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A Sulfonium Triggered Thiol-yne Reaction for Cysteine Modification
Zhanfeng Hou1,2, Dongyuan Wang1,3, Yang Li1
1State Key Laboratory of Chemical Oncogenomics, School of Chemical Biology and Biotechnology , Peking University Shenzhen Graduate School , Shenzhen , 518055 , China.
The Journal of Organic Chemistry
|January 4, 2020
Summary
A new thiol-yne reaction using sulfonium centers enables facile peptide modification. This method creates stable cyclic peptides and versatile probes for cysteine-containing biomolecules.
Area of Science:
- Organic Chemistry
- Biochemistry
- Chemical Biology
Background:
- Thiol-yne reactions are valuable for bioconjugation.
- Sulfonium chemistry offers unique reactivity.
- Peptide cyclization enhances stability and cellular uptake.
Purpose of the Study:
- To develop a novel, facile thiol-yne reaction triggered by a sulfonium center.
- To apply this reaction for the synthesis of cyclic peptides.
- To explore the use of propargylated sulfoniums as probes for biomolecules.
Main Methods:
- Propargylation of thioethers to form sulfonium intermediates.
- Facile addition of thiols to sulfoniums in aqueous media at ambient temperature.
- Application in unprotected peptides containing methionine and cysteine residues.
Main Results:
- Demonstrated a facile thiol-yne type reaction initiated by a sulfonium center.
- Successfully synthesized cyclic peptides with enhanced stability and glutathione resistance.
- Achieved increased cellular uptake of the modified peptides.
- Showcased the potential of propargylated sulfoniums as versatile probes.
Conclusions:
- The developed sulfonium-centered thiol-yne reaction provides an efficient method for peptide modification.
- This approach facilitates the construction of robust cyclic peptides with improved biological properties.
- Propargylated sulfoniums represent promising tools for targeting cysteine-containing biomolecules.
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