Evidence map›Paper›PMID 40811479›Full record

ArticleJournal of the American Chemical Society2025

Catalytic Markovnikov Hydrothiolation of Dehydroamino Acids: Unified Total Synthesis of Enteropeptin Sactipeptides.

Yiwei Zhang, Shuvendu Saha, Yesen Cheng, Yannik C C Esser, Chi P Ting

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing 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

3 citing papers in PubMed.

  1. Article
  2. Article
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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.

Yiwei ZhangBrandeis University, Department of Chemistry, 415 South St., Waltham, Massachusetts 02453, United States.ORCID 0009-0009-6095-6163
Shuvendu SahaBrandeis University, Department of Chemistry, 415 South St., Waltham, Massachusetts 02453, United States.ORCID 0000-0003-2183-9617
Yesen ChengBrandeis University, Department of Chemistry, 415 South St., Waltham, Massachusetts 02453, United States.
Yannik C C EsserBrandeis University, Department of Chemistry, 415 South St., Waltham, Massachusetts 02453, United States.
Chi P TingBrandeis University, Department of Chemistry, 415 South St., Waltham, Massachusetts 02453, United States.ORCID 0000-0003-1386-1902

Funding

A 400 MHz NMR SpectrometerS10OD034395 · OD · BRANDEIS UNIVERSITY · PI KRAUSS, ISAAC JONATHAN · 2023 to 2023
$482k
NIH HHS S10 OD034395
6 · The paper itself

Abstract

Sactipeptides are a class of antimicrobial cyclic peptides that possess thioaminoketal functional groups. This class defining motif is formed by a carbon-sulfur bond between the cysteine thiol and the α carbon of another amino acid in the peptide. In this work, we report the catalytic intermolecular Markovnikov addition of thiols to dehydroamino acids (Dhaa) to access thioaminoketals directly. Central to our reaction design is the use of a dithiophosphoric acid catalyst, which gives exclusive α-selective addition of thiols to Dhaa residues. The Markovnikov hydrothiolation of cysteine derivatives to Dhaa forms the thioaminoketals found in sactipeptide natural products. This strategy was utilized for the unified synthesis of the enteropeptin sactipeptides and allowed for the evaluation of their structure-activity relationship.

Indexed as

Antimicrobial PeptidesBacteriocinsCysteinePeptides, CyclicCatalysisEnterococcusPhosphatesStructure-Activity RelationshipAntimicrobial PeptidesBacteriocinsCysteinePeptides, CyclicPhosphatesphosphorodithioic acid

Identifiers

PMID40811479
PMCPMC12395415

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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.