Total synthesis and cyclization strategy of samoamide A, a cytotoxic cyclic octapeptide rich in proline and phenlalanine isolated from marine cyanobacterium.

Abstract

Samoamide A is a cyclic octapeptide rich in proline and phenylalanine residues isolated from an American Samoa marine cyanobacterium, which exhibits potent activity against H460 human non-small-cell lung cancer cells (IC50 of 1.1 μM). The first total synthesis of samoamide A was achieved by employing a strategy of a solid-phase peptide synthesis (SPPS) and a head-to-tail cyclization selecting free steric-hinrance connection sites. Then the final product was purified and identified. This strategy not only provides a basis in producing potent cytotoxic agents for drug discovery, but also provides a reference to the total synthesis of proline-rich peptides.

• Authors: Qi Chang, Yu-Lei Li, Xia Zhao
• Journal: Journal of Asian natural products research (J Asian Nat Prod Res) Vol. 21 Issue 2 Pg. 171-177 (Feb 2019) ISSN: 1477-2213 [Electronic] England
• PMID: 29671350 (Publication Type: Journal Article)

Chemical References

• Antineoplastic Agents
• Peptides, Cyclic
• samoamide A
• Phenylalanine
• Proline

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Aquatic Organisms
• Carcinoma, Non-Small-Cell Lung
• Cell Line, Tumor
• Cyanobacteria (chemistry)
• Humans
• Lung Neoplasms
• Molecular Structure
• Peptides, Cyclic (chemical synthesis, chemistry, pharmacology)
• Phenylalanine (chemistry)
• Proline (chemistry)