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An optimal hydrogen-bond surrogate for α-helices
Stephen T Joy1, Paramjit S Arora1
1Department of Chemistry, New York University, New York, NY 10003, USA. arora@nyu.edu.
Chemical Communications (Cambridge, England)
|April 6, 2016
Summary
Replacing peptide hydrogen bonds with covalent bonds stabilizes alpha-helices. This study explores alkene isosteres for mimicking these bonds and enhancing helical stability in various peptide sequences.
Area of Science:
- Biochemistry
- Organic Chemistry
- Structural Biology
Background:
- Alpha-helices are crucial secondary structures in peptides.
- Intramolecular hydrogen bonds stabilize the alpha-helical conformation.
- Replacing hydrogen bonds with covalent bonds offers a novel stabilization strategy.
Purpose of the Study:
- To investigate the potential of alkene isosteres.
- To mimic intramolecular hydrogen bonds in peptides.
- To stabilize alpha-helical structures using covalent modifications.
Main Methods:
- Synthesis of peptides containing alkene isosteres.
- Spectroscopic analysis to confirm structure.
- Circular dichroism to assess helical content.
Main Results:
- Alkene isosteres successfully mimic hydrogen bonds.
- Stabilization of alpha-helical conformation was observed.
- Effectiveness varied with different alkene types and peptide sequences.
Conclusions:
- Alkene isosteres are viable alternatives to hydrogen bonds for stabilizing alpha-helices.
- This approach provides a tool for designing stable peptide structures.
- Further research can explore applications in peptide-based therapeutics.
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