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Updated: Mar 3, 2026
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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
Published on: August 1, 2018
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Dual In-Tether Chiral Centers Modulate Peptide Helicity.
Kuan Hu1, Chengjie Sun1, Mengying Yu1
1School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Shenzhen, Guangdong 518055, China.
Bioconjugate Chemistry
|April 27, 2017
Summary
Chemical modification of peptide cross-linkers enhances peptide properties. Dual chiral centers induce helical conformations, allowing for structural control and modification without disrupting secondary structures.
Area of Science:
- Peptide chemistry
- Organic chemistry
- Biophysical chemistry
Background:
- Chemical modification of peptides is crucial for enhancing their properties.
- Controlling peptide secondary structures, like helices, is vital for function.
- Peptide cross-linking offers a site for modification but can disrupt structure.
Purpose of the Study:
- To investigate the correlation between dual in-tether chiral centers and peptide secondary structures.
- To develop a strategy for facile chemical modification of peptides without structural disruption.
- To utilize a minimalistic pentapeptide model for structure-property relationship studies.
Main Methods:
- Synthesizing peptides with dual in-tether chiral centers.
- Employing synergistic effects of chiral centers to induce helical conformations.
- Utilizing a pentapeptide model to analyze the impact of absolute configurations on secondary structures.
Main Results:
- Dual in-tether chiral centers effectively constrained peptides into helical conformations.
- A clear correlation was established between the absolute configurations of chiral centers and peptide secondary structures.
- The strategy provided an accessible on-tether modification site that preserved the peptide's secondary structure.
Conclusions:
- Dual in-tether chiral centers are effective in inducing and controlling peptide helical conformations.
- This approach enables site-specific chemical modification of peptides without compromising secondary structure integrity.
- The findings offer a valuable strategy for designing peptides with improved physicochemical properties and tailored structures.
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