Evidence map›Paper›PMID 29629104›Full record

ArticleChemical science2018

Epimerization-free access to C-terminal cysteine peptide acids, carboxamides, secondary amides, and esters

Christine A Arbour, Thilini D Kondasinghe, Hasina Y Saraha, Teanna L Vorlicek, Jennifer L Stockdill

Abstract read
In one paragraph

Article in Chemical science, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.

0numbers the graph read from it
0cells of the map it votes in
9citing 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

9 citing papers in PubMed.

  1. Review
  2. Review on the o-Aminoaniline Moiety in Peptide and Protein Chemistry.Chembiochem : a European journal of chemical biology · 2025
    Review
  3. Safety-Catch Linkers for Solid-Phase Peptide Synthesis.Molecules (Basel, Switzerland) · 2024
    Review
  4. Epimerisation in Peptide Synthesis.Molecules (Basel, Switzerland) · 2023
    Review
  5. A versatileChemical science · 2022
    Article
  6. Review
  7. Article
  8. Directed C(spChemical science · 2019
    Article
  9. 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

5 authors.

Christine A ArbourWayne State University , Department of Chemistry , Detroit , MI , USA 48202 . Email: stockdill@wayne.edu.ORCID 0000-0001-6056-296X
Thilini D KondasingheWayne State University , Department of Chemistry , Detroit , MI , USA 48202 . Email: stockdill@wayne.edu.
Hasina Y SarahaWayne State University , Department of Chemistry , Detroit , MI , USA 48202 . Email: stockdill@wayne.edu.
Teanna L VorlicekWayne State University , Department of Chemistry , Detroit , MI , USA 48202 . Email: stockdill@wayne.edu.
Jennifer L StockdillWayne State University , Department of Chemistry , Detroit , MI , USA 48202 . Email: stockdill@wayne.edu.ORCID 0000-0003-4238-6530

Funding

C-N Bond-Forming Methodologies for the Synthesis of Small Molecules and PeptidesR00GM097095 · NIGMS · WAYNE STATE UNIVERSITY · PI STOCKDILL, JENNIFER LYNN · 2012 to 2014
$837k
NIGMS NIH HHS R00 GM097095
6 · The paper itself

Abstract

C-Terminal cysteine peptide acids are difficult to access without epimerization of the cysteine α-stereocenter. Diversification of the C-terminus after solid-phase peptide synthesis poses an even greater challenge because of the proclivity of the cysteine α-stereocenter to undergo deprotonation upon activation of the C-terminal carboxylic acid. We present herein two general strategies to access C-terminal cysteine peptide derivatives without detectable epimerization, diketopiperazine formation, or piperidinylalanine side products.

Identifiers

PMID29629104
PMCPMC5868297

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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.