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07:11
Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
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Cyclic and Lasso Peptides: Sequence Determination, Topology Analysis, and Rotaxane Formation
Hader E Elashal1, Ryan D Cohen2, Heidi E Elashal1
1Department of Chemistry and Biochemistry, Seton Hall University, South Orange, NJ, 07079, USA.
Angewandte Chemie (International Ed. in English)
|April 13, 2018
Summary
A new chemical method enables MS/MS sequencing of macrocyclic and lasso peptides, overcoming limitations of existing techniques. This breakthrough also facilitated the synthesis of novel peptide-based rotaxanes.
Area of Science:
- Chemical Biology
- Peptide Chemistry
- Drug Discovery
Background:
- Macrocyclic and lasso peptides show therapeutic potential but are challenging to sequence.
- Current sequencing methods like Edman degradation and enzymatic digestion are ineffective for these constrained peptides.
Purpose of the Study:
- To develop a broadly applicable chemical cleavage methodology for MS/MS sequencing of macrocyclic and lasso peptides.
- To utilize the new method for synthesizing unique peptide-based rotaxanes.
Main Methods:
- Development of a novel chemical cleavage strategy.
- Application of the cleavage method to macrocyclic and lasso peptides.
- Synthesis of peptide-based rotaxanes using the developed methodology.
Main Results:
- Successfully established a versatile chemical cleavage technique for challenging peptide structures.
- Demonstrated the method's efficacy in facilitating MS/MS sequencing.
- Synthesized a unique cyclic and threaded peptide-based rotaxane from benenodin-1 ΔC5.
Conclusions:
- The new chemical cleavage method significantly advances the sequencing of macrocyclic and lasso peptides.
- This methodology opens new avenues for therapeutic peptide development and complex molecular synthesis.
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