title: Lipase-catalyzed synthesis of palmitanilide: Kinetic model and antimicrobial activity study.
abstract: Enzymatic syntheses of fatty acid anilides are important owing to their wide range of industrial applications in detergents, shampoo, cosmetics, and surfactant formulations. The amidation reaction of Mucor miehei lipase Lipozyme IM20 was investigated for direct amidation of triacylglycerol in organic solvents. The process parameters (reaction temperature, substrate molar ratio, enzyme amount) were optimized to achieve the highest yield of anilide. The maximum yield of palmitanilide (88.9%) was achieved after 24 h of reaction at 40 °C at an enzyme concentration of 1.4% (70 mg). Kinetics of lipase-catalyzed amidation of aniline with tripalmitin has been investigated. The reaction rate could be described in terms of the Michaelis-Menten equation with a Ping-Pong Bi-Bi mechanism and competitive inhibition by both the substrates. The kinetic constants were estimated by using non-linear regression method using enzyme kinetic modules. The enzyme operational stability study showed that Lipozyme IM20 retained 38.1% of the initial activity for the synthesis of palmitanilide (even after repeated use for 48 h). Palmitanilide, a fatty acid amide, exhibited potent antimicrobial activity toward Bacillus cereus.
authors.affiliation: School of Medical Applied Chemistry, Chung Shan Medical University, Taichung 40201, Taiwan, ROC; Department of Medical Education, Chung Shan Medical University Hospital, Taichung 40201, Taiwan, ROC.
authors.forename: Kuan-Miao
authors.initials: KM
authors.lastname: Liu
authors.affiliation: Department of Food Science, National Penghu University of Science and Technology, Makung City, Penghu 88046, Taiwan, ROC. Electronic address: kjliu@npu.edu.tw.
authors.forename: Kuan-Ju
authors.initials: KJ
authors.lastname: Liu
mesh_terms: D000813:Anilides / Q000378:metabolism* / Q000494:pharmacology; D000814:Aniline Compounds / Q000378:metabolism; D000900:Anti-Bacterial Agents / Q000096:biosynthesis*; D001409:Bacillus cereus / Q000187:drug effects; D052978:Disk Diffusion Antimicrobial Tests; D004800:Enzymes, Immobilized / Q000378:metabolism; D005656:Fungal Proteins / Q000378:metabolism*; D007218:Industrial Microbiology / Q000379:methods; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D009994:Osmolar Concentration; D010169:Palmitic Acids / Q000378:metabolism* / Q000494:pharmacology; D012476:Salmonella arizonae / Q000187:drug effects; D012997:Solvents; D013501:Surface-Active Agents / Q000378:metabolism; D013696:Temperature; D014280:Triglycerides / Q000378:metabolism
chemical_list: D000813:Anilides; D000814:Aniline Compounds; D000900:Anti-Bacterial Agents; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D010169:Palmitic Acids; D012997:Solvents; D013501:Surface-Active Agents; D014280:Triglycerides; C000611429:palmitanilide; C005859:tripalmitin; C093666:Lipozyme; D008049:Lipase; C023650:aniline
keywords: Amidation; Aniline; Lipase; Organic Solvent; Palmitanilide