Direct separation of regio- and enantiomeric isomers of diacylglycerols by a tandem column high-performance liquid chromatography
A novel HPLC-based method for direct separation of the three isomers of mono-acid diacylglycerols (DAGs), i.e., 1,2-DAG, 2,3-DAG and 1,3-DAG, has been established. The method employs a tandem column system, in which two different columns (a conventional silica gel column and a chiral stationary phas...
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| Veröffentlicht in: | Journal of Chromatography A 2005-03, Vol.1068 (2), p.243-248 |
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| creator | Piyatheerawong, Weera Iwasaki, Yugo Yamane, Tsuneo |
| description | A novel HPLC-based method for direct separation of the three isomers of mono-acid diacylglycerols (DAGs), i.e., 1,2-DAG, 2,3-DAG and 1,3-DAG, has been established. The method employs a tandem column system, in which two different columns (a conventional silica gel column and a chiral stationary phase column) are connected in series. Two isomeric mixtures of DAGs (i.e., dicapryloylglycerol and dioleoylglycerol) and lipase-catalyzed reaction mixtures were successfully resolved on the tandem column HPLC system without any derivatization prior to the analysis. According to the established analytical method, stereoselectivity of two lipases toward mono-acid triacylglycerols in ethanolysis reaction was investigated. The tested enzymes were immobilized
Candida antarctica lipase B (CALB) and
Rhizomucor miehei lipase (RML). Analyses of the enantiomeric purity of 1,2-DAG and 2,3-DAG, generated as intermediates during the reaction, revealed that CALB and RML have
sn-3 and
sn-1 stereopreference, respectively. |
| doi_str_mv | 10.1016/j.chroma.2005.01.075 |
| format | Article |
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Candida antarctica lipase B (CALB) and
Rhizomucor miehei lipase (RML). Analyses of the enantiomeric purity of 1,2-DAG and 2,3-DAG, generated as intermediates during the reaction, revealed that CALB and RML have
sn-3 and
sn-1 stereopreference, respectively.</description><identifier>ISSN: 0021-9673</identifier><identifier>DOI: 10.1016/j.chroma.2005.01.075</identifier><identifier>PMID: 15830930</identifier><identifier>CODEN: JOCRAM</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Analytical chemistry ; Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; Chemistry ; Chiral stationary phase ; Chromatographic methods and physical methods associated with chromatography ; Chromatography, High Pressure Liquid - methods ; Diacylglycerols ; Diglycerides - isolation & purification ; Enantiomeric resolution ; Ethanolysis ; Exact sciences and technology ; Fundamental and applied biological sciences. Psychology ; Fungal Proteins ; Glycerol - analogs & derivatives ; Glycerol - isolation & purification ; Isomerism ; Lipase - metabolism ; Methods. Procedures. Technologies ; Oleic Acids - isolation & purification ; Other chromatographic methods ; Rhizomucor - enzymology ; Stereoisomerism ; Tandem column ; Triglycerides - metabolism</subject><ispartof>Journal of Chromatography A, 2005-03, Vol.1068 (2), p.243-248</ispartof><rights>2005 Elsevier B.V.</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c456t-f1b3b81f0ee525f16125a426fb324d4c9536491e7e9d00f75570c4760a0fd9523</citedby><cites>FETCH-LOGICAL-c456t-f1b3b81f0ee525f16125a426fb324d4c9536491e7e9d00f75570c4760a0fd9523</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.chroma.2005.01.075$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27926,27927,45997</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16627743$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15830930$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Piyatheerawong, Weera</creatorcontrib><creatorcontrib>Iwasaki, Yugo</creatorcontrib><creatorcontrib>Yamane, Tsuneo</creatorcontrib><title>Direct separation of regio- and enantiomeric isomers of diacylglycerols by a tandem column high-performance liquid chromatography</title><title>Journal of Chromatography A</title><addtitle>J Chromatogr A</addtitle><description>A novel HPLC-based method for direct separation of the three isomers of mono-acid diacylglycerols (DAGs), i.e., 1,2-DAG, 2,3-DAG and 1,3-DAG, has been established. The method employs a tandem column system, in which two different columns (a conventional silica gel column and a chiral stationary phase column) are connected in series. Two isomeric mixtures of DAGs (i.e., dicapryloylglycerol and dioleoylglycerol) and lipase-catalyzed reaction mixtures were successfully resolved on the tandem column HPLC system without any derivatization prior to the analysis. According to the established analytical method, stereoselectivity of two lipases toward mono-acid triacylglycerols in ethanolysis reaction was investigated. The tested enzymes were immobilized
Candida antarctica lipase B (CALB) and
Rhizomucor miehei lipase (RML). Analyses of the enantiomeric purity of 1,2-DAG and 2,3-DAG, generated as intermediates during the reaction, revealed that CALB and RML have
sn-3 and
sn-1 stereopreference, respectively.</description><subject>Analytical chemistry</subject><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Chemistry</subject><subject>Chiral stationary phase</subject><subject>Chromatographic methods and physical methods associated with chromatography</subject><subject>Chromatography, High Pressure Liquid - methods</subject><subject>Diacylglycerols</subject><subject>Diglycerides - isolation & purification</subject><subject>Enantiomeric resolution</subject><subject>Ethanolysis</subject><subject>Exact sciences and technology</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Fungal Proteins</subject><subject>Glycerol - analogs & derivatives</subject><subject>Glycerol - isolation & purification</subject><subject>Isomerism</subject><subject>Lipase - metabolism</subject><subject>Methods. Procedures. Technologies</subject><subject>Oleic Acids - isolation & purification</subject><subject>Other chromatographic methods</subject><subject>Rhizomucor - enzymology</subject><subject>Stereoisomerism</subject><subject>Tandem column</subject><subject>Triglycerides - metabolism</subject><issn>0021-9673</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kU1v1DAQhnMA0VL4Bwj5AreEsR3bzQUJtXxJlbjA2XLs8a5XSZzaCVKO_HO8ZKXeOI01et7RzOOqekOhoUDlh1NjjymOpmEAogHagBLPqmsARutOKn5Vvcz5BEAVKPaiuqLilkPH4br6cx8S2oVknE0yS4gTiZ4kPIRYEzM5gpOZSnvEFCwJ-fzIZ8QFY7fhMGwWUxwy6TdiyFISOBIbh3WcyDEcjvWMycc0mskiGcLjGhzZd13iIZn5uL2qnnszZHx9qTfVry-ff959qx9-fP1-9-mhtq2QS-1pz_tb6gFRMOGppEyYlknfc9a61naCy7ajqLBzAF4JocC2SoIB7zrB-E31fp87p_i4Yl70GLLFYTATxjVrqRTvKO8K2O6gTTHnhF7PKYwmbZqCPuvWJ72foM-6NVBddJfY28v8tR_RPYUurgvw7gKYbM3gU3ES8hMnJVOq5YX7uHNYbPwOmHS2AYs_9--rtIvh_5v8BU4-o_w</recordid><startdate>20050318</startdate><enddate>20050318</enddate><creator>Piyatheerawong, Weera</creator><creator>Iwasaki, Yugo</creator><creator>Yamane, Tsuneo</creator><general>Elsevier B.V</general><general>Elsevier</general><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>20050318</creationdate><title>Direct separation of regio- and enantiomeric isomers of diacylglycerols by a tandem column high-performance liquid chromatography</title><author>Piyatheerawong, Weera ; Iwasaki, Yugo ; Yamane, Tsuneo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c456t-f1b3b81f0ee525f16125a426fb324d4c9536491e7e9d00f75570c4760a0fd9523</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Analytical chemistry</topic><topic>Bioconversions. Hemisynthesis</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Chemistry</topic><topic>Chiral stationary phase</topic><topic>Chromatographic methods and physical methods associated with chromatography</topic><topic>Chromatography, High Pressure Liquid - methods</topic><topic>Diacylglycerols</topic><topic>Diglycerides - isolation & purification</topic><topic>Enantiomeric resolution</topic><topic>Ethanolysis</topic><topic>Exact sciences and technology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Fungal Proteins</topic><topic>Glycerol - analogs & derivatives</topic><topic>Glycerol - isolation & purification</topic><topic>Isomerism</topic><topic>Lipase - metabolism</topic><topic>Methods. Procedures. Technologies</topic><topic>Oleic Acids - isolation & purification</topic><topic>Other chromatographic methods</topic><topic>Rhizomucor - enzymology</topic><topic>Stereoisomerism</topic><topic>Tandem column</topic><topic>Triglycerides - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Piyatheerawong, Weera</creatorcontrib><creatorcontrib>Iwasaki, Yugo</creatorcontrib><creatorcontrib>Yamane, Tsuneo</creatorcontrib><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 Chromatography A</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Piyatheerawong, Weera</au><au>Iwasaki, Yugo</au><au>Yamane, Tsuneo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Direct separation of regio- and enantiomeric isomers of diacylglycerols by a tandem column high-performance liquid chromatography</atitle><jtitle>Journal of Chromatography A</jtitle><addtitle>J Chromatogr A</addtitle><date>2005-03-18</date><risdate>2005</risdate><volume>1068</volume><issue>2</issue><spage>243</spage><epage>248</epage><pages>243-248</pages><issn>0021-9673</issn><coden>JOCRAM</coden><abstract>A novel HPLC-based method for direct separation of the three isomers of mono-acid diacylglycerols (DAGs), i.e., 1,2-DAG, 2,3-DAG and 1,3-DAG, has been established. The method employs a tandem column system, in which two different columns (a conventional silica gel column and a chiral stationary phase column) are connected in series. Two isomeric mixtures of DAGs (i.e., dicapryloylglycerol and dioleoylglycerol) and lipase-catalyzed reaction mixtures were successfully resolved on the tandem column HPLC system without any derivatization prior to the analysis. According to the established analytical method, stereoselectivity of two lipases toward mono-acid triacylglycerols in ethanolysis reaction was investigated. The tested enzymes were immobilized
Candida antarctica lipase B (CALB) and
Rhizomucor miehei lipase (RML). Analyses of the enantiomeric purity of 1,2-DAG and 2,3-DAG, generated as intermediates during the reaction, revealed that CALB and RML have
sn-3 and
sn-1 stereopreference, respectively.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><pmid>15830930</pmid><doi>10.1016/j.chroma.2005.01.075</doi><tpages>6</tpages></addata></record> |
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| subjects | Analytical chemistry Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Chemistry Chiral stationary phase Chromatographic methods and physical methods associated with chromatography Chromatography, High Pressure Liquid - methods Diacylglycerols Diglycerides - isolation & purification Enantiomeric resolution Ethanolysis Exact sciences and technology Fundamental and applied biological sciences. Psychology Fungal Proteins Glycerol - analogs & derivatives Glycerol - isolation & purification Isomerism Lipase - metabolism Methods. Procedures. Technologies Oleic Acids - isolation & purification Other chromatographic methods Rhizomucor - enzymology Stereoisomerism Tandem column Triglycerides - metabolism |
| title | Direct separation of regio- and enantiomeric isomers of diacylglycerols by a tandem column high-performance liquid chromatography |
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