Transition state isosteres of the γ-glutamyl peptide bond hydrolysis: synthesis and characterization of the ψ[CH2NH] pseudopeptide analogue of glutathione

The fully deprotected glutathione analogue containing the aminomethylene unit as transition state isostere of the γ‐Glu‐Cys peptide bond was synthesized for the first time and characterized in both the reduced and oxidized forms. Copyright © 2003 European Peptide Society and John Wiley & Sons, L...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of peptide science 2004-02, Vol.10 (2), p.109-114
Hauptverfasser: Cacciatore, Ivana, Stefano, Antonio Di, Luisi, Grazia, Pinnen, Francesco, Sozio, Piera
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 114
container_issue 2
container_start_page 109
container_title Journal of peptide science
container_volume 10
creator Cacciatore, Ivana
Stefano, Antonio Di
Luisi, Grazia
Pinnen, Francesco
Sozio, Piera
description The fully deprotected glutathione analogue containing the aminomethylene unit as transition state isostere of the γ‐Glu‐Cys peptide bond was synthesized for the first time and characterized in both the reduced and oxidized forms. Copyright © 2003 European Peptide Society and John Wiley & Sons, Ltd.
doi_str_mv 10.1002/psc.501
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_71693738</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>71693738</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3761-803616c138334a4e7e48b35bba4963b383329f053d5dbdaa72a3485348803ed03</originalsourceid><addsrcrecordid>eNp1kUGO0zAUhi0EYoaCuAHyChYogx0nccIORdCiqcpIDGKBkPUSv04NaRxsRxBOwCG4BfeAK-FOCqxYWH7y-95n2T8h9zk744ylTwbfnuWM3yCnnFVVwkUpbx5qmSdpweUJueP9B8ZiLy9ukxOeVVVWldUp-X7poPcmGNtTHyAgNd76gA49tVsadkh__kiuujHAfurogEMwGmlje013k3a2m7zxT6mf-sjGkkLstDtw0EaL-QrX6qPq17d39SrdrN7TweOo7R8d9NDZqxEP3PVdYRen8C65tYXO473jviBvXjy_rFfJ-tXyZf1snbRCFjwpmSh40cZHC5FBhhKzshF500BWFaI5HKfVluVC57rRADIFkZV5XHESNRML8nD2Ds5-GtEHtTe-xa6DHu3oleRFJWT0LMijGWyd9d7hVg3O7MFNijN1CELFIFQMIpIPjsqx2aP-xx1_PgKPZ-Cz6XD6n0ddvK5nXTLTJmbz5S8N7qMqpJC5ertZqo24OF-e16lai9946aS7</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>71693738</pqid></control><display><type>article</type><title>Transition state isosteres of the γ-glutamyl peptide bond hydrolysis: synthesis and characterization of the ψ[CH2NH] pseudopeptide analogue of glutathione</title><source>MEDLINE</source><source>Wiley Online Library Journals Frontfile Complete</source><creator>Cacciatore, Ivana ; Stefano, Antonio Di ; Luisi, Grazia ; Pinnen, Francesco ; Sozio, Piera</creator><creatorcontrib>Cacciatore, Ivana ; Stefano, Antonio Di ; Luisi, Grazia ; Pinnen, Francesco ; Sozio, Piera</creatorcontrib><description>The fully deprotected glutathione analogue containing the aminomethylene unit as transition state isostere of the γ‐Glu‐Cys peptide bond was synthesized for the first time and characterized in both the reduced and oxidized forms. Copyright © 2003 European Peptide Society and John Wiley &amp; Sons, Ltd.</description><identifier>ISSN: 1075-2617</identifier><identifier>EISSN: 1099-1387</identifier><identifier>DOI: 10.1002/psc.501</identifier><identifier>PMID: 14994989</identifier><language>eng</language><publisher>Chichester, UK: John Wiley &amp; Sons, Ltd</publisher><subject>glutathione ; Glutathione - analogs &amp; derivatives ; Glutathione - chemical synthesis ; Glutathione - chemistry ; Hydrolysis ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Peptides - chemical synthesis ; Peptides - chemistry ; reduced peptides ; transition state analogue ; γ-glutamyl peptide bond</subject><ispartof>Journal of peptide science, 2004-02, Vol.10 (2), p.109-114</ispartof><rights>Copyright © 2003 European Peptide Society and John Wiley &amp; Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3761-803616c138334a4e7e48b35bba4963b383329f053d5dbdaa72a3485348803ed03</citedby><cites>FETCH-LOGICAL-c3761-803616c138334a4e7e48b35bba4963b383329f053d5dbdaa72a3485348803ed03</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fpsc.501$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fpsc.501$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14994989$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Cacciatore, Ivana</creatorcontrib><creatorcontrib>Stefano, Antonio Di</creatorcontrib><creatorcontrib>Luisi, Grazia</creatorcontrib><creatorcontrib>Pinnen, Francesco</creatorcontrib><creatorcontrib>Sozio, Piera</creatorcontrib><title>Transition state isosteres of the γ-glutamyl peptide bond hydrolysis: synthesis and characterization of the ψ[CH2NH] pseudopeptide analogue of glutathione</title><title>Journal of peptide science</title><addtitle>J. Peptide Sci</addtitle><description>The fully deprotected glutathione analogue containing the aminomethylene unit as transition state isostere of the γ‐Glu‐Cys peptide bond was synthesized for the first time and characterized in both the reduced and oxidized forms. Copyright © 2003 European Peptide Society and John Wiley &amp; Sons, Ltd.</description><subject>glutathione</subject><subject>Glutathione - analogs &amp; derivatives</subject><subject>Glutathione - chemical synthesis</subject><subject>Glutathione - chemistry</subject><subject>Hydrolysis</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Structure</subject><subject>Peptides - chemical synthesis</subject><subject>Peptides - chemistry</subject><subject>reduced peptides</subject><subject>transition state analogue</subject><subject>γ-glutamyl peptide bond</subject><issn>1075-2617</issn><issn>1099-1387</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kUGO0zAUhi0EYoaCuAHyChYogx0nccIORdCiqcpIDGKBkPUSv04NaRxsRxBOwCG4BfeAK-FOCqxYWH7y-95n2T8h9zk744ylTwbfnuWM3yCnnFVVwkUpbx5qmSdpweUJueP9B8ZiLy9ukxOeVVVWldUp-X7poPcmGNtTHyAgNd76gA49tVsadkh__kiuujHAfurogEMwGmlje013k3a2m7zxT6mf-sjGkkLstDtw0EaL-QrX6qPq17d39SrdrN7TweOo7R8d9NDZqxEP3PVdYRen8C65tYXO473jviBvXjy_rFfJ-tXyZf1snbRCFjwpmSh40cZHC5FBhhKzshF500BWFaI5HKfVluVC57rRADIFkZV5XHESNRML8nD2Ds5-GtEHtTe-xa6DHu3oleRFJWT0LMijGWyd9d7hVg3O7MFNijN1CELFIFQMIpIPjsqx2aP-xx1_PgKPZ-Cz6XD6n0ddvK5nXTLTJmbz5S8N7qMqpJC5ertZqo24OF-e16lai9946aS7</recordid><startdate>200402</startdate><enddate>200402</enddate><creator>Cacciatore, Ivana</creator><creator>Stefano, Antonio Di</creator><creator>Luisi, Grazia</creator><creator>Pinnen, Francesco</creator><creator>Sozio, Piera</creator><general>John Wiley &amp; Sons, Ltd</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>200402</creationdate><title>Transition state isosteres of the γ-glutamyl peptide bond hydrolysis: synthesis and characterization of the ψ[CH2NH] pseudopeptide analogue of glutathione</title><author>Cacciatore, Ivana ; Stefano, Antonio Di ; Luisi, Grazia ; Pinnen, Francesco ; Sozio, Piera</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3761-803616c138334a4e7e48b35bba4963b383329f053d5dbdaa72a3485348803ed03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>glutathione</topic><topic>Glutathione - analogs &amp; derivatives</topic><topic>Glutathione - chemical synthesis</topic><topic>Glutathione - chemistry</topic><topic>Hydrolysis</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Structure</topic><topic>Peptides - chemical synthesis</topic><topic>Peptides - chemistry</topic><topic>reduced peptides</topic><topic>transition state analogue</topic><topic>γ-glutamyl peptide bond</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cacciatore, Ivana</creatorcontrib><creatorcontrib>Stefano, Antonio Di</creatorcontrib><creatorcontrib>Luisi, Grazia</creatorcontrib><creatorcontrib>Pinnen, Francesco</creatorcontrib><creatorcontrib>Sozio, Piera</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 peptide science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cacciatore, Ivana</au><au>Stefano, Antonio Di</au><au>Luisi, Grazia</au><au>Pinnen, Francesco</au><au>Sozio, Piera</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Transition state isosteres of the γ-glutamyl peptide bond hydrolysis: synthesis and characterization of the ψ[CH2NH] pseudopeptide analogue of glutathione</atitle><jtitle>Journal of peptide science</jtitle><addtitle>J. Peptide Sci</addtitle><date>2004-02</date><risdate>2004</risdate><volume>10</volume><issue>2</issue><spage>109</spage><epage>114</epage><pages>109-114</pages><issn>1075-2617</issn><eissn>1099-1387</eissn><abstract>The fully deprotected glutathione analogue containing the aminomethylene unit as transition state isostere of the γ‐Glu‐Cys peptide bond was synthesized for the first time and characterized in both the reduced and oxidized forms. Copyright © 2003 European Peptide Society and John Wiley &amp; Sons, Ltd.</abstract><cop>Chichester, UK</cop><pub>John Wiley &amp; Sons, Ltd</pub><pmid>14994989</pmid><doi>10.1002/psc.501</doi><tpages>6</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1075-2617
ispartof Journal of peptide science, 2004-02, Vol.10 (2), p.109-114
issn 1075-2617
1099-1387
language eng
recordid cdi_proquest_miscellaneous_71693738
source MEDLINE; Wiley Online Library Journals Frontfile Complete
subjects glutathione
Glutathione - analogs & derivatives
Glutathione - chemical synthesis
Glutathione - chemistry
Hydrolysis
Magnetic Resonance Spectroscopy
Molecular Structure
Peptides - chemical synthesis
Peptides - chemistry
reduced peptides
transition state analogue
γ-glutamyl peptide bond
title Transition state isosteres of the γ-glutamyl peptide bond hydrolysis: synthesis and characterization of the ψ[CH2NH] pseudopeptide analogue of glutathione
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-20T07%3A45%3A41IST&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=Transition%20state%20isosteres%20of%20the%20%CE%B3-glutamyl%20peptide%20bond%20hydrolysis:%20synthesis%20and%20characterization%20of%20the%20%CF%88%5BCH2NH%5D%20pseudopeptide%20analogue%20of%20glutathione&rft.jtitle=Journal%20of%20peptide%20science&rft.au=Cacciatore,%20Ivana&rft.date=2004-02&rft.volume=10&rft.issue=2&rft.spage=109&rft.epage=114&rft.pages=109-114&rft.issn=1075-2617&rft.eissn=1099-1387&rft_id=info:doi/10.1002/psc.501&rft_dat=%3Cproquest_cross%3E71693738%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=71693738&rft_id=info:pmid/14994989&rfr_iscdi=true