title: Topochemical exploration of potent compounds using retro-enantiomer libraries of cyclic pentapeptides.
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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Hirokazu
authors.initials: H
authors.lastname: Tamamura
authors.forename: Makiko
authors.initials: M
authors.lastname: Mizumoto
authors.forename: Kenichi
authors.initials: K
authors.lastname: Hiramatsu
authors.forename: Shuichi
authors.initials: S
authors.lastname: Kusano
authors.forename: Shigemi
authors.initials: S
authors.lastname: Terakubo
authors.forename: Naoki
authors.initials: N
authors.lastname: Yamamoto
authors.forename: John O
authors.initials: JO
authors.lastname: Trent
authors.forename: Zixuan
authors.initials: Z
authors.lastname: Wang
authors.forename: Stephen C
authors.initials: SC
authors.lastname: Peiper
authors.forename: Hideki
authors.initials: H
authors.lastname: Nakashima
authors.forename: Akira
authors.initials: A
authors.lastname: Otaka
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Fujii
mesh_terms: D000595:Amino Acid Sequence; D009842:Oligopeptides / Q000737:chemistry*; D019151:Peptide Library; D010456:Peptides, Cyclic / Q000737:chemistry*; D011487:Protein Conformation; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D009842:Oligopeptides; D019151:Peptide Library; D010456:Peptides, Cyclic