title: Lipase-catalyzed production of a bioactive fatty amide derivative of 7,10-dihydroxy-8(E)-octadecenoic acid.
abstract: Enzymatic syntheses of fatty amides are of considerable interest due to their wide ranging industrial applications in detergents, shampoo, cosmetics and surfactant formulations. Amidation reaction of Candida antarctica lipase B (CALB) was investigated for direct amidation of carboxylic acid in organic solvent. CALB-mediated production of a novel secondary amide was carried out by reacting the hydroxy oleic acid derivative, 7,10-dihydroxy-8(E)-octadecenoic acid (DOD), with N-methylethanol amine in organic solvent medium. A single, new product peak corresponding to the secondary amide of DOD (D2AM) was detected by high-performance liquid chromatography and thin-layer chromatography. The production of D2AM was achieved in high yields (95%) after 72 h at 50 degrees C in a CALB-catalyzed reaction that contained 100 IU enzyme activity, 50 mM DOD, and 100 mM N-methylethanol amine in isoamyl alcohol. The new fatty amide D2AM displayed potent antimicrobial activity towards Gram-positive (Bacillus subtilis and Staphylococcus aureus) and Gram-negative bacteria (Proteus vulgaris and Klebsiella pneumonae). D2AM also exhibited antioxidative activity by its alpha,alpha-diphenyl-beta-picryl-hydrazyl (DPPH) radicals scavenging effects.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Hauz-Khas, New Delhi, India. skhare@rocketmail.com
authors.forename: Sunil K
authors.initials: SK
authors.lastname: Khare
authors.forename: Anand
authors.initials: A
authors.lastname: Kumar
authors.forename: Tsung Min
authors.initials: TM
authors.lastname: Kuo
mesh_terms: D000577:Amides / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D005227:Fatty Acids / Q000737:chemistry*; D005656:Fungal Proteins; D008049:Lipase / Q000737:chemistry*; D009829:Oleic Acids / Q000138:chemical synthesis*
chemical_list: C477043:7,10-dihydroxy-8-octadecenoic acid; D000577:Amides; D002264:Carboxylic Acids; D005227:Fatty Acids; D005656:Fungal Proteins; D009829:Oleic Acids; D008049:Lipase; C431349:lipase B, Candida antarctica