title: Synthesis and study of a lipophilic alpha-keto amide inhibitor of pancreatic lipase.
abstract: [reaction: see text] A lipophilic alpha-keto amide, inhibitor of pancreatic lipase, was synthesized using a lipidic 2-amino alcohol as backbone. The chiral key intermediate 2-(tert-butyloxycarbonylamino)-D-undecen-5-ol was synthesized starting from D-glutamic acid. The inhibitor formed a stable monomolecular film at the air/water interface as shown by a force/area curve. Inhibition studies using the monomolecular film technique with mixed films of 1,2-dicaprin containing variable proportions of the inhibitor showed a 50% decrease in lipase activity at a 0.14 molar fraction.
authors.affiliation: Department of Chemistry, University of Athens, Greece.
authors.forename: A
authors.initials: A
authors.lastname: Chiou
authors.forename: T
authors.initials: T
authors.lastname: Markidis
authors.forename: V
authors.initials: V
authors.lastname: Constantinou-Kokotou
authors.forename: R
authors.initials: R
authors.lastname: Verger
authors.forename: G
authors.initials: G
authors.lastname: Kokotos
mesh_terms: D000577:Amides / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D007659:Ketones / Q000737:chemistry; D008049:Lipase / Q000037:antagonists & inhibitors*; D050356:Lipid Metabolism; D008055:Lipids / Q000737:chemistry; D010179:Pancreas / Q000201:enzymology*; D020799:Pancrelipase / Q000737:chemistry*; D013499:Surface Properties
chemical_list: D000577:Amides; D004791:Enzyme Inhibitors; D007659:Ketones; D008055:Lipids; D020799:Pancrelipase; D008049:Lipase