Conversion of (3S,4R)-Tetrahydrodaidzein to (3S)-Equol by THD Reductase: Proposed Mechanism Involving a Radical Intermediate
To elucidate the mechanism of (3S)-equol biosynthesis, (2,3,4-d 3)-trans-THD was synthesized and converted to (3S)-equol by THD reductase in Eggerthella strain Julong 732. The position of the deuterium atoms in (3S)-equol was determined by 1H NMR and 2H NMR spectroscopy, and the product was identifi...
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| Veröffentlicht in: | Biochemistry (Easton) 2010-07, Vol.49 (26), p.5582-5587 |
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| container_issue | 26 |
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| container_title | Biochemistry (Easton) |
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| creator | Kim, Mihyang Marsh, E. Neil G Kim, Soo-Un Han, Jaehong |
| description | To elucidate the mechanism of (3S)-equol biosynthesis, (2,3,4-d 3)-trans-THD was synthesized and converted to (3S)-equol by THD reductase in Eggerthella strain Julong 732. The position of the deuterium atoms in (3S)-equol was determined by 1H NMR and 2H NMR spectroscopy, and the product was identified as (2,3,4α-d 3)-(3S)-equol. All the deuterium atoms were retained, while the OH group at C-4 was replaced by a hydrogen atom with retention of configuration. To explain the deuterium retention in this stereospecific reduction, we propose a mechanism involving radical intermediates. |
| doi_str_mv | 10.1021/bi100465y |
| format | Article |
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To explain the deuterium retention in this stereospecific reduction, we propose a mechanism involving radical intermediates.</description><identifier>ISSN: 0006-2960</identifier><identifier>EISSN: 1520-4995</identifier><identifier>DOI: 10.1021/bi100465y</identifier><identifier>PMID: 20515029</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Bacteria, Anaerobic - metabolism ; Deuterium ; Equol ; Free Radicals - metabolism ; Isoflavones - biosynthesis ; Isoflavones - metabolism ; Magnetic Resonance Spectroscopy ; Molecular Conformation ; Organic Chemistry Phenomena ; Oxidoreductases - metabolism ; Stereoisomerism</subject><ispartof>Biochemistry (Easton), 2010-07, Vol.49 (26), p.5582-5587</ispartof><rights>Copyright © 2010 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a380t-f5a0b200b92116e3118e313ccae86ce0c5d2005af4d2d5a5d2d0efc6e57f55b53</citedby><cites>FETCH-LOGICAL-a380t-f5a0b200b92116e3118e313ccae86ce0c5d2005af4d2d5a5d2d0efc6e57f55b53</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/bi100465y$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/bi100465y$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56716,56766</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20515029$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kim, Mihyang</creatorcontrib><creatorcontrib>Marsh, E. Neil G</creatorcontrib><creatorcontrib>Kim, Soo-Un</creatorcontrib><creatorcontrib>Han, Jaehong</creatorcontrib><title>Conversion of (3S,4R)-Tetrahydrodaidzein to (3S)-Equol by THD Reductase: Proposed Mechanism Involving a Radical Intermediate</title><title>Biochemistry (Easton)</title><addtitle>Biochemistry</addtitle><description>To elucidate the mechanism of (3S)-equol biosynthesis, (2,3,4-d 3)-trans-THD was synthesized and converted to (3S)-equol by THD reductase in Eggerthella strain Julong 732. The position of the deuterium atoms in (3S)-equol was determined by 1H NMR and 2H NMR spectroscopy, and the product was identified as (2,3,4α-d 3)-(3S)-equol. All the deuterium atoms were retained, while the OH group at C-4 was replaced by a hydrogen atom with retention of configuration. To explain the deuterium retention in this stereospecific reduction, we propose a mechanism involving radical intermediates.</description><subject>Bacteria, Anaerobic - metabolism</subject><subject>Deuterium</subject><subject>Equol</subject><subject>Free Radicals - metabolism</subject><subject>Isoflavones - biosynthesis</subject><subject>Isoflavones - metabolism</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Conformation</subject><subject>Organic Chemistry Phenomena</subject><subject>Oxidoreductases - metabolism</subject><subject>Stereoisomerism</subject><issn>0006-2960</issn><issn>1520-4995</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkF9L60AQxRdRtFd98AvIvoi3YHQ2ySaNb9LrP1CUWp_DZHeiK2m23U0KlfvhXan65MsMM-fHgXMYOxBwKiAWZ5URAGkmVxtsIGQMUVoUcpMNACCL4iKDHfbH-7dwppCn22wnBikkxMWA_R_bdknOG9tyW_O_ydNJOhlGU-ocvq60sxqNfifT8s5-qsPoctHbhlcrPr35xyeke9Whp3P-6OzcetL8ntQrtsbP-G27tM3StC8c-QS1UdiEX0duRtpgR3tsq8bG0_7X3mXPV5fT8U1093B9O764izAZQRfVEqGKAaoiFiKjRIhRGIlSSKNMESipgyqxTnWsJYZLA9UqI5nXUlYy2WXHa9-5s4uefFfOjFfUNNiS7X2ZJ0maZyLPAjlck8pZ7x3V5dyZGbpVKaD87Lr86Tqwh1-ufRUC_ZDf5QbgaA2g8uWb7V0bQv5i9AHR_oUK</recordid><startdate>20100706</startdate><enddate>20100706</enddate><creator>Kim, Mihyang</creator><creator>Marsh, E. 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Neil G ; Kim, Soo-Un ; Han, Jaehong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a380t-f5a0b200b92116e3118e313ccae86ce0c5d2005af4d2d5a5d2d0efc6e57f55b53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Bacteria, Anaerobic - metabolism</topic><topic>Deuterium</topic><topic>Equol</topic><topic>Free Radicals - metabolism</topic><topic>Isoflavones - biosynthesis</topic><topic>Isoflavones - metabolism</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Conformation</topic><topic>Organic Chemistry Phenomena</topic><topic>Oxidoreductases - metabolism</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kim, Mihyang</creatorcontrib><creatorcontrib>Marsh, E. Neil G</creatorcontrib><creatorcontrib>Kim, Soo-Un</creatorcontrib><creatorcontrib>Han, Jaehong</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>Biochemistry (Easton)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kim, Mihyang</au><au>Marsh, E. 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To explain the deuterium retention in this stereospecific reduction, we propose a mechanism involving radical intermediates.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>20515029</pmid><doi>10.1021/bi100465y</doi><tpages>6</tpages></addata></record> |
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| source | MEDLINE; ACS Publications |
| subjects | Bacteria, Anaerobic - metabolism Deuterium Equol Free Radicals - metabolism Isoflavones - biosynthesis Isoflavones - metabolism Magnetic Resonance Spectroscopy Molecular Conformation Organic Chemistry Phenomena Oxidoreductases - metabolism Stereoisomerism |
| title | Conversion of (3S,4R)-Tetrahydrodaidzein to (3S)-Equol by THD Reductase: Proposed Mechanism Involving a Radical Intermediate |
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