title: Double bond isosteres of the peptide bond: synthesis and biological activity of cholecystokinin (CCK) C-terminal hexapeptide analogs.
abstract: New and existing methodologies were used to prepare a series of modified CCK analogs in which each amide bond was replaced by a trans-alkene unit. The data indicate that every amide linkage at C-terminal tetrapeptide (CCK-4) region is crucial for biological activity. While the amide bond beyond the Trp residue in the N-terminal direction can be replaced by a trans-alkene and still retain most of the binding potency and functional activity.
authors.affiliation: Pharmaceutical Product Division, Abbott Laboratories, Abbott Park, IL 60064.
authors.forename: Y K
authors.initials: YK
authors.lastname: Shue
authors.forename: M D
authors.initials: MD
authors.lastname: Tufano
authors.forename: G M
authors.initials: GM
authors.lastname: Carrera
authors.forename: H
authors.initials: H
authors.lastname: Kopecka
authors.forename: S L
authors.initials: SL
authors.lastname: Kuyper
authors.forename: M W
authors.initials: MW
authors.lastname: Holladay
authors.forename: C W
authors.initials: CW
authors.lastname: Lin
authors.forename: D G
authors.initials: DG
authors.lastname: Witte
authors.forename: T R
authors.initials: TR
authors.lastname: Miller
authors.forename: M
authors.initials: M
authors.lastname: Stashko
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D002540:Cerebral Cortex / Q000378:metabolism; D002766:Cholecystokinin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D006168:Guinea Pigs; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010179:Pancreas / Q000378:metabolism; D010446:Peptide Fragments / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D011869:Radioligand Assay; D013329:Structure-Activity Relationship
chemical_list: D010446:Peptide Fragments; D002766:Cholecystokinin