[Synthesis of peptide and pseudo-peptide analogs of cholecystokinin].
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.
Jeannin
L
L
UA CNRS 492, Université de Reims, Champagne-Ardenne, Faculté de Pharmacie, Reims.
Sapi
J
J
Cartier
D
D
Laronze
J Y
JY
Maigret
B
B
Penke
B
B
D002766:Cholecystokinin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D011949:Receptors, Cholecystokinin / Q000037:antagonists & inhibitors
D011949:Receptors, Cholecystokinin; D002766:Cholecystokinin
Synthèses d'analogues peptidiques et pseudo-peptidiques de la cholécystokinine.