Synthesis and study of a lipophilic α-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-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.