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Synthetic routes and lipase‐inhibiting activity of long‐chain α‐keto amides
Author(s) -
Chiou Antonia,
Verger Robert,
Kokotos George
Publication year - 2001
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-001-0754-0
Subject(s) - chemistry , amide , alkyl , lipase , organic chemistry , pyridinium , yield (engineering) , enzyme , materials science , metallurgy
Synthetic routes to primary and N ‐alkyl α‐keto amides are presented in this paper. Primary α‐keto amides may be prepared by using an aldehyde as starting material. Commercially available α‐keto acids may be coupled in high yield with primary amines by the mixed carbonic anhydride method affording N ‐alkyl α‐keto amides. Alternatively, N ‐alkyl α‐keto amides may be prepared by coupling long‐chain α‐hydroxy acids with amino components, followed by oxidation with pyridinium dichromate or NaOCl in the presence of 4‐acetamido‐2,2,6,6‐tetramethyl‐1‐piperidinyloxy free radical. The α‐keto amide derivatives prepared according to these procedures were tested for their ability to form stable monomolecular films at the air/water interface. The inhibition of porcine pancreatic lipase by the α‐keto amides, spread as mixed films with 1,2‐dicaprin, was studied with the monolayet technique. Among the compounds tested in this study, methyl 2‐[(2‐ketododecanoyl)aminol]hexadecanoate was shown to be the most potent inhibitor, causing a 50% decrease in lipase activity at a 0.09 molar fraction.