Formation of a Highly Oxidized Iron Biliverdin Complex upon Treatment of a Five-Coordinate Verdoheme with Dioxygen
Treatment of a green solution of the five-coordinate octaethylverdoheme, XFeII(OEOP) 1 (X = Cl or Br), with dioxygen results in the formation of a new iron complex of octaethylbiliverdin, 2, within a matter of minutes. The reaction has been monitored by 1H NMR spectroscopy, and the product 2 (X = Cl...
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| Veröffentlicht in: | Journal of the American Chemical Society 2004-05, Vol.126 (20), p.6210-6211 |
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| container_title | Journal of the American Chemical Society |
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| creator | Nguyen, Khoi T Rath, Sankar Prasad Latos-Grażyński, Lechosław Olmstead, Marilyn M Balch, Alan L |
| description | Treatment of a green solution of the five-coordinate octaethylverdoheme, XFeII(OEOP) 1 (X = Cl or Br), with dioxygen results in the formation of a new iron complex of octaethylbiliverdin, 2, within a matter of minutes. The reaction has been monitored by 1H NMR spectroscopy, and the product 2 (X = Cl) has been isolated and examined by X-ray crystallography. The structure of 2 (X = Cl) shows that the iron is five-coordinate with bonds to the four nitrogen atoms of the helical tetrapyrrole ligand and to an axial chloride. Treatment of 2 (X = Cl or Br) with zinc amalgam produces the known iron(III) complex of biliverdin, {FeIII(OEB)}2. The unusual pattern of resonances in the 1H NMR spectrum of 2 and its facile reduction to {FeIII(OEB)}2 indicate that 2 is an oxidized complex that can be formulated by resonance structures involving either an Fe(IV) ion bound to a bilindione trianion or an Fe(III) ion bound to an oxidized, dianionic, radical form of the ligand. |
| doi_str_mv | 10.1021/ja049222d |
| format | Article |
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The reaction has been monitored by 1H NMR spectroscopy, and the product 2 (X = Cl) has been isolated and examined by X-ray crystallography. The structure of 2 (X = Cl) shows that the iron is five-coordinate with bonds to the four nitrogen atoms of the helical tetrapyrrole ligand and to an axial chloride. Treatment of 2 (X = Cl or Br) with zinc amalgam produces the known iron(III) complex of biliverdin, {FeIII(OEB)}2. The unusual pattern of resonances in the 1H NMR spectrum of 2 and its facile reduction to {FeIII(OEB)}2 indicate that 2 is an oxidized complex that can be formulated by resonance structures involving either an Fe(IV) ion bound to a bilindione trianion or an Fe(III) ion bound to an oxidized, dianionic, radical form of the ligand.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja049222d</identifier><identifier>PMID: 15149200</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Biliverdine - chemistry ; Biological and medical sciences ; Fundamental and applied biological sciences. Psychology ; Heme - analogs & derivatives ; Heme - chemistry ; Indicators and Reagents ; Iron - chemistry ; Magnetic Resonance Spectroscopy ; Mechanisms. Catalysis. Electron transfer. Models ; Models, Molecular ; Molecular biophysics ; Molecular Conformation ; Oxidation-Reduction ; Oxygen - chemistry ; Physical chemistry in biology</subject><ispartof>Journal of the American Chemical Society, 2004-05, Vol.126 (20), p.6210-6211</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-b3e5a6f470dd5305f7ee8810ea3713d56d68989cb7e792c8a5326f28a3ef0813</citedby><cites>FETCH-LOGICAL-a379t-b3e5a6f470dd5305f7ee8810ea3713d56d68989cb7e792c8a5326f28a3ef0813</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ja049222d$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja049222d$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15770557$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15149200$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nguyen, Khoi T</creatorcontrib><creatorcontrib>Rath, Sankar Prasad</creatorcontrib><creatorcontrib>Latos-Grażyński, Lechosław</creatorcontrib><creatorcontrib>Olmstead, Marilyn M</creatorcontrib><creatorcontrib>Balch, Alan L</creatorcontrib><title>Formation of a Highly Oxidized Iron Biliverdin Complex upon Treatment of a Five-Coordinate Verdoheme with Dioxygen</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Treatment of a green solution of the five-coordinate octaethylverdoheme, XFeII(OEOP) 1 (X = Cl or Br), with dioxygen results in the formation of a new iron complex of octaethylbiliverdin, 2, within a matter of minutes. The reaction has been monitored by 1H NMR spectroscopy, and the product 2 (X = Cl) has been isolated and examined by X-ray crystallography. The structure of 2 (X = Cl) shows that the iron is five-coordinate with bonds to the four nitrogen atoms of the helical tetrapyrrole ligand and to an axial chloride. Treatment of 2 (X = Cl or Br) with zinc amalgam produces the known iron(III) complex of biliverdin, {FeIII(OEB)}2. The unusual pattern of resonances in the 1H NMR spectrum of 2 and its facile reduction to {FeIII(OEB)}2 indicate that 2 is an oxidized complex that can be formulated by resonance structures involving either an Fe(IV) ion bound to a bilindione trianion or an Fe(III) ion bound to an oxidized, dianionic, radical form of the ligand.</description><subject>Biliverdine - chemistry</subject><subject>Biological and medical sciences</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Heme - analogs & derivatives</subject><subject>Heme - chemistry</subject><subject>Indicators and Reagents</subject><subject>Iron - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mechanisms. Catalysis. Electron transfer. Models</subject><subject>Models, Molecular</subject><subject>Molecular biophysics</subject><subject>Molecular Conformation</subject><subject>Oxidation-Reduction</subject><subject>Oxygen - chemistry</subject><subject>Physical chemistry in biology</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E9P2zAYBnALbYLCduALTL5sEoeA_9SxcxwZXZHQ2LRqBy6WG7-h7pK42Am0fPoZWsEOnCz7-b2vrAehY0pOKWH0bGnIuGCM2T00ooKRTFCWv0MjQgjLpMr5ATqMcZmuY6boPjqggqYBQkYoTHxoTe98h32NDZ6620WzwddrZ90jWHwZUnLuGncPwboOl75dNbDGwyq9zwKYvoWu385OEspK75-g6QH_SSN-AS3gB9cv8Dfn15tb6D6g97VpInzcnUdoNrmYldPs6vr7Zfn1KjNcFn025yBMXo8lsVZwImoJoBQlkGLKrchtrgpVVHMJsmCVMoKzvGbKcKiJovwIfdmuXQV_N0DsdetiBU1jOvBD1JIWYyGf4ckWVsHHGKDWq-BaEzaaEv3Ur37pN9lPu6XDvAX7KneFJvB5B0ysTFMH01Uu_uekJELI5LKtc7GH9Utuwl-dSy6Fnv38rac_fpU3bCr0-eteU0W99EPoUnVvfPAfjMqdrw</recordid><startdate>20040526</startdate><enddate>20040526</enddate><creator>Nguyen, Khoi T</creator><creator>Rath, Sankar Prasad</creator><creator>Latos-Grażyński, Lechosław</creator><creator>Olmstead, Marilyn M</creator><creator>Balch, Alan L</creator><general>American Chemical Society</general><scope>BSCLL</scope><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>20040526</creationdate><title>Formation of a Highly Oxidized Iron Biliverdin Complex upon Treatment of a Five-Coordinate Verdoheme with Dioxygen</title><author>Nguyen, Khoi T ; Rath, Sankar Prasad ; Latos-Grażyński, Lechosław ; Olmstead, Marilyn M ; Balch, Alan L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-b3e5a6f470dd5305f7ee8810ea3713d56d68989cb7e792c8a5326f28a3ef0813</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Biliverdine - chemistry</topic><topic>Biological and medical sciences</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Heme - analogs & derivatives</topic><topic>Heme - chemistry</topic><topic>Indicators and Reagents</topic><topic>Iron - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mechanisms. Catalysis. Electron transfer. Models</topic><topic>Models, Molecular</topic><topic>Molecular biophysics</topic><topic>Molecular Conformation</topic><topic>Oxidation-Reduction</topic><topic>Oxygen - chemistry</topic><topic>Physical chemistry in biology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nguyen, Khoi T</creatorcontrib><creatorcontrib>Rath, Sankar Prasad</creatorcontrib><creatorcontrib>Latos-Grażyński, Lechosław</creatorcontrib><creatorcontrib>Olmstead, Marilyn M</creatorcontrib><creatorcontrib>Balch, Alan L</creatorcontrib><collection>Istex</collection><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 the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nguyen, Khoi T</au><au>Rath, Sankar Prasad</au><au>Latos-Grażyński, Lechosław</au><au>Olmstead, Marilyn M</au><au>Balch, Alan L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Formation of a Highly Oxidized Iron Biliverdin Complex upon Treatment of a Five-Coordinate Verdoheme with Dioxygen</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2004-05-26</date><risdate>2004</risdate><volume>126</volume><issue>20</issue><spage>6210</spage><epage>6211</epage><pages>6210-6211</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>Treatment of a green solution of the five-coordinate octaethylverdoheme, XFeII(OEOP) 1 (X = Cl or Br), with dioxygen results in the formation of a new iron complex of octaethylbiliverdin, 2, within a matter of minutes. The reaction has been monitored by 1H NMR spectroscopy, and the product 2 (X = Cl) has been isolated and examined by X-ray crystallography. The structure of 2 (X = Cl) shows that the iron is five-coordinate with bonds to the four nitrogen atoms of the helical tetrapyrrole ligand and to an axial chloride. Treatment of 2 (X = Cl or Br) with zinc amalgam produces the known iron(III) complex of biliverdin, {FeIII(OEB)}2. The unusual pattern of resonances in the 1H NMR spectrum of 2 and its facile reduction to {FeIII(OEB)}2 indicate that 2 is an oxidized complex that can be formulated by resonance structures involving either an Fe(IV) ion bound to a bilindione trianion or an Fe(III) ion bound to an oxidized, dianionic, radical form of the ligand.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15149200</pmid><doi>10.1021/ja049222d</doi><tpages>2</tpages></addata></record> |
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| subjects | Biliverdine - chemistry Biological and medical sciences Fundamental and applied biological sciences. Psychology Heme - analogs & derivatives Heme - chemistry Indicators and Reagents Iron - chemistry Magnetic Resonance Spectroscopy Mechanisms. Catalysis. Electron transfer. Models Models, Molecular Molecular biophysics Molecular Conformation Oxidation-Reduction Oxygen - chemistry Physical chemistry in biology |
| title | Formation of a Highly Oxidized Iron Biliverdin Complex upon Treatment of a Five-Coordinate Verdoheme with Dioxygen |
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