcinaldehyde substrates directly to the corresponding linear tricyclic azaphilones in a single reaction vessel was achieved. Further, mechanistic studies support that a substrate equilibrium together with enzyme substrate selectivity play an import role in the selectivity of the final cyclization step. Using this strategy, five azaphilone natural products were synthesized for the first time as well as a number of unnatural derivatives thereof.

Identifiers

PMID38559303
PMCPMC10979483
OpenAlexW4392296798

What OpenQuestion holds

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LicenceCC BY
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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.