Synthesis of methyl 3-(2-octadecylcyclopropen-1-yl)propanoate and methyl 3-(2-octadecylcyclopropen-1-yl)pentanoate and cyclopropane fatty acids as possible inhibitors of mycolic acid biosynthesis
( Z)-Tetracos-5-enoic acid is a key intermediate in the biosynthesis of mycobacterial mycolic acids. Recently the methyl ester of its cyclopropene analogue, methyl 4-(2-octadecylcyclopropen-1-yl)butanoate, was shown to act as an inhibitor of mycolic acid biosynthesis. The related analogues methyl 5-...
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| Veröffentlicht in: | Chemistry and physics of lipids 1994-05, Vol.71 (1), p.99-108 |
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| container_title | Chemistry and physics of lipids |
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| creator | Hartmann, S. Minnikin, D.E. Römming, H.-J. Baird, M.S. Ratledge, C. Wheeler, P.R. |
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Z)-Tetracos-5-enoic acid is a key intermediate in the biosynthesis of mycobacterial mycolic acids. Recently the methyl ester of its cyclopropene analogue, methyl 4-(2-octadecylcyclopropen-1-yl)butanoate, was shown to act as an inhibitor of mycolic acid biosynthesis. The related analogues methyl 5-(2-octadecylcyclopropen-1-yl)pentanoate and methyl 3-(2-octadecylcyclopropen-1-yl)propanoate have been synthesised, as well as the related cyclopropane esters methyl (
Z)-4-(2-octadecylcyclopropan-1-yl)butanoate and methyl (
Z)-5-(2-octadecylcyclopropan-1-yl)pentanoate. The synthesis of methyl 3-(2-octadecylcyclopropen-1-yl)propanoate involved protection of the cyclopropene ring by iodination to allow oxidation of an alcohol to a carboxylic acid; the diiodocyclopropane was deprotected by a new mild procedure using activated zinc. |
| doi_str_mv | 10.1016/0009-3084(94)02315-8 |
| format | Article |
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Z)-Tetracos-5-enoic acid is a key intermediate in the biosynthesis of mycobacterial mycolic acids. Recently the methyl ester of its cyclopropene analogue, methyl 4-(2-octadecylcyclopropen-1-yl)butanoate, was shown to act as an inhibitor of mycolic acid biosynthesis. The related analogues methyl 5-(2-octadecylcyclopropen-1-yl)pentanoate and methyl 3-(2-octadecylcyclopropen-1-yl)propanoate have been synthesised, as well as the related cyclopropane esters methyl (
Z)-4-(2-octadecylcyclopropan-1-yl)butanoate and methyl (
Z)-5-(2-octadecylcyclopropan-1-yl)pentanoate. The synthesis of methyl 3-(2-octadecylcyclopropen-1-yl)propanoate involved protection of the cyclopropene ring by iodination to allow oxidation of an alcohol to a carboxylic acid; the diiodocyclopropane was deprotected by a new mild procedure using activated zinc.</description><identifier>ISSN: 0009-3084</identifier><identifier>EISSN: 1873-2941</identifier><identifier>DOI: 10.1016/0009-3084(94)02315-8</identifier><identifier>PMID: 8039261</identifier><language>eng</language><publisher>Ireland: Elsevier Ireland Ltd</publisher><subject>Activated zinc ; Biosynthetic intermediate ; Cyclopentanes ; Cyclopropane fatty acid ; Cyclopropanes - chemical synthesis ; Cyclopropanes - chemistry ; Cyclopropanes - pharmacology ; Cyclopropene fatty acid ; Diiodocyclopropane ; Fatty Acids, Nonesterified - chemical synthesis ; Fatty Acids, Nonesterified - chemistry ; Fatty Acids, Nonesterified - pharmacology ; Indicators and Reagents ; Inhibitor ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Molecular Structure ; Mycobacterium - drug effects ; Mycobacterium - metabolism ; Mycolic acid ; Mycolic Acids - antagonists & inhibitors ; Mycolic Acids - metabolism ; Propionates - chemical synthesis ; Propionates - chemistry ; Propionates - pharmacology ; Tetracosenoic acid ; Valerates - chemistry ; Valerates - pharmacology</subject><ispartof>Chemistry and physics of lipids, 1994-05, Vol.71 (1), p.99-108</ispartof><rights>1994</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c357t-daac01cede4e560639ac3c73ed82fc33be8f057cad4653c8db68e2aa63632f463</citedby><cites>FETCH-LOGICAL-c357t-daac01cede4e560639ac3c73ed82fc33be8f057cad4653c8db68e2aa63632f463</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/0009-3084(94)02315-8$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,45974</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/8039261$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hartmann, S.</creatorcontrib><creatorcontrib>Minnikin, D.E.</creatorcontrib><creatorcontrib>Römming, H.-J.</creatorcontrib><creatorcontrib>Baird, M.S.</creatorcontrib><creatorcontrib>Ratledge, C.</creatorcontrib><creatorcontrib>Wheeler, P.R.</creatorcontrib><title>Synthesis of methyl 3-(2-octadecylcyclopropen-1-yl)propanoate and methyl 3-(2-octadecylcyclopropen-1-yl)pentanoate and cyclopropane fatty acids as possible inhibitors of mycolic acid biosynthesis</title><title>Chemistry and physics of lipids</title><addtitle>Chem Phys Lipids</addtitle><description>(
Z)-Tetracos-5-enoic acid is a key intermediate in the biosynthesis of mycobacterial mycolic acids. Recently the methyl ester of its cyclopropene analogue, methyl 4-(2-octadecylcyclopropen-1-yl)butanoate, was shown to act as an inhibitor of mycolic acid biosynthesis. The related analogues methyl 5-(2-octadecylcyclopropen-1-yl)pentanoate and methyl 3-(2-octadecylcyclopropen-1-yl)propanoate have been synthesised, as well as the related cyclopropane esters methyl (
Z)-4-(2-octadecylcyclopropan-1-yl)butanoate and methyl (
Z)-5-(2-octadecylcyclopropan-1-yl)pentanoate. The synthesis of methyl 3-(2-octadecylcyclopropen-1-yl)propanoate involved protection of the cyclopropene ring by iodination to allow oxidation of an alcohol to a carboxylic acid; the diiodocyclopropane was deprotected by a new mild procedure using activated zinc.</description><subject>Activated zinc</subject><subject>Biosynthetic intermediate</subject><subject>Cyclopentanes</subject><subject>Cyclopropane fatty acid</subject><subject>Cyclopropanes - chemical synthesis</subject><subject>Cyclopropanes - chemistry</subject><subject>Cyclopropanes - pharmacology</subject><subject>Cyclopropene fatty acid</subject><subject>Diiodocyclopropane</subject><subject>Fatty Acids, Nonesterified - chemical synthesis</subject><subject>Fatty Acids, Nonesterified - chemistry</subject><subject>Fatty Acids, Nonesterified - pharmacology</subject><subject>Indicators and Reagents</subject><subject>Inhibitor</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Molecular Structure</subject><subject>Mycobacterium - drug effects</subject><subject>Mycobacterium - metabolism</subject><subject>Mycolic acid</subject><subject>Mycolic Acids - antagonists & inhibitors</subject><subject>Mycolic Acids - metabolism</subject><subject>Propionates - chemical synthesis</subject><subject>Propionates - chemistry</subject><subject>Propionates - pharmacology</subject><subject>Tetracosenoic acid</subject><subject>Valerates - chemistry</subject><subject>Valerates - pharmacology</subject><issn>0009-3084</issn><issn>1873-2941</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1994</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNUU2LFDEUDKKss6v_QCEn2T1E89GdTl8EWXRdWNjD6jmkX14zkUxn7GSE_n3-MTM74-BJ9vTyqKqXKoqQN4K_F1zoD5zznilumsu-ueJSiZaZZ2QlTKeY7BvxnKxOlJfkPOcfdeVtK87ImeGql1qsyO-HZSprzCHTNNINlvUSqWKXkiUoziMsERaIaTunLU5MsCVe7d9uSq4gdZN_qgin8o_ohLsJ6ehKWaiD4DN1mW5TzmGISMO0DkMoaT6YWyDFAI88OoSU_zp_RV6MLmZ8fZwX5PuXz9-uv7K7-5vb6093DFTbFeadAy4APTbYaq5V70BBp9AbOYJSA5qRtx043-hWgfGDNiid00orOTZaXZB3h7vV988d5mI3IQPGWDOkXbad1kLKjldicyDCXKPMONrtHDZuXqzgdt-d3Rdj98XYvrGP3VlTZW-P93fDBv1JdCyr4h8PONaQvwLONkPAqSYKM0KxPoX_f_AHKw-t7A</recordid><startdate>19940506</startdate><enddate>19940506</enddate><creator>Hartmann, S.</creator><creator>Minnikin, D.E.</creator><creator>Römming, H.-J.</creator><creator>Baird, M.S.</creator><creator>Ratledge, C.</creator><creator>Wheeler, P.R.</creator><general>Elsevier Ireland Ltd</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>7X8</scope></search><sort><creationdate>19940506</creationdate><title>Synthesis of methyl 3-(2-octadecylcyclopropen-1-yl)propanoate and methyl 3-(2-octadecylcyclopropen-1-yl)pentanoate and cyclopropane fatty acids as possible inhibitors of mycolic acid biosynthesis</title><author>Hartmann, S. ; Minnikin, D.E. ; Römming, H.-J. ; Baird, M.S. ; Ratledge, C. ; Wheeler, P.R.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c357t-daac01cede4e560639ac3c73ed82fc33be8f057cad4653c8db68e2aa63632f463</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1994</creationdate><topic>Activated zinc</topic><topic>Biosynthetic intermediate</topic><topic>Cyclopentanes</topic><topic>Cyclopropane fatty acid</topic><topic>Cyclopropanes - chemical synthesis</topic><topic>Cyclopropanes - chemistry</topic><topic>Cyclopropanes - pharmacology</topic><topic>Cyclopropene fatty acid</topic><topic>Diiodocyclopropane</topic><topic>Fatty Acids, Nonesterified - chemical synthesis</topic><topic>Fatty Acids, Nonesterified - chemistry</topic><topic>Fatty Acids, Nonesterified - pharmacology</topic><topic>Indicators and Reagents</topic><topic>Inhibitor</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Molecular Structure</topic><topic>Mycobacterium - drug effects</topic><topic>Mycobacterium - metabolism</topic><topic>Mycolic acid</topic><topic>Mycolic Acids - antagonists & inhibitors</topic><topic>Mycolic Acids - metabolism</topic><topic>Propionates - chemical synthesis</topic><topic>Propionates - chemistry</topic><topic>Propionates - pharmacology</topic><topic>Tetracosenoic acid</topic><topic>Valerates - chemistry</topic><topic>Valerates - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hartmann, S.</creatorcontrib><creatorcontrib>Minnikin, D.E.</creatorcontrib><creatorcontrib>Römming, H.-J.</creatorcontrib><creatorcontrib>Baird, M.S.</creatorcontrib><creatorcontrib>Ratledge, C.</creatorcontrib><creatorcontrib>Wheeler, P.R.</creatorcontrib><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>Chemistry and physics of lipids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hartmann, S.</au><au>Minnikin, D.E.</au><au>Römming, H.-J.</au><au>Baird, M.S.</au><au>Ratledge, C.</au><au>Wheeler, P.R.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of methyl 3-(2-octadecylcyclopropen-1-yl)propanoate and methyl 3-(2-octadecylcyclopropen-1-yl)pentanoate and cyclopropane fatty acids as possible inhibitors of mycolic acid biosynthesis</atitle><jtitle>Chemistry and physics of lipids</jtitle><addtitle>Chem Phys Lipids</addtitle><date>1994-05-06</date><risdate>1994</risdate><volume>71</volume><issue>1</issue><spage>99</spage><epage>108</epage><pages>99-108</pages><issn>0009-3084</issn><eissn>1873-2941</eissn><abstract>(
Z)-Tetracos-5-enoic acid is a key intermediate in the biosynthesis of mycobacterial mycolic acids. Recently the methyl ester of its cyclopropene analogue, methyl 4-(2-octadecylcyclopropen-1-yl)butanoate, was shown to act as an inhibitor of mycolic acid biosynthesis. The related analogues methyl 5-(2-octadecylcyclopropen-1-yl)pentanoate and methyl 3-(2-octadecylcyclopropen-1-yl)propanoate have been synthesised, as well as the related cyclopropane esters methyl (
Z)-4-(2-octadecylcyclopropan-1-yl)butanoate and methyl (
Z)-5-(2-octadecylcyclopropan-1-yl)pentanoate. The synthesis of methyl 3-(2-octadecylcyclopropen-1-yl)propanoate involved protection of the cyclopropene ring by iodination to allow oxidation of an alcohol to a carboxylic acid; the diiodocyclopropane was deprotected by a new mild procedure using activated zinc.</abstract><cop>Ireland</cop><pub>Elsevier Ireland Ltd</pub><pmid>8039261</pmid><doi>10.1016/0009-3084(94)02315-8</doi><tpages>10</tpages></addata></record> |
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| ispartof | Chemistry and physics of lipids, 1994-05, Vol.71 (1), p.99-108 |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Activated zinc Biosynthetic intermediate Cyclopentanes Cyclopropane fatty acid Cyclopropanes - chemical synthesis Cyclopropanes - chemistry Cyclopropanes - pharmacology Cyclopropene fatty acid Diiodocyclopropane Fatty Acids, Nonesterified - chemical synthesis Fatty Acids, Nonesterified - chemistry Fatty Acids, Nonesterified - pharmacology Indicators and Reagents Inhibitor Magnetic Resonance Spectroscopy Mass Spectrometry Molecular Structure Mycobacterium - drug effects Mycobacterium - metabolism Mycolic acid Mycolic Acids - antagonists & inhibitors Mycolic Acids - metabolism Propionates - chemical synthesis Propionates - chemistry Propionates - pharmacology Tetracosenoic acid Valerates - chemistry Valerates - pharmacology |
| title | Synthesis of methyl 3-(2-octadecylcyclopropen-1-yl)propanoate and methyl 3-(2-octadecylcyclopropen-1-yl)pentanoate and cyclopropane fatty acids as possible inhibitors of mycolic acid biosynthesis |
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