Synthesis of peptide and pseudo-peptide analogs of cholecystokinin
Jeannin, L.; Sapi, J.; Cartier, D.; Laronze, J.Y.; Maigret, B.; Penke, B.
Annales Pharmaceutiques Francaises 55(3): 135-140
1997
ISSN/ISBN: 0003-4509 PMID: 9239862 Document Number: 470100
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.
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