Synthesis and study of a lipophilic alpha-keto amide inhibitor of pancreatic lipase.
[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.
Chiou
A
A
Department of Chemistry, University of Athens, Greece.
Markidis
T
T
Constantinou-Kokotou
V
V
Verger
R
R
Kokotos
G
G
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
D000577:Amides; D004791:Enzyme Inhibitors; D007659:Ketones; D008055:Lipids; D020799:Pancrelipase; D008049:Lipase