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310-Helix stabilization and screw sense control via stereochemically configured 4-atom hydrocarbon staples
Duc V H Tran1, Ha T N Nguyen1, Hee-Chul Ahn1
1College of Pharmacy, Dongguk University-Seoul, Goyang 10326, Republic of Korea; Intergrated Research Institute for Drug Development, College of Pharmacy, Dongguk University-Seoul, Goyang 10326, Republic of Korea.
Bioorganic & Medicinal Chemistry
|October 25, 2024
Summary
Stabilizing 310-helices in peptides is challenging. This study shows 4-atom hydrocarbon staples, particularly the Ri,i+3S(4) configuration, effectively stabilize these structures and control their handedness.
Area of Science:
- Biochemistry
- Peptide Chemistry
- Structural Biology
Background:
- The 310-helix is a key protein secondary structure involved in protein interactions.
- Stabilizing 310-helices in peptides is difficult but crucial for biological applications.
Purpose of the Study:
- To investigate the use of 4-atom hydrocarbon staples for stabilizing 310-helices in peptides.
- To determine the role of staple configuration in helix stabilization and screw sense control.
Main Methods:
- Peptide synthesis utilizing ring-closing metathesis.
- Circular dichroism (CD) spectroscopy to analyze secondary structure.
- Employing Ri,i+3S(4) staples with specific stereochemistry.
Main Results:
- The configuration of the 4-atom hydrocarbon staple critically influences 310-helix stabilization and screw sense.
- The Ri,i+3S(4) staple strongly induces right-handed 310-helices, particularly in l-amino acid sequences.
- Multiple staples effectively stabilized longer peptide chains.
Conclusions:
- 4-atom hydrocarbon staples are effective tools for stabilizing 310-helices.
- Staple configuration dictates helix handedness, offering precise structural control.
- This method holds promise for peptide therapeutics and biomolecular engineering.
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