Models for cytochrome P450 prosthetic heme alkylation. Reaction of diazoacetophenone with (tetraphenylporphyrinato)iron(II) chloride
The reaction of diazoacetophenone with (tetraphenylporphyrinato)iron(II) yields (N-(2-phenyl-2-oxoethyl)tetraphenylporphyrinato)iron(II) chloride. The structure of this product has been established by spectroscopic methods and by x-ray crystallography. The crystal structure shows that the first carb...
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| Veröffentlicht in: | Inorg. Chem.; (United States) 1988-09, Vol.27 (18), p.3112-3117 |
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| creator | Komives, Elizabeth A Tew, David Olmstead, Marilyn M Ortiz de Montellano, Paul R |
| description | The reaction of diazoacetophenone with (tetraphenylporphyrinato)iron(II) yields (N-(2-phenyl-2-oxoethyl)tetraphenylporphyrinato)iron(II) chloride. The structure of this product has been established by spectroscopic methods and by x-ray crystallography. The crystal structure shows that the first carbon of the N-alkyl group is 2.94 /angstrom/ from the iron atom and that the oxygen of the N-alkyl group points away from the iron. No evidence is seen for the Fe-C-N product expected from insertion of the diazo carbon into the metalloporphyrin iron-nitrogen bond or for intermediates in which the oxygen of the N-(2-phenyl-2-oxoethyl) group is coordinated to the iron. These results suggest it is unlikely that carbene-insertion or oxygen-coordinated intermediates will be detected during the N-alkylation of cytochrome P450 by diazo ketones. The results also rationalize the failure to detect iron-chelated enol species during N-alkylation of the prosthetic group of cytochrome P450 by catalytically activated phenylacetylene. 43 references, 5 figures, 4 tables. |
| doi_str_mv | 10.1021/ic00291a014 |
| format | Article |
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Reaction of diazoacetophenone with (tetraphenylporphyrinato)iron(II) chloride</title><source>ACS Publications</source><creator>Komives, Elizabeth A ; Tew, David ; Olmstead, Marilyn M ; Ortiz de Montellano, Paul R</creator><creatorcontrib>Komives, Elizabeth A ; Tew, David ; Olmstead, Marilyn M ; Ortiz de Montellano, Paul R ; Univ. of California, San Francisco (USA)</creatorcontrib><description>The reaction of diazoacetophenone with (tetraphenylporphyrinato)iron(II) yields (N-(2-phenyl-2-oxoethyl)tetraphenylporphyrinato)iron(II) chloride. The structure of this product has been established by spectroscopic methods and by x-ray crystallography. The crystal structure shows that the first carbon of the N-alkyl group is 2.94 /angstrom/ from the iron atom and that the oxygen of the N-alkyl group points away from the iron. No evidence is seen for the Fe-C-N product expected from insertion of the diazo carbon into the metalloporphyrin iron-nitrogen bond or for intermediates in which the oxygen of the N-(2-phenyl-2-oxoethyl) group is coordinated to the iron. These results suggest it is unlikely that carbene-insertion or oxygen-coordinated intermediates will be detected during the N-alkylation of cytochrome P450 by diazo ketones. The results also rationalize the failure to detect iron-chelated enol species during N-alkylation of the prosthetic group of cytochrome P450 by catalytically activated phenylacetylene. 43 references, 5 figures, 4 tables.</description><identifier>ISSN: 0020-1669</identifier><identifier>EISSN: 1520-510X</identifier><identifier>DOI: 10.1021/ic00291a014</identifier><identifier>CODEN: INOCAJ</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>400201 - Chemical & Physicochemical Properties ; 400202 - Isotope Effects, Isotope Exchange, & Isotope Separation ; Bioinorganic chemistry ; CARBON 13 ; CARBON ISOTOPES ; CARBOXYLIC ACIDS ; Chemistry ; CHLORIDES ; CHLORINE COMPOUNDS ; CRYSTALLOGRAPHY ; DATA ; ELECTROMAGNETIC RADIATION ; EVEN-ODD NUCLEI ; Exact sciences and technology ; EXPERIMENTAL DATA ; HALIDES ; HALOGEN COMPOUNDS ; HETEROCYCLIC ACIDS ; HETEROCYCLIC COMPOUNDS ; INFORMATION ; Inorganic chemistry and origins of life ; INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY ; IONIZING RADIATIONS ; IRON CHLORIDES ; IRON COMPOUNDS ; ISOTOPE APPLICATIONS ; ISOTOPES ; LABELLED COMPOUNDS ; LIGHT NUCLEI ; MOLECULAR STRUCTURE ; NUCLEI ; NUMERICAL DATA ; ORGANIC ACIDS ; ORGANIC COMPOUNDS ; ORGANIC NITROGEN COMPOUNDS ; PORPHYRINS ; RADIATIONS ; SPECTROSCOPY ; STABLE ISOTOPES ; TRACER TECHNIQUES ; TRANSITION ELEMENT COMPOUNDS ; X RADIATION</subject><ispartof>Inorg. Chem.; (United States), 1988-09, Vol.27 (18), p.3112-3117</ispartof><rights>1989 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a357t-5ce9f34e22d3bf7cded62fa532a64a01c023dd18b13ba2002f5b40c62ebdc45f3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ic00291a014$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ic00291a014$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,881,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=6998081$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/5852979$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Komives, Elizabeth A</creatorcontrib><creatorcontrib>Tew, David</creatorcontrib><creatorcontrib>Olmstead, Marilyn M</creatorcontrib><creatorcontrib>Ortiz de Montellano, Paul R</creatorcontrib><creatorcontrib>Univ. of California, San Francisco (USA)</creatorcontrib><title>Models for cytochrome P450 prosthetic heme alkylation. Reaction of diazoacetophenone with (tetraphenylporphyrinato)iron(II) chloride</title><title>Inorg. Chem.; (United States)</title><addtitle>Inorg. Chem</addtitle><description>The reaction of diazoacetophenone with (tetraphenylporphyrinato)iron(II) yields (N-(2-phenyl-2-oxoethyl)tetraphenylporphyrinato)iron(II) chloride. The structure of this product has been established by spectroscopic methods and by x-ray crystallography. The crystal structure shows that the first carbon of the N-alkyl group is 2.94 /angstrom/ from the iron atom and that the oxygen of the N-alkyl group points away from the iron. No evidence is seen for the Fe-C-N product expected from insertion of the diazo carbon into the metalloporphyrin iron-nitrogen bond or for intermediates in which the oxygen of the N-(2-phenyl-2-oxoethyl) group is coordinated to the iron. These results suggest it is unlikely that carbene-insertion or oxygen-coordinated intermediates will be detected during the N-alkylation of cytochrome P450 by diazo ketones. The results also rationalize the failure to detect iron-chelated enol species during N-alkylation of the prosthetic group of cytochrome P450 by catalytically activated phenylacetylene. 43 references, 5 figures, 4 tables.</description><subject>400201 - Chemical & Physicochemical Properties</subject><subject>400202 - Isotope Effects, Isotope Exchange, & Isotope Separation</subject><subject>Bioinorganic chemistry</subject><subject>CARBON 13</subject><subject>CARBON ISOTOPES</subject><subject>CARBOXYLIC ACIDS</subject><subject>Chemistry</subject><subject>CHLORIDES</subject><subject>CHLORINE COMPOUNDS</subject><subject>CRYSTALLOGRAPHY</subject><subject>DATA</subject><subject>ELECTROMAGNETIC RADIATION</subject><subject>EVEN-ODD NUCLEI</subject><subject>Exact sciences and technology</subject><subject>EXPERIMENTAL DATA</subject><subject>HALIDES</subject><subject>HALOGEN COMPOUNDS</subject><subject>HETEROCYCLIC ACIDS</subject><subject>HETEROCYCLIC COMPOUNDS</subject><subject>INFORMATION</subject><subject>Inorganic chemistry and origins of life</subject><subject>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</subject><subject>IONIZING RADIATIONS</subject><subject>IRON CHLORIDES</subject><subject>IRON COMPOUNDS</subject><subject>ISOTOPE APPLICATIONS</subject><subject>ISOTOPES</subject><subject>LABELLED COMPOUNDS</subject><subject>LIGHT NUCLEI</subject><subject>MOLECULAR STRUCTURE</subject><subject>NUCLEI</subject><subject>NUMERICAL DATA</subject><subject>ORGANIC ACIDS</subject><subject>ORGANIC COMPOUNDS</subject><subject>ORGANIC NITROGEN COMPOUNDS</subject><subject>PORPHYRINS</subject><subject>RADIATIONS</subject><subject>SPECTROSCOPY</subject><subject>STABLE ISOTOPES</subject><subject>TRACER TECHNIQUES</subject><subject>TRANSITION ELEMENT COMPOUNDS</subject><subject>X RADIATION</subject><issn>0020-1669</issn><issn>1520-510X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1988</creationdate><recordtype>article</recordtype><recordid>eNptkEFv1DAQhSNEJZbCiT9gISRaVSm2EyebI5SWLlpEVYrUmzWZjBW3aRzZRpCe-8PrVVDFgdOM3nwzmvey7I3gx4JL8cEi57IRwEX5LFsJJXmuBL9-nq2SznNRVc2L7GUIN5zzpiirVfbwzXU0BGacZzhHh713d8QuSsXZ5F2IPUWLrKckwnA7DxCtG4_ZJQHuOuYM6yzcO0CKbuppdCOx3zb27CBS9LCT5mFyfupnb0eI7tB6Nx5sNocM-8F529GrbM_AEOj137qf_Tw7vTo5z7ffv2xOPm5zKFQdc4XUmKIkKbuiNTV21FXSgCokVGXyjFwWXSfWrShakMmxUW3JsZLUdlgqU-xnb5e7yZfVAW0k7NGNI2HUaq1kUzcJOlogTPaDJ6Mnb-_Az1pwvUtZ_5Nyot8t9AQBYTAeRrThaaVqmjVfi4TlC2ZDpD9PY_C3uqqLWumrix_68_arOj-7vtSfEv9-4QGDvnG__Jhy-e8Dj_JXmq8</recordid><startdate>19880901</startdate><enddate>19880901</enddate><creator>Komives, Elizabeth A</creator><creator>Tew, David</creator><creator>Olmstead, Marilyn M</creator><creator>Ortiz de Montellano, Paul R</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>OTOTI</scope></search><sort><creationdate>19880901</creationdate><title>Models for cytochrome P450 prosthetic heme alkylation. Reaction of diazoacetophenone with (tetraphenylporphyrinato)iron(II) chloride</title><author>Komives, Elizabeth A ; Tew, David ; Olmstead, Marilyn M ; Ortiz de Montellano, Paul R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a357t-5ce9f34e22d3bf7cded62fa532a64a01c023dd18b13ba2002f5b40c62ebdc45f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1988</creationdate><topic>400201 - Chemical & Physicochemical Properties</topic><topic>400202 - Isotope Effects, Isotope Exchange, & Isotope Separation</topic><topic>Bioinorganic chemistry</topic><topic>CARBON 13</topic><topic>CARBON ISOTOPES</topic><topic>CARBOXYLIC ACIDS</topic><topic>Chemistry</topic><topic>CHLORIDES</topic><topic>CHLORINE COMPOUNDS</topic><topic>CRYSTALLOGRAPHY</topic><topic>DATA</topic><topic>ELECTROMAGNETIC RADIATION</topic><topic>EVEN-ODD NUCLEI</topic><topic>Exact sciences and technology</topic><topic>EXPERIMENTAL DATA</topic><topic>HALIDES</topic><topic>HALOGEN COMPOUNDS</topic><topic>HETEROCYCLIC ACIDS</topic><topic>HETEROCYCLIC COMPOUNDS</topic><topic>INFORMATION</topic><topic>Inorganic chemistry and origins of life</topic><topic>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</topic><topic>IONIZING RADIATIONS</topic><topic>IRON CHLORIDES</topic><topic>IRON COMPOUNDS</topic><topic>ISOTOPE APPLICATIONS</topic><topic>ISOTOPES</topic><topic>LABELLED COMPOUNDS</topic><topic>LIGHT NUCLEI</topic><topic>MOLECULAR STRUCTURE</topic><topic>NUCLEI</topic><topic>NUMERICAL DATA</topic><topic>ORGANIC ACIDS</topic><topic>ORGANIC COMPOUNDS</topic><topic>ORGANIC NITROGEN COMPOUNDS</topic><topic>PORPHYRINS</topic><topic>RADIATIONS</topic><topic>SPECTROSCOPY</topic><topic>STABLE ISOTOPES</topic><topic>TRACER TECHNIQUES</topic><topic>TRANSITION ELEMENT COMPOUNDS</topic><topic>X RADIATION</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Komives, Elizabeth A</creatorcontrib><creatorcontrib>Tew, David</creatorcontrib><creatorcontrib>Olmstead, Marilyn M</creatorcontrib><creatorcontrib>Ortiz de Montellano, Paul R</creatorcontrib><creatorcontrib>Univ. of California, San Francisco (USA)</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>OSTI.GOV</collection><jtitle>Inorg. Chem.; (United States)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Komives, Elizabeth A</au><au>Tew, David</au><au>Olmstead, Marilyn M</au><au>Ortiz de Montellano, Paul R</au><aucorp>Univ. of California, San Francisco (USA)</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Models for cytochrome P450 prosthetic heme alkylation. Reaction of diazoacetophenone with (tetraphenylporphyrinato)iron(II) chloride</atitle><jtitle>Inorg. Chem.; (United States)</jtitle><addtitle>Inorg. Chem</addtitle><date>1988-09-01</date><risdate>1988</risdate><volume>27</volume><issue>18</issue><spage>3112</spage><epage>3117</epage><pages>3112-3117</pages><issn>0020-1669</issn><eissn>1520-510X</eissn><coden>INOCAJ</coden><abstract>The reaction of diazoacetophenone with (tetraphenylporphyrinato)iron(II) yields (N-(2-phenyl-2-oxoethyl)tetraphenylporphyrinato)iron(II) chloride. The structure of this product has been established by spectroscopic methods and by x-ray crystallography. The crystal structure shows that the first carbon of the N-alkyl group is 2.94 /angstrom/ from the iron atom and that the oxygen of the N-alkyl group points away from the iron. No evidence is seen for the Fe-C-N product expected from insertion of the diazo carbon into the metalloporphyrin iron-nitrogen bond or for intermediates in which the oxygen of the N-(2-phenyl-2-oxoethyl) group is coordinated to the iron. These results suggest it is unlikely that carbene-insertion or oxygen-coordinated intermediates will be detected during the N-alkylation of cytochrome P450 by diazo ketones. The results also rationalize the failure to detect iron-chelated enol species during N-alkylation of the prosthetic group of cytochrome P450 by catalytically activated phenylacetylene. 43 references, 5 figures, 4 tables.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><doi>10.1021/ic00291a014</doi><tpages>6</tpages></addata></record> |
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| identifier | ISSN: 0020-1669 |
| ispartof | Inorg. Chem.; (United States), 1988-09, Vol.27 (18), p.3112-3117 |
| issn | 0020-1669 1520-510X |
| language | eng |
| recordid | cdi_crossref_primary_10_1021_ic00291a014 |
| source | ACS Publications |
| subjects | 400201 - Chemical & Physicochemical Properties 400202 - Isotope Effects, Isotope Exchange, & Isotope Separation Bioinorganic chemistry CARBON 13 CARBON ISOTOPES CARBOXYLIC ACIDS Chemistry CHLORIDES CHLORINE COMPOUNDS CRYSTALLOGRAPHY DATA ELECTROMAGNETIC RADIATION EVEN-ODD NUCLEI Exact sciences and technology EXPERIMENTAL DATA HALIDES HALOGEN COMPOUNDS HETEROCYCLIC ACIDS HETEROCYCLIC COMPOUNDS INFORMATION Inorganic chemistry and origins of life INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY IONIZING RADIATIONS IRON CHLORIDES IRON COMPOUNDS ISOTOPE APPLICATIONS ISOTOPES LABELLED COMPOUNDS LIGHT NUCLEI MOLECULAR STRUCTURE NUCLEI NUMERICAL DATA ORGANIC ACIDS ORGANIC COMPOUNDS ORGANIC NITROGEN COMPOUNDS PORPHYRINS RADIATIONS SPECTROSCOPY STABLE ISOTOPES TRACER TECHNIQUES TRANSITION ELEMENT COMPOUNDS X RADIATION |
| title | Models for cytochrome P450 prosthetic heme alkylation. Reaction of diazoacetophenone with (tetraphenylporphyrinato)iron(II) chloride |
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