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The First Solid-phase Synthesis and Structural Studies on Phakellistatin 15 Farzana Shaheen, Muhammad Asad Ziaee, Syed Abid Ali, Shabana U. Simjee, Aqeel Ahmed and M. Iqbal Choudhary H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan Dr. Panjwani Center for Molecular Medicine and Drug Research,, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan Department of Biochemistry, Faculty of Science, King Abdulaziz University, Jeddah-21412, Saudi Arabia 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. © 2016 ACG Publications. All rights reserved.
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