One-electron reduction of selenomethionine oxide
Experimental evidence is provided that selenomethionine oxide (MetSeO) is more readily reducible than its sulfur analogue, methionine sulfoxide (MetSO). Pulse radiolysis experiments reveal an efficient reaction of MetSeO with one-electron reductants, such as e-aq (k = 1.2 × 1010M-1s-1), CO·-2 (k = 5...
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| Veröffentlicht in: | Free radical research 2000-01, Vol.32 (4), p.371-376 |
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| creator | Assmann, A Bonifacic, M Briviba, K Sies, H Asmus, K.-D |
| description | Experimental evidence is provided that selenomethionine oxide (MetSeO) is more readily reducible than its sulfur analogue, methionine sulfoxide (MetSO). Pulse radiolysis experiments reveal an efficient reaction of MetSeO with one-electron reductants, such as e-aq (k = 1.2 × 1010M-1s-1), CO·-2 (k = 5.9 × 108 M-1s-1) and (CH3)2) C·OH (k = 3.5 × 107M-1s-1), forming an intermediate selenium-nitrogen coupled zwitterionic radical with the positive charge at an intramolecularly formed Se∴ N 2σ/1σ* three-electron bond, which is characterized by an optical absorption with λmax at 375 nm, and a half-life of about 70 μs. The same transient is generated upon HO· radical-induced one-electron oxidation of selenomethionine (MetSe). This radical thus constitutes the redox intermediate between the two oxidation states, MetSeO and MetSe. Time-resolved optical data further indicate sulfur-selenium interactions between the Se∴ N transient and GSH. The Se∴ N transient appears to play a key role in the reduction of selenomethionine oxide by glutathione. |
| doi_str_mv | 10.1080/10715760000300371 |
| format | Article |
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Inst. fuer Ernaehrungsphysiologie</creatorcontrib><description>Experimental evidence is provided that selenomethionine oxide (MetSeO) is more readily reducible than its sulfur analogue, methionine sulfoxide (MetSO). Pulse radiolysis experiments reveal an efficient reaction of MetSeO with one-electron reductants, such as e-aq (k = 1.2 × 1010M-1s-1), CO·-2 (k = 5.9 × 108 M-1s-1) and (CH3)2) C·OH (k = 3.5 × 107M-1s-1), forming an intermediate selenium-nitrogen coupled zwitterionic radical with the positive charge at an intramolecularly formed Se∴ N 2σ/1σ* three-electron bond, which is characterized by an optical absorption with λmax at 375 nm, and a half-life of about 70 μs. The same transient is generated upon HO· radical-induced one-electron oxidation of selenomethionine (MetSe). This radical thus constitutes the redox intermediate between the two oxidation states, MetSeO and MetSe. Time-resolved optical data further indicate sulfur-selenium interactions between the Se∴ N transient and GSH. The Se∴ N transient appears to play a key role in the reduction of selenomethionine oxide by glutathione.</description><identifier>ISSN: 1071-5762</identifier><identifier>EISSN: 1029-2470</identifier><identifier>DOI: 10.1080/10715760000300371</identifier><identifier>PMID: 10741858</identifier><language>eng</language><publisher>England: Informa UK Ltd</publisher><subject>Chemical Phenomena ; Chemistry, Physical ; Electrons ; glutathione ; Glutathione - chemistry ; Hydroxyl Radical - chemistry ; Kinetics ; METHIONINE ; METIONINA ; odd-electron bonds ; Oxidation-Reduction ; OXIDOREDUCTIONS ; OXIRREDUCION ; OXYDOREDUCTION ; Pulse Radiolysis ; SELENIO ; SELENIUM ; Selenomethionine - chemistry ; Selenomethionine oxide ; Solutions ; Spectrophotometry ; Water</subject><ispartof>Free radical research, 2000-01, Vol.32 (4), p.371-376</ispartof><rights>2000 Informa UK Ltd All rights reserved: reproduction in whole or part not permitted 2000</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c424t-4048af6f8e008a50162d00489c7656666276b0d73ac03abddd3842daed9778923</citedby><cites>FETCH-LOGICAL-c424t-4048af6f8e008a50162d00489c7656666276b0d73ac03abddd3842daed9778923</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.1080/10715760000300371$$EPDF$$P50$$Ginformaworld$$H</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.1080/10715760000300371$$EHTML$$P50$$Ginformaworld$$H</linktohtml><link.rule.ids>314,780,784,27922,27923,59645,60434,61219,61400</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10741858$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Assmann, A</creatorcontrib><creatorcontrib>Bonifacic, M</creatorcontrib><creatorcontrib>Briviba, K</creatorcontrib><creatorcontrib>Sies, H</creatorcontrib><creatorcontrib>Asmus, K.-D</creatorcontrib><creatorcontrib>Bundesforschungsanstalt fuer Ernaehrung, Karlsruhe (Germany). Inst. fuer Ernaehrungsphysiologie</creatorcontrib><title>One-electron reduction of selenomethionine oxide</title><title>Free radical research</title><addtitle>Free Radic Res</addtitle><description>Experimental evidence is provided that selenomethionine oxide (MetSeO) is more readily reducible than its sulfur analogue, methionine sulfoxide (MetSO). Pulse radiolysis experiments reveal an efficient reaction of MetSeO with one-electron reductants, such as e-aq (k = 1.2 × 1010M-1s-1), CO·-2 (k = 5.9 × 108 M-1s-1) and (CH3)2) C·OH (k = 3.5 × 107M-1s-1), forming an intermediate selenium-nitrogen coupled zwitterionic radical with the positive charge at an intramolecularly formed Se∴ N 2σ/1σ* three-electron bond, which is characterized by an optical absorption with λmax at 375 nm, and a half-life of about 70 μs. The same transient is generated upon HO· radical-induced one-electron oxidation of selenomethionine (MetSe). This radical thus constitutes the redox intermediate between the two oxidation states, MetSeO and MetSe. Time-resolved optical data further indicate sulfur-selenium interactions between the Se∴ N transient and GSH. The Se∴ N transient appears to play a key role in the reduction of selenomethionine oxide by glutathione.</description><subject>Chemical Phenomena</subject><subject>Chemistry, Physical</subject><subject>Electrons</subject><subject>glutathione</subject><subject>Glutathione - chemistry</subject><subject>Hydroxyl Radical - chemistry</subject><subject>Kinetics</subject><subject>METHIONINE</subject><subject>METIONINA</subject><subject>odd-electron bonds</subject><subject>Oxidation-Reduction</subject><subject>OXIDOREDUCTIONS</subject><subject>OXIRREDUCION</subject><subject>OXYDOREDUCTION</subject><subject>Pulse Radiolysis</subject><subject>SELENIO</subject><subject>SELENIUM</subject><subject>Selenomethionine - chemistry</subject><subject>Selenomethionine oxide</subject><subject>Solutions</subject><subject>Spectrophotometry</subject><subject>Water</subject><issn>1071-5762</issn><issn>1029-2470</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9UE1LxDAQDaLouvoDPCh78ladfLRJ0Yvo-gELXvQcssnUrbTNmrTo_nsj9aAIDgMzvHnvJTxCjiicUVBwTkHSXBaQiqeWdItMKLAyY0LC9tcuaZYIbI_sx_gKQLnI5S7ZSwdBVa4mBB47zLBB2wffzQK6wfZ12nw1iwnufIv9KgF1hzP_UTs8IDuVaSIefs8peb6dP13fZ4vHu4frq0VmBRN9JkAoUxWVQgBlcqAFc5Cw0soiL1IxWSzBSW4scLN0znElmDPoSilVyfiUnI6-6-DfBoy9butosWlMh36IWkKpcl4UiUhHog0-xoCVXoe6NWGjKeivmPSfmJLm5Nt8WLbofijGXBLhciTUXeVDa959aJzuzabxoQqms3XU_D__i1_yFZqmX1kTUL_6IXQpuH9_dzyqK-O1eQnprZs5S_dFCVRQ_glb1o5m</recordid><startdate>20000101</startdate><enddate>20000101</enddate><creator>Assmann, A</creator><creator>Bonifacic, M</creator><creator>Briviba, K</creator><creator>Sies, H</creator><creator>Asmus, K.-D</creator><general>Informa UK Ltd</general><general>Taylor & Francis</general><scope>FBQ</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>20000101</creationdate><title>One-electron reduction of selenomethionine oxide</title><author>Assmann, A ; Bonifacic, M ; Briviba, K ; Sies, H ; Asmus, K.-D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c424t-4048af6f8e008a50162d00489c7656666276b0d73ac03abddd3842daed9778923</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Chemical Phenomena</topic><topic>Chemistry, Physical</topic><topic>Electrons</topic><topic>glutathione</topic><topic>Glutathione - chemistry</topic><topic>Hydroxyl Radical - chemistry</topic><topic>Kinetics</topic><topic>METHIONINE</topic><topic>METIONINA</topic><topic>odd-electron bonds</topic><topic>Oxidation-Reduction</topic><topic>OXIDOREDUCTIONS</topic><topic>OXIRREDUCION</topic><topic>OXYDOREDUCTION</topic><topic>Pulse Radiolysis</topic><topic>SELENIO</topic><topic>SELENIUM</topic><topic>Selenomethionine - chemistry</topic><topic>Selenomethionine oxide</topic><topic>Solutions</topic><topic>Spectrophotometry</topic><topic>Water</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Assmann, A</creatorcontrib><creatorcontrib>Bonifacic, M</creatorcontrib><creatorcontrib>Briviba, K</creatorcontrib><creatorcontrib>Sies, H</creatorcontrib><creatorcontrib>Asmus, K.-D</creatorcontrib><creatorcontrib>Bundesforschungsanstalt fuer Ernaehrung, Karlsruhe (Germany). Inst. fuer Ernaehrungsphysiologie</creatorcontrib><collection>AGRIS</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>Free radical research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Assmann, A</au><au>Bonifacic, M</au><au>Briviba, K</au><au>Sies, H</au><au>Asmus, K.-D</au><aucorp>Bundesforschungsanstalt fuer Ernaehrung, Karlsruhe (Germany). Inst. fuer Ernaehrungsphysiologie</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One-electron reduction of selenomethionine oxide</atitle><jtitle>Free radical research</jtitle><addtitle>Free Radic Res</addtitle><date>2000-01-01</date><risdate>2000</risdate><volume>32</volume><issue>4</issue><spage>371</spage><epage>376</epage><pages>371-376</pages><issn>1071-5762</issn><eissn>1029-2470</eissn><abstract>Experimental evidence is provided that selenomethionine oxide (MetSeO) is more readily reducible than its sulfur analogue, methionine sulfoxide (MetSO). Pulse radiolysis experiments reveal an efficient reaction of MetSeO with one-electron reductants, such as e-aq (k = 1.2 × 1010M-1s-1), CO·-2 (k = 5.9 × 108 M-1s-1) and (CH3)2) C·OH (k = 3.5 × 107M-1s-1), forming an intermediate selenium-nitrogen coupled zwitterionic radical with the positive charge at an intramolecularly formed Se∴ N 2σ/1σ* three-electron bond, which is characterized by an optical absorption with λmax at 375 nm, and a half-life of about 70 μs. The same transient is generated upon HO· radical-induced one-electron oxidation of selenomethionine (MetSe). This radical thus constitutes the redox intermediate between the two oxidation states, MetSeO and MetSe. Time-resolved optical data further indicate sulfur-selenium interactions between the Se∴ N transient and GSH. The Se∴ N transient appears to play a key role in the reduction of selenomethionine oxide by glutathione.</abstract><cop>England</cop><pub>Informa UK Ltd</pub><pmid>10741858</pmid><doi>10.1080/10715760000300371</doi><tpages>6</tpages></addata></record> |
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| source | MEDLINE; Taylor & Francis:Master (3349 titles) |
| subjects | Chemical Phenomena Chemistry, Physical Electrons glutathione Glutathione - chemistry Hydroxyl Radical - chemistry Kinetics METHIONINE METIONINA odd-electron bonds Oxidation-Reduction OXIDOREDUCTIONS OXIRREDUCION OXYDOREDUCTION Pulse Radiolysis SELENIO SELENIUM Selenomethionine - chemistry Selenomethionine oxide Solutions Spectrophotometry Water |
| title | One-electron reduction of selenomethionine oxide |
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