Functionalized Phosphanyl-Phosphonic Acids as Unusual Complexing Units as Analogues of Fosmidomycin
Fosmidomycin (1a) and FR‐90098 are potent inhibitors of 1‐deoxy‐D‐xylulose‐5‐phosphate reductoisomerase (DXR), the second enzyme of the non‐mevalonate (MEP) pathway responsible for the biosynthesis of isoprenoids. This paper describes the synthesis of four types of targets bearing a phosphanyl‐phosp...
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| Veröffentlicht in: | European journal of organic chemistry 2012-06, Vol.2012 (17), p.3237-3248 |
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| container_title | European journal of organic chemistry |
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| creator | Montel, Sonia Midrier, Camille Volle, Jean-Noël Braun, Ralf Haaf, Klaus Willms, Lothar Pirat, Jean-Luc Virieux, David |
| description | Fosmidomycin (1a) and FR‐90098 are potent inhibitors of 1‐deoxy‐D‐xylulose‐5‐phosphate reductoisomerase (DXR), the second enzyme of the non‐mevalonate (MEP) pathway responsible for the biosynthesis of isoprenoids. This paper describes the synthesis of four types of targets bearing a phosphanyl‐phosphonic acid motif as the common core for the inhibition of DXR. In these structures, the hydroxamic acid was replaced by various chelators based on a phosphinic acid linked to different functional groups capable of forming five‐ or six‐membered chelating rings.
Fosmidomycin (1a) and FR‐90098 are potent inhibitors of 1‐deoxy‐D‐xylulose‐5‐phosphate reductoisomerase (DXR). The replacement of the hydroxamic acid by functionalized phosphinic acids led to four types of targets which could act as analogues of fosmidomycin. |
| doi_str_mv | 10.1002/ejoc.201200210 |
| format | Article |
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Fosmidomycin (1a) and FR‐90098 are potent inhibitors of 1‐deoxy‐D‐xylulose‐5‐phosphate reductoisomerase (DXR). The replacement of the hydroxamic acid by functionalized phosphinic acids led to four types of targets which could act as analogues of fosmidomycin.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201200210</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Arylation ; Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; Chemical Sciences ; Chemistry ; Coordination compounds ; Enzymes ; Exact sciences and technology ; Fundamental and applied biological sciences. Psychology ; Inhibitors ; Inorganic chemistry and origins of life ; Methods. Procedures. Technologies ; Natural products ; Organic chemistry ; Organometalloidal and organometallic compounds ; P derivatives ; Palladium ; Phosphorus ; Preparations and properties ; Synthetic methods</subject><ispartof>European journal of organic chemistry, 2012-06, Vol.2012 (17), p.3237-3248</ispartof><rights>Copyright © 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3910-8de29867e5a94146c590d8ee2c63770bdcb8cd2328f4dd81ec0de082476663d03</citedby><cites>FETCH-LOGICAL-c3910-8de29867e5a94146c590d8ee2c63770bdcb8cd2328f4dd81ec0de082476663d03</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.201200210$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201200210$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,315,781,785,886,1418,27928,27929,45578,45579</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26042670$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00993938$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Montel, Sonia</creatorcontrib><creatorcontrib>Midrier, Camille</creatorcontrib><creatorcontrib>Volle, Jean-Noël</creatorcontrib><creatorcontrib>Braun, Ralf</creatorcontrib><creatorcontrib>Haaf, Klaus</creatorcontrib><creatorcontrib>Willms, Lothar</creatorcontrib><creatorcontrib>Pirat, Jean-Luc</creatorcontrib><creatorcontrib>Virieux, David</creatorcontrib><title>Functionalized Phosphanyl-Phosphonic Acids as Unusual Complexing Units as Analogues of Fosmidomycin</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>Fosmidomycin (1a) and FR‐90098 are potent inhibitors of 1‐deoxy‐D‐xylulose‐5‐phosphate reductoisomerase (DXR), the second enzyme of the non‐mevalonate (MEP) pathway responsible for the biosynthesis of isoprenoids. This paper describes the synthesis of four types of targets bearing a phosphanyl‐phosphonic acid motif as the common core for the inhibition of DXR. In these structures, the hydroxamic acid was replaced by various chelators based on a phosphinic acid linked to different functional groups capable of forming five‐ or six‐membered chelating rings.
Fosmidomycin (1a) and FR‐90098 are potent inhibitors of 1‐deoxy‐D‐xylulose‐5‐phosphate reductoisomerase (DXR). The replacement of the hydroxamic acid by functionalized phosphinic acids led to four types of targets which could act as analogues of fosmidomycin.</description><subject>Arylation</subject><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Chemical Sciences</subject><subject>Chemistry</subject><subject>Coordination compounds</subject><subject>Enzymes</subject><subject>Exact sciences and technology</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Inhibitors</subject><subject>Inorganic chemistry and origins of life</subject><subject>Methods. Procedures. Technologies</subject><subject>Natural products</subject><subject>Organic chemistry</subject><subject>Organometalloidal and organometallic compounds</subject><subject>P derivatives</subject><subject>Palladium</subject><subject>Phosphorus</subject><subject>Preparations and properties</subject><subject>Synthetic methods</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqFkM1PwjAYxhejiYhePe_iwcPwbTu69bgsAhoixohwa0rbQXGsZGUK_vUOZxZvnt6PPr_nTR_Pu0bQQwD4Tq-t7GFAuB4QnHgdBIwFQBmc1n1IwgAxMj_3LpxbAwCjFHU8OagKuTO2ELn50sp_Xlm3XYnikAdNawsj_UQa5Xzh_GlRuUrkfmo321zvTbGsV2b385bUHnZZaefbzB9YtzHKbg7SFJfeWSZyp69-a9ebDu5f01Ewngwf0mQcSMIQBLHSmMU00n3BQhRS2WegYq2xpCSKYKHkIpYKExxnoVIx0hKUhhiHEaWUKCBd77bxXYmcb0uzEeWBW2H4KBnz467-NCOMxB-o1vYarSytc6XOWgABP8bJj3HyNs4auGmArXBS5FkpCmlcS2EKIabRUcca3afJ9eEfV37_OEn_3gga1rid3resKN85jUjU57OnIU_fZrNR-jLmc_INjmaWQQ</recordid><startdate>201206</startdate><enddate>201206</enddate><creator>Montel, Sonia</creator><creator>Midrier, Camille</creator><creator>Volle, Jean-Noël</creator><creator>Braun, Ralf</creator><creator>Haaf, Klaus</creator><creator>Willms, Lothar</creator><creator>Pirat, Jean-Luc</creator><creator>Virieux, David</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><general>Wiley-VCH Verlag</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope></search><sort><creationdate>201206</creationdate><title>Functionalized Phosphanyl-Phosphonic Acids as Unusual Complexing Units as Analogues of Fosmidomycin</title><author>Montel, Sonia ; Midrier, Camille ; Volle, Jean-Noël ; Braun, Ralf ; Haaf, Klaus ; Willms, Lothar ; Pirat, Jean-Luc ; Virieux, David</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3910-8de29867e5a94146c590d8ee2c63770bdcb8cd2328f4dd81ec0de082476663d03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Arylation</topic><topic>Bioconversions. Hemisynthesis</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Chemical Sciences</topic><topic>Chemistry</topic><topic>Coordination compounds</topic><topic>Enzymes</topic><topic>Exact sciences and technology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Inhibitors</topic><topic>Inorganic chemistry and origins of life</topic><topic>Methods. Procedures. Technologies</topic><topic>Natural products</topic><topic>Organic chemistry</topic><topic>Organometalloidal and organometallic compounds</topic><topic>P derivatives</topic><topic>Palladium</topic><topic>Phosphorus</topic><topic>Preparations and properties</topic><topic>Synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Montel, Sonia</creatorcontrib><creatorcontrib>Midrier, Camille</creatorcontrib><creatorcontrib>Volle, Jean-Noël</creatorcontrib><creatorcontrib>Braun, Ralf</creatorcontrib><creatorcontrib>Haaf, Klaus</creatorcontrib><creatorcontrib>Willms, Lothar</creatorcontrib><creatorcontrib>Pirat, Jean-Luc</creatorcontrib><creatorcontrib>Virieux, David</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Montel, Sonia</au><au>Midrier, Camille</au><au>Volle, Jean-Noël</au><au>Braun, Ralf</au><au>Haaf, Klaus</au><au>Willms, Lothar</au><au>Pirat, Jean-Luc</au><au>Virieux, David</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Functionalized Phosphanyl-Phosphonic Acids as Unusual Complexing Units as Analogues of Fosmidomycin</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2012-06</date><risdate>2012</risdate><volume>2012</volume><issue>17</issue><spage>3237</spage><epage>3248</epage><pages>3237-3248</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Fosmidomycin (1a) and FR‐90098 are potent inhibitors of 1‐deoxy‐D‐xylulose‐5‐phosphate reductoisomerase (DXR), the second enzyme of the non‐mevalonate (MEP) pathway responsible for the biosynthesis of isoprenoids. This paper describes the synthesis of four types of targets bearing a phosphanyl‐phosphonic acid motif as the common core for the inhibition of DXR. In these structures, the hydroxamic acid was replaced by various chelators based on a phosphinic acid linked to different functional groups capable of forming five‐ or six‐membered chelating rings.
Fosmidomycin (1a) and FR‐90098 are potent inhibitors of 1‐deoxy‐D‐xylulose‐5‐phosphate reductoisomerase (DXR). The replacement of the hydroxamic acid by functionalized phosphinic acids led to four types of targets which could act as analogues of fosmidomycin.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201200210</doi><tpages>12</tpages></addata></record> |
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| subjects | Arylation Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Chemical Sciences Chemistry Coordination compounds Enzymes Exact sciences and technology Fundamental and applied biological sciences. Psychology Inhibitors Inorganic chemistry and origins of life Methods. Procedures. Technologies Natural products Organic chemistry Organometalloidal and organometallic compounds P derivatives Palladium Phosphorus Preparations and properties Synthetic methods |
| title | Functionalized Phosphanyl-Phosphonic Acids as Unusual Complexing Units as Analogues of Fosmidomycin |
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