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Tuning Peptide Structure and Function through Fluorobenzene Stapling.

Niklas H Fischer¹, Erik Fumi¹, Maria Teresa Oliveira¹

¹Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100, Copenhagen, Denmark.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|December 13, 2021

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A new catalyst-free method enables precise control over cyclic peptide macrocycle structure. This technique fine-tunes peptide secondary structures and biological activity for targeted therapeutic development.

Area of Science:

Medicinal Chemistry
Organic Chemistry
Biochemistry

Background:

Cyclic peptides offer enhanced stability and activity as next-generation therapeutics.
Developing methods for controlled synthesis of cyclic peptides is crucial for drug discovery.

Purpose of the Study:

To develop a catalyst-free method for synthesizing cyclic peptides.
To demonstrate the ability to fine-tune macrocycle structure and peptide properties.
To apply the method to generate potential agonists for melanocortin receptors.

Main Methods:

A catalyst-free stapling reaction using fluorobenzene linkers on cysteine-containing peptides.
On-resin synthesis of stapled peptides for convenience.
Characterization using NMR spectroscopy and circular dichroism.

Keywords:

SNAr cyclization fluorobenzenes melanocortin peptide stapling

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Application to synthesize ligands for melanocortin receptors.

Main Results:

Successful catalyst-free stapling of unprotected peptides and on-resin.
Demonstrated tuning of peptide secondary structures by varying linker regioisomers.
Generated a library of macrocyclic ligands with varying thioether relationships (ortho, meta, para).
Showcased facile fine-tuning of potency and efficacy towards biological targets.

Conclusions:

The developed method provides facile control over cyclic peptide macrocycle formation.
This technique allows for the fine-tuning of secondary structures and biological activity.
The approach is valuable for optimizing cyclic peptides as therapeutics, exemplified by melanocortin receptor agonists.