Application of chemoenzymatic hydrolysis in the synthesis of 2-monoacylglycerols
The selective biocatalyzed synthesis of 2-monoacylglycerols (2-MAGs) through the use of commercially available immobilized Candida antarctica (Novozym435) and Rhizomucor miehei is explored. Reactions at room temperature result in the formation of a 2-MAG and a corresponding ethyl ester of the fatty...
Gespeichert in:
| Veröffentlicht in: | Tetrahedron 2012-07, Vol.68 (27-28), p.5422-5428 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 5428 |
|---|---|
| container_issue | 27-28 |
| container_start_page | 5422 |
| container_title | Tetrahedron |
| container_volume | 68 |
| creator | Whitten, Kyle M. Makriyannis, Alexandros Vadivel, Subramanian K. |
| description | The selective biocatalyzed synthesis of 2-monoacylglycerols (2-MAGs) through the use of commercially available immobilized Candida antarctica (Novozym435) and Rhizomucor miehei is explored. Reactions at room temperature result in the formation of a 2-MAG and a corresponding ethyl ester of the fatty acid with immobilized C. antarctica within 2h with yields ranging from 36% to 83%. Similar reaction conditions with immobilized R. miehei yielded exclusively the 2-MAG after 24h with yields ranging from 37% to 88%. Yields vary on the acyl group at the sn-2 position and choice of enzyme involved.
[Display omitted] The selective biocatalyzed synthesis of 2-monoacylglycerols (2-MAGs) through the use of commercially available immobilized Candida antarctica (Novozym435) and Rhizomucor miehei is explored. Reactions at room temperature result in the formation of a 2-MAG and a corresponding ethyl ester of the fatty acid with immobilized C. antarctica within 2h with yields ranging from 36% to 83%. Similar reaction conditions with immobilized R. miehei yielded exclusively the 2-MAG after 24h with yields ranging from 37% to 88%. Yields vary on the acyl group at the sn-2 position and choice of enzyme involved. |
| doi_str_mv | 10.1016/j.tet.2012.04.101 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_3398708</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0040402012006540</els_id><sourcerecordid>1744690368</sourcerecordid><originalsourceid>FETCH-LOGICAL-c514t-8cc8d90653a583739b3e47a8c9c14a32e8181892eefe801b6910c7bdfd66acdc3</originalsourceid><addsrcrecordid>eNqFkU2LFDEQhoMo7rj6A7xIXwQvPear02kEYVn8goXdg55Dprp6J0M6GZOehfbXm2bGVS-75FDw5qk3lXoJec3omlGm3u_WE05rThlfU7lIT8iKSSXrRjL1lKwolbSWlNMz8iLnHaWUMS6ekzPONee8FStyc7Hfewd2cjFUcahgi2PE8GseiwTVdu5T9HN2uXKhmrZY5TmUsgiF5vUYQ7Qw-1s_AxY0vyTPBuszvjrVc_Lj86fvl1_rq-sv3y4vrmpomJxqDaD7jqpG2EaLVnQbgbK1Gjpg0gqOmpXTccQBNWUb1TEK7aYfeqUs9CDOycej7_6wGbEHDFOy3uyTG22aTbTO_H8T3NbcxjsjRKdbqovBu5NBij8PmCczugzovQ0YD9kwzVXTtEKxx9FWStVRoRZXdkQhxZwTDvcTMWqW0MzOlNDMEpqhcpFKz5t_v3Lf8SelArw9ATaD9UOyAVz-yzVd2WS7PP7hyGFZ_J3DZDI4DIC9SwiT6aN7YIzf0R62YQ</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1744690368</pqid></control><display><type>article</type><title>Application of chemoenzymatic hydrolysis in the synthesis of 2-monoacylglycerols</title><source>ScienceDirect Journals (5 years ago - present)</source><creator>Whitten, Kyle M. ; Makriyannis, Alexandros ; Vadivel, Subramanian K.</creator><creatorcontrib>Whitten, Kyle M. ; Makriyannis, Alexandros ; Vadivel, Subramanian K.</creatorcontrib><description>The selective biocatalyzed synthesis of 2-monoacylglycerols (2-MAGs) through the use of commercially available immobilized Candida antarctica (Novozym435) and Rhizomucor miehei is explored. Reactions at room temperature result in the formation of a 2-MAG and a corresponding ethyl ester of the fatty acid with immobilized C. antarctica within 2h with yields ranging from 36% to 83%. Similar reaction conditions with immobilized R. miehei yielded exclusively the 2-MAG after 24h with yields ranging from 37% to 88%. Yields vary on the acyl group at the sn-2 position and choice of enzyme involved.
[Display omitted] The selective biocatalyzed synthesis of 2-monoacylglycerols (2-MAGs) through the use of commercially available immobilized Candida antarctica (Novozym435) and Rhizomucor miehei is explored. Reactions at room temperature result in the formation of a 2-MAG and a corresponding ethyl ester of the fatty acid with immobilized C. antarctica within 2h with yields ranging from 36% to 83%. Similar reaction conditions with immobilized R. miehei yielded exclusively the 2-MAG after 24h with yields ranging from 37% to 88%. Yields vary on the acyl group at the sn-2 position and choice of enzyme involved.</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2012.04.101</identifier><identifier>PMID: 22822273</identifier><identifier>CODEN: TETRAB</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>2-Monoacylglycerol ; Antarctica ; Biocatalysis ; Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; Candida antarctica ; Cannabinoid ; Chemistry ; Drug addictions ; Endogenous ligand ; Ethyl esters ; Exact sciences and technology ; Fatty acids ; Fundamental and applied biological sciences. Psychology ; Hydrolysis ; Lipids ; Medical sciences ; Methods. Procedures. Technologies ; Organic chemistry ; Preparations and properties ; Receptor ; Rhizomucor miehei ; Synthesis ; Tetrahedrons ; Toxicology</subject><ispartof>Tetrahedron, 2012-07, Vol.68 (27-28), p.5422-5428</ispartof><rights>2012 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>2012 Elsevier Ltd. All rights reserved. 2012</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c514t-8cc8d90653a583739b3e47a8c9c14a32e8181892eefe801b6910c7bdfd66acdc3</citedby><cites>FETCH-LOGICAL-c514t-8cc8d90653a583739b3e47a8c9c14a32e8181892eefe801b6910c7bdfd66acdc3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tet.2012.04.101$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,315,781,785,886,3551,27929,27930,46000</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25990678$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22822273$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Whitten, Kyle M.</creatorcontrib><creatorcontrib>Makriyannis, Alexandros</creatorcontrib><creatorcontrib>Vadivel, Subramanian K.</creatorcontrib><title>Application of chemoenzymatic hydrolysis in the synthesis of 2-monoacylglycerols</title><title>Tetrahedron</title><addtitle>Tetrahedron</addtitle><description>The selective biocatalyzed synthesis of 2-monoacylglycerols (2-MAGs) through the use of commercially available immobilized Candida antarctica (Novozym435) and Rhizomucor miehei is explored. Reactions at room temperature result in the formation of a 2-MAG and a corresponding ethyl ester of the fatty acid with immobilized C. antarctica within 2h with yields ranging from 36% to 83%. Similar reaction conditions with immobilized R. miehei yielded exclusively the 2-MAG after 24h with yields ranging from 37% to 88%. Yields vary on the acyl group at the sn-2 position and choice of enzyme involved.
[Display omitted] The selective biocatalyzed synthesis of 2-monoacylglycerols (2-MAGs) through the use of commercially available immobilized Candida antarctica (Novozym435) and Rhizomucor miehei is explored. Reactions at room temperature result in the formation of a 2-MAG and a corresponding ethyl ester of the fatty acid with immobilized C. antarctica within 2h with yields ranging from 36% to 83%. Similar reaction conditions with immobilized R. miehei yielded exclusively the 2-MAG after 24h with yields ranging from 37% to 88%. Yields vary on the acyl group at the sn-2 position and choice of enzyme involved.</description><subject>2-Monoacylglycerol</subject><subject>Antarctica</subject><subject>Biocatalysis</subject><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Candida antarctica</subject><subject>Cannabinoid</subject><subject>Chemistry</subject><subject>Drug addictions</subject><subject>Endogenous ligand</subject><subject>Ethyl esters</subject><subject>Exact sciences and technology</subject><subject>Fatty acids</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hydrolysis</subject><subject>Lipids</subject><subject>Medical sciences</subject><subject>Methods. Procedures. Technologies</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Receptor</subject><subject>Rhizomucor miehei</subject><subject>Synthesis</subject><subject>Tetrahedrons</subject><subject>Toxicology</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqFkU2LFDEQhoMo7rj6A7xIXwQvPear02kEYVn8goXdg55Dprp6J0M6GZOehfbXm2bGVS-75FDw5qk3lXoJec3omlGm3u_WE05rThlfU7lIT8iKSSXrRjL1lKwolbSWlNMz8iLnHaWUMS6ekzPONee8FStyc7Hfewd2cjFUcahgi2PE8GseiwTVdu5T9HN2uXKhmrZY5TmUsgiF5vUYQ7Qw-1s_AxY0vyTPBuszvjrVc_Lj86fvl1_rq-sv3y4vrmpomJxqDaD7jqpG2EaLVnQbgbK1Gjpg0gqOmpXTccQBNWUb1TEK7aYfeqUs9CDOycej7_6wGbEHDFOy3uyTG22aTbTO_H8T3NbcxjsjRKdbqovBu5NBij8PmCczugzovQ0YD9kwzVXTtEKxx9FWStVRoRZXdkQhxZwTDvcTMWqW0MzOlNDMEpqhcpFKz5t_v3Lf8SelArw9ATaD9UOyAVz-yzVd2WS7PP7hyGFZ_J3DZDI4DIC9SwiT6aN7YIzf0R62YQ</recordid><startdate>20120708</startdate><enddate>20120708</enddate><creator>Whitten, Kyle M.</creator><creator>Makriyannis, Alexandros</creator><creator>Vadivel, Subramanian K.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20120708</creationdate><title>Application of chemoenzymatic hydrolysis in the synthesis of 2-monoacylglycerols</title><author>Whitten, Kyle M. ; Makriyannis, Alexandros ; Vadivel, Subramanian K.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c514t-8cc8d90653a583739b3e47a8c9c14a32e8181892eefe801b6910c7bdfd66acdc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>2-Monoacylglycerol</topic><topic>Antarctica</topic><topic>Biocatalysis</topic><topic>Bioconversions. Hemisynthesis</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Candida antarctica</topic><topic>Cannabinoid</topic><topic>Chemistry</topic><topic>Drug addictions</topic><topic>Endogenous ligand</topic><topic>Ethyl esters</topic><topic>Exact sciences and technology</topic><topic>Fatty acids</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Hydrolysis</topic><topic>Lipids</topic><topic>Medical sciences</topic><topic>Methods. Procedures. Technologies</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Receptor</topic><topic>Rhizomucor miehei</topic><topic>Synthesis</topic><topic>Tetrahedrons</topic><topic>Toxicology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Whitten, Kyle M.</creatorcontrib><creatorcontrib>Makriyannis, Alexandros</creatorcontrib><creatorcontrib>Vadivel, Subramanian K.</creatorcontrib><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Whitten, Kyle M.</au><au>Makriyannis, Alexandros</au><au>Vadivel, Subramanian K.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Application of chemoenzymatic hydrolysis in the synthesis of 2-monoacylglycerols</atitle><jtitle>Tetrahedron</jtitle><addtitle>Tetrahedron</addtitle><date>2012-07-08</date><risdate>2012</risdate><volume>68</volume><issue>27-28</issue><spage>5422</spage><epage>5428</epage><pages>5422-5428</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><coden>TETRAB</coden><abstract>The selective biocatalyzed synthesis of 2-monoacylglycerols (2-MAGs) through the use of commercially available immobilized Candida antarctica (Novozym435) and Rhizomucor miehei is explored. Reactions at room temperature result in the formation of a 2-MAG and a corresponding ethyl ester of the fatty acid with immobilized C. antarctica within 2h with yields ranging from 36% to 83%. Similar reaction conditions with immobilized R. miehei yielded exclusively the 2-MAG after 24h with yields ranging from 37% to 88%. Yields vary on the acyl group at the sn-2 position and choice of enzyme involved.
[Display omitted] The selective biocatalyzed synthesis of 2-monoacylglycerols (2-MAGs) through the use of commercially available immobilized Candida antarctica (Novozym435) and Rhizomucor miehei is explored. Reactions at room temperature result in the formation of a 2-MAG and a corresponding ethyl ester of the fatty acid with immobilized C. antarctica within 2h with yields ranging from 36% to 83%. Similar reaction conditions with immobilized R. miehei yielded exclusively the 2-MAG after 24h with yields ranging from 37% to 88%. Yields vary on the acyl group at the sn-2 position and choice of enzyme involved.</abstract><cop>Kidlington</cop><pub>Elsevier Ltd</pub><pmid>22822273</pmid><doi>10.1016/j.tet.2012.04.101</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0040-4020 |
| ispartof | Tetrahedron, 2012-07, Vol.68 (27-28), p.5422-5428 |
| issn | 0040-4020 1464-5416 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_3398708 |
| source | ScienceDirect Journals (5 years ago - present) |
| subjects | 2-Monoacylglycerol Antarctica Biocatalysis Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Candida antarctica Cannabinoid Chemistry Drug addictions Endogenous ligand Ethyl esters Exact sciences and technology Fatty acids Fundamental and applied biological sciences. Psychology Hydrolysis Lipids Medical sciences Methods. Procedures. Technologies Organic chemistry Preparations and properties Receptor Rhizomucor miehei Synthesis Tetrahedrons Toxicology |
| title | Application of chemoenzymatic hydrolysis in the synthesis of 2-monoacylglycerols |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-15T13%3A27%3A02IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Application%20of%20chemoenzymatic%20hydrolysis%20in%20the%20synthesis%20of%202-monoacylglycerols&rft.jtitle=Tetrahedron&rft.au=Whitten,%20Kyle%20M.&rft.date=2012-07-08&rft.volume=68&rft.issue=27-28&rft.spage=5422&rft.epage=5428&rft.pages=5422-5428&rft.issn=0040-4020&rft.eissn=1464-5416&rft.coden=TETRAB&rft_id=info:doi/10.1016/j.tet.2012.04.101&rft_dat=%3Cproquest_pubme%3E1744690368%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1744690368&rft_id=info:pmid/22822273&rft_els_id=S0040402012006540&rfr_iscdi=true |