A short, concise route to diphosphatidylglycerol (Cardiolipin) and its variants
A new approach is described for the synthesis of the cardiolipin family of phospholipids that uses phosphonium salt methodology. The method involves the reaction of 2‐O‐protected glycerol with a trialkyl phosphite derived from 1,2‐diacyl‐sn‐glycerol in the presence of pyridinium bromide perbromide a...
Gespeichert in:
| Veröffentlicht in: | Lipids 2004-06, Vol.39 (6), p.595-600 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 600 |
|---|---|
| container_issue | 6 |
| container_start_page | 595 |
| container_title | Lipids |
| container_volume | 39 |
| creator | Krishna, U. Murali Ahmad, Moghis U. Ali, Shoukath M. Ahmad, Imran |
| description | A new approach is described for the synthesis of the cardiolipin family of phospholipids that uses phosphonium salt methodology. The method involves the reaction of 2‐O‐protected glycerol with a trialkyl phosphite derived from 1,2‐diacyl‐sn‐glycerol in the presence of pyridinium bromide perbromide and triethylamine to afford the phosphoric triesters. The synthesis involves three steps and allows the preparation of a wide range of cardiolipins with different substitution patterns and chain lengths, including unsaturated derivatives. The use of inexpensive protecting groups and the ease of purification facilitate this synthetic route and allow its scale‐up in a higher overall yield (72%) than the literature methods. |
| doi_str_mv | 10.1007/s11745-004-1269-4 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_67077972</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>738078791</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4385-f5a9258115d9cf7aa838a7835fa31c74ce41fb8fe72ac1e93ada5f9cf4af85b53</originalsourceid><addsrcrecordid>eNqFkEtr3DAUhUVoSSaPH5BNEVmUFOpUVw_LXoZJH4GBdNGuxR1Z6ih4LEeyG-bfV2EGAtl0dTnwncPlI-QS2A0wpr9kAC1VxZisgNdtJY_IApRqqlYw_Y4sGOOykpzBCTnN-bFEkK06JicFUhJqWJCHW5o3MU2fqY2DDdnRFOfJ0SnSLoybmMcNTqHb9X_6nXUp9vR6iakLsQ9jGD5RHDoapkz_Ygo4TPmcvPfYZ3dxuGfk97evv5Y_qtXD9_vl7aqyUjSq8gpbrhoA1bXWa8RGNKgboTwKsFpaJ8GvG-80RwuuFdih8gWV6Bu1VuKMfNzvjik-zS5PZhuydX2Pg4tzNrVmWreaF_DqDfgY5zSU3wxXnNeC67pAsIdsijkn582YwhbTzgAzL6rNXrUpqs2LaiNL58NheF5vXffaOLgtgN4Dz6F3u_8vmtX9zzumWiX-AbR3igs</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>252263276</pqid></control><display><type>article</type><title>A short, concise route to diphosphatidylglycerol (Cardiolipin) and its variants</title><source>Wiley Online Library - AutoHoldings Journals</source><source>MEDLINE</source><source>SpringerLink Journals</source><creator>Krishna, U. Murali ; Ahmad, Moghis U. ; Ali, Shoukath M. ; Ahmad, Imran</creator><creatorcontrib>Krishna, U. Murali ; Ahmad, Moghis U. ; Ali, Shoukath M. ; Ahmad, Imran</creatorcontrib><description>A new approach is described for the synthesis of the cardiolipin family of phospholipids that uses phosphonium salt methodology. The method involves the reaction of 2‐O‐protected glycerol with a trialkyl phosphite derived from 1,2‐diacyl‐sn‐glycerol in the presence of pyridinium bromide perbromide and triethylamine to afford the phosphoric triesters. The synthesis involves three steps and allows the preparation of a wide range of cardiolipins with different substitution patterns and chain lengths, including unsaturated derivatives. The use of inexpensive protecting groups and the ease of purification facilitate this synthetic route and allow its scale‐up in a higher overall yield (72%) than the literature methods.</description><identifier>ISSN: 0024-4201</identifier><identifier>EISSN: 1558-9307</identifier><identifier>DOI: 10.1007/s11745-004-1269-4</identifier><identifier>PMID: 15554161</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer‐Verlag</publisher><subject>Cardiolipins - chemistry ; Methods ; Organophosphonates - chemistry ; Organophosphorus Compounds - chemistry</subject><ispartof>Lipids, 2004-06, Vol.39 (6), p.595-600</ispartof><rights>2004 American Oil Chemists' Society (AOCS)</rights><rights>Copyright AOCS Press Jun 2004</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4385-f5a9258115d9cf7aa838a7835fa31c74ce41fb8fe72ac1e93ada5f9cf4af85b53</citedby><cites>FETCH-LOGICAL-c4385-f5a9258115d9cf7aa838a7835fa31c74ce41fb8fe72ac1e93ada5f9cf4af85b53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1007%2Fs11745-004-1269-4$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1007%2Fs11745-004-1269-4$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15554161$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Krishna, U. Murali</creatorcontrib><creatorcontrib>Ahmad, Moghis U.</creatorcontrib><creatorcontrib>Ali, Shoukath M.</creatorcontrib><creatorcontrib>Ahmad, Imran</creatorcontrib><title>A short, concise route to diphosphatidylglycerol (Cardiolipin) and its variants</title><title>Lipids</title><addtitle>Lipids</addtitle><description>A new approach is described for the synthesis of the cardiolipin family of phospholipids that uses phosphonium salt methodology. The method involves the reaction of 2‐O‐protected glycerol with a trialkyl phosphite derived from 1,2‐diacyl‐sn‐glycerol in the presence of pyridinium bromide perbromide and triethylamine to afford the phosphoric triesters. The synthesis involves three steps and allows the preparation of a wide range of cardiolipins with different substitution patterns and chain lengths, including unsaturated derivatives. The use of inexpensive protecting groups and the ease of purification facilitate this synthetic route and allow its scale‐up in a higher overall yield (72%) than the literature methods.</description><subject>Cardiolipins - chemistry</subject><subject>Methods</subject><subject>Organophosphonates - chemistry</subject><subject>Organophosphorus Compounds - chemistry</subject><issn>0024-4201</issn><issn>1558-9307</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><recordid>eNqFkEtr3DAUhUVoSSaPH5BNEVmUFOpUVw_LXoZJH4GBdNGuxR1Z6ih4LEeyG-bfV2EGAtl0dTnwncPlI-QS2A0wpr9kAC1VxZisgNdtJY_IApRqqlYw_Y4sGOOykpzBCTnN-bFEkK06JicFUhJqWJCHW5o3MU2fqY2DDdnRFOfJ0SnSLoybmMcNTqHb9X_6nXUp9vR6iakLsQ9jGD5RHDoapkz_Ygo4TPmcvPfYZ3dxuGfk97evv5Y_qtXD9_vl7aqyUjSq8gpbrhoA1bXWa8RGNKgboTwKsFpaJ8GvG-80RwuuFdih8gWV6Bu1VuKMfNzvjik-zS5PZhuydX2Pg4tzNrVmWreaF_DqDfgY5zSU3wxXnNeC67pAsIdsijkn582YwhbTzgAzL6rNXrUpqs2LaiNL58NheF5vXffaOLgtgN4Dz6F3u_8vmtX9zzumWiX-AbR3igs</recordid><startdate>200406</startdate><enddate>200406</enddate><creator>Krishna, U. Murali</creator><creator>Ahmad, Moghis U.</creator><creator>Ali, Shoukath M.</creator><creator>Ahmad, Imran</creator><general>Springer‐Verlag</general><general>Springer Nature B.V</general><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>3V.</scope><scope>7QL</scope><scope>7QP</scope><scope>7QR</scope><scope>7T7</scope><scope>7TK</scope><scope>7U9</scope><scope>7X7</scope><scope>7XB</scope><scope>88A</scope><scope>88E</scope><scope>8AO</scope><scope>8C1</scope><scope>8FD</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>BKSAR</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M7N</scope><scope>M7P</scope><scope>P64</scope><scope>PCBAR</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>7X8</scope></search><sort><creationdate>200406</creationdate><title>A short, concise route to diphosphatidylglycerol (Cardiolipin) and its variants</title><author>Krishna, U. Murali ; Ahmad, Moghis U. ; Ali, Shoukath M. ; Ahmad, Imran</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4385-f5a9258115d9cf7aa838a7835fa31c74ce41fb8fe72ac1e93ada5f9cf4af85b53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Cardiolipins - chemistry</topic><topic>Methods</topic><topic>Organophosphonates - chemistry</topic><topic>Organophosphorus Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Krishna, U. Murali</creatorcontrib><creatorcontrib>Ahmad, Moghis U.</creatorcontrib><creatorcontrib>Ali, Shoukath M.</creatorcontrib><creatorcontrib>Ahmad, Imran</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Neurosciences Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Biology Database (Alumni Edition)</collection><collection>Medical Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>Public Health Database</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Natural Science Collection</collection><collection>Earth, Atmospheric & Aquatic Science Collection</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Engineering Research Database</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>ProQuest Biological Science Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biological Science Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Earth, Atmospheric & Aquatic Science Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>MEDLINE - Academic</collection><jtitle>Lipids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Krishna, U. Murali</au><au>Ahmad, Moghis U.</au><au>Ali, Shoukath M.</au><au>Ahmad, Imran</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A short, concise route to diphosphatidylglycerol (Cardiolipin) and its variants</atitle><jtitle>Lipids</jtitle><addtitle>Lipids</addtitle><date>2004-06</date><risdate>2004</risdate><volume>39</volume><issue>6</issue><spage>595</spage><epage>600</epage><pages>595-600</pages><issn>0024-4201</issn><eissn>1558-9307</eissn><abstract>A new approach is described for the synthesis of the cardiolipin family of phospholipids that uses phosphonium salt methodology. The method involves the reaction of 2‐O‐protected glycerol with a trialkyl phosphite derived from 1,2‐diacyl‐sn‐glycerol in the presence of pyridinium bromide perbromide and triethylamine to afford the phosphoric triesters. The synthesis involves three steps and allows the preparation of a wide range of cardiolipins with different substitution patterns and chain lengths, including unsaturated derivatives. The use of inexpensive protecting groups and the ease of purification facilitate this synthetic route and allow its scale‐up in a higher overall yield (72%) than the literature methods.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer‐Verlag</pub><pmid>15554161</pmid><doi>10.1007/s11745-004-1269-4</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0024-4201 |
| ispartof | Lipids, 2004-06, Vol.39 (6), p.595-600 |
| issn | 0024-4201 1558-9307 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_67077972 |
| source | Wiley Online Library - AutoHoldings Journals; MEDLINE; SpringerLink Journals |
| subjects | Cardiolipins - chemistry Methods Organophosphonates - chemistry Organophosphorus Compounds - chemistry |
| title | A short, concise route to diphosphatidylglycerol (Cardiolipin) and its variants |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-02T06%3A41%3A49IST&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=A%20short,%20concise%20route%20to%20diphosphatidylglycerol%20(Cardiolipin)%20and%20its%20variants&rft.jtitle=Lipids&rft.au=Krishna,%20U.%20Murali&rft.date=2004-06&rft.volume=39&rft.issue=6&rft.spage=595&rft.epage=600&rft.pages=595-600&rft.issn=0024-4201&rft.eissn=1558-9307&rft_id=info:doi/10.1007/s11745-004-1269-4&rft_dat=%3Cproquest_cross%3E738078791%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=252263276&rft_id=info:pmid/15554161&rfr_iscdi=true |