Mono-thioesters and di-thioesters by lipase-catalyzed reactions of alpha,omega-alkanedithiols with palmitic acid or its methyl ester
1-S-Mono-palmitoyl-hexanedithiol and 1-S-mono-palmitoyl-octanedithiol were prepared in high yield (80-90%) by solvent-free lipase-catalyzed thioesterification of palmitic acid with the corresponding alpha,omega-alkanedithiols in vacuo. Similarly, 1,6-di-S-palmitoyl-hexanedithiol and 1,8-di-S-palmito...
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| Veröffentlicht in: | Applied microbiology and biotechnology 2004-06, Vol.64 (6), p.800-805 |
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| creator | Weber, N Klein, E Vosman, K Mukherjee, K.D |
| description | 1-S-Mono-palmitoyl-hexanedithiol and 1-S-mono-palmitoyl-octanedithiol were prepared in high yield (80-90%) by solvent-free lipase-catalyzed thioesterification of palmitic acid with the corresponding alpha,omega-alkanedithiols in vacuo. Similarly, 1,6-di-S-palmitoyl-hexanedithiol and 1,8-di-S-palmitoyl-octanedithiol were prepared in moderate yield (50-60%) by solvent-free lipase-catalyzed thioesterification of palmitic acid with 1-S-Mono-palmitoyl-hexanedithiol and 1-S-mono-palmitoyl-octanedithiol, respectively. An immobilized lipase preparation from Rhizomucor miehei (Lipozyme RM IM) was more effective than a lipase B preparation from Candida antarctica (Novozym 435) or a lipase preparation from Thermomyces lanuginosus (Lipozyme TL IM). Lipase-catalyzed transthioesterifications of methyl palmitate with alpha,omega-alkanedithiols using the same enzymes were less effective than thioesterification for the preparation of the corresponding 1-S-mono-palmitoyl thioesters. |
| doi_str_mv | 10.1007/s00253-004-1604-8 |
| format | Article |
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Similarly, 1,6-di-S-palmitoyl-hexanedithiol and 1,8-di-S-palmitoyl-octanedithiol were prepared in moderate yield (50-60%) by solvent-free lipase-catalyzed thioesterification of palmitic acid with 1-S-Mono-palmitoyl-hexanedithiol and 1-S-mono-palmitoyl-octanedithiol, respectively. An immobilized lipase preparation from Rhizomucor miehei (Lipozyme RM IM) was more effective than a lipase B preparation from Candida antarctica (Novozym 435) or a lipase preparation from Thermomyces lanuginosus (Lipozyme TL IM). Lipase-catalyzed transthioesterifications of methyl palmitate with alpha,omega-alkanedithiols using the same enzymes were less effective than thioesterification for the preparation of the corresponding 1-S-mono-palmitoyl thioesters.</description><identifier>ISSN: 0175-7598</identifier><identifier>EISSN: 1432-0614</identifier><identifier>DOI: 10.1007/s00253-004-1604-8</identifier><identifier>PMID: 15048592</identifier><identifier>CODEN: AMBIDG</identifier><language>eng</language><publisher>Berlin: Springer</publisher><subject>Ascomycota ; Biological and medical sciences ; Biological Sciences ; Biotechnology ; Candida ; Candida antarctica ; Enzymes, Immobilized ; Esters - chemical synthesis ; Fundamental and applied biological sciences. Psychology ; Lipase - chemistry ; Lipase - isolation & purification ; Lipase - metabolism ; Molecular Structure ; Palmitic Acid - chemistry ; Rhizomucor ; Rhizomucor miehei ; Sulfhydryl Compounds - chemical synthesis ; Thermomyces lanuginosus</subject><ispartof>Applied microbiology and biotechnology, 2004-06, Vol.64 (6), p.800-805</ispartof><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15908152$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15048592$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Weber, N</creatorcontrib><creatorcontrib>Klein, E</creatorcontrib><creatorcontrib>Vosman, K</creatorcontrib><creatorcontrib>Mukherjee, K.D</creatorcontrib><title>Mono-thioesters and di-thioesters by lipase-catalyzed reactions of alpha,omega-alkanedithiols with palmitic acid or its methyl ester</title><title>Applied microbiology and biotechnology</title><addtitle>Appl Microbiol Biotechnol</addtitle><description>1-S-Mono-palmitoyl-hexanedithiol and 1-S-mono-palmitoyl-octanedithiol were prepared in high yield (80-90%) by solvent-free lipase-catalyzed thioesterification of palmitic acid with the corresponding alpha,omega-alkanedithiols in vacuo. Similarly, 1,6-di-S-palmitoyl-hexanedithiol and 1,8-di-S-palmitoyl-octanedithiol were prepared in moderate yield (50-60%) by solvent-free lipase-catalyzed thioesterification of palmitic acid with 1-S-Mono-palmitoyl-hexanedithiol and 1-S-mono-palmitoyl-octanedithiol, respectively. An immobilized lipase preparation from Rhizomucor miehei (Lipozyme RM IM) was more effective than a lipase B preparation from Candida antarctica (Novozym 435) or a lipase preparation from Thermomyces lanuginosus (Lipozyme TL IM). Lipase-catalyzed transthioesterifications of methyl palmitate with alpha,omega-alkanedithiols using the same enzymes were less effective than thioesterification for the preparation of the corresponding 1-S-mono-palmitoyl thioesters.</description><subject>Ascomycota</subject><subject>Biological and medical sciences</subject><subject>Biological Sciences</subject><subject>Biotechnology</subject><subject>Candida</subject><subject>Candida antarctica</subject><subject>Enzymes, Immobilized</subject><subject>Esters - chemical synthesis</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Lipase - chemistry</subject><subject>Lipase - isolation & purification</subject><subject>Lipase - metabolism</subject><subject>Molecular Structure</subject><subject>Palmitic Acid - chemistry</subject><subject>Rhizomucor</subject><subject>Rhizomucor miehei</subject><subject>Sulfhydryl Compounds - chemical synthesis</subject><subject>Thermomyces lanuginosus</subject><issn>0175-7598</issn><issn>1432-0614</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0EtP3DAQAGCralUW2h_QS_GlnGoY2_EjR4T6QAJxAM7RxHFYFydO46yq7ZkfjilbiRuXGcv6xuMZQj5xOOYA5iQDCCUZQMW4LsG-ISteScFA8-otWQE3ihlV2z2yn_MvAC6s1u_JHldQWVWLFXm4TGNiyzoknxc_Z4pjR7vw8qbd0hgmzJ45XDBu__qOzh7dEtKYaeopxmmNX9Pg75BhvMfRd-GpPmb6pxzohHEIS3AUXehommlYMh38st5G-q_HB_Kux5j9x10-ILffv92c_WQXVz_Oz04vWC9qsTBr6lY57cHqyrhWaRSttFUvpGlbUSJXlnPrhCzzy16BrnQPHTcFVka28oAcPb87zen3prRuhpCdj7F8OW1yY3ity4rsq5BbUFppUeDnHdy0g--aaQ4Dztvm_4IL-LIDmB3GfsbRhfzC1WC5enKHz67H1ODdXMzttQAuAWolysTyEVEnlDQ</recordid><startdate>20040601</startdate><enddate>20040601</enddate><creator>Weber, N</creator><creator>Klein, E</creator><creator>Vosman, K</creator><creator>Mukherjee, K.D</creator><general>Springer</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>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20040601</creationdate><title>Mono-thioesters and di-thioesters by lipase-catalyzed reactions of alpha,omega-alkanedithiols with palmitic acid or its methyl ester</title><author>Weber, N ; Klein, E ; Vosman, K ; Mukherjee, K.D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-f292t-879b5c6e08647cb56a2b384f237bb2237158118c230613f50646f0d176a2473b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Ascomycota</topic><topic>Biological and medical sciences</topic><topic>Biological Sciences</topic><topic>Biotechnology</topic><topic>Candida</topic><topic>Candida antarctica</topic><topic>Enzymes, Immobilized</topic><topic>Esters - chemical synthesis</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Lipase - chemistry</topic><topic>Lipase - isolation & purification</topic><topic>Lipase - metabolism</topic><topic>Molecular Structure</topic><topic>Palmitic Acid - chemistry</topic><topic>Rhizomucor</topic><topic>Rhizomucor miehei</topic><topic>Sulfhydryl Compounds - chemical synthesis</topic><topic>Thermomyces lanuginosus</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Weber, N</creatorcontrib><creatorcontrib>Klein, E</creatorcontrib><creatorcontrib>Vosman, K</creatorcontrib><creatorcontrib>Mukherjee, K.D</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>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>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Applied microbiology and biotechnology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Weber, N</au><au>Klein, E</au><au>Vosman, K</au><au>Mukherjee, K.D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Mono-thioesters and di-thioesters by lipase-catalyzed reactions of alpha,omega-alkanedithiols with palmitic acid or its methyl ester</atitle><jtitle>Applied microbiology and biotechnology</jtitle><addtitle>Appl Microbiol Biotechnol</addtitle><date>2004-06-01</date><risdate>2004</risdate><volume>64</volume><issue>6</issue><spage>800</spage><epage>805</epage><pages>800-805</pages><issn>0175-7598</issn><eissn>1432-0614</eissn><coden>AMBIDG</coden><abstract>1-S-Mono-palmitoyl-hexanedithiol and 1-S-mono-palmitoyl-octanedithiol were prepared in high yield (80-90%) by solvent-free lipase-catalyzed thioesterification of palmitic acid with the corresponding alpha,omega-alkanedithiols in vacuo. Similarly, 1,6-di-S-palmitoyl-hexanedithiol and 1,8-di-S-palmitoyl-octanedithiol were prepared in moderate yield (50-60%) by solvent-free lipase-catalyzed thioesterification of palmitic acid with 1-S-Mono-palmitoyl-hexanedithiol and 1-S-mono-palmitoyl-octanedithiol, respectively. An immobilized lipase preparation from Rhizomucor miehei (Lipozyme RM IM) was more effective than a lipase B preparation from Candida antarctica (Novozym 435) or a lipase preparation from Thermomyces lanuginosus (Lipozyme TL IM). Lipase-catalyzed transthioesterifications of methyl palmitate with alpha,omega-alkanedithiols using the same enzymes were less effective than thioesterification for the preparation of the corresponding 1-S-mono-palmitoyl thioesters.</abstract><cop>Berlin</cop><pub>Springer</pub><pmid>15048592</pmid><doi>10.1007/s00253-004-1604-8</doi><tpages>6</tpages></addata></record> |
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| identifier | ISSN: 0175-7598 |
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| issn | 0175-7598 1432-0614 |
| language | eng |
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| source | MEDLINE; SpringerNature Journals |
| subjects | Ascomycota Biological and medical sciences Biological Sciences Biotechnology Candida Candida antarctica Enzymes, Immobilized Esters - chemical synthesis Fundamental and applied biological sciences. Psychology Lipase - chemistry Lipase - isolation & purification Lipase - metabolism Molecular Structure Palmitic Acid - chemistry Rhizomucor Rhizomucor miehei Sulfhydryl Compounds - chemical synthesis Thermomyces lanuginosus |
| title | Mono-thioesters and di-thioesters by lipase-catalyzed reactions of alpha,omega-alkanedithiols with palmitic acid or its methyl ester |
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