title: Conformationally homogeneous heterocyclic pseudotetrapeptides as three-dimensional scaffolds for rational drug design: receptor-selective somatostatin analogues.
abstract: A would-be amide: A 1,4-disubstituted 1,2,3-triazole was used as a surrogate for a trans amide bond to create a library of 16 diastereomeric pseudotetrapeptides as beta-turn mimetics. High-resolution structural analysis indicated that these scaffolds adopt distinct, rigid, conformationally homogeneous beta-turn-like structures (see example), some of which bind somatostatin receptor subtypes selectively, and some of which show broad-spectrum activity.
authors.affiliation: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
authors.forename: John M
authors.initials: JM
authors.lastname: Beierle
authors.forename: W Seth
authors.initials: WS
authors.lastname: Horne
authors.forename: Jan H
authors.initials: JH
authors.lastname: van Maarseveen
authors.forename: Beatrice
authors.initials: B
authors.lastname: Waser
authors.forename: Jean Claude
authors.initials: JC
authors.lastname: Reubi
authors.forename: M Reza
authors.initials: MR
authors.lastname: Ghadiri
mesh_terms: D018360:Crystallography, X-Ray; D015195:Drug Design; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D008968:Molecular Conformation; D009842:Oligopeptides / Q000737:chemistry*; D011485:Protein Binding; D020033:Protein Isoforms / Q000737:chemistry / Q000378:metabolism; D017481:Receptors, Somatostatin / Q000737:chemistry* / Q000378:metabolism; D013004:Somatostatin / Q000031:analogs & derivatives*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D006571:Heterocyclic Compounds; D009842:Oligopeptides; D020033:Protein Isoforms; D017481:Receptors, Somatostatin; D013004:Somatostatin