Abstract
The total synthesis of PF1171B, D, and E, and avellanins A, B, and C, which are cyclic pentapeptides containing non-proteinogenic amino acid residues, was achieved by solid-phase peptide elongation and solution-phase macrolactamization. PF1171B and D and avellanins A and C were found to inhibit apolipoprotein B production in Hep G2 cells without exhibiting cytotoxicity. PF1171B had the most potent inhibitory activity against apolipoprotein B production. The synthesis and bioactivity evaluation of the enantiomer and a linear analog of PF1171B suggested its essential structural features.
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