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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
Solid-phase total synthesis of cyclic decapeptide phakellistatin 12
Liaqat Ali1, Syed Ghulam Musharraf, Farzana Shaheen
1H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan.
Journal of Natural Products
|May 21, 2008
Summary
Scientists synthesized Pakellistatin 12, a novel cyclodecapeptide from marine sponges, demonstrating potent cancer cell growth inhibition. The synthetic compound matched the natural substance
Area of Science:
- Marine natural products chemistry
- Medicinal chemistry
- Synthetic organic chemistry
Background:
- Pakellistatin 12 is a cyclodecapeptide isolated from the marine sponge Phakellia sp.
- This compound exhibits significant cancer cell growth inhibitory properties.
Purpose of the Study:
- To achieve the first total synthesis of Pakellistatin 12.
- To confirm the structure and identity of the synthetic compound against the natural isolate.
Main Methods:
- Solid-phase peptide synthesis utilizing a safety-catch linker strategy.
- Analysis of the synthesized peptide's amino acid sequence using MALDI TOF/TOF mass spectrometry.
Main Results:
- Successful synthesis of Pakellistatin 12 was accomplished.
- The synthetic Pakellistatin 12 was found to be chemically and spectroscopically identical to the naturally occurring compound.
- The synthetic peptide retained the cancer cell growth inhibitory activity.
Conclusions:
- The total synthesis of Pakellistatin 12 provides a reliable method for obtaining this potent anticancer agent.
- The structural confirmation validates the synthetic approach and the identity of the natural product.
