Thiophosphorylation of Histidine
The preparation of a novel phosphorus species, thiophosphoramidate, has enabled the specific thiophosphorylation of histidine at its 3-position. The rates of phosphorylation and thiophosphorylation of histidine are reported, as well as the spectroscopic properties of both thiophosphoramidate and 3-t...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2000-12, Vol.65 (25), p.8448-8453 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 8453 |
|---|---|
| container_issue | 25 |
| container_start_page | 8448 |
| container_title | Journal of organic chemistry |
| container_volume | 65 |
| creator | Pirrung, Michael C James, Kenneth D Rana, Vipul S |
| description | The preparation of a novel phosphorus species, thiophosphoramidate, has enabled the specific thiophosphorylation of histidine at its 3-position. The rates of phosphorylation and thiophosphorylation of histidine are reported, as well as the spectroscopic properties of both thiophosphoramidate and 3-thiophosphohistidine. Structural assignment of the latter was made by analogy to the NMR properties of the known 3-phosphohistidine. The alkylation of 3-thiophosphohistidine by phenacyl bromide serves as a model for the introduction of labeling or probe reagents into histidine phosphorothioate-containing proteins. |
| doi_str_mv | 10.1021/jo000771l |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_72469772</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>72469772</sourcerecordid><originalsourceid>FETCH-LOGICAL-a349t-f09304a21a7ac18c1ca98aa23afea9d63e2d83fa66290ec02d54179964cd864d3</originalsourceid><addsrcrecordid>eNpt0MFKAzEQBuAgiq3Vgy8gvSh4WJ0ku8nmKEVbsVbBeg5jNku3bpua7IJ9eyNb6sWBMId8zDA_IecUbigwert0ACAlrQ9In2YMEqEgPSR9AMYSzgTvkZMQlhFBlmXHpEdjsUywPhnOF5XbLFyIz29rbCq3HrpyOKlCUxXV2p6SoxLrYM92fUDeH-7no0kyfRk_ju6mCfJUNUkJikOKjKJEQ3NDDaockXEsLapCcMuKnJcoBFNgDbAiS6lUSqSmyEVa8AG56uZuvPtqbWj0qgrG1jWurWuDliwVSkoW4XUHjXcheFvqja9W6Leagv6NQ-_jiPZiN7T9WNniT-7ujyDpQDzXfu__0X9qIbnM9Pz1TU9nT3xMn2daRn_ZeTQh7mn9Ombyz-IfYDx0Lg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>72469772</pqid></control><display><type>article</type><title>Thiophosphorylation of Histidine</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Pirrung, Michael C ; James, Kenneth D ; Rana, Vipul S</creator><creatorcontrib>Pirrung, Michael C ; James, Kenneth D ; Rana, Vipul S</creatorcontrib><description>The preparation of a novel phosphorus species, thiophosphoramidate, has enabled the specific thiophosphorylation of histidine at its 3-position. The rates of phosphorylation and thiophosphorylation of histidine are reported, as well as the spectroscopic properties of both thiophosphoramidate and 3-thiophosphohistidine. Structural assignment of the latter was made by analogy to the NMR properties of the known 3-phosphohistidine. The alkylation of 3-thiophosphohistidine by phenacyl bromide serves as a model for the introduction of labeling or probe reagents into histidine phosphorothioate-containing proteins.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo000771l</identifier><identifier>PMID: 11112562</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Chromatography, High Pressure Liquid ; Histidine - chemistry ; Kinetics ; Magnetic Resonance Spectroscopy ; Phosphorylation ; Spectrometry, Mass, Fast Atom Bombardment ; Sulfhydryl Compounds - physiology</subject><ispartof>Journal of organic chemistry, 2000-12, Vol.65 (25), p.8448-8453</ispartof><rights>Copyright © 2000 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a349t-f09304a21a7ac18c1ca98aa23afea9d63e2d83fa66290ec02d54179964cd864d3</citedby><cites>FETCH-LOGICAL-a349t-f09304a21a7ac18c1ca98aa23afea9d63e2d83fa66290ec02d54179964cd864d3</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/jo000771l$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo000771l$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11112562$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pirrung, Michael C</creatorcontrib><creatorcontrib>James, Kenneth D</creatorcontrib><creatorcontrib>Rana, Vipul S</creatorcontrib><title>Thiophosphorylation of Histidine</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The preparation of a novel phosphorus species, thiophosphoramidate, has enabled the specific thiophosphorylation of histidine at its 3-position. The rates of phosphorylation and thiophosphorylation of histidine are reported, as well as the spectroscopic properties of both thiophosphoramidate and 3-thiophosphohistidine. Structural assignment of the latter was made by analogy to the NMR properties of the known 3-phosphohistidine. The alkylation of 3-thiophosphohistidine by phenacyl bromide serves as a model for the introduction of labeling or probe reagents into histidine phosphorothioate-containing proteins.</description><subject>Chromatography, High Pressure Liquid</subject><subject>Histidine - chemistry</subject><subject>Kinetics</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Phosphorylation</subject><subject>Spectrometry, Mass, Fast Atom Bombardment</subject><subject>Sulfhydryl Compounds - physiology</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MFKAzEQBuAgiq3Vgy8gvSh4WJ0ku8nmKEVbsVbBeg5jNku3bpua7IJ9eyNb6sWBMId8zDA_IecUbigwert0ACAlrQ9In2YMEqEgPSR9AMYSzgTvkZMQlhFBlmXHpEdjsUywPhnOF5XbLFyIz29rbCq3HrpyOKlCUxXV2p6SoxLrYM92fUDeH-7no0kyfRk_ju6mCfJUNUkJikOKjKJEQ3NDDaockXEsLapCcMuKnJcoBFNgDbAiS6lUSqSmyEVa8AG56uZuvPtqbWj0qgrG1jWurWuDliwVSkoW4XUHjXcheFvqja9W6Leagv6NQ-_jiPZiN7T9WNniT-7ujyDpQDzXfu__0X9qIbnM9Pz1TU9nT3xMn2daRn_ZeTQh7mn9Ombyz-IfYDx0Lg</recordid><startdate>20001215</startdate><enddate>20001215</enddate><creator>Pirrung, Michael C</creator><creator>James, Kenneth D</creator><creator>Rana, Vipul S</creator><general>American Chemical Society</general><scope>BSCLL</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>20001215</creationdate><title>Thiophosphorylation of Histidine</title><author>Pirrung, Michael C ; James, Kenneth D ; Rana, Vipul S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a349t-f09304a21a7ac18c1ca98aa23afea9d63e2d83fa66290ec02d54179964cd864d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Chromatography, High Pressure Liquid</topic><topic>Histidine - chemistry</topic><topic>Kinetics</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Phosphorylation</topic><topic>Spectrometry, Mass, Fast Atom Bombardment</topic><topic>Sulfhydryl Compounds - physiology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pirrung, Michael C</creatorcontrib><creatorcontrib>James, Kenneth D</creatorcontrib><creatorcontrib>Rana, Vipul S</creatorcontrib><collection>Istex</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>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pirrung, Michael C</au><au>James, Kenneth D</au><au>Rana, Vipul S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Thiophosphorylation of Histidine</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2000-12-15</date><risdate>2000</risdate><volume>65</volume><issue>25</issue><spage>8448</spage><epage>8453</epage><pages>8448-8453</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>The preparation of a novel phosphorus species, thiophosphoramidate, has enabled the specific thiophosphorylation of histidine at its 3-position. The rates of phosphorylation and thiophosphorylation of histidine are reported, as well as the spectroscopic properties of both thiophosphoramidate and 3-thiophosphohistidine. Structural assignment of the latter was made by analogy to the NMR properties of the known 3-phosphohistidine. The alkylation of 3-thiophosphohistidine by phenacyl bromide serves as a model for the introduction of labeling or probe reagents into histidine phosphorothioate-containing proteins.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>11112562</pmid><doi>10.1021/jo000771l</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2000-12, Vol.65 (25), p.8448-8453 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_72469772 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Chromatography, High Pressure Liquid Histidine - chemistry Kinetics Magnetic Resonance Spectroscopy Phosphorylation Spectrometry, Mass, Fast Atom Bombardment Sulfhydryl Compounds - physiology |
| title | Thiophosphorylation of Histidine |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-26T08%3A12%3A49IST&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=Thiophosphorylation%20of%20Histidine&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Pirrung,%20Michael%20C&rft.date=2000-12-15&rft.volume=65&rft.issue=25&rft.spage=8448&rft.epage=8453&rft.pages=8448-8453&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/jo000771l&rft_dat=%3Cproquest_cross%3E72469772%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=72469772&rft_id=info:pmid/11112562&rfr_iscdi=true |