Experimental and theoretical evidence for cyclic selenurane formation during selenomethionine oxidation
The oxidation products of selenomethionine (SeMet) have been studied via experimental (77)Se NMR and theoretical (77)Se chemical shifts. Four signals are observed: a diastereomeric pair of selenoxides at 840 ppm and two unidentified resonances at 703 and 716 ppm. Theoretical DeltaG and chemical shif...
Gespeichert in:
| Veröffentlicht in: | Organic & biomolecular chemistry 2005-12, Vol.3 (24), p.4337-4342 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 4342 |
|---|---|
| container_issue | 24 |
| container_start_page | 4337 |
| container_title | Organic & biomolecular chemistry |
| container_volume | 3 |
| creator | Ritchey, Joshua A Davis, Bonnie M Pleban, Patricia A Bayse, Craig A |
| description | The oxidation products of selenomethionine (SeMet) have been studied via experimental (77)Se NMR and theoretical (77)Se chemical shifts. Four signals are observed: a diastereomeric pair of selenoxides at 840 ppm and two unidentified resonances at 703 and 716 ppm. Theoretical DeltaG and chemical shifts suggest the 703 and 716 ppm resonances correspond to hypervalent selenium heterocycles, called selenuranes, formed by reaction with the amine or acid group of the amino acid and the selenoxide. To identify which of these selenuranes is formed, the amine and acid groups were individually protected. The N-formyl SeMet formed only the selenoxide pair at 840 ppm. The oxidized SeMet methyl ester produced signals at 703 and 716 ppm which are assigned as the Se-N selenurane. |
| doi_str_mv | 10.1039/b513238j |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_68864310</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>68864310</sourcerecordid><originalsourceid>FETCH-LOGICAL-c281t-7735dca30d554e56a86a547a584bbd88d3475e1e365b7c0a801f615b247363bb3</originalsourceid><addsrcrecordid>eNpFkE1Lw0AQhhdRbK2Cv0ByEi_R3exnj1LqBxS86Dnsx6TdkmTrbiLtvze2VU8z887DMDwIXRN8TzCdPhhOaEHV-gSNCZMyx5xOT__6Ao_QRUprjMlUCnaORkTQQqopG6PlfLuB6BtoO11nunVZt4IQofN2mOHLO2gtZFWImd3Z2tssQQ1tH3W7Txvd-dBmro--XR52oYFuNYR-IMLWuz1xic4qXSe4OtYJ-niav89e8sXb8-vscZHbQpEul5JyZzXFjnMGXGglNGdSc8WMcUo5yiQHAlRwIy3WCpNKEG4KJqmgxtAJuj3c3cTw2UPqysYnC3U9_Bv6VAqlBKODtAm6O4A2hpQiVOVm0KDjriS4_JFa_kod0Jvjzd404P7Bo0X6DTToc6c</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>68864310</pqid></control><display><type>article</type><title>Experimental and theoretical evidence for cyclic selenurane formation during selenomethionine oxidation</title><source>MEDLINE</source><source>Royal Society Of Chemistry Journals</source><source>Royal Society of Chemistry Journals Archive (1841-2007)</source><source>Alma/SFX Local Collection</source><creator>Ritchey, Joshua A ; Davis, Bonnie M ; Pleban, Patricia A ; Bayse, Craig A</creator><creatorcontrib>Ritchey, Joshua A ; Davis, Bonnie M ; Pleban, Patricia A ; Bayse, Craig A</creatorcontrib><description>The oxidation products of selenomethionine (SeMet) have been studied via experimental (77)Se NMR and theoretical (77)Se chemical shifts. Four signals are observed: a diastereomeric pair of selenoxides at 840 ppm and two unidentified resonances at 703 and 716 ppm. Theoretical DeltaG and chemical shifts suggest the 703 and 716 ppm resonances correspond to hypervalent selenium heterocycles, called selenuranes, formed by reaction with the amine or acid group of the amino acid and the selenoxide. To identify which of these selenuranes is formed, the amine and acid groups were individually protected. The N-formyl SeMet formed only the selenoxide pair at 840 ppm. The oxidized SeMet methyl ester produced signals at 703 and 716 ppm which are assigned as the Se-N selenurane.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/b513238j</identifier><identifier>PMID: 16327894</identifier><language>eng</language><publisher>England</publisher><subject>Magnetic Resonance Spectroscopy ; Molecular Structure ; Oxidation-Reduction ; Selenomethionine - analogs & derivatives ; Selenomethionine - chemistry</subject><ispartof>Organic & biomolecular chemistry, 2005-12, Vol.3 (24), p.4337-4342</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c281t-7735dca30d554e56a86a547a584bbd88d3475e1e365b7c0a801f615b247363bb3</citedby><cites>FETCH-LOGICAL-c281t-7735dca30d554e56a86a547a584bbd88d3475e1e365b7c0a801f615b247363bb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,2831,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16327894$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ritchey, Joshua A</creatorcontrib><creatorcontrib>Davis, Bonnie M</creatorcontrib><creatorcontrib>Pleban, Patricia A</creatorcontrib><creatorcontrib>Bayse, Craig A</creatorcontrib><title>Experimental and theoretical evidence for cyclic selenurane formation during selenomethionine oxidation</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>The oxidation products of selenomethionine (SeMet) have been studied via experimental (77)Se NMR and theoretical (77)Se chemical shifts. Four signals are observed: a diastereomeric pair of selenoxides at 840 ppm and two unidentified resonances at 703 and 716 ppm. Theoretical DeltaG and chemical shifts suggest the 703 and 716 ppm resonances correspond to hypervalent selenium heterocycles, called selenuranes, formed by reaction with the amine or acid group of the amino acid and the selenoxide. To identify which of these selenuranes is formed, the amine and acid groups were individually protected. The N-formyl SeMet formed only the selenoxide pair at 840 ppm. The oxidized SeMet methyl ester produced signals at 703 and 716 ppm which are assigned as the Se-N selenurane.</description><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Structure</subject><subject>Oxidation-Reduction</subject><subject>Selenomethionine - analogs & derivatives</subject><subject>Selenomethionine - chemistry</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkE1Lw0AQhhdRbK2Cv0ByEi_R3exnj1LqBxS86Dnsx6TdkmTrbiLtvze2VU8z887DMDwIXRN8TzCdPhhOaEHV-gSNCZMyx5xOT__6Ao_QRUprjMlUCnaORkTQQqopG6PlfLuB6BtoO11nunVZt4IQofN2mOHLO2gtZFWImd3Z2tssQQ1tH3W7Txvd-dBmro--XR52oYFuNYR-IMLWuz1xic4qXSe4OtYJ-niav89e8sXb8-vscZHbQpEul5JyZzXFjnMGXGglNGdSc8WMcUo5yiQHAlRwIy3WCpNKEG4KJqmgxtAJuj3c3cTw2UPqysYnC3U9_Bv6VAqlBKODtAm6O4A2hpQiVOVm0KDjriS4_JFa_kod0Jvjzd404P7Bo0X6DTToc6c</recordid><startdate>20051221</startdate><enddate>20051221</enddate><creator>Ritchey, Joshua A</creator><creator>Davis, Bonnie M</creator><creator>Pleban, Patricia A</creator><creator>Bayse, Craig A</creator><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>20051221</creationdate><title>Experimental and theoretical evidence for cyclic selenurane formation during selenomethionine oxidation</title><author>Ritchey, Joshua A ; Davis, Bonnie M ; Pleban, Patricia A ; Bayse, Craig A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c281t-7735dca30d554e56a86a547a584bbd88d3475e1e365b7c0a801f615b247363bb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Structure</topic><topic>Oxidation-Reduction</topic><topic>Selenomethionine - analogs & derivatives</topic><topic>Selenomethionine - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ritchey, Joshua A</creatorcontrib><creatorcontrib>Davis, Bonnie M</creatorcontrib><creatorcontrib>Pleban, Patricia A</creatorcontrib><creatorcontrib>Bayse, Craig A</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>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ritchey, Joshua A</au><au>Davis, Bonnie M</au><au>Pleban, Patricia A</au><au>Bayse, Craig A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Experimental and theoretical evidence for cyclic selenurane formation during selenomethionine oxidation</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2005-12-21</date><risdate>2005</risdate><volume>3</volume><issue>24</issue><spage>4337</spage><epage>4342</epage><pages>4337-4342</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>The oxidation products of selenomethionine (SeMet) have been studied via experimental (77)Se NMR and theoretical (77)Se chemical shifts. Four signals are observed: a diastereomeric pair of selenoxides at 840 ppm and two unidentified resonances at 703 and 716 ppm. Theoretical DeltaG and chemical shifts suggest the 703 and 716 ppm resonances correspond to hypervalent selenium heterocycles, called selenuranes, formed by reaction with the amine or acid group of the amino acid and the selenoxide. To identify which of these selenuranes is formed, the amine and acid groups were individually protected. The N-formyl SeMet formed only the selenoxide pair at 840 ppm. The oxidized SeMet methyl ester produced signals at 703 and 716 ppm which are assigned as the Se-N selenurane.</abstract><cop>England</cop><pmid>16327894</pmid><doi>10.1039/b513238j</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2005-12, Vol.3 (24), p.4337-4342 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_68864310 |
| source | MEDLINE; Royal Society Of Chemistry Journals; Royal Society of Chemistry Journals Archive (1841-2007); Alma/SFX Local Collection |
| subjects | Magnetic Resonance Spectroscopy Molecular Structure Oxidation-Reduction Selenomethionine - analogs & derivatives Selenomethionine - chemistry |
| title | Experimental and theoretical evidence for cyclic selenurane formation during selenomethionine oxidation |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T10%3A42%3A21IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Experimental%20and%20theoretical%20evidence%20for%20cyclic%20selenurane%20formation%20during%20selenomethionine%20oxidation&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Ritchey,%20Joshua%20A&rft.date=2005-12-21&rft.volume=3&rft.issue=24&rft.spage=4337&rft.epage=4342&rft.pages=4337-4342&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/b513238j&rft_dat=%3Cproquest_cross%3E68864310%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=68864310&rft_id=info:pmid/16327894&rfr_iscdi=true |