Evidence map›Paper›PMID 28326777›Full record

ArticleJournal of the American Chemical Society2017

Peptide Macrocyclization Inspired by Non-Ribosomal Imine Natural Products.

Lara R Malins, Justine N deGruyter, Kevin J Robbins, Paul M Scola, Martin D Eastgate, M Reza Ghadiri, Phil S Baran

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.

0numbers the graph read from it
0cells of the map it votes in
31citing papers in PubMed
6.0field-weighted citation impact, top 3% 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

31 citing papers in PubMed, 125 citations in OpenAlex.

  1. Article
  2. Diverse thioether macrocyclized peptides through a radical SAM maturase.Proceedings of the National Academy of Sciences of the United States of America · 2025
    Article
  3. Pseudo-Ring Methodology to Control the Conformations of Macrocyclic Peptides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025
    Article
  4. Article
  5. Review
  6. Peptide macrocyclisationChemical science · 2024
    Article
  7. Article
  8. Article
  9. Article
  10. A Tag-Free Platform for Synthesis and Screening of Cyclic Peptide Libraries.Angewandte Chemie (International ed. in English) · 2024
    Article
  11. Article
  12. Review
  13. Article
  14. Article
  15. Article
  16. Article
  17. Review
  18. Article
  19. Review
  20. Ideality in Context: Motivations for Total Synthesis.Accounts of chemical research · 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

7 authors at 2 institutions in 1 country.

Lara R MalinsDepartment of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Justine N deGruyterDepartment of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.ORCID http://orcid.org/0000-0003-0465-8988
Kevin J RobbinsDepartment of Discovery Chemistry, Bristol-Myers Squibb Research and Development , 5 Research Parkway, Wallingford, Connecticut 06492, United States.
Paul M ScolaDepartment of Discovery Chemistry, Bristol-Myers Squibb Research and Development , 5 Research Parkway, Wallingford, Connecticut 06492, United States.
Martin D EastgateChemical Development, Bristol-Myers Squibb , One Squibb Drive, New Brunswick, New Jersey 08903, United States.
M Reza GhadiriDepartment of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Phil S BaranDepartment of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.ORCID http://orcid.org/0000-0001-9193-9053
Scripps Research Institute · USBristol-Myers Squibb (United States) · US

Funding

Scalable Synthesis and New Bond DisconnectionsR35GM118176 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI BARAN, PHIL S · 2016 to 2025
$11.5M
A C-H Functionalization Approach to Heterocyclic Amino Acids for Application in Drug DiscoveryF32GM117816 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI MALINS, LARA REBECCA · 2016 to 2017
$96k
NIGMS NIH HHS F32 GM117816NIGMS NIH HHS R35 GM118176
6 · The paper itself

Abstract

A thermodynamic approach to peptide macrocyclization inspired by the cyclization of non-ribosomal peptide aldehydes is presented. The method provides access to structurally diverse macrocycles by exploiting the reactivity of transient macrocyclic peptide imines toward inter- and intramolecular nucleophiles. Reactions are performed in aqueous media, in the absence of side chain protecting groups, and are tolerant of all proteinogenic functional groups. Macrocyclic products bearing non-native and rigidifying structural motifs, isotopic labels, and a variety of bioorthogonal handles are prepared, along with analogues of four distinct natural products. Structural interrogation of the linear and macrocyclic peptides using variable-temperature NMR and circular dichroism suggests that preorganization of linear substrates is not a prerequisite for macrocyclization.

Identifiers

PMID28326777
PMCPMC5391502
OpenAlexW2598535577

What OpenQuestion holds

Textmetadata
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.