Synthesis and study of a lipophilic alpha-keto amide inhibitor of pancreatic lipase

[GRAPHICS] A lipophilic a 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 was synthesized starting from D-glut amic acid. The inhibitor formed a stable monomolecular film at the air/wate r interface as shown by a force/area curve, Inhibition studies using the mo nomolecular film technique with mixed films of 1,2 dicaprin containing vari able proportions of the inhibitor showed a 50% decrease in lipase activity at a 0.14 molar fraction.