Solution-Phase Automated Synthesis of Tripeptide Derivatives
An improved general method for automated synthesis of tripeptides was developed, in which methanesulfonic acid (MSA) was used in place of trifluoroacetic acid (TFA), thus making it possible to avoid, 1) corrosion of the apparatus by strong acid vapor, 2) formation of emulsions, and 3) use of the res...
Gespeichert in:
| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2001, Vol.49(9), pp.1138-1146 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1146 |
|---|---|
| container_issue | 9 |
| container_start_page | 1138 |
| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 49 |
| creator | KURODA, Noritaka HATTORI, Taeko KITADA, Chieko SUGAWARA, Tohru |
| description | An improved general method for automated synthesis of tripeptides was developed, in which methanesulfonic acid (MSA) was used in place of trifluoroacetic acid (TFA), thus making it possible to avoid, 1) corrosion of the apparatus by strong acid vapor, 2) formation of emulsions, and 3) use of the restricted solvent, dichloromethane. As an application of the automated synthesis apparatus, 216 fragment tripeptide derivatives were synthesized systematically using the MSA method, in excellent yield and with increased efficiency. |
| doi_str_mv | 10.1248/cpb.49.1138 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_71171377</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3133455301</sourcerecordid><originalsourceid>FETCH-LOGICAL-c629t-7b83e4adc3f5cef9259749be2b534f9a3e6f2b4dbbdd04f5a28df8e0ab593aa93</originalsourceid><addsrcrecordid>eNpd0E1r3DAQBmBRWppN2lPvxVCaS_FWn5YFPTSknxBoIelZjORRV4vXdiQ5kH9fL7vtQi8zh3mYGV5CXjG6Zly27_3k1tKsGRPtE7JiQupacS6ekhWl1NRcNOKMnOe8pZQrqsVzcsaYUm1D6Yp8uB37ucRxqH9uIGN1NZdxBwW76vZxKBvMMVdjqO5SnHAqscPqE6b4ACU-YH5BngXoM7489gvy68vnu-tv9c2Pr9-vr25q33BTau1agRI6L4LyGAxXRkvjkDslZDAgsAncyc65rqMyKOBtF1qk4JQRAEZckMvD3imN9zPmYncxe-x7GHCcs9WMaSa0XuCb_-B2nNOw_GaZbKgQjeF79e6gfBpzThjslOIO0qNl1O4jtUukVhq7j3TRr487Z7fD7mSPGS7g7RFA9tCHBIOP-eQk1VS0bHEfD26bC_zGfwBSib7Hv0fNoexvn0YbSBYH8QdI3JXD</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1460336927</pqid></control><display><type>article</type><title>Solution-Phase Automated Synthesis of Tripeptide Derivatives</title><source>J-STAGE Free</source><source>MEDLINE</source><source>EZB-FREE-00999 freely available EZB journals</source><source>Free Full-Text Journals in Chemistry</source><creator>KURODA, Noritaka ; HATTORI, Taeko ; KITADA, Chieko ; SUGAWARA, Tohru</creator><creatorcontrib>KURODA, Noritaka ; HATTORI, Taeko ; KITADA, Chieko ; SUGAWARA, Tohru</creatorcontrib><description>An improved general method for automated synthesis of tripeptides was developed, in which methanesulfonic acid (MSA) was used in place of trifluoroacetic acid (TFA), thus making it possible to avoid, 1) corrosion of the apparatus by strong acid vapor, 2) formation of emulsions, and 3) use of the restricted solvent, dichloromethane. As an application of the automated synthesis apparatus, 216 fragment tripeptide derivatives were synthesized systematically using the MSA method, in excellent yield and with increased efficiency.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.49.1138</identifier><identifier>PMID: 11558600</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>automated synthesis ; Automation ; Carbonates - chemistry ; Chemical Phenomena ; Chemistry ; Chemistry, Physical ; Exact sciences and technology ; fragment tripeptide ; Indicators and Reagents ; Mesylates - chemistry ; methanesulfonic acid method ; Oligopeptides - chemical synthesis ; Organic chemistry ; Peptide Fragments - chemistry ; Peptides ; Preparations and properties ; solution-phase peptide synthesis ; Solutions ; trifluoroacetic acid method</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2001, Vol.49(9), pp.1138-1146</ispartof><rights>2001 The Pharmaceutical Society of Japan</rights><rights>2002 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 2001</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c629t-7b83e4adc3f5cef9259749be2b534f9a3e6f2b4dbbdd04f5a28df8e0ab593aa93</citedby><cites>FETCH-LOGICAL-c629t-7b83e4adc3f5cef9259749be2b534f9a3e6f2b4dbbdd04f5a28df8e0ab593aa93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1882,4023,27922,27923,27924</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14070381$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11558600$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>KURODA, Noritaka</creatorcontrib><creatorcontrib>HATTORI, Taeko</creatorcontrib><creatorcontrib>KITADA, Chieko</creatorcontrib><creatorcontrib>SUGAWARA, Tohru</creatorcontrib><title>Solution-Phase Automated Synthesis of Tripeptide Derivatives</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>An improved general method for automated synthesis of tripeptides was developed, in which methanesulfonic acid (MSA) was used in place of trifluoroacetic acid (TFA), thus making it possible to avoid, 1) corrosion of the apparatus by strong acid vapor, 2) formation of emulsions, and 3) use of the restricted solvent, dichloromethane. As an application of the automated synthesis apparatus, 216 fragment tripeptide derivatives were synthesized systematically using the MSA method, in excellent yield and with increased efficiency.</description><subject>automated synthesis</subject><subject>Automation</subject><subject>Carbonates - chemistry</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>Chemistry, Physical</subject><subject>Exact sciences and technology</subject><subject>fragment tripeptide</subject><subject>Indicators and Reagents</subject><subject>Mesylates - chemistry</subject><subject>methanesulfonic acid method</subject><subject>Oligopeptides - chemical synthesis</subject><subject>Organic chemistry</subject><subject>Peptide Fragments - chemistry</subject><subject>Peptides</subject><subject>Preparations and properties</subject><subject>solution-phase peptide synthesis</subject><subject>Solutions</subject><subject>trifluoroacetic acid method</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpd0E1r3DAQBmBRWppN2lPvxVCaS_FWn5YFPTSknxBoIelZjORRV4vXdiQ5kH9fL7vtQi8zh3mYGV5CXjG6Zly27_3k1tKsGRPtE7JiQupacS6ekhWl1NRcNOKMnOe8pZQrqsVzcsaYUm1D6Yp8uB37ucRxqH9uIGN1NZdxBwW76vZxKBvMMVdjqO5SnHAqscPqE6b4ACU-YH5BngXoM7489gvy68vnu-tv9c2Pr9-vr25q33BTau1agRI6L4LyGAxXRkvjkDslZDAgsAncyc65rqMyKOBtF1qk4JQRAEZckMvD3imN9zPmYncxe-x7GHCcs9WMaSa0XuCb_-B2nNOw_GaZbKgQjeF79e6gfBpzThjslOIO0qNl1O4jtUukVhq7j3TRr487Z7fD7mSPGS7g7RFA9tCHBIOP-eQk1VS0bHEfD26bC_zGfwBSib7Hv0fNoexvn0YbSBYH8QdI3JXD</recordid><startdate>2001</startdate><enddate>2001</enddate><creator>KURODA, Noritaka</creator><creator>HATTORI, Taeko</creator><creator>KITADA, Chieko</creator><creator>SUGAWARA, Tohru</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope></search><sort><creationdate>2001</creationdate><title>Solution-Phase Automated Synthesis of Tripeptide Derivatives</title><author>KURODA, Noritaka ; HATTORI, Taeko ; KITADA, Chieko ; SUGAWARA, Tohru</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c629t-7b83e4adc3f5cef9259749be2b534f9a3e6f2b4dbbdd04f5a28df8e0ab593aa93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>automated synthesis</topic><topic>Automation</topic><topic>Carbonates - chemistry</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>Chemistry, Physical</topic><topic>Exact sciences and technology</topic><topic>fragment tripeptide</topic><topic>Indicators and Reagents</topic><topic>Mesylates - chemistry</topic><topic>methanesulfonic acid method</topic><topic>Oligopeptides - chemical synthesis</topic><topic>Organic chemistry</topic><topic>Peptide Fragments - chemistry</topic><topic>Peptides</topic><topic>Preparations and properties</topic><topic>solution-phase peptide synthesis</topic><topic>Solutions</topic><topic>trifluoroacetic acid method</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>KURODA, Noritaka</creatorcontrib><creatorcontrib>HATTORI, Taeko</creatorcontrib><creatorcontrib>KITADA, Chieko</creatorcontrib><creatorcontrib>SUGAWARA, Tohru</creatorcontrib><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>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>KURODA, Noritaka</au><au>HATTORI, Taeko</au><au>KITADA, Chieko</au><au>SUGAWARA, Tohru</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Solution-Phase Automated Synthesis of Tripeptide Derivatives</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2001</date><risdate>2001</risdate><volume>49</volume><issue>9</issue><spage>1138</spage><epage>1146</epage><pages>1138-1146</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>An improved general method for automated synthesis of tripeptides was developed, in which methanesulfonic acid (MSA) was used in place of trifluoroacetic acid (TFA), thus making it possible to avoid, 1) corrosion of the apparatus by strong acid vapor, 2) formation of emulsions, and 3) use of the restricted solvent, dichloromethane. As an application of the automated synthesis apparatus, 216 fragment tripeptide derivatives were synthesized systematically using the MSA method, in excellent yield and with increased efficiency.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>11558600</pmid><doi>10.1248/cpb.49.1138</doi><tpages>9</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 2001, Vol.49(9), pp.1138-1146 |
| issn | 0009-2363 1347-5223 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_71171377 |
| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | automated synthesis Automation Carbonates - chemistry Chemical Phenomena Chemistry Chemistry, Physical Exact sciences and technology fragment tripeptide Indicators and Reagents Mesylates - chemistry methanesulfonic acid method Oligopeptides - chemical synthesis Organic chemistry Peptide Fragments - chemistry Peptides Preparations and properties solution-phase peptide synthesis Solutions trifluoroacetic acid method |
| title | Solution-Phase Automated Synthesis of Tripeptide Derivatives |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-09T00%3A05%3A00IST&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=Solution-Phase%20Automated%20Synthesis%20of%20Tripeptide%20Derivatives&rft.jtitle=Chemical%20&%20pharmaceutical%20bulletin&rft.au=KURODA,%20Noritaka&rft.date=2001&rft.volume=49&rft.issue=9&rft.spage=1138&rft.epage=1146&rft.pages=1138-1146&rft.issn=0009-2363&rft.eissn=1347-5223&rft.coden=CPBTAL&rft_id=info:doi/10.1248/cpb.49.1138&rft_dat=%3Cproquest_cross%3E3133455301%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=1460336927&rft_id=info:pmid/11558600&rfr_iscdi=true |