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

Bioresource Technology

Volumn 100, Issue 3, 2009, Pages 1482-1485

  Khare, Sunil K ^a   Kumar, Anand ^a   Kuo, Tsung Min ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY DELHI   (India)

^b NATIONAL CENTER FOR AGRICULTURAL UTILIZATION RESEARCH   (United States)

Author keywords

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

Indexed keywords

AMINES; BACTERIA; BACTERIOLOGY; CARBOXYLIC ACIDS; CHROMATOGRAPHIC ANALYSIS; CHROMATOGRAPHY; ENZYME ACTIVITY; HIGH PRESSURE LIQUID CHROMATOGRAPHY; INDUSTRIAL APPLICATIONS; ISOMERS; LIQUID CHROMATOGRAPHY; OLEIC ACID; ORGANIC ACIDS; ORGANIC COMPOUNDS; ORGANIC POLYMERS; ORGANIC SOLVENTS; SOAPS (DETERGENTS); SOLVENTS; SURFACE ACTIVE AGENTS;

7,10-DIHYDROXY-8(E)-OCTADECENOIC ACID (DOD); ACID DERIVATIVES; AMIDATION; AMIDATION REACTIONS; ANTIMICROBIAL ACTIVITIES; ANTIOXIDATIVE ACTIVITIES; BACILLUS SUBTILIS; BIOACTIVE LIPID; CANDIDA ANTARCTICA LIPASE B; CANDIDA ANTARCTICA LIPASE B (CALB); CATALYZED REACTIONS; ENZYMATIC SYNTHESES; FATTY AMIDE; FATTY AMIDES; HIGH YIELDS; HIGH-PERFORMANCE LIQUID CHROMATOGRAPHIES; ISOAMYL ALCOHOLS; NEW PRODUCTS; ORGANIC SOLVENT MEDIUMS; PROTEUS VULGARIS; SCAVENGING EFFECTS; SECONDARY AMIDES; STAPHYLOCOCCUS AUREUS; SURFACTANT FORMULATIONS;

AMIDES;

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 2 METHYLAMINOETHANOL; 7,10 DIHYDROXY 8 OCTADECENOIC ACID; AMIDE; CARBOXYLIC ACID; FUNGAL ENZYME; ISOPENTYL ALCOHOL; LIPASE B; OLEIC ACID; ORGANIC SOLVENT; RADICAL; UNCLASSIFIED DRUG;

CARBOXYLIC ACID; CATALYSIS; DETERGENT; ENZYME; SURFACTANT;

AMIDATION; ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CANDIDA ANTARCTICA; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DETERMINATION; ENZYME ACTIVITY; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KLEBSIELLA PNEUMONIAE; NONHUMAN; PRIORITY JOURNAL; PROTEUS VULGARIS; STAPHYLOCOCCUS AUREUS; THIN LAYER CHROMATOGRAPHY;

AMIDES; CARBOXYLIC ACIDS; CATALYSIS; FATTY ACIDS; LIPASE; OLEIC ACIDS;

BACILLUS SUBTILIS; CANDIDA ANTARCTICA; KLEBSIELLA; NEGIBACTERIA; POSIBACTERIA; PROTEUS VULGARIS; STAPHYLOCOCCUS AUREUS;

EID: 55549132606     PISSN: 09608524     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biortech.2008.08.011     Document Type: Article

References (22)

1. Awasthi N.P., and Singh R.P. Lipase catalyzed synthesis of fatty acid amide (erucamide) using fatty acid and urea. J. Oleo Sci. 56 (2007) 507-509
2. Chung Y.-C., Chang C.-T., Chao W.-W., Lin C.-F., and Chou S.-T. Antioxidative activity and safety of the 50% ethanolic extract from red bean fermented by Bacillus subtilis IMR-NKI. J. Agric. Food Chem. 50 (2002) 2454-2458
3. de Zoete M.C., Kock-van Dalen A.C., van Rantwijk F., and Sheldon R.A. Lipase catalyzed ammoniolysis of lipids: a facile synthesis of fatty acid amides. J. Mol. Catal. B: Enz. 1 (1996) 109-113
4. Gotor-Fernández V., Busto E., and Gotor V. Candida antarctica lipase B: an ideal biocatalyst for the preparation of nitrogenated organic compounds. Adv. Synth. Catal. 348 (2006) 797-812
5. Izumi T., Yaginuma Y., and Haga M. Enzymatic synthesis of N-lauroyl-β-alanine homologues in organic media. J. Am. Chem. Soc. 74 (1997) 875-879
6. Johnson E.W., and Fritz E. Fatty Acids in Industries (1989), Dekker, New York pp. 177-199
7. Kabara J.J., Conley A.J., and Truant J.P. Relationship of chemical structure and antimicrobial activity of alkyl amides and amines. Antimicrob. Agents Chemother. 2 6 (1972) 492-498
8. Kabara J.J., Swieczkowski D.M., Conley A.J., and Truant J.P. Fatty acids and derivatives as antimicrobial agents. Antimicrob. Agents Chemother. 2 1 (1972) 23-28
9. Kraus R.L., Pasieczny R., Lariosa-Willingham K., Turner M.S., Jiang A., and Trauger J.W. Antioxidant properties of minocycline: neuroprotection in an oxidative stress assay and direct radical-scavenging activity. J. Neurochem. 94 (2005) 819-827
10. Kuo T.M., Kim H., and Hou C.T. Production of novel compound 7,10,12-trihydroxy-8(E)-octadecenoic acid from ricinoleic acid by Pseudomonas aeruginosa PR3. Curr. Microbiol. 43 (2001) 198-203
11. Kuo T.M., and Gardner H.W. Lipid Biotechnology (2002), Marcel and Dekker, New York pp. 605-628
12. Kuo T.M., and Lanser A.C. Factors influencing the production of novel compound 7,10-dihydroxy-8(E)-octadecenoic acid from oleic acid conversion by Pseudomonas aeruginosa PR3 (NRRL B-18602). Curr. Microbiol. 47 (2003) 186-191
13. Kuo T.M., Ray K.J., and Manthey L.K. A facile reactor process for producing 7,10-dihydroxy-8(E)-octadecenoic acid from oleic acid conversion by Pseudomonas aeruginosa. Biotechnol. Lett. 25 (2003) 29-33
14. Levinson W.E., Kuo T.M., and Kurtzman C.P. Lipase catalyzed production of novel hydroxylated fatty amides in organic solvents. Enz. Microb. Technol. 37 (2005) 126-130
15. Litjens M.J., Sha M., Straathof A.J., Jongejan J.A., and Heijnen J.J. Competitive lipase catalyzed ester hydrolysis and ammoniolysis in organic solvents: equilibrium model of solid liquid vapor system. Biotechnol. Bioeng. 65 (1999) 347-356
16. Maag H. Fatty acid derivatives: important surfactants for household, cosmetics and industrial purposes. J. Am. Oil Chem. Soc. 61 (1984) 259-267
17. Meckenna A.L. Fatty Amide Synthesis Properties Reactions and Applications (1982), Witco Chemical Corp., Memphis, TN pp. 111-194
18. Moree W.J., Sears P., Kawashiro K., Witte K., and Wong C.H. Exploitation of subtilisin BPN' as catalysts for the synthesis of peptides containing noncoded amino acids, peptide mimetics and peptide conjugates. J. Am. Chem. Soc. 119 (1997) 3942-3947
19. Omura S., Katagiri M., Awaya J., Furukawa T., Umezawa I., Oi N., Mizoguchi M., Aoki B., and Shindo M. Relationship between the structures of fatty acid amide derivatives and their antimicrobial activities. Antimicrob. Agents Chemother. 6 2 (1974) 207-215
20. Shapiro S.H. Commercial nitrogen derivatives of fatty acid. In: Scott E. (Ed). Fatty Acid and their Industrial Applications (1968), Dekker, New York 77-154
21. Sharma J., Batovska D., Kuwamori Y., and Asano Y. Enzymatic chemoselective synthesis of secondary amide surfactant from N-methylethanol amine. J. Biosci. Bioeng. 100 (2005) 662-666
22. Slotema W.F., Sandoval G., Guieysse D., Straathop A.J.J., and Marty A. Economically pertinent continuous amide formation by direct lipase catalyzed amidation with ammonia. Biotechnol. Bioeng. 82 (2003) 664-669