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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

Light-responsive bicyclic peptides.

Mohammad R Jafari¹, Hongtao Yu, Jessica M Wickware

¹Department of Chemistry, University of Alberta, Edmonton, AB T6G2G2, Canada. ratmir@ualberta.ca.

Organic & Biomolecular Chemistry

|August 2, 2018

Summary

This summary is machine-generated.

Researchers developed a novel light-responsive (LR) linker to synthesize bicyclic peptides. This method enables reversible control over peptide function using visible light, advancing photopharmacology and optochemical genetics.

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Area of Science:

Chemical Synthesis
Biotechnology
Molecular Engineering

Background:

Light-responsive (LR) molecules, including small molecules, peptide macrocycles, and protein conjugates, are crucial for photopharmacology and optochemical genetics.
Bicyclic peptides offer enhanced binding and stability compared to monocyclic peptides, but their light-responsive design is challenging.
Existing methods for creating LR bicyclic architectures are limited, necessitating new synthetic strategies.

Purpose of the Study:

To develop a novel method for synthesizing light-responsive (LR) bicyclic peptides.
To create a versatile linker enabling the construction of bicyclic peptides with light-controlled conformational changes.
To establish a scalable synthetic route for producing these advanced peptide architectures.

Main Methods:

Development of a tridentate C2-symmetric hydroxyl amine and di-chlorobenzene containing azobenzene (HADCAz) LR-linker.
Utilized orthogonally reactive functionalities (chlorobenzyl and hydroxylamine) for a one-pot, two-step conversion of linear peptides to bicyclic peptides.
Demonstrated linker application in synthesizing bicyclic peptides with varying loop lengths (2-5 amino acids) and light-induced isomerization (trans to cis) using blue light (365 nm).

Main Results:

Successful synthesis of light-responsive bicyclic peptides from linear peptides using the HADCAz linker.
The HADCAz linker enables reversible isomerization upon blue light irradiation, modulating peptide conformation.
A scalable synthetic route for the HADCAz linker was established, facilitating its application in diverse peptide designs.

Conclusions:

The developed HADCAz linker provides a robust and scalable method for constructing light-responsive bicyclic peptides.
This approach expands the toolkit for designing advanced peptide-based therapeutics and molecular tools.
The ability to control peptide conformation with light opens new avenues in drug delivery and molecular sensing.