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Total Synthesis of Alloviroidin
Carol M Taylor1, Samuel K Kutty1, Benson J Edagwa1
1Department of Chemistry , Louisiana State University , Baton Rouge , Louisiana 70803 , United States.
Organic Letters
|March 13, 2019
Summary
Alloviroidin, a cyclic heptapeptide from Amanita mushrooms, was synthesized using a [3 + 4] fragment condensation. The study confirmed its structure and properties, aligning with natural alloviroidin.
Area of Science:
- Natural product chemistry
- Peptide synthesis
- Mycotoxicology
Background:
- Alloviroidin is a cyclic heptapeptide found in Amanita mushrooms.
- It exhibits high affinity for F-actin, similar to virotoxins and phallotoxins.
Purpose of the Study:
- To synthesize alloviroidin.
- To confirm the structure and properties of synthesized alloviroidin.
Main Methods:
- Solid-phase peptide synthesis using a [3 + 4] fragment condensation strategy.
- Global deprotection and High-Performance Liquid Chromatography (HPLC) purification.
- Nuclear Magnetic Resonance (NMR) spectroscopy for structural characterization.
Main Results:
- Successful synthesis of alloviroidin via fragment condensation.
- The linear heptapeptide adopted a turn conformation, facilitating cyclization.
- NMR spectra of the synthetic product were in excellent agreement with the natural product.
Conclusions:
- The synthetic route provides a reliable method for producing alloviroidin.
- The study validates the structure of alloviroidin and its characteristic properties.
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