Selectivity of Candida antarctica B Lipase toward Fatty Acid and (Iso)propanol Substrates in Esterification Reactions in Organic Media
Fatty acid (FA) selectivity of immobilized Candida antarctica B lipase was assessed as influenced by various cosubstrate systems for ester synthesis. Reaction mixtures contained a homologous series of even-chain n-acyl donor (C4 - 16) substrates (FA or their methyl esters, FAME) and a single alcohol...
Gespeichert in:
| Veröffentlicht in: | Journal of agricultural and food chemistry 2000-08, Vol.48 (8), p.3738-3743 |
|---|---|
| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3743 |
|---|---|
| container_issue | 8 |
| container_start_page | 3738 |
| container_title | Journal of agricultural and food chemistry |
| container_volume | 48 |
| creator | Arsan, Jad Parkin, Kirk L |
| description | Fatty acid (FA) selectivity of immobilized Candida antarctica B lipase was assessed as influenced by various cosubstrate systems for ester synthesis. Reaction mixtures contained a homologous series of even-chain n-acyl donor (C4 - 16) substrates (FA or their methyl esters, FAME) and a single alcohol cosubstrate (propanol, 2-propanol, or their acetate derivatives) in hexane. Multiple FA optima were often observed, with preferences for C6 (or C4) followed by C14 and sometimes C10. The degree of selectivity among acyl donors was modest (up to 1.28−2.60, based on ratios of selectivity constants) and was dependent on the choice of cosubstrate system. Acyl group selectivity ranged up to 1.31−1.36 for [FA + alcohol], 1.48−2.60 for [FAME + alcohol], 1.30−1.72 for [FA + alcohol acetate], and 1.28−1.88 [FAME + alcohol acetate] reaction systems. General shifts in selectivity were observed between short-chain (C4 - 8) and long-chain (C10 - 16) FA as groups with propanol cosubstrate, whereas shifts in reaction selectivity were observed toward specific FA(s) for 2-propanol cosubstrate. Selectivity among a series of alcohol cosubstrates ranged up to 13-fold in esterification reactions with C6 FA. Keywords: Lipase; anhydrous; selectivity; ester modification; Candida antarctica |
| doi_str_mv | 10.1021/jf990640p |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_72203694</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>72203694</sourcerecordid><originalsourceid>FETCH-LOGICAL-a378t-6b630d22f6686fd15a7ad2835ecfc8c6b0c2a9510cd876aa5b6b0b624938f0bb3</originalsourceid><addsrcrecordid>eNpt0c1u1DAQB3ALgehSOPACyAdA9BCwnY3jHMvSLZW2KmKLxM2a-AN5ydrBdoC-AM-NS1aFAydbMz-NRv9B6Cklrylh9M3Odh3hSzLeQwvaMFI1lIr7aEFKsxINp0foUUo7QohoWvIQHVHSlaogC_Rrawajsvvu8g0OFq_Aa6cBg88QS10Bfos3boRkcA4_IGq8hlzsqXK6KI1fXaRwMsYwgg8D3k59yhGySdh5fJayic6WKdkFjz8aULefP72r-AW8U_jSaAeP0QMLQzJPDu8x-rQ-u169rzZX5xer000FdStyxXteE82Y5Vxwq2kDLWgm6sYoq4TiPVEMuoYSpUXLAZq-lHrOll0tLOn7-hi9nOeWhb9NJmW5d0mZYQBvwpRkyxipebcs8GSGKoaUorFyjG4P8UZSIm9Dl3ehF_vsMHTq90b_I-eUC3h-AJAUDDaCVy79deVkHeWFVTNzJbafd22IXyVv67aR1x-28nO3Pl-3l-_kpvgXsweV5C5M0Zfo_rPfb6CMpa8</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>72203694</pqid></control><display><type>article</type><title>Selectivity of Candida antarctica B Lipase toward Fatty Acid and (Iso)propanol Substrates in Esterification Reactions in Organic Media</title><source>MEDLINE</source><source>ACS Publications</source><creator>Arsan, Jad ; Parkin, Kirk L</creator><creatorcontrib>Arsan, Jad ; Parkin, Kirk L</creatorcontrib><description>Fatty acid (FA) selectivity of immobilized Candida antarctica B lipase was assessed as influenced by various cosubstrate systems for ester synthesis. Reaction mixtures contained a homologous series of even-chain n-acyl donor (C4 - 16) substrates (FA or their methyl esters, FAME) and a single alcohol cosubstrate (propanol, 2-propanol, or their acetate derivatives) in hexane. Multiple FA optima were often observed, with preferences for C6 (or C4) followed by C14 and sometimes C10. The degree of selectivity among acyl donors was modest (up to 1.28−2.60, based on ratios of selectivity constants) and was dependent on the choice of cosubstrate system. Acyl group selectivity ranged up to 1.31−1.36 for [FA + alcohol], 1.48−2.60 for [FAME + alcohol], 1.30−1.72 for [FA + alcohol acetate], and 1.28−1.88 [FAME + alcohol acetate] reaction systems. General shifts in selectivity were observed between short-chain (C4 - 8) and long-chain (C10 - 16) FA as groups with propanol cosubstrate, whereas shifts in reaction selectivity were observed toward specific FA(s) for 2-propanol cosubstrate. Selectivity among a series of alcohol cosubstrates ranged up to 13-fold in esterification reactions with C6 FA. Keywords: Lipase; anhydrous; selectivity; ester modification; Candida antarctica</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf990640p</identifier><identifier>PMID: 10956180</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>2-Propanol - metabolism ; Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; Candida - enzymology ; Esterification ; Fatty Acids - metabolism ; Fundamental and applied biological sciences. Psychology ; Lipase - metabolism ; Methods. Procedures. Technologies ; Organic Chemicals - chemistry ; Solvents - chemistry ; Substrate Specificity</subject><ispartof>Journal of agricultural and food chemistry, 2000-08, Vol.48 (8), p.3738-3743</ispartof><rights>Copyright © 2000 American Chemical Society</rights><rights>2000 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a378t-6b630d22f6686fd15a7ad2835ecfc8c6b0c2a9510cd876aa5b6b0b624938f0bb3</citedby><cites>FETCH-LOGICAL-a378t-6b630d22f6686fd15a7ad2835ecfc8c6b0c2a9510cd876aa5b6b0b624938f0bb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf990640p$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf990640p$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27081,27929,27930,56743,56793</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1520916$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10956180$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Arsan, Jad</creatorcontrib><creatorcontrib>Parkin, Kirk L</creatorcontrib><title>Selectivity of Candida antarctica B Lipase toward Fatty Acid and (Iso)propanol Substrates in Esterification Reactions in Organic Media</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Fatty acid (FA) selectivity of immobilized Candida antarctica B lipase was assessed as influenced by various cosubstrate systems for ester synthesis. Reaction mixtures contained a homologous series of even-chain n-acyl donor (C4 - 16) substrates (FA or their methyl esters, FAME) and a single alcohol cosubstrate (propanol, 2-propanol, or their acetate derivatives) in hexane. Multiple FA optima were often observed, with preferences for C6 (or C4) followed by C14 and sometimes C10. The degree of selectivity among acyl donors was modest (up to 1.28−2.60, based on ratios of selectivity constants) and was dependent on the choice of cosubstrate system. Acyl group selectivity ranged up to 1.31−1.36 for [FA + alcohol], 1.48−2.60 for [FAME + alcohol], 1.30−1.72 for [FA + alcohol acetate], and 1.28−1.88 [FAME + alcohol acetate] reaction systems. General shifts in selectivity were observed between short-chain (C4 - 8) and long-chain (C10 - 16) FA as groups with propanol cosubstrate, whereas shifts in reaction selectivity were observed toward specific FA(s) for 2-propanol cosubstrate. Selectivity among a series of alcohol cosubstrates ranged up to 13-fold in esterification reactions with C6 FA. Keywords: Lipase; anhydrous; selectivity; ester modification; Candida antarctica</description><subject>2-Propanol - metabolism</subject><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Candida - enzymology</subject><subject>Esterification</subject><subject>Fatty Acids - metabolism</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Lipase - metabolism</subject><subject>Methods. Procedures. Technologies</subject><subject>Organic Chemicals - chemistry</subject><subject>Solvents - chemistry</subject><subject>Substrate Specificity</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0c1u1DAQB3ALgehSOPACyAdA9BCwnY3jHMvSLZW2KmKLxM2a-AN5ydrBdoC-AM-NS1aFAydbMz-NRv9B6Cklrylh9M3Odh3hSzLeQwvaMFI1lIr7aEFKsxINp0foUUo7QohoWvIQHVHSlaogC_Rrawajsvvu8g0OFq_Aa6cBg88QS10Bfos3boRkcA4_IGq8hlzsqXK6KI1fXaRwMsYwgg8D3k59yhGySdh5fJayic6WKdkFjz8aULefP72r-AW8U_jSaAeP0QMLQzJPDu8x-rQ-u169rzZX5xer000FdStyxXteE82Y5Vxwq2kDLWgm6sYoq4TiPVEMuoYSpUXLAZq-lHrOll0tLOn7-hi9nOeWhb9NJmW5d0mZYQBvwpRkyxipebcs8GSGKoaUorFyjG4P8UZSIm9Dl3ehF_vsMHTq90b_I-eUC3h-AJAUDDaCVy79deVkHeWFVTNzJbafd22IXyVv67aR1x-28nO3Pl-3l-_kpvgXsweV5C5M0Zfo_rPfb6CMpa8</recordid><startdate>20000801</startdate><enddate>20000801</enddate><creator>Arsan, Jad</creator><creator>Parkin, Kirk L</creator><general>American Chemical Society</general><scope>BSCLL</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>7X8</scope></search><sort><creationdate>20000801</creationdate><title>Selectivity of Candida antarctica B Lipase toward Fatty Acid and (Iso)propanol Substrates in Esterification Reactions in Organic Media</title><author>Arsan, Jad ; Parkin, Kirk L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a378t-6b630d22f6686fd15a7ad2835ecfc8c6b0c2a9510cd876aa5b6b0b624938f0bb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>2-Propanol - metabolism</topic><topic>Bioconversions. Hemisynthesis</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Candida - enzymology</topic><topic>Esterification</topic><topic>Fatty Acids - metabolism</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Lipase - metabolism</topic><topic>Methods. Procedures. Technologies</topic><topic>Organic Chemicals - chemistry</topic><topic>Solvents - chemistry</topic><topic>Substrate Specificity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Arsan, Jad</creatorcontrib><creatorcontrib>Parkin, Kirk L</creatorcontrib><collection>Istex</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>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Arsan, Jad</au><au>Parkin, Kirk L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selectivity of Candida antarctica B Lipase toward Fatty Acid and (Iso)propanol Substrates in Esterification Reactions in Organic Media</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2000-08-01</date><risdate>2000</risdate><volume>48</volume><issue>8</issue><spage>3738</spage><epage>3743</epage><pages>3738-3743</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Fatty acid (FA) selectivity of immobilized Candida antarctica B lipase was assessed as influenced by various cosubstrate systems for ester synthesis. Reaction mixtures contained a homologous series of even-chain n-acyl donor (C4 - 16) substrates (FA or their methyl esters, FAME) and a single alcohol cosubstrate (propanol, 2-propanol, or their acetate derivatives) in hexane. Multiple FA optima were often observed, with preferences for C6 (or C4) followed by C14 and sometimes C10. The degree of selectivity among acyl donors was modest (up to 1.28−2.60, based on ratios of selectivity constants) and was dependent on the choice of cosubstrate system. Acyl group selectivity ranged up to 1.31−1.36 for [FA + alcohol], 1.48−2.60 for [FAME + alcohol], 1.30−1.72 for [FA + alcohol acetate], and 1.28−1.88 [FAME + alcohol acetate] reaction systems. General shifts in selectivity were observed between short-chain (C4 - 8) and long-chain (C10 - 16) FA as groups with propanol cosubstrate, whereas shifts in reaction selectivity were observed toward specific FA(s) for 2-propanol cosubstrate. Selectivity among a series of alcohol cosubstrates ranged up to 13-fold in esterification reactions with C6 FA. Keywords: Lipase; anhydrous; selectivity; ester modification; Candida antarctica</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>10956180</pmid><doi>10.1021/jf990640p</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0021-8561 |
| ispartof | Journal of agricultural and food chemistry, 2000-08, Vol.48 (8), p.3738-3743 |
| issn | 0021-8561 1520-5118 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_72203694 |
| source | MEDLINE; ACS Publications |
| subjects | 2-Propanol - metabolism Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Candida - enzymology Esterification Fatty Acids - metabolism Fundamental and applied biological sciences. Psychology Lipase - metabolism Methods. Procedures. Technologies Organic Chemicals - chemistry Solvents - chemistry Substrate Specificity |
| title | Selectivity of Candida antarctica B Lipase toward Fatty Acid and (Iso)propanol Substrates in Esterification Reactions in Organic Media |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-12T03%3A44%3A25IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Selectivity%20of%20Candida%20antarctica%20B%20Lipase%20toward%20Fatty%20Acid%20and%20(Iso)propanol%20Substrates%20in%20Esterification%20Reactions%20in%20Organic%20Media&rft.jtitle=Journal%20of%20agricultural%20and%20food%20chemistry&rft.au=Arsan,%20Jad&rft.date=2000-08-01&rft.volume=48&rft.issue=8&rft.spage=3738&rft.epage=3743&rft.pages=3738-3743&rft.issn=0021-8561&rft.eissn=1520-5118&rft.coden=JAFCAU&rft_id=info:doi/10.1021/jf990640p&rft_dat=%3Cproquest_cross%3E72203694%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=72203694&rft_id=info:pmid/10956180&rfr_iscdi=true |