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Attempting to synthesize lasso peptides using high pressure.
Mateusz Waliczek1, Magdalena Wierzbicka1, Maciej Arkuszewski1
1Faculty of Chemistry, University of Wrocław, Wroclaw, Poland.
Plos One
|June 25, 2020
Summary
High pressure does not induce cyclization in lasso peptide precursors, unlike mechanically interlocked molecules. This study explored high-pressure synthesis for these unique threaded peptides, finding it ineffective for forming the lasso structure.
Area of Science:
- Biochemistry
- Organic Chemistry
- Peptide Science
Background:
- Lasso peptides feature a unique structure where the tail threads through a macrolactam ring.
- Recent discoveries have increased scientific interest in lasso peptides due to their unusual structure and biological activities.
- Microbial synthesis of lasso peptides is efficient, but chemical assembly remains challenging.
Purpose of the Study:
- To investigate the potential of high pressure to induce cyclization in linear lasso peptide precursors.
- To explore novel synthetic routes for challenging lasso peptide structures.
Main Methods:
- Investigated the effect of high pressure (up to 14,000 kbar) on linear precursors of lasso peptides.
- Compared the high-pressure response of lasso peptide precursors to other mechanically interlocked molecules like rotaxanes.
Main Results:
- High pressure, even up to 14,000 kbar, did not induce the formation of the threaded lasso peptide structure.
- Unlike rotaxanes, lasso peptides did not mechanically interlock or cyclize under high-pressure conditions.
Conclusions:
- High pressure is not a viable method for inducing the cyclization of lasso peptide precursors.
- The unique threaded structure of lasso peptides presents significant challenges for high-pressure chemical synthesis.
