Lipase-catalyzed production of a bioactive fatty amide derivative of 7,10-dihydroxy-8( E)-octadecenoic acid

• Published in: Bioresource technology Vol. 100; no. 3; pp. 1482 - 1485
• Main Authors: Khare, Sunil K., Kumar, Anand, Kuo, Tsung Min
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 01.02.2009; [New York, NY]: Elsevier Ltd; Elsevier
• Subjects: 7,10-Dihydroxy-8( E)-octadecenoic acid (DOD); amides; Amides - chemical synthesis; antibacterial properties; antioxidant activity; Bacillus subtilis; Bioactive lipid; Biological and medical sciences; Biotechnology; Candida antarctica; Candida antarctica lipase B (CALB); carboxylic acids; Carboxylic Acids - chemistry; Catalysis; enzyme activity; Fatty Acids - chemistry; Fatty amide; fatty amides; Fundamental and applied biological sciences. Psychology; Fungal Proteins; Klebsiella; Lipase; Lipase - chemistry; octadecenoic acid; Oleic Acids - chemical synthesis; Proteus vulgaris; Staphylococcus aureus; triacylglycerol lipase; Fatty amide; Bioactive lipid; Lipase; Candida antarctica lipase B (CALB); 7,10-Dihydroxy-8( E)-octadecenoic acid (DOD); candida antarctica; Enzyme; Enzymatic catalysis; Lipids; 7,10-Dihydroxy-8(E)-octadecenoic acid; Biological activity; Fungi; DOD; Fungi Imperfecti; Lipolytic enzyme
• ISSN: 0960-8524; 1873-2976
• DOI: 10.1016/j.biortech.2008.08.011

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 °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 α,α-diphenyl-β-picryl-hydrazyl (DPPH) radicals scavenging effects.