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Updated: Apr 10, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

Published on: September 28, 2022

Twisted amide electrophiles enable cyclic peptide sequencing.

Serge Zaretsky¹, Vishal Rai, Gerald Gish

¹Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON M5S 3H6, Canada. ayudin@chem.utoronto.ca.

Organic & Biomolecular Chemistry

|June 17, 2015

Summary

This summary is machine-generated.

New synthetic methods using aziridine amides enable peptide macrocyclization and downstream applications. These amides reduce unwanted biological interactions and allow for peptide sequencing via mass spectrometry.

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Area of Science:

Synthetic organic chemistry
Chemical biology
Mass spectrometry

Background:

Peptide macrocycles are important in drug discovery.
Current synthetic methods for macrocyclization often lack facile downstream applications.
Understanding and controlling interactions of synthetic molecules with biological systems is crucial.

Purpose of the Study:

To develop novel synthetic methodologies for peptide macrocyclization.
To engineer macrocyclic peptides with reduced non-specific biological interactions.
To enable facile downstream analysis of synthesized macrocycles, specifically peptide sequencing.

Main Methods:

Synthesis of novel peptide macrocycles incorporating aziridine amide functionalities.
Investigation of the stereoelectronic properties of aziridine amides within a macrocyclic context.
Exploration of the reactivity of aziridine amides under varying pH conditions.
Application of mass spectrometry for peptide sequencing of aziridine amide-containing macrocycles.

Main Results:

Aziridine amides exhibit stereoelectronic attenuation in macrocyclic environments, significantly reducing non-specific interactions with biological nucleophiles.
Electrophilic reactivity of aziridine amides is unmasked at high pH.
This pH-dependent reactivity enables efficient peptide sequencing using mass spectrometry.
Aziridine amide-containing macrocycles demonstrate broadened utility for downstream applications.

Conclusions:

Aziridine amides represent a versatile tool for designing peptide macrocycles with controlled biological interactions.
The developed method provides a pathway for facile peptide sequencing, enhancing the utility of macrocyclic libraries.
This research expands the toolkit for synthetic chemists and chemical biologists working with macrocyclic peptides.