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Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.
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Indirect-acting cholinergic agonists are agents that interact with the acetylcholinesterase enzyme in the synaptic cleft, preventing the breakdown of acetylcholine into choline and acetate. Consequently, the concentration of acetylcholine in the synaptic cleft increases. These agonists can be classified into reversible and irreversible inhibitors based on their duration of action.
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Related Experiment Video

Updated: Nov 17, 2025

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
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Solid-phase synthesis and bioactivity evaluation of cherimolacyclopeptide E.

Yuka Yoshida1, Minoru Inagaki1, Yuichi Masuda1

  • 1Graduate School of Bioresources, Mie University, Tsu, Japan.

Journal of Peptide Science : an Official Publication of the European Peptide Society
|February 15, 2021
PubMed
Summary

Total synthesis confirmed the structure of cherimolacyclopeptide E, a cyclic hexapeptide from Annona cherimola. However, synthetic peptide 1 showed significantly lower cytotoxicity and antibacterial activity than previously reported.

Keywords:
Annona cherimolacyclic peptidescytotoxicitysolid-phase synthesis

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Area of Science:

  • Natural Product Chemistry
  • Synthetic Organic Chemistry
  • Medicinal Chemistry

Background:

  • Cherimolacylopeptide E (1) is a cyclic hexapeptide isolated from Annona cherimola seeds.
  • Previous reports indicated potent cytotoxicity of peptide 1 against KB cells (IC50 0.017 μM).

Purpose of the Study:

  • To confirm the proposed structure of cherimolacyclopeptide E through total synthesis.
  • To re-evaluate the bioactivity, specifically cytotoxicity and antibacterial effects, of synthetic cherimolacyclopeptide E.

Main Methods:

  • Solid-phase peptide elongation using Fmoc/OAll-protected amino acids on 2-Cl-trityl resin.
  • Macrocyclization and subsequent structural confirmation via NMR analysis.
  • Cytotoxicity assays against KB cells and antibacterial assays against Escherichia coli.

Main Results:

  • The total synthesis successfully yielded cherimolacyclopeptide E, confirming its structure.
  • Synthetic peptide 1 exhibited two conformations in pyridine-d5, with the major conformer matching natural peptide 1's spectroscopic data.
  • Synthetic cherimolacyclopeptide E demonstrated significantly reduced cytotoxicity (IC50 > 100 μM) compared to prior reports.
  • Antibacterial activity against Escherichia coli was found to be minimal.

Conclusions:

  • The structure of cherimolacyclopeptide E was confirmed via total synthesis.
  • The bioactivity of synthetic cherimolacyclopeptide E, particularly its cytotoxicity, is considerably lower than previously documented.
  • Discrepancies in reported bioactivity highlight the importance of independent synthesis and verification in natural product research.