Triphosgene: an efficient carbonylating agent for liquid and solid-phase aza-peptide synthesis. Application to the synthesis of two aza-analogues of the AChR MIR decapeptide
The Nα/CαH exchange in aza‐peptides has the advantage of preserving the side chain. Bis(trichloromethyl)carbonate or triphosgene is a solid, stable phosgene substitute which retains its high reactivity. Temperature and coupling times are greatly reduced with reference to other usually recommended ca...
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| Veröffentlicht in: | Journal of peptide science 1997-11, Vol.3 (6), p.429-441 |
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| container_issue | 6 |
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| container_title | Journal of peptide science |
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| creator | André, Frédéric Marraud, Michel Tsouloufis, Theodoros Tzartos, Socrates J. Boussard, Guy |
| description | The Nα/CαH exchange in aza‐peptides has the advantage of preserving the side chain. Bis(trichloromethyl)carbonate or triphosgene is a solid, stable phosgene substitute which retains its high reactivity. Temperature and coupling times are greatly reduced with reference to other usually recommended carbonylating agents, while purity and yield are increased. It has been used, in both liquid‐ and solid‐phase procedures, for the synthesis of various aza‐analogues of dipeptides, tripeptides and decapeptides containing the alanine, aspartic acid and asparagine aza‐residue. ©1997 European Peptide Society and John Wiley & Sons, Ltd. |
| doi_str_mv | 10.1002/(SICI)1099-1387(199711)3:6<429::AID-PSC115>3.0.CO;2-C |
| format | Article |
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It has been used, in both liquid‐ and solid‐phase procedures, for the synthesis of various aza‐analogues of dipeptides, tripeptides and decapeptides containing the alanine, aspartic acid and asparagine aza‐residue. ©1997 European Peptide Society and John Wiley & Sons, Ltd.</description><subject>Aza Compounds - chemical synthesis</subject><subject>Aza Compounds - immunology</subject><subject>aza-alanine</subject><subject>aza-asparagine</subject><subject>aza-aspartic acid</subject><subject>aza-peptides</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Immunodominant Epitopes - chemistry</subject><subject>Indicators and Reagents</subject><subject>Oligopeptides - chemical synthesis</subject><subject>Oligopeptides - immunology</subject><subject>Phosgene - analogs & derivatives</subject><subject>Radioimmunoassay</subject><subject>Receptors, Cholinergic - chemistry</subject><subject>Receptors, Cholinergic - immunology</subject><subject>triphosgene</subject><issn>1075-2617</issn><issn>1099-1387</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1997</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kV1v0zAUhiMEGmPwE5B8hbaLFH80cVI-pCobJdJY0Tq0yyMntluzNM7iVFv5T_xHHBKVCxBXtt5z_JwjP0HwgeAJwZi-PV3lWX5GcJqGhCX8lKQpJ-SMzeL3U5rOZvP8PPy6ygiJPrIJnmTLdzTMngTHhxdP-zuPQhoT_jx44dx3jH0tio-Co3Qac487Dn7etKbZWLdWtZohUSOltSmNqjtUiraw9b4SnanXSKz7TNsWVeZ-Z6TvlcjZysiw2QinkPghwkY1nZEKuX3dbZQzboLmTVOZ0jNsjTqLfPyniqxG3YP9_VTUorLrnRpC3zXPNtfoS36NpCrFCH4ZPNOicurVeJ4E3z5d3GSfw8vlIs_ml2E5ZSwKZUFYiXEpWMrTiBRxQbVglEZaEs4TRZnWEWUSJ4WkWHIVaaqjUmCp-DQRCTsJ3gzcprX3fqcOtsaVqqpErezOAfW_Tgjj7LBA2VrnWqWhac1WtHsgGHqNAL1G6KVALwUGjcAgBq8RwGuEQaPPMGRLoJB57utxgV2xVfJAHb35-u1QfzCV2v819P8z_zlyTDw5HMjGderxQBbtHcSc8QhurxaQXpHzVZwtgLNfGnvKmA</recordid><startdate>199711</startdate><enddate>199711</enddate><creator>André, Frédéric</creator><creator>Marraud, Michel</creator><creator>Tsouloufis, Theodoros</creator><creator>Tzartos, Socrates J.</creator><creator>Boussard, Guy</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></search><sort><creationdate>199711</creationdate><title>Triphosgene: an efficient carbonylating agent for liquid and solid-phase aza-peptide synthesis. Application to the synthesis of two aza-analogues of the AChR MIR decapeptide</title><author>André, Frédéric ; Marraud, Michel ; Tsouloufis, Theodoros ; Tzartos, Socrates J. ; Boussard, Guy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4335-db13c00ca397951b6b2fa3225fd1778e23ff523d08bd20d7e5f2f5ca0de748a83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1997</creationdate><topic>Aza Compounds - chemical synthesis</topic><topic>Aza Compounds - immunology</topic><topic>aza-alanine</topic><topic>aza-asparagine</topic><topic>aza-aspartic acid</topic><topic>aza-peptides</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Immunodominant Epitopes - chemistry</topic><topic>Indicators and Reagents</topic><topic>Oligopeptides - chemical synthesis</topic><topic>Oligopeptides - immunology</topic><topic>Phosgene - analogs & derivatives</topic><topic>Radioimmunoassay</topic><topic>Receptors, Cholinergic - chemistry</topic><topic>Receptors, Cholinergic - immunology</topic><topic>triphosgene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>André, Frédéric</creatorcontrib><creatorcontrib>Marraud, Michel</creatorcontrib><creatorcontrib>Tsouloufis, Theodoros</creatorcontrib><creatorcontrib>Tzartos, Socrates J.</creatorcontrib><creatorcontrib>Boussard, Guy</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><jtitle>Journal of peptide science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>André, Frédéric</au><au>Marraud, Michel</au><au>Tsouloufis, Theodoros</au><au>Tzartos, Socrates J.</au><au>Boussard, Guy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Triphosgene: an efficient carbonylating agent for liquid and solid-phase aza-peptide synthesis. 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It has been used, in both liquid‐ and solid‐phase procedures, for the synthesis of various aza‐analogues of dipeptides, tripeptides and decapeptides containing the alanine, aspartic acid and asparagine aza‐residue. ©1997 European Peptide Society and John Wiley & Sons, Ltd.</abstract><cop>Chichester, UK</cop><pub>John Wiley & Sons, Ltd</pub><pmid>9467971</pmid><doi>10.1002/(SICI)1099-1387(199711)3:6<429::AID-PSC115>3.0.CO;2-C</doi><tpages>13</tpages></addata></record> |
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| ispartof | Journal of peptide science, 1997-11, Vol.3 (6), p.429-441 |
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| language | eng |
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| subjects | Aza Compounds - chemical synthesis Aza Compounds - immunology aza-alanine aza-asparagine aza-aspartic acid aza-peptides Chromatography, High Pressure Liquid Immunodominant Epitopes - chemistry Indicators and Reagents Oligopeptides - chemical synthesis Oligopeptides - immunology Phosgene - analogs & derivatives Radioimmunoassay Receptors, Cholinergic - chemistry Receptors, Cholinergic - immunology triphosgene |
| title | Triphosgene: an efficient carbonylating agent for liquid and solid-phase aza-peptide synthesis. Application to the synthesis of two aza-analogues of the AChR MIR decapeptide |
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