Fmoc solid-phase synthesis of peptide thioesters using an intramolecularn,S-acyl shift
[reaction: see text] We describe the Fmoc solid-phase synthesis of peptide thioesters based on the alkylation of the safety-catch sulfonamide linker with a protected 2-mercaptoethanol derivative. The thioester is generated on the solid phase after the peptide chain assembly as a consequence of an in...
Gespeichert in:
| Veröffentlicht in: | Organic letters 2005-06, Vol.7 (13), p.2647-2650 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 2650 |
|---|---|
| container_issue | 13 |
| container_start_page | 2647 |
| container_title | Organic letters |
| container_volume | 7 |
| creator | Ollivier, Nathalie Behr, Jean-Bernard El-Mahdi, Ouafâa Blanpain, Annick Melnyk, Oleg |
| description | [reaction: see text] We describe the Fmoc solid-phase synthesis of peptide thioesters based on the alkylation of the safety-catch sulfonamide linker with a protected 2-mercaptoethanol derivative. The thioester is generated on the solid phase after the peptide chain assembly as a consequence of an intramolecular N,S-acyl shift. Depending on the stability of the spacer separating the sulfonamide linker from the resin toward TFA, treatment of the peptidyl resin with TFA led to a soluble or supported deprotected thioester. |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_proquest_miscellaneous_67937596</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>67937596</sourcerecordid><originalsourceid>FETCH-LOGICAL-p542-f03913d78a4d146abc0974f858d18556cfeeea81b8ab066cb20696f2399325573</originalsourceid><addsrcrecordid>eNo1kMFKxDAURbNQnHH0FyQrVxaSpkmapQyOCgMuHNyWNH2xkbSpfe2if2_BmdWFy-FwuVdky2UuMs0U25BbxB_G-NqYG7Lh0khteL4lX4cuOYophiYbWotAcemnFjAgTZ4OMEyhATq1IQFOMCKdMfTf1PY09NNouxTBzdGO_dNnZt0SKbbBT3fk2tuIcH_OHTkdXk77t-z48fq-fz5mgyzyzDNhuGh0aYuGF8rWjhld-FKWDS-lVM4DgC15XdqaKeXqnCmjfC6MEbmUWuzI4792GNPvvA6suoAOYrQ9pBkrpY3Q0qgVfDiDc91BUw1j6Oy4VJcjxB8aHlle</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>67937596</pqid></control><display><type>article</type><title>Fmoc solid-phase synthesis of peptide thioesters using an intramolecularn,S-acyl shift</title><source>ACS Publications</source><source>MEDLINE</source><creator>Ollivier, Nathalie ; Behr, Jean-Bernard ; El-Mahdi, Ouafâa ; Blanpain, Annick ; Melnyk, Oleg</creator><creatorcontrib>Ollivier, Nathalie ; Behr, Jean-Bernard ; El-Mahdi, Ouafâa ; Blanpain, Annick ; Melnyk, Oleg</creatorcontrib><description>[reaction: see text] We describe the Fmoc solid-phase synthesis of peptide thioesters based on the alkylation of the safety-catch sulfonamide linker with a protected 2-mercaptoethanol derivative. The thioester is generated on the solid phase after the peptide chain assembly as a consequence of an intramolecular N,S-acyl shift. Depending on the stability of the spacer separating the sulfonamide linker from the resin toward TFA, treatment of the peptidyl resin with TFA led to a soluble or supported deprotected thioester.</description><identifier>ISSN: 1523-7060</identifier><identifier>PMID: 15957912</identifier><language>eng</language><publisher>United States</publisher><subject>Amino Acid Sequence ; Amino Acids - chemistry ; Combinatorial Chemistry Techniques ; Esters ; Molecular Sequence Data ; Peptides - chemical synthesis ; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</subject><ispartof>Organic letters, 2005-06, Vol.7 (13), p.2647-2650</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15957912$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ollivier, Nathalie</creatorcontrib><creatorcontrib>Behr, Jean-Bernard</creatorcontrib><creatorcontrib>El-Mahdi, Ouafâa</creatorcontrib><creatorcontrib>Blanpain, Annick</creatorcontrib><creatorcontrib>Melnyk, Oleg</creatorcontrib><title>Fmoc solid-phase synthesis of peptide thioesters using an intramolecularn,S-acyl shift</title><title>Organic letters</title><addtitle>Org Lett</addtitle><description>[reaction: see text] We describe the Fmoc solid-phase synthesis of peptide thioesters based on the alkylation of the safety-catch sulfonamide linker with a protected 2-mercaptoethanol derivative. The thioester is generated on the solid phase after the peptide chain assembly as a consequence of an intramolecular N,S-acyl shift. Depending on the stability of the spacer separating the sulfonamide linker from the resin toward TFA, treatment of the peptidyl resin with TFA led to a soluble or supported deprotected thioester.</description><subject>Amino Acid Sequence</subject><subject>Amino Acids - chemistry</subject><subject>Combinatorial Chemistry Techniques</subject><subject>Esters</subject><subject>Molecular Sequence Data</subject><subject>Peptides - chemical synthesis</subject><subject>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</subject><issn>1523-7060</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo1kMFKxDAURbNQnHH0FyQrVxaSpkmapQyOCgMuHNyWNH2xkbSpfe2if2_BmdWFy-FwuVdky2UuMs0U25BbxB_G-NqYG7Lh0khteL4lX4cuOYophiYbWotAcemnFjAgTZ4OMEyhATq1IQFOMCKdMfTf1PY09NNouxTBzdGO_dNnZt0SKbbBT3fk2tuIcH_OHTkdXk77t-z48fq-fz5mgyzyzDNhuGh0aYuGF8rWjhld-FKWDS-lVM4DgC15XdqaKeXqnCmjfC6MEbmUWuzI4792GNPvvA6suoAOYrQ9pBkrpY3Q0qgVfDiDc91BUw1j6Oy4VJcjxB8aHlle</recordid><startdate>20050623</startdate><enddate>20050623</enddate><creator>Ollivier, Nathalie</creator><creator>Behr, Jean-Bernard</creator><creator>El-Mahdi, Ouafâa</creator><creator>Blanpain, Annick</creator><creator>Melnyk, Oleg</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20050623</creationdate><title>Fmoc solid-phase synthesis of peptide thioesters using an intramolecularn,S-acyl shift</title><author>Ollivier, Nathalie ; Behr, Jean-Bernard ; El-Mahdi, Ouafâa ; Blanpain, Annick ; Melnyk, Oleg</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p542-f03913d78a4d146abc0974f858d18556cfeeea81b8ab066cb20696f2399325573</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Amino Acid Sequence</topic><topic>Amino Acids - chemistry</topic><topic>Combinatorial Chemistry Techniques</topic><topic>Esters</topic><topic>Molecular Sequence Data</topic><topic>Peptides - chemical synthesis</topic><topic>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ollivier, Nathalie</creatorcontrib><creatorcontrib>Behr, Jean-Bernard</creatorcontrib><creatorcontrib>El-Mahdi, Ouafâa</creatorcontrib><creatorcontrib>Blanpain, Annick</creatorcontrib><creatorcontrib>Melnyk, Oleg</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ollivier, Nathalie</au><au>Behr, Jean-Bernard</au><au>El-Mahdi, Ouafâa</au><au>Blanpain, Annick</au><au>Melnyk, Oleg</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Fmoc solid-phase synthesis of peptide thioesters using an intramolecularn,S-acyl shift</atitle><jtitle>Organic letters</jtitle><addtitle>Org Lett</addtitle><date>2005-06-23</date><risdate>2005</risdate><volume>7</volume><issue>13</issue><spage>2647</spage><epage>2650</epage><pages>2647-2650</pages><issn>1523-7060</issn><abstract>[reaction: see text] We describe the Fmoc solid-phase synthesis of peptide thioesters based on the alkylation of the safety-catch sulfonamide linker with a protected 2-mercaptoethanol derivative. The thioester is generated on the solid phase after the peptide chain assembly as a consequence of an intramolecular N,S-acyl shift. Depending on the stability of the spacer separating the sulfonamide linker from the resin toward TFA, treatment of the peptidyl resin with TFA led to a soluble or supported deprotected thioester.</abstract><cop>United States</cop><pmid>15957912</pmid><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2005-06, Vol.7 (13), p.2647-2650 |
| issn | 1523-7060 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_67937596 |
| source | ACS Publications; MEDLINE |
| subjects | Amino Acid Sequence Amino Acids - chemistry Combinatorial Chemistry Techniques Esters Molecular Sequence Data Peptides - chemical synthesis Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization |
| title | Fmoc solid-phase synthesis of peptide thioesters using an intramolecularn,S-acyl shift |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-05T13%3A38%3A02IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Fmoc%20solid-phase%20synthesis%20of%20peptide%20thioesters%20using%20an%20intramolecularn,S-acyl%20shift&rft.jtitle=Organic%20letters&rft.au=Ollivier,%20Nathalie&rft.date=2005-06-23&rft.volume=7&rft.issue=13&rft.spage=2647&rft.epage=2650&rft.pages=2647-2650&rft.issn=1523-7060&rft_id=info:doi/&rft_dat=%3Cproquest_pubme%3E67937596%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=67937596&rft_id=info:pmid/15957912&rfr_iscdi=true |