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Updated: Apr 22, 2026
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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
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Facile method to sequence cyclic peptides/peptoids via one-pot ring-opening/cleavage reaction.
1Department of Chemistry, Pohang University of Science and Technology (POSTECH) , Pohang 790-784, South Korea.
Organic Letters
|October 14, 2014
Summary
A new method simplifies cyclic peptide sequencing. This approach uses a one-pot reaction to linearize peptides for efficient analysis by tandem mass spectrometry, aiding drug discovery.
Area of Science:
- Biochemistry
- Organic Chemistry
- Analytical Chemistry
Background:
- Cyclic peptides and peptoids are important biomolecules with diverse applications.
- Determining the sequence of cyclic peptides is challenging due to their constrained structures.
- Existing sequencing methods can be laborious and inefficient.
Purpose of the Study:
- To develop a facile and efficient method for the sequence determination of cyclic peptides and peptoids.
- To enable the analysis of macrocyclic peptides and peptoids with 3-10 residues.
Main Methods:
- Synthesis of thioether-embedded cyclic peptides/peptoids.
- One-pot reaction involving cyanogen bromide-mediated ring-opening and cleavage.
- Sequencing of linearized molecules using tandem mass spectrometry.
Main Results:
- Efficient synthesis of macrocyclic peptides/peptoids (3-10 residues) via thioether formation.
- Successful linearization of cyclic peptides/peptoids using a one-pot cyanogen bromide reaction.
- High efficiency in sequencing the linearized molecules by tandem mass spectrometry.
Conclusions:
- The described method provides a facile route for cyclic peptide and peptoid sequence determination.
- This technique simplifies the analysis of challenging macrocyclic structures.
- The method is suitable for peptides and peptoids ranging from 3 to 10 residues.
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