New tris-alkoxycarbonyl arginine derivatives for peptide synthesis
α‐Alkoxycarbonyl protected ornithines were treated with N,N′‐[Z(2Cl)]2‐S‐methylisothiourea and N,N′‐[Z(2Br)]2‐S‐methylisothiourea, N,N′‐Z2‐S‐methylisothiourea and N,N′‐Boc2‐S‐methylisothiourea to form Nα, ω, ω′‐tris‐alkoxycarbonyl arginines. Two of them, Boc‐Arg‐{ω,ω′‐[Z(2Br)]2}‐OH and Boc‐Arg‐{ω,ω′...
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Veröffentlicht in: | Journal of peptide science 2005-01, Vol.11 (1), p.60-64 |
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creator | Izdebski, Jan Gers, Tomasz Kunce, Danuta Markowski, Paweł |
description | α‐Alkoxycarbonyl protected ornithines were treated with N,N′‐[Z(2Cl)]2‐S‐methylisothiourea and N,N′‐[Z(2Br)]2‐S‐methylisothiourea, N,N′‐Z2‐S‐methylisothiourea and N,N′‐Boc2‐S‐methylisothiourea to form Nα, ω, ω′‐tris‐alkoxycarbonyl arginines. Two of them, Boc‐Arg‐{ω,ω′‐[Z(2Br)]2}‐OH and Boc‐Arg‐{ω,ω′‐[Z(2Cl)]2}‐OH, were used for the synthesis of dermorphin fragments containing two or three arginine residues. Examination of the products by HPLC and ESI‐MS revealed that the purity of the materials obtained with the use of the new derivatives was higher than that obtained in concurrent syntheses in which Boc‐Arg(Tos) was used. Copyright © 2004 European Peptide Society and John Wiley & Sons, Ltd. |
doi_str_mv | 10.1002/psc.585 |
format | Article |
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Two of them, Boc‐Arg‐{ω,ω′‐[Z(2Br)]2}‐OH and Boc‐Arg‐{ω,ω′‐[Z(2Cl)]2}‐OH, were used for the synthesis of dermorphin fragments containing two or three arginine residues. Examination of the products by HPLC and ESI‐MS revealed that the purity of the materials obtained with the use of the new derivatives was higher than that obtained in concurrent syntheses in which Boc‐Arg(Tos) was used. Copyright © 2004 European Peptide Society and John Wiley & Sons, Ltd.</description><identifier>ISSN: 1075-2617</identifier><identifier>EISSN: 1099-1387</identifier><identifier>DOI: 10.1002/psc.585</identifier><identifier>PMID: 15635728</identifier><language>eng</language><publisher>Chichester, UK: John Wiley & Sons, Ltd</publisher><subject>Arginine - analogs & derivatives ; Arginine - chemistry ; arginine protection ; dynorphin ; Dynorphins - chemical synthesis ; guanidinylation ; Methods ; Peptide Fragments - chemical synthesis ; Peptides - chemical synthesis ; SPPS ; Thiourea - analogs & derivatives</subject><ispartof>Journal of peptide science, 2005-01, Vol.11 (1), p.60-64</ispartof><rights>Copyright © 2004 European Peptide Society and John Wiley & Sons, Ltd.</rights><rights>Copyright (c) 2004 European Peptide Society and John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4175-819b6b9e466b596a18bc84ef95ffa25e696691e62ebfb11a09f43bdaf26681d33</citedby><cites>FETCH-LOGICAL-c4175-819b6b9e466b596a18bc84ef95ffa25e696691e62ebfb11a09f43bdaf26681d33</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.585$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fpsc.585$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15635728$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Izdebski, Jan</creatorcontrib><creatorcontrib>Gers, Tomasz</creatorcontrib><creatorcontrib>Kunce, Danuta</creatorcontrib><creatorcontrib>Markowski, Paweł</creatorcontrib><title>New tris-alkoxycarbonyl arginine derivatives for peptide synthesis</title><title>Journal of peptide science</title><addtitle>J. Peptide Sci</addtitle><description>α‐Alkoxycarbonyl protected ornithines were treated with N,N′‐[Z(2Cl)]2‐S‐methylisothiourea and N,N′‐[Z(2Br)]2‐S‐methylisothiourea, N,N′‐Z2‐S‐methylisothiourea and N,N′‐Boc2‐S‐methylisothiourea to form Nα, ω, ω′‐tris‐alkoxycarbonyl arginines. Two of them, Boc‐Arg‐{ω,ω′‐[Z(2Br)]2}‐OH and Boc‐Arg‐{ω,ω′‐[Z(2Cl)]2}‐OH, were used for the synthesis of dermorphin fragments containing two or three arginine residues. Examination of the products by HPLC and ESI‐MS revealed that the purity of the materials obtained with the use of the new derivatives was higher than that obtained in concurrent syntheses in which Boc‐Arg(Tos) was used. Copyright © 2004 European Peptide Society and John Wiley & Sons, Ltd.</description><subject>Arginine - analogs & derivatives</subject><subject>Arginine - chemistry</subject><subject>arginine protection</subject><subject>dynorphin</subject><subject>Dynorphins - chemical synthesis</subject><subject>guanidinylation</subject><subject>Methods</subject><subject>Peptide Fragments - chemical synthesis</subject><subject>Peptides - chemical synthesis</subject><subject>SPPS</subject><subject>Thiourea - analogs & derivatives</subject><issn>1075-2617</issn><issn>1099-1387</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0MtKxDAUBuAgipdRfAPpShfSsSdt0map4xVExQsuQ9KeaLTT1qQz2re3QwddiascyMfPOT8huxCNIYroUePzMcvYCtmESIgQ4ixdXcwpCymHdINsef8WRf0f4-tkAxiPWUqzTXJyg59B66wPVflef3W5crquujJQ7sVWtsKgQGfnqrVz9IGpXdBg09oCA99V7St667fJmlGlx53lOyJP52ePk8vw-vbianJ8HeYJ9HtkIDTXAhPONRNcQabzLEEjmDGKMuSCcwHIKWqjAVQkTBLrQhnKeQZFHI_I_pDbuPpjhr6VU-tzLEtVYT3zkqdxIjL4H1KAJAEhengwwNzV3js0snF2qlwnIZKLXmXfq-x77eXeMnKmp1j8umWRPTgcwKctsfsrR949TIa4cNDWt_j1o5V7X1yRMvl8cyHvKaeP5_xZnsbf3KCQhQ</recordid><startdate>200501</startdate><enddate>200501</enddate><creator>Izdebski, Jan</creator><creator>Gers, Tomasz</creator><creator>Kunce, Danuta</creator><creator>Markowski, Paweł</creator><general>John Wiley & 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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>200501</creationdate><title>New tris-alkoxycarbonyl arginine derivatives for peptide synthesis</title><author>Izdebski, Jan ; Gers, Tomasz ; Kunce, Danuta ; Markowski, Paweł</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4175-819b6b9e466b596a18bc84ef95ffa25e696691e62ebfb11a09f43bdaf26681d33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Arginine - analogs & derivatives</topic><topic>Arginine - chemistry</topic><topic>arginine protection</topic><topic>dynorphin</topic><topic>Dynorphins - chemical synthesis</topic><topic>guanidinylation</topic><topic>Methods</topic><topic>Peptide Fragments - chemical synthesis</topic><topic>Peptides - chemical synthesis</topic><topic>SPPS</topic><topic>Thiourea - analogs & derivatives</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Izdebski, Jan</creatorcontrib><creatorcontrib>Gers, Tomasz</creatorcontrib><creatorcontrib>Kunce, Danuta</creatorcontrib><creatorcontrib>Markowski, Paweł</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>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of peptide science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Izdebski, Jan</au><au>Gers, Tomasz</au><au>Kunce, Danuta</au><au>Markowski, Paweł</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New tris-alkoxycarbonyl arginine derivatives for peptide synthesis</atitle><jtitle>Journal of peptide science</jtitle><addtitle>J. Peptide Sci</addtitle><date>2005-01</date><risdate>2005</risdate><volume>11</volume><issue>1</issue><spage>60</spage><epage>64</epage><pages>60-64</pages><issn>1075-2617</issn><eissn>1099-1387</eissn><abstract>α‐Alkoxycarbonyl protected ornithines were treated with N,N′‐[Z(2Cl)]2‐S‐methylisothiourea and N,N′‐[Z(2Br)]2‐S‐methylisothiourea, N,N′‐Z2‐S‐methylisothiourea and N,N′‐Boc2‐S‐methylisothiourea to form Nα, ω, ω′‐tris‐alkoxycarbonyl arginines. Two of them, Boc‐Arg‐{ω,ω′‐[Z(2Br)]2}‐OH and Boc‐Arg‐{ω,ω′‐[Z(2Cl)]2}‐OH, were used for the synthesis of dermorphin fragments containing two or three arginine residues. Examination of the products by HPLC and ESI‐MS revealed that the purity of the materials obtained with the use of the new derivatives was higher than that obtained in concurrent syntheses in which Boc‐Arg(Tos) was used. Copyright © 2004 European Peptide Society and John Wiley & Sons, Ltd.</abstract><cop>Chichester, UK</cop><pub>John Wiley & Sons, Ltd</pub><pmid>15635728</pmid><doi>10.1002/psc.585</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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source | MEDLINE; Wiley Journals |
subjects | Arginine - analogs & derivatives Arginine - chemistry arginine protection dynorphin Dynorphins - chemical synthesis guanidinylation Methods Peptide Fragments - chemical synthesis Peptides - chemical synthesis SPPS Thiourea - analogs & derivatives |
title | New tris-alkoxycarbonyl arginine derivatives for peptide synthesis |
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