Evidence map›Paper›PMID 29081961›Full record

ArticleChemical science2017

Divergent unprotected peptide macrocyclisation by palladium-mediated cysteine arylation.

Anthony J Rojas, Chi Zhang, Ekaterina V Vinogradova, Nathan H Buchwald, John Reilly, Bradley L Pentelute, Stephen L Buchwald

Open access · diamondAbstract read
In one paragraph

Article in Chemical science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 43 papers.

0numbers the graph read from it
0cells of the map it votes in
43citing papers in PubMed
6.8field-weighted citation impact, top 2% of its field
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

43 citing papers in PubMed, 113 citations in OpenAlex.

  1. Article
  2. Article
  3. Review
  4. Article
  5. Review
  6. Review
  7. Fast Cysteine Bioconjugation Chemistry.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022
    Article
  8. Article
  9. Article
  10. Article
  11. Pd(II)-Mediated C-H Activation for Cysteine Bioconjugation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022
    Article
  12. Article
  13. Article
  14. Peptide stapling by late-stage Suzuki-Miyaura cross-coupling.Beilstein journal of organic chemistry · 2022
    Article
  15. Article
  16. Review
  17. Article
  18. Article
  19. DeaminativeChemical science · 2021
    Article
  20. 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

7 authors at 2 institutions in 3 countries.

Anthony J RojasDepartment of Chemistry , Massachusetts Institute of Technology , Cambridge , Massachusetts 02139 , USA . Email: blp@mit.edu ; Email: sbuchwal@mit.edu.ORCID 0000-0002-1975-7113
Chi ZhangDepartment of Chemistry , Massachusetts Institute of Technology , Cambridge , Massachusetts 02139 , USA . Email: blp@mit.edu ; Email: sbuchwal@mit.edu.ORCID 0000-0001-9519-7456
Ekaterina V VinogradovaDepartment of Chemistry , Massachusetts Institute of Technology , Cambridge , Massachusetts 02139 , USA . Email: blp@mit.edu ; Email: sbuchwal@mit.edu.
Nathan H BuchwaldDepartment of Chemistry , Massachusetts Institute of Technology , Cambridge , Massachusetts 02139 , USA . Email: blp@mit.edu ; Email: sbuchwal@mit.edu.
John ReillyNovartis , Novartis Institutes for Biomedical Research Inc. , Cambridge , Massachusetts 02139 , USA.
Bradley L PenteluteDepartment of Chemistry , Massachusetts Institute of Technology , Cambridge , Massachusetts 02139 , USA . Email: blp@mit.edu ; Email: sbuchwal@mit.edu.ORCID 0000-0002-7242-801X
Stephen L BuchwaldDepartment of Chemistry , Massachusetts Institute of Technology , Cambridge , Massachusetts 02139 , USA . Email: blp@mit.edu ; Email: sbuchwal@mit.edu.ORCID 0000-0003-3875-4775
Massachusetts Institute of Technology · USNovartis (Switzerland) · CH

Funding

TOXICOLOGY CORE UNITP30ES002109 · NIEHS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI LEVINE, STUART S · 1985 to 2020
$25.6M
Metal-Catalyzed Methods for Organic SynthesisR35GM122483 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI STEPHEN L BUCHWALD · 2017 to 2026
$11.4M
CATALYTIC METHODS FOR ORGANIC SYNTHESISR37GM046059 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI BUCHWALD, STEPHEN L · 2000 to 2009
$8.1M
EARLY TRANSITION METAL CATALYSTS IN ORGANIC SYNTHESISR01GM046059 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI BUCHWALD, STEPHEN L · 1992 to 2016
$5.4M
Acquisition of Octet Biolayer Interferometry system for MIT biophysics facilityS10OD016326 · OD · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI IMPERIALI, BARBARA · 2014 to 2014
$180k
NIEHS NIH HHS P30 ES002109NIGMS NIH HHS R01 GM046059NIGMS NIH HHS R35 GM122483NIGMS NIH HHS R37 GM046059NIH HHS S10 OD016326
6 · The paper itself

Abstract

Macrocyclic peptides are important therapeutic candidates due to their improved physicochemical properties in comparison to their linear counterparts. Here we detail a method for a divergent macrocyclisation of unprotected peptides by crosslinking two cysteine residues with bis-palladium organometallic reagents. These synthetic intermediates are prepared in a single step from commercially available aryl bis-halides. Two bioactive linear peptides with cysteine residues at

Identifiers

PMID29081961
PMCPMC5635729
OpenAlexW2599690337

What OpenQuestion holds

Textmetadata
LicenceCC BY-NC
Read underepoch 390

Registered trials

None linked

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.