title: [Synthesis of peptide and pseudo-peptide analogs of cholecystokinin].
abstract: We describe selective CCKA receptor antagonists, based on the 1-oxo-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid core. Selectivity A vs B is discussed on the basis of molecular modelling. Chemical preparation uses electrophilic cyclization of isocyanates derivating from unnatural tryptophan esters. A stereoselective version of the reaction is given. A few peptides incorporating unnatural tryptophans are prepared, with a view of SAR.
authors.affiliation: UA CNRS 492, Université de Reims, Champagne-Ardenne, Faculté de Pharmacie, Reims.
authors.forename: L
authors.initials: L
authors.lastname: Jeannin
authors.forename: J
authors.initials: J
authors.lastname: Sapi
authors.forename: D
authors.initials: D
authors.lastname: Cartier
authors.forename: J Y
authors.initials: JY
authors.lastname: Laronze
authors.forename: B
authors.initials: B
authors.lastname: Maigret
authors.forename: B
authors.initials: B
authors.lastname: Penke
mesh_terms: D002766:Cholecystokinin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D011949:Receptors, Cholecystokinin / Q000037:antagonists & inhibitors
chemical_list: D011949:Receptors, Cholecystokinin; D002766:Cholecystokinin
vernacular_title: Synthèses d'analogues peptidiques et pseudo-peptidiques de la cholécystokinine.