Lipase-catalyzed production of a bioactive fatty amide derivative of 7,10-dihydroxy-8( E)-octadecenoic acid
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 organ...
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| Veröffentlicht in: | Bioresource technology 2009-02, Vol.100 (3), p.1482-1485 |
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| creator | Khare, Sunil K. Kumar, Anand Kuo, Tsung Min |
| description | 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. |
| doi_str_mv | 10.1016/j.biortech.2008.08.011 |
| format | Article |
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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.</description><identifier>ISSN: 0960-8524</identifier><identifier>EISSN: 1873-2976</identifier><identifier>DOI: 10.1016/j.biortech.2008.08.011</identifier><identifier>PMID: 18793843</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>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</subject><ispartof>Bioresource technology, 2009-02, Vol.100 (3), p.1482-1485</ispartof><rights>2008 Elsevier Ltd</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c451t-5f3c33d2af3f18d70a488f1f808c1a5cdc580ce34574e9f6b3776355a90e13023</citedby><cites>FETCH-LOGICAL-c451t-5f3c33d2af3f18d70a488f1f808c1a5cdc580ce34574e9f6b3776355a90e13023</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960852408006834$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20897903$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18793843$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Khare, Sunil K.</creatorcontrib><creatorcontrib>Kumar, Anand</creatorcontrib><creatorcontrib>Kuo, Tsung Min</creatorcontrib><title>Lipase-catalyzed production of a bioactive fatty amide derivative of 7,10-dihydroxy-8( E)-octadecenoic acid</title><title>Bioresource technology</title><addtitle>Bioresour Technol</addtitle><description>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.</description><subject>7,10-Dihydroxy-8( E)-octadecenoic acid (DOD)</subject><subject>amides</subject><subject>Amides - chemical synthesis</subject><subject>antibacterial properties</subject><subject>antioxidant activity</subject><subject>Bacillus subtilis</subject><subject>Bioactive lipid</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Candida antarctica</subject><subject>Candida antarctica lipase B (CALB)</subject><subject>carboxylic acids</subject><subject>Carboxylic Acids - chemistry</subject><subject>Catalysis</subject><subject>enzyme activity</subject><subject>Fatty Acids - chemistry</subject><subject>Fatty amide</subject><subject>fatty amides</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Fungal Proteins</subject><subject>Klebsiella</subject><subject>Lipase</subject><subject>Lipase - chemistry</subject><subject>octadecenoic acid</subject><subject>Oleic Acids - chemical synthesis</subject><subject>Proteus vulgaris</subject><subject>Staphylococcus aureus</subject><subject>triacylglycerol lipase</subject><issn>0960-8524</issn><issn>1873-2976</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0V9v0zAQAPAIgVg3-AojLyCQSPHFie28DU3jj1SJB9izdbXPzCWNi51WhE8_hxZ4nHSSZet3Pp-vKC6BLYGBeLdZrn2II5m7Zc2YWs4B8KhYgJK8qjspHhcL1glWqbZuzorzlDaMMQ6yflqcZdRx1fBF8WPld5ioMjhiP_0mW-5isHsz-jCUwZVY5jqYtwcqHY7jVOLWWyotRX_AP8dZybfAKuvvJhvDr6lSr8ubN1UwI1oyNARvSjTePiueOOwTPT-tF8Xth5tv15-q1ZePn6_fryrTtDBWreOGc1uj4w6UlQwbpRw4xZQBbI01rWKGeNPKhjon1lxKwdsWO0bAWc0vilfHe3MrP_eURr31yVDf40Bhn7QQEoTKOQ9B6BQA4zJDcYQmhpQiOb2Lfotx0sD0PA-90X_noed56DkAcuLlqcJ-vSX7P-00gAxengAmg72LOBif_rmaqU52bHYvjs5h0Pg9ZnP7tWa5X2hFnVkWV0dB-WsPnqJOxtNgyPpIZtQ2-Ideew-hirS4</recordid><startdate>20090201</startdate><enddate>20090201</enddate><creator>Khare, Sunil K.</creator><creator>Kumar, Anand</creator><creator>Kuo, Tsung Min</creator><general>Elsevier Ltd</general><general>[New York, NY]: Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>7QO</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20090201</creationdate><title>Lipase-catalyzed production of a bioactive fatty amide derivative of 7,10-dihydroxy-8( E)-octadecenoic acid</title><author>Khare, Sunil K. ; Kumar, Anand ; Kuo, Tsung Min</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c451t-5f3c33d2af3f18d70a488f1f808c1a5cdc580ce34574e9f6b3776355a90e13023</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>7,10-Dihydroxy-8( E)-octadecenoic acid (DOD)</topic><topic>amides</topic><topic>Amides - chemical synthesis</topic><topic>antibacterial properties</topic><topic>antioxidant activity</topic><topic>Bacillus subtilis</topic><topic>Bioactive lipid</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Candida antarctica</topic><topic>Candida antarctica lipase B (CALB)</topic><topic>carboxylic acids</topic><topic>Carboxylic Acids - chemistry</topic><topic>Catalysis</topic><topic>enzyme activity</topic><topic>Fatty Acids - chemistry</topic><topic>Fatty amide</topic><topic>fatty amides</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Fungal Proteins</topic><topic>Klebsiella</topic><topic>Lipase</topic><topic>Lipase - chemistry</topic><topic>octadecenoic acid</topic><topic>Oleic Acids - chemical synthesis</topic><topic>Proteus vulgaris</topic><topic>Staphylococcus aureus</topic><topic>triacylglycerol lipase</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Khare, Sunil K.</creatorcontrib><creatorcontrib>Kumar, Anand</creatorcontrib><creatorcontrib>Kuo, Tsung Min</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioresource technology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Khare, Sunil K.</au><au>Kumar, Anand</au><au>Kuo, Tsung Min</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Lipase-catalyzed production of a bioactive fatty amide derivative of 7,10-dihydroxy-8( E)-octadecenoic acid</atitle><jtitle>Bioresource technology</jtitle><addtitle>Bioresour Technol</addtitle><date>2009-02-01</date><risdate>2009</risdate><volume>100</volume><issue>3</issue><spage>1482</spage><epage>1485</epage><pages>1482-1485</pages><issn>0960-8524</issn><eissn>1873-2976</eissn><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
°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.</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><pmid>18793843</pmid><doi>10.1016/j.biortech.2008.08.011</doi><tpages>4</tpages></addata></record> |
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| ispartof | Bioresource technology, 2009-02, Vol.100 (3), p.1482-1485 |
| issn | 0960-8524 1873-2976 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_66716876 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| 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 |
| title | Lipase-catalyzed production of a bioactive fatty amide derivative of 7,10-dihydroxy-8( E)-octadecenoic acid |
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