Evidence map›Paper›PMID 29780547›Full record

ArticleChemical science2018

Protecting group free radical C-H trifluoromethylation of peptides.

Naoko Ichiishi, John P Caldwell, Melissa Lin, Wendy Zhong, Xiaohong Zhu, Eric Streckfuss, Hai-Young Kim, Craig A Parish, Shane W Krska

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 44 papers.

0numbers the graph read from it
0cells of the map it votes in
44citing 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

44 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Article
  5. Article
  6. Manganese-Catalyzed Electrochemical Diazidation of Dehydroalanine Peptides.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025
    Article
  7. Article
  8. C-H Labeling with [ACS central science · 2024
    Review
  9. Article
  10. Article
  11. Article
  12. Review
  13. Article
  14. Review
  15. Article
  16. Article
  17. Article
  18. Review
  19. Closing the gap betweenEJNMMI radiopharmacy and chemistry · 2021
    Review
  20. Organometallic AlaChem catalysis · 2021
    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.

Naoko IchiishiChemistry Capabilities and Screening , Merck Sharp & Dohme Corp. , Kenilworth , New Jersey 07033 , USA . Email: shane_krska@merck.com.
John P CaldwellKenilworth Discovery Chemistry , Merck Sharp & Dohme Corp. , Kenilworth , New Jersey 07033 , USA.
Melissa LinAnalytical Research & Development , Merck Sharp & Dohme Corp. , Rahway , NJ , USA.
Wendy ZhongAnalytical Research & Development , Merck Sharp & Dohme Corp. , Rahway , NJ , USA.
Xiaohong ZhuKenilworth Discovery Chemistry , Merck Sharp & Dohme Corp. , Kenilworth , New Jersey 07033 , USA.
Eric StreckfussWest Point Discovery Chemistry , Merck Sharp & Dohme Corp. , West Point , Pennsylvania 19486 , USA.
Hai-Young KimAnalytical Research & Development , Merck Sharp & Dohme Corp. , Rahway , NJ , USA.
Craig A ParishDiscovery Chemistry Modalities , Merck Sharp & Dohme Corp. , Kenilworth , New Jersey 07033 , USA . Email: craig_parish@merck.com.
Shane W KrskaChemistry Capabilities and Screening , Merck Sharp & Dohme Corp. , Kenilworth , New Jersey 07033 , USA . Email: shane_krska@merck.com.ORCID 0000-0001-9757-9036

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Two radical-based approaches have been developed to effect the trifluoromethylation of aryl C-H bonds in native peptides either using stoichiometric oxidant or visible light photoredox catalysis. The reported methods are able to derivatize tyrosine and tryptophan sidechains under biocompatible conditions, and a number of examples are reported involving fully unprotected peptides with up to 51 amino acids. The development of this chemistry adds to the growing array of chemical methods for selectively modifying amino acid residues in the context of complex peptides. The direct incorporation of trifluoromethyl groups into biopolymers enables the study of a range of biological and biochemical systems, and preliminary results indicate this method can be extended to the incorporation of other fluoroalkyl groups for bioconjugation applications.

Identifiers

PMID29780547
PMCPMC5941281

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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.