4.8 Article

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

期刊

BIORESOURCE TECHNOLOGY
卷 100, 期 3, 页码 1482-1485

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ELSEVIER SCI LTD
DOI: 10.1016/j.biortech.2008.08.011

关键词

Bioactive lipid; Fatty amide; Lipase; Candida antarctica lipase B (CALB); 7,10-Dihydroxy-8(E)-octadecenoic acid (DOD)

资金

  1. Department of Biotechnology (Government of India)

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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. (c) 2008 Elsevier Ltd. All rights reserved.

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