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Phakellistatin peptides from marine organisms are the sources of proline-rich cyclic peptides with reported significant antitumor activities. Phakellistatin 18 ( 1 ), reported from marine sponge  Phakellia fusca , contains three proline-peptide linkages in  cis  form. We attempted the total synthesis of natural product  1  through solution-phase macrocyclization approach, as a result, the synthetic cyclic peptide  2  was obtained as a rotamer of natural product having all three proline residues in  trans -conformation. Here, we describe the synthesis, structural, and cytotoxicity studies of  trans -Phakellistatin 18 ( 2 ), and its analog [Ala 1,3,6 ]-Phakellistatin 18 ( 3 ). Detailed NMR studies were carried out to characterize the synthesized peptides, and anti-cancer screening was performed by using MTT assay. The synthetic  trans -Phakellistatin 18 ( 2 ) (IC 50 =67.5 ± 2.938 µM) showed comparable cytotoxicity against HepG2 cancer cell line with standard drug doxorubicin (IC 50 =63.88 ± 6.48 µM). Here, the first synthetic and structural studies on  trans -Phakellistatin 18 ( 2 ), and its anticancer screening against HepG2 cell line was reported.

First report on the synthesis and structural studies of trans -Phakellistatin 18: a rotamer of marine natural product phakellistatin 18