Stereocontrolled synthesis of Ψ[CH=CH] dipeptide isosteres
A new Stereocontrolled synthesis of the Ψ[CH=CH] dipeptide isostere is described. They key step of the sequence relies on the stereospecific α‐alkylation of δ‐amino‐γ‐mesyloxy‐α,β‐unsaturated esters. The broad availability of nucleophilic α‐side chains by this method allows the preparation of a wide...
Gespeichert in:
Veröffentlicht in: | International Journal of Peptide and Protein Research 1991-09, Vol.38 (3), p.237-241 |
---|---|
Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 241 |
---|---|
container_issue | 3 |
container_start_page | 237 |
container_title | International Journal of Peptide and Protein Research |
container_volume | 38 |
creator | KEMPF, DALE J. WANG, XIU CHUN SPANTON, STEPHEN G. |
description | A new Stereocontrolled synthesis of the Ψ[CH=CH] dipeptide isostere is described. They key step of the sequence relies on the stereospecific α‐alkylation of δ‐amino‐γ‐mesyloxy‐α,β‐unsaturated esters. The broad availability of nucleophilic α‐side chains by this method allows the preparation of a wide variety of Ψ[CH=CH] isosteres with predictable stereochemistry. |
doi_str_mv | 10.1111/j.1399-3011.1991.tb01434.x |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_72578643</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>72578643</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4687-38a704a0e9bedbe4a1fb23ce329e51105ac76a7e8d3e7f2066c7cc4c8f3f28d43</originalsourceid><addsrcrecordid>eNqVkdFu0zAUhi3ENMrgEZAihLhLsGPHxwYhxDK2TprgAtAQCFmOcyLcpU1np6J9I56GZ1qiVN0lwje-ON__--gzIc8ZzdhwXi0yxrVOOWUsY1qzrK8oE1xk2wdkdhg9JDPKJaSKAzwij2NcUMoFh_yYHDOQjAOdkTefewzYuW7Vh65tsU7ibtX_wuhj0jXJ3z8_yvnbcv4zqf0a172vMfGxi2MoPiFHjW0jPt3fJ-Tr-Ycv5Ty9-nRxWb6_Sp2QClKuLFBhKeoK6wqFZU2Vc4c811gwRgvrQFpAVXOEJqdSOnBOONXwJle14Cfk5dS7Dt3tBmNvlj46bFu7wm4TDeQFKCn4P0EmWS5loQbw9QS60MUYsDHr4Jc27AyjZlRsFmb0aEaPZlRs9orNdgg_27-yqZZY30cnp8P8xX5uo7NtE-zK-XjAhJZMCzZg7ybst29x9x8LmPL07CznMDSkU4Mf_mN7aLDhxkjgUJjrjxfmXKvv3xS9NsDvAIslqAk</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>16126658</pqid></control><display><type>article</type><title>Stereocontrolled synthesis of Ψ[CH=CH] dipeptide isosteres</title><source>Wiley Online Library - AutoHoldings Journals</source><source>MEDLINE</source><creator>KEMPF, DALE J. ; WANG, XIU CHUN ; SPANTON, STEPHEN G.</creator><creatorcontrib>KEMPF, DALE J. ; WANG, XIU CHUN ; SPANTON, STEPHEN G.</creatorcontrib><description>A new Stereocontrolled synthesis of the Ψ[CH=CH] dipeptide isostere is described. They key step of the sequence relies on the stereospecific α‐alkylation of δ‐amino‐γ‐mesyloxy‐α,β‐unsaturated esters. The broad availability of nucleophilic α‐side chains by this method allows the preparation of a wide variety of Ψ[CH=CH] isosteres with predictable stereochemistry.</description><identifier>ISSN: 0367-8377</identifier><identifier>EISSN: 1399-3011</identifier><identifier>DOI: 10.1111/j.1399-3011.1991.tb01434.x</identifier><identifier>PMID: 1761370</identifier><identifier>CODEN: IJPPC3</identifier><language>eng</language><publisher>Oxford, UK: Blackwell Publishing Ltd</publisher><subject>Aliphatic compounds ; Alkylation ; Chemistry ; dipeptide isostere ; Dipeptides - chemistry ; Esters - chemistry ; Exact sciences and technology ; Models, Molecular ; Organic chemistry ; peptidomimetic ; Preparations and properties ; Stereoisomerism</subject><ispartof>International Journal of Peptide and Protein Research, 1991-09, Vol.38 (3), p.237-241</ispartof><rights>1992 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4687-38a704a0e9bedbe4a1fb23ce329e51105ac76a7e8d3e7f2066c7cc4c8f3f28d43</citedby><cites>FETCH-LOGICAL-c4687-38a704a0e9bedbe4a1fb23ce329e51105ac76a7e8d3e7f2066c7cc4c8f3f28d43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1111%2Fj.1399-3011.1991.tb01434.x$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1111%2Fj.1399-3011.1991.tb01434.x$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=4961941$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/1761370$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>KEMPF, DALE J.</creatorcontrib><creatorcontrib>WANG, XIU CHUN</creatorcontrib><creatorcontrib>SPANTON, STEPHEN G.</creatorcontrib><title>Stereocontrolled synthesis of Ψ[CH=CH] dipeptide isosteres</title><title>International Journal of Peptide and Protein Research</title><addtitle>Int J Pept Protein Res</addtitle><description>A new Stereocontrolled synthesis of the Ψ[CH=CH] dipeptide isostere is described. They key step of the sequence relies on the stereospecific α‐alkylation of δ‐amino‐γ‐mesyloxy‐α,β‐unsaturated esters. The broad availability of nucleophilic α‐side chains by this method allows the preparation of a wide variety of Ψ[CH=CH] isosteres with predictable stereochemistry.</description><subject>Aliphatic compounds</subject><subject>Alkylation</subject><subject>Chemistry</subject><subject>dipeptide isostere</subject><subject>Dipeptides - chemistry</subject><subject>Esters - chemistry</subject><subject>Exact sciences and technology</subject><subject>Models, Molecular</subject><subject>Organic chemistry</subject><subject>peptidomimetic</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><issn>0367-8377</issn><issn>1399-3011</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1991</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqVkdFu0zAUhi3ENMrgEZAihLhLsGPHxwYhxDK2TprgAtAQCFmOcyLcpU1np6J9I56GZ1qiVN0lwje-ON__--gzIc8ZzdhwXi0yxrVOOWUsY1qzrK8oE1xk2wdkdhg9JDPKJaSKAzwij2NcUMoFh_yYHDOQjAOdkTefewzYuW7Vh65tsU7ibtX_wuhj0jXJ3z8_yvnbcv4zqf0a172vMfGxi2MoPiFHjW0jPt3fJ-Tr-Ycv5Ty9-nRxWb6_Sp2QClKuLFBhKeoK6wqFZU2Vc4c811gwRgvrQFpAVXOEJqdSOnBOONXwJle14Cfk5dS7Dt3tBmNvlj46bFu7wm4TDeQFKCn4P0EmWS5loQbw9QS60MUYsDHr4Jc27AyjZlRsFmb0aEaPZlRs9orNdgg_27-yqZZY30cnp8P8xX5uo7NtE-zK-XjAhJZMCzZg7ybst29x9x8LmPL07CznMDSkU4Mf_mN7aLDhxkjgUJjrjxfmXKvv3xS9NsDvAIslqAk</recordid><startdate>199109</startdate><enddate>199109</enddate><creator>KEMPF, DALE J.</creator><creator>WANG, XIU CHUN</creator><creator>SPANTON, STEPHEN G.</creator><general>Blackwell Publishing Ltd</general><general>Munksgaard</general><scope>BSCLL</scope><scope>IQODW</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>7QL</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>M81</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>199109</creationdate><title>Stereocontrolled synthesis of Ψ[CH=CH] dipeptide isosteres</title><author>KEMPF, DALE J. ; WANG, XIU CHUN ; SPANTON, STEPHEN G.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4687-38a704a0e9bedbe4a1fb23ce329e51105ac76a7e8d3e7f2066c7cc4c8f3f28d43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1991</creationdate><topic>Aliphatic compounds</topic><topic>Alkylation</topic><topic>Chemistry</topic><topic>dipeptide isostere</topic><topic>Dipeptides - chemistry</topic><topic>Esters - chemistry</topic><topic>Exact sciences and technology</topic><topic>Models, Molecular</topic><topic>Organic chemistry</topic><topic>peptidomimetic</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>KEMPF, DALE J.</creatorcontrib><creatorcontrib>WANG, XIU CHUN</creatorcontrib><creatorcontrib>SPANTON, STEPHEN G.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biochemistry Abstracts 3</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>International Journal of Peptide and Protein Research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>KEMPF, DALE J.</au><au>WANG, XIU CHUN</au><au>SPANTON, STEPHEN G.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereocontrolled synthesis of Ψ[CH=CH] dipeptide isosteres</atitle><jtitle>International Journal of Peptide and Protein Research</jtitle><addtitle>Int J Pept Protein Res</addtitle><date>1991-09</date><risdate>1991</risdate><volume>38</volume><issue>3</issue><spage>237</spage><epage>241</epage><pages>237-241</pages><issn>0367-8377</issn><eissn>1399-3011</eissn><coden>IJPPC3</coden><abstract>A new Stereocontrolled synthesis of the Ψ[CH=CH] dipeptide isostere is described. They key step of the sequence relies on the stereospecific α‐alkylation of δ‐amino‐γ‐mesyloxy‐α,β‐unsaturated esters. The broad availability of nucleophilic α‐side chains by this method allows the preparation of a wide variety of Ψ[CH=CH] isosteres with predictable stereochemistry.</abstract><cop>Oxford, UK</cop><pub>Blackwell Publishing Ltd</pub><pmid>1761370</pmid><doi>10.1111/j.1399-3011.1991.tb01434.x</doi><tpages>5</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0367-8377 |
ispartof | International Journal of Peptide and Protein Research, 1991-09, Vol.38 (3), p.237-241 |
issn | 0367-8377 1399-3011 |
language | eng |
recordid | cdi_proquest_miscellaneous_72578643 |
source | Wiley Online Library - AutoHoldings Journals; MEDLINE |
subjects | Aliphatic compounds Alkylation Chemistry dipeptide isostere Dipeptides - chemistry Esters - chemistry Exact sciences and technology Models, Molecular Organic chemistry peptidomimetic Preparations and properties Stereoisomerism |
title | Stereocontrolled synthesis of Ψ[CH=CH] dipeptide isosteres |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-03T06%3A58%3A06IST&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=Stereocontrolled%20synthesis%20of%20%CE%A8%5BCH=CH%5D%20dipeptide%20isosteres&rft.jtitle=International%20Journal%20of%20Peptide%20and%20Protein%20Research&rft.au=KEMPF,%20DALE%20J.&rft.date=1991-09&rft.volume=38&rft.issue=3&rft.spage=237&rft.epage=241&rft.pages=237-241&rft.issn=0367-8377&rft.eissn=1399-3011&rft.coden=IJPPC3&rft_id=info:doi/10.1111/j.1399-3011.1991.tb01434.x&rft_dat=%3Cproquest_cross%3E72578643%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=16126658&rft_id=info:pmid/1761370&rfr_iscdi=true |