Whole-Cell Biocatalysis for 1-Naphthol Production in Liquid-Liquid Biphasic Systems
Whole-cell biocatalysis to oxidize naphthalene to 1-naphthol in liquid-liquid biphasic systems was performed. Escherichia coli expressing TOM-Green, a variant of toluene ortho-monooxygenase (TOM), was used for this oxidation. Three different solvents, dodecane, dioctyl phthalate, and lauryl acetate,...
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| creator | Garikipati, S.V.B. Janardhan McIver, Angela M Peeples, Tonya L |
| description | Whole-cell biocatalysis to oxidize naphthalene to 1-naphthol in liquid-liquid biphasic systems was performed. Escherichia coli expressing TOM-Green, a variant of toluene ortho-monooxygenase (TOM), was used for this oxidation. Three different solvents, dodecane, dioctyl phthalate, and lauryl acetate, were screened for biotransformations in biphasic media. Of the solvents tested, lauryl acetate gave the best results, producing 0.72 ± 0.03 g/liter 1-naphthol with a productivity of 0.46 ± 0.02 g/g (dry weight) cells after 48 h. The effects of the organic phase ratio and the naphthalene concentration in the organic phase were investigated. The highest 1-naphthol concentration (1.43 g/liter) and the highest 1-naphthol productivity (0.55 g/g [dry weight] cells) were achieved by optimization of the organic phase. The ability to recycle both free cells and cells immobilized in calcium alginate was tested. Both free and immobilized cells lost more than ~60% of their activity after the first run, which could be attributed to product toxicity. On a constant-volume basis, an eightfold improvement in 1-naphthol production was achieved using biphasic media compared to biotransformation in aqueous media. |
| doi_str_mv | 10.1128/AEM.00434-09 |
| format | Article |
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Janardhan ; McIver, Angela M ; Peeples, Tonya L</creator><creatorcontrib>Garikipati, S.V.B. Janardhan ; McIver, Angela M ; Peeples, Tonya L</creatorcontrib><description>Whole-cell biocatalysis to oxidize naphthalene to 1-naphthol in liquid-liquid biphasic systems was performed. Escherichia coli expressing TOM-Green, a variant of toluene ortho-monooxygenase (TOM), was used for this oxidation. Three different solvents, dodecane, dioctyl phthalate, and lauryl acetate, were screened for biotransformations in biphasic media. Of the solvents tested, lauryl acetate gave the best results, producing 0.72 ± 0.03 g/liter 1-naphthol with a productivity of 0.46 ± 0.02 g/g (dry weight) cells after 48 h. The effects of the organic phase ratio and the naphthalene concentration in the organic phase were investigated. The highest 1-naphthol concentration (1.43 g/liter) and the highest 1-naphthol productivity (0.55 g/g [dry weight] cells) were achieved by optimization of the organic phase. The ability to recycle both free cells and cells immobilized in calcium alginate was tested. Both free and immobilized cells lost more than ~60% of their activity after the first run, which could be attributed to product toxicity. On a constant-volume basis, an eightfold improvement in 1-naphthol production was achieved using biphasic media compared to biotransformation in aqueous media.</description><identifier>ISSN: 0099-2240</identifier><identifier>EISSN: 1098-5336</identifier><identifier>EISSN: 1098-6596</identifier><identifier>DOI: 10.1128/AEM.00434-09</identifier><identifier>PMID: 19700554</identifier><identifier>CODEN: AEMIDF</identifier><language>eng</language><publisher>Washington, DC: American Society for Microbiology</publisher><subject>Acetates ; Acetic acid ; Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; Biotransformation ; Catalysis ; Catalysts ; Cell cycle ; Cells, Immobilized ; Chemical Engineering ; E coli ; Escherichia coli ; Escherichia coli - drug effects ; Escherichia coli - genetics ; Escherichia coli - metabolism ; Fundamental and applied biological sciences. Psychology ; Methods. Procedures. Technologies ; Microbiology ; Mixed Function Oxygenases - genetics ; Mixed Function Oxygenases - metabolism ; Naphthalenes - metabolism ; Naphthalenes - toxicity ; Naphthols - metabolism ; Naphthols - toxicity ; Oxidation ; Recombinant Proteins - genetics ; Recombinant Proteins - metabolism ; Solvents ; Toxicity</subject><ispartof>Applied and Environmental Microbiology, 2009-10, Vol.75 (20), p.6545-6552</ispartof><rights>2009 INIST-CNRS</rights><rights>Copyright American Society for Microbiology Oct 2009</rights><rights>Copyright © 2009, American Society for Microbiology</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c522t-1cd9f49580eb792e4eca99c7d4ccc42864536652a94a3017a5eb26c3ac4393e63</citedby><cites>FETCH-LOGICAL-c522t-1cd9f49580eb792e4eca99c7d4ccc42864536652a94a3017a5eb26c3ac4393e63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC2765131/pdf/$$EPDF$$P50$$Gpubmedcentral$$H</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC2765131/$$EHTML$$P50$$Gpubmedcentral$$H</linktohtml><link.rule.ids>230,314,723,776,780,881,3175,3176,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22019277$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19700554$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Garikipati, S.V.B. Janardhan</creatorcontrib><creatorcontrib>McIver, Angela M</creatorcontrib><creatorcontrib>Peeples, Tonya L</creatorcontrib><title>Whole-Cell Biocatalysis for 1-Naphthol Production in Liquid-Liquid Biphasic Systems</title><title>Applied and Environmental Microbiology</title><addtitle>Appl Environ Microbiol</addtitle><description>Whole-cell biocatalysis to oxidize naphthalene to 1-naphthol in liquid-liquid biphasic systems was performed. Escherichia coli expressing TOM-Green, a variant of toluene ortho-monooxygenase (TOM), was used for this oxidation. Three different solvents, dodecane, dioctyl phthalate, and lauryl acetate, were screened for biotransformations in biphasic media. Of the solvents tested, lauryl acetate gave the best results, producing 0.72 ± 0.03 g/liter 1-naphthol with a productivity of 0.46 ± 0.02 g/g (dry weight) cells after 48 h. The effects of the organic phase ratio and the naphthalene concentration in the organic phase were investigated. The highest 1-naphthol concentration (1.43 g/liter) and the highest 1-naphthol productivity (0.55 g/g [dry weight] cells) were achieved by optimization of the organic phase. The ability to recycle both free cells and cells immobilized in calcium alginate was tested. Both free and immobilized cells lost more than ~60% of their activity after the first run, which could be attributed to product toxicity. On a constant-volume basis, an eightfold improvement in 1-naphthol production was achieved using biphasic media compared to biotransformation in aqueous media.</description><subject>Acetates</subject><subject>Acetic acid</subject><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Biotransformation</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Cell cycle</subject><subject>Cells, Immobilized</subject><subject>Chemical Engineering</subject><subject>E coli</subject><subject>Escherichia coli</subject><subject>Escherichia coli - drug effects</subject><subject>Escherichia coli - genetics</subject><subject>Escherichia coli - metabolism</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Methods. Procedures. Technologies</subject><subject>Microbiology</subject><subject>Mixed Function Oxygenases - genetics</subject><subject>Mixed Function Oxygenases - metabolism</subject><subject>Naphthalenes - metabolism</subject><subject>Naphthalenes - toxicity</subject><subject>Naphthols - metabolism</subject><subject>Naphthols - toxicity</subject><subject>Oxidation</subject><subject>Recombinant Proteins - genetics</subject><subject>Recombinant Proteins - metabolism</subject><subject>Solvents</subject><subject>Toxicity</subject><issn>0099-2240</issn><issn>1098-5336</issn><issn>1098-6596</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkc1v1DAQxS0EokvhxhkiJDiRMv5MfEEqq_IhLR_SUnG0Zh1n4yqJt3YC2v8el121wGkO85unN-8R8pTCGaWsfnN-8fkMQHBRgr5HFhR0XUrO1X2yANC6ZEzACXmU0hVkDFT9kJxQXQFIKRZk_aMLvSuXru-Ldz5YnLDfJ5-KNsSCll9w102ZKL7F0Mx28mEs_Fis_PXsm_Iw8t2uw-Rtsd6nyQ3pMXnQYp_ck-M8JZfvL74vP5arrx8-Lc9XpZWMTSW1jW6FljW4TaWZE86i1rZqhLVWsFoJyZWSDLVADrRC6TZMWY5WcM2d4qfk7UF3N28G11g3ThF7s4t-wLg3Ab35dzP6zmzDT8MqJSmnWeDVUSCG69mlyQw-2RwFji7MyTAqQeSQM_jiP_AqzHHMzxkGUsuK1zJDrw-QjSGl6NpbJxTMTVUmV2X-VGVAZ_zZ3-7v4GM3GXh5BDBZ7NuIo_XplmMMqGZVdWeu89vul4_OYBoMusFUMtszSoobc88PUIvB4DZmoct1VsjBqloDo_w31_Gvpg</recordid><startdate>200910</startdate><enddate>200910</enddate><creator>Garikipati, S.V.B. 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Janardhan ; McIver, Angela M ; Peeples, Tonya L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c522t-1cd9f49580eb792e4eca99c7d4ccc42864536652a94a3017a5eb26c3ac4393e63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Acetates</topic><topic>Acetic acid</topic><topic>Bioconversions. Hemisynthesis</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Biotransformation</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Cell cycle</topic><topic>Cells, Immobilized</topic><topic>Chemical Engineering</topic><topic>E coli</topic><topic>Escherichia coli</topic><topic>Escherichia coli - drug effects</topic><topic>Escherichia coli - genetics</topic><topic>Escherichia coli - metabolism</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Methods. Procedures. 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Janardhan</au><au>McIver, Angela M</au><au>Peeples, Tonya L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Whole-Cell Biocatalysis for 1-Naphthol Production in Liquid-Liquid Biphasic Systems</atitle><jtitle>Applied and Environmental Microbiology</jtitle><addtitle>Appl Environ Microbiol</addtitle><date>2009-10</date><risdate>2009</risdate><volume>75</volume><issue>20</issue><spage>6545</spage><epage>6552</epage><pages>6545-6552</pages><issn>0099-2240</issn><eissn>1098-5336</eissn><eissn>1098-6596</eissn><coden>AEMIDF</coden><abstract>Whole-cell biocatalysis to oxidize naphthalene to 1-naphthol in liquid-liquid biphasic systems was performed. Escherichia coli expressing TOM-Green, a variant of toluene ortho-monooxygenase (TOM), was used for this oxidation. Three different solvents, dodecane, dioctyl phthalate, and lauryl acetate, were screened for biotransformations in biphasic media. Of the solvents tested, lauryl acetate gave the best results, producing 0.72 ± 0.03 g/liter 1-naphthol with a productivity of 0.46 ± 0.02 g/g (dry weight) cells after 48 h. The effects of the organic phase ratio and the naphthalene concentration in the organic phase were investigated. The highest 1-naphthol concentration (1.43 g/liter) and the highest 1-naphthol productivity (0.55 g/g [dry weight] cells) were achieved by optimization of the organic phase. The ability to recycle both free cells and cells immobilized in calcium alginate was tested. Both free and immobilized cells lost more than ~60% of their activity after the first run, which could be attributed to product toxicity. On a constant-volume basis, an eightfold improvement in 1-naphthol production was achieved using biphasic media compared to biotransformation in aqueous media.</abstract><cop>Washington, DC</cop><pub>American Society for Microbiology</pub><pmid>19700554</pmid><doi>10.1128/AEM.00434-09</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Acetates Acetic acid Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Biotransformation Catalysis Catalysts Cell cycle Cells, Immobilized Chemical Engineering E coli Escherichia coli Escherichia coli - drug effects Escherichia coli - genetics Escherichia coli - metabolism Fundamental and applied biological sciences. Psychology Methods. Procedures. Technologies Microbiology Mixed Function Oxygenases - genetics Mixed Function Oxygenases - metabolism Naphthalenes - metabolism Naphthalenes - toxicity Naphthols - metabolism Naphthols - toxicity Oxidation Recombinant Proteins - genetics Recombinant Proteins - metabolism Solvents Toxicity |
| title | Whole-Cell Biocatalysis for 1-Naphthol Production in Liquid-Liquid Biphasic Systems |
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