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  • Title: Topochemical exploration of potent compounds using retro-enantiomer libraries of cyclic pentapeptides.
    Author: Tamamura H, Mizumoto M, Hiramatsu K, Kusano S, Terakubo S, Yamamoto N, Trent JO, Wang Z, Peiper SC, Nakashima H, Otaka A, Fujii N.
    Journal: Org Biomol Chem; 2004 Apr 21; 2(8):1255-7. PubMed ID: 15064805.
    Abstract:
    Cyclic pentapeptides have been adopted as conformationally restricted peptide templates to dispose pharmacophores of bioactive peptides. In our recent study, use of two orthogonal cyclic pentapeptide libraries involving conformation-based and sequence-based libraries containing critical residues of a bioactive peptide led to the discovery of potent downsized peptides that possess activity comparable to that of the parent peptide. The present study demonstrates that a third library consisting of retro-enantiomers (retro-inverso peptides) that possess not only all residues with the opposite configuration to those in the corresponding original peptide but also amino acid sequences with reversed arrangement, is important as an alternative library for rationally finding active compounds.
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