JOURNAL 386


Records of Natural Products
VOLUME & ISSUE
Year: 2016 Issue: 4 July-August
PAGES
p.397 - 406
STATISTICS
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AUTHORS
    Farzana Shaheen, Muhammad Asad Ziaee, Syed Abid Ali, Shabana U. Simjee, Aqeel Ahmed and M. Iqbal Choudhary
PDF OF ARTICLE

GRAPHICAL ABSTRACT


ABSTRACT


 Phakellistatin 15 (1) is a cyclic octapeptide, containing three proline moieties, all in the trans form. It is a constituent of South China Sea sponge Phakella fusca and reported to have antitumor activity. This study describes the first solid-phase total synthesis of peptide 1 by using Kenner's N-acyl sulfonamide "safety-catch" linker. The structural analysis of peptide 1 was performed by mass, NMR and CD studies. The spectral data of synthetic peptide 1 was found to be identical to that reported for natural peptide. However, the synthetic peptide was found to be inactive on human glioblastoma (U-87), pancreatic cancer (PSN-1) and human non-small cell lung cancer (NCI-H460) cells.

KEYWORDS
  • Cyclic peptide
  • phakellistatin
  • solid-phase synthesis
  • safety-catch linker

SUPPORTING INFORMATION


Supporting Information
Download File 50-RNP-1503-049-SI.pdf (708.26 KB)