Evidence map›Paper›PMID 29861887›Full record

ArticleChemical science2015

Mechanistic investigation of aziridine aldehyde-driven peptide macrocyclization: the imidoanhydride pathway.

Serge Zaretsky, Jennifer L Hickey, Joanne Tan, Dmitry Pichugin, Megan A St Denis, Spencer Ler, Benjamin K W Chung, Conor C G Scully, Andrei K Yudin

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Chemical science, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.

0numbers the graph read from it
0cells of the map it votes in
6citing 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

6 citing papers in PubMed.

  1. Article
  2. Article
  3. Review
  4. Article
  5. Article
  6. Article
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

9 authors.

Serge ZaretskyDavenport Research Laboratories , Department of Chemistry , University of Toronto , 80 St. George Street , Toronto , Ontario M5S 3H6 , Canada . Email: ayudin@chem.utoronto.ca.
Jennifer L HickeyDavenport Research Laboratories , Department of Chemistry , University of Toronto , 80 St. George Street , Toronto , Ontario M5S 3H6 , Canada . Email: ayudin@chem.utoronto.ca.
Joanne TanDavenport Research Laboratories , Department of Chemistry , University of Toronto , 80 St. George Street , Toronto , Ontario M5S 3H6 , Canada . Email: ayudin@chem.utoronto.ca.
Dmitry PichuginCenter for Structural Investigations of Complex Organic Molecules and Polymers , Department of Chemistry , University of Toronto , 80 St. George Street , Toronto , Ontario M5S 3H6 , Canada.
Megan A St DenisDavenport Research Laboratories , Department of Chemistry , University of Toronto , 80 St. George Street , Toronto , Ontario M5S 3H6 , Canada . Email: ayudin@chem.utoronto.ca.
Spencer LerDavenport Research Laboratories , Department of Chemistry , University of Toronto , 80 St. George Street , Toronto , Ontario M5S 3H6 , Canada . Email: ayudin@chem.utoronto.ca.
Benjamin K W ChungDavenport Research Laboratories , Department of Chemistry , University of Toronto , 80 St. George Street , Toronto , Ontario M5S 3H6 , Canada . Email: ayudin@chem.utoronto.ca.
Conor C G ScullyDavenport Research Laboratories , Department of Chemistry , University of Toronto , 80 St. George Street , Toronto , Ontario M5S 3H6 , Canada . Email: ayudin@chem.utoronto.ca.
Andrei K YudinDavenport Research Laboratories , Department of Chemistry , University of Toronto , 80 St. George Street , Toronto , Ontario M5S 3H6 , Canada . Email: ayudin@chem.utoronto.ca.

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Aziridine aldehyde dimers, peptides, and isocyanides participate in a multicomponent reaction to yield peptide macrocycles. We have investigated the selectivity and kinetics of this process and performed a detailed analysis of its chemoselectivity. While the reactants encompass all of the elements of the traditional Ugi four-component condensation, there is a significant deviation from the previously proposed mechanism. Our results provide evidence for an imidoanhydride pathway in peptide macrocyclization and lend justification for the diastereoselectivity and high effective molarity observed in the reaction.

Identifiers

PMID29861887
PMCPMC5949604

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.