Intramolecular isotope effects associated with meta-hydroxylation of biphenyl catalyzed by cytochrome P-450
Intramolecular isotope effects and the degree of deuterium retention were determined for the meta-hydroxylation of biphenyl as catalyzed by microsomal cytochrome P-450 obtained from rats pretreated with phenobarbital. The percent deuterium retention after meta-hydroxylation of 3,5,3′,5′-[ 2H 4]-biph...
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| Veröffentlicht in: | Biochemical and biophysical research communications 1984-02, Vol.118 (3), p.867-872 |
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| container_title | Biochemical and biophysical research communications |
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| creator | Swinney, D.C. Howald, W.N. Trager, W.F. |
| description | Intramolecular isotope effects and the degree of deuterium retention were determined for the meta-hydroxylation of biphenyl as catalyzed by microsomal cytochrome P-450 obtained from rats pretreated with phenobarbital. The percent deuterium retention after meta-hydroxylation of 3,5,3′,5′-[
2H
4]-biphenyl was found to be 77.3% ± 1.9. The intramolecular isotope effects associated with 3,3′-[
2H
2]-biphenyl and 3,5-[
2H
2]-biphenyl were found to be 0.90 ± .05 and 1.05 ± .06, respectively. These data demonstrate conclusively that a direct insertion or abstraction mechanism is not operable in the meta-hydroxylation of biphenyl and suggest the possibility of an addition-rearrangement mechanism as opposed to initial and direct arene oxide formation. |
| doi_str_mv | 10.1016/0006-291X(84)91475-X |
| format | Article |
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2H
4]-biphenyl was found to be 77.3% ± 1.9. The intramolecular isotope effects associated with 3,3′-[
2H
2]-biphenyl and 3,5-[
2H
2]-biphenyl were found to be 0.90 ± .05 and 1.05 ± .06, respectively. These data demonstrate conclusively that a direct insertion or abstraction mechanism is not operable in the meta-hydroxylation of biphenyl and suggest the possibility of an addition-rearrangement mechanism as opposed to initial and direct arene oxide formation.</description><identifier>ISSN: 0006-291X</identifier><identifier>EISSN: 1090-2104</identifier><identifier>DOI: 10.1016/0006-291X(84)91475-X</identifier><identifier>PMID: 6704111</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Animals ; Biphenyl Compounds - metabolism ; Chemical Phenomena ; Chemistry ; Cytochrome P-450 Enzyme System - metabolism ; Deuterium ; Hydroxylation ; Male ; Microsomes, Liver - enzymology ; Molecular Conformation ; Rats ; Rats, Inbred Strains</subject><ispartof>Biochemical and biophysical research communications, 1984-02, Vol.118 (3), p.867-872</ispartof><rights>1984</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c357t-588495c7198fb8af6ac760ed4a762b8e2d2e9fc1375216c036222d9b0880fe173</citedby><cites>FETCH-LOGICAL-c357t-588495c7198fb8af6ac760ed4a762b8e2d2e9fc1375216c036222d9b0880fe173</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/0006-291X(84)91475-X$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/6704111$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Swinney, D.C.</creatorcontrib><creatorcontrib>Howald, W.N.</creatorcontrib><creatorcontrib>Trager, W.F.</creatorcontrib><title>Intramolecular isotope effects associated with meta-hydroxylation of biphenyl catalyzed by cytochrome P-450</title><title>Biochemical and biophysical research communications</title><addtitle>Biochem Biophys Res Commun</addtitle><description>Intramolecular isotope effects and the degree of deuterium retention were determined for the meta-hydroxylation of biphenyl as catalyzed by microsomal cytochrome P-450 obtained from rats pretreated with phenobarbital. The percent deuterium retention after meta-hydroxylation of 3,5,3′,5′-[
2H
4]-biphenyl was found to be 77.3% ± 1.9. The intramolecular isotope effects associated with 3,3′-[
2H
2]-biphenyl and 3,5-[
2H
2]-biphenyl were found to be 0.90 ± .05 and 1.05 ± .06, respectively. These data demonstrate conclusively that a direct insertion or abstraction mechanism is not operable in the meta-hydroxylation of biphenyl and suggest the possibility of an addition-rearrangement mechanism as opposed to initial and direct arene oxide formation.</description><subject>Animals</subject><subject>Biphenyl Compounds - metabolism</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>Cytochrome P-450 Enzyme System - metabolism</subject><subject>Deuterium</subject><subject>Hydroxylation</subject><subject>Male</subject><subject>Microsomes, Liver - enzymology</subject><subject>Molecular Conformation</subject><subject>Rats</subject><subject>Rats, Inbred Strains</subject><issn>0006-291X</issn><issn>1090-2104</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1984</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1v1DAQhi0Earcf_4BKPqFySDv2Oo59QUJVKZUq0QNIe7McZ6w1JPFie6Hpr2-WXfXIaQ7zvO9oHkLeM7hiwOQ1AMiKa7a6VOKjZqKpq9UbsmCgoeIMxFuyeEWOyUnOPwEYE1IfkSPZgGCMLciv-7EkO8Qe3ba3iYYcS9wgRe_RlUxtztEFW7Cjf0NZ0wGLrdZTl-LT1NsS4kijp23YrHGceupssf30PNPtRN1UolunOCB9rEQNZ-Sdt33G88M8JT--3H6_-Vo9fLu7v_n8ULll3ZSqVkro2jVMK98q66V1jQTshG0kbxXyjqP2ji2bmjPpYCk5551uQSnwyJrlKfmw792k-HuLuZghZId9b0eM22wUaK2lrmdQ7EGXYs4JvdmkMNg0GQZm59jsBJqdQKOE-efYrObYxaF_2w7YvYYOUuf9p_0e5yf_BEwmu4Cjwy6kWarpYvj_gRc-KI0N</recordid><startdate>19840214</startdate><enddate>19840214</enddate><creator>Swinney, D.C.</creator><creator>Howald, W.N.</creator><creator>Trager, W.F.</creator><general>Elsevier Inc</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>19840214</creationdate><title>Intramolecular isotope effects associated with meta-hydroxylation of biphenyl catalyzed by cytochrome P-450</title><author>Swinney, D.C. ; Howald, W.N. ; Trager, W.F.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c357t-588495c7198fb8af6ac760ed4a762b8e2d2e9fc1375216c036222d9b0880fe173</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1984</creationdate><topic>Animals</topic><topic>Biphenyl Compounds - metabolism</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>Cytochrome P-450 Enzyme System - metabolism</topic><topic>Deuterium</topic><topic>Hydroxylation</topic><topic>Male</topic><topic>Microsomes, Liver - enzymology</topic><topic>Molecular Conformation</topic><topic>Rats</topic><topic>Rats, Inbred Strains</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Swinney, D.C.</creatorcontrib><creatorcontrib>Howald, W.N.</creatorcontrib><creatorcontrib>Trager, W.F.</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>Biochemical and biophysical research communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Swinney, D.C.</au><au>Howald, W.N.</au><au>Trager, W.F.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Intramolecular isotope effects associated with meta-hydroxylation of biphenyl catalyzed by cytochrome P-450</atitle><jtitle>Biochemical and biophysical research communications</jtitle><addtitle>Biochem Biophys Res Commun</addtitle><date>1984-02-14</date><risdate>1984</risdate><volume>118</volume><issue>3</issue><spage>867</spage><epage>872</epage><pages>867-872</pages><issn>0006-291X</issn><eissn>1090-2104</eissn><abstract>Intramolecular isotope effects and the degree of deuterium retention were determined for the meta-hydroxylation of biphenyl as catalyzed by microsomal cytochrome P-450 obtained from rats pretreated with phenobarbital. The percent deuterium retention after meta-hydroxylation of 3,5,3′,5′-[
2H
4]-biphenyl was found to be 77.3% ± 1.9. The intramolecular isotope effects associated with 3,3′-[
2H
2]-biphenyl and 3,5-[
2H
2]-biphenyl were found to be 0.90 ± .05 and 1.05 ± .06, respectively. These data demonstrate conclusively that a direct insertion or abstraction mechanism is not operable in the meta-hydroxylation of biphenyl and suggest the possibility of an addition-rearrangement mechanism as opposed to initial and direct arene oxide formation.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>6704111</pmid><doi>10.1016/0006-291X(84)91475-X</doi><tpages>6</tpages></addata></record> |
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| identifier | ISSN: 0006-291X |
| ispartof | Biochemical and biophysical research communications, 1984-02, Vol.118 (3), p.867-872 |
| issn | 0006-291X 1090-2104 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_80999695 |
| source | MEDLINE; ScienceDirect |
| subjects | Animals Biphenyl Compounds - metabolism Chemical Phenomena Chemistry Cytochrome P-450 Enzyme System - metabolism Deuterium Hydroxylation Male Microsomes, Liver - enzymology Molecular Conformation Rats Rats, Inbred Strains |
| title | Intramolecular isotope effects associated with meta-hydroxylation of biphenyl catalyzed by cytochrome P-450 |
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