Evidence map›Paper›PMID 42038488›Full record

ArticleACS central science2026

Propellane Alkaloid Biosynthesis and Total Synthesis via Interrupted Reaction Pathways.

John M Billingsley, Jiaming Ding, Allison T Hands, Kanji Niwa, Nathan J Adamson, Lukas A Wein, Bruno Perlatti, Neil K Garg, Yi Tang

Erratum issuedAbstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in ACS central science, 2026. 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 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing 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

1 citing paper in PubMed.

  1. Article
4 · The record

Corrections and comments

5 · Who and what money

Authors and funding

9 authors.

John M BillingsleyDepartment of Chemical and Biomolecular Engineering, University of California, Los Angeles, California 90095, United States.ORCID https://orcid.org/0000-0001-9300-9378
Jiaming DingDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
Allison T HandsDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
Kanji NiwaDepartment of Chemical and Biomolecular Engineering, University of California, Los Angeles, California 90095, United States.
Nathan J AdamsonDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
Lukas A WeinDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
Bruno PerlattiDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
Neil K GargDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.ORCID https://orcid.org/0000-0002-7793-2629
Yi TangDepartment of Chemical and Biomolecular Engineering, University of California, Los Angeles, California 90095, United States.ORCID https://orcid.org/0000-0003-1597-0141

Funding

MIRA: Enzymology and Self-Resistance of Natural Product BiosynthesisR35GM118056 · NIGMS · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI Yi Tang · 2016 to 2026
$6.1M
NMR Console and Prodigy CryoProbeS10OD028644 · OD · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI GARG, NEIL K · 2021 to 2021
$600k
Time-of-Flight Mass Spectrometer for Synthesis Supporting Biomedical ResearchS10RR025631 · NCRR · UNIVERSITY OF CALIFORNIA LOS ANGELES · PI HOUK, KENDALL N · 2009 to 2009
$328k
NCRR NIH HHS S10 RR025631NIGMS NIH HHS R35 GM118056NIH HHS S10 OD028644
6 · The paper itself

Abstract

Interrupted reactions, in which an intermediate is redirected from its conventional mechanistic pathway, offer a unique approach to the assembly of complex natural products. This study details the biosynthesis of a newly discovered family of alkaloids named the subrubines alongside the total synthesis of the penultimate member, pensubrubine, featuring distinct interrupted reaction pathways. These natural products, identified using high-resolution genome mining of an active site mutation, represent the only reported microbial diaza[3.3.3]-propellane pyrrolidinoindolines. We demonstrate through complete pathway reconstitution that the putatively annotated ene-reductase SubF functions as the propellane synthase that directs an enolate intermediate toward an intramolecular Mannich cyclization. Concurrently, a concise 7-step total synthesis of pensubrubine was developed, employing a diastereoselective interrupted Fischer indolization reaction to rapidly construct the diaza[3.3.3]-propellane core and establish the absolute configuration of pensubrubine. The reported bio- and total syntheses of subrubines showcase the value of interrupted pathways in assembling complex scaffolds.

Identifiers

PMID42038488
PMCPMC13107220

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.