ff1588d761d55f48f61a52249e1dcc24

Micron Document

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<th colspan="2" style="background:#FFDEAD; color:#202122;">Strukturformel

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<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines

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<td style="width:33%;">Name

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<td>HCTU

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<td>Andere Namen

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<ul><li>(2-(6-Chlor-1<i>H</i>-benzotriazol-1-yl)-1,1,3,3-tetramethylaminium-hexafluorophosphat)</li>

<li><i>O</i>-(6-Chlorbenzotriazol-1-yl)-<i>N</i>,<i>N</i>,<i>N</i>′,<i>N</i>′-tetramethyluronium-hexafluorophosphat</li>

<li>1-[Bis(dimethylamino)methylen]-5-chlorbenzotriazolium 3-oxid-hexafluorophosphat</li>

<li><i>N</i>,<i>N</i>,<i>N</i>′,<i>N</i>′-Tetramethyl-<i>O</i>-(6-chlor-1<i>H</i>-benzotriazol-1-yl)uronium hexafluorophosphat</li></ul>

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<td><a href="Summenformel" title="Summenformel">Summenformel</a>

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<td>C<sub>11</sub>H<sub>15</sub>ClF<sub>6</sub>N<sub>5</sub>OP

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<td>Kurzbeschreibung

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<p>weißes Pulver<sup id="cite_ref-Sigma_1-0" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>

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<th colspan="2" style="background:#FFDEAD; color:#202122;">Externe Identifikatoren/Datenbanken

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<td style="width:33%;"><a href="CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a>

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<td><a href="EG-Nummer" title="EG-Nummer">EG-Nummer</a> (<a href="EG-Nummer#Listennummern" title="EG-Nummer">Listennummer</a>)

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<td colspan="2">608-825-3

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<td><a href="Europ%C3%A4ische_Chemikalienagentur" title="Europäische Chemikalienagentur">ECHA</a>-InfoCard

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<td><a href="PubChem" title="PubChem">PubChem</a>

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<td><a href="ChemSpider" title="ChemSpider">ChemSpider</a>

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<td style="border-right:1px solid #a2a9b1;"><a href="Wikidata" title="Wikidata">Wikidata</a>

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<th colspan="2" style="background:#FFDEAD; color:#202122;">Eigenschaften

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<td><a href="Molare_Masse" title="Molare Masse">Molare Masse</a>

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<td><a href="Aggregatzustand" title="Aggregatzustand">Aggregatzustand</a>

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<p>fest

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<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>

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<th colspan="2" style="background:#FFDEAD; color:#202122;">Sicherheitshinweise

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<td colspan="2" style="text-align:center"><b><a href="Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien" title="Global harmonisiertes System zur Einstufung und Kennzeichnung von Chemikalien">GHS-Gefahrstoffkennzeichnung</a></b><sup id="cite_ref-Sigma_1-2" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>

<td><i>keine GHS-Piktogramme</i>

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<td rowspan="2" width="33%" style="border-top:1px #A7A7A7 dashed; border-right:1px #A7A7A7 dashed;"><a href="H-_und_P-S%C3%A4tze" title="H- und P-Sätze">H- und P-Sätze</a>

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<td style="border-top:1px #A7A7A7 dashed;">H: <span title="Untervorlage eingebunden: H-Sätze"></span><i>keine H-Sätze</i>

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<td style="border-top:1px #A7A7A7 dashed;">P: <span title="Untervorlage eingebunden: P-Sätze"></span><i>keine P-Sätze</i><sup id="cite_ref-Sigma_1-3" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>

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<td colspan="2" style="background:#FFDEAD; color:#202122; font-size:80%; text-align:center; line-height:150%; padding:.25em;">Wenn nicht anders vermerkt, gelten die angegebenen Daten bei <a href="Standardbedingungen" title="Standardbedingungen">Standardbedingungen</a> (0 °C, 1000 hPa).

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</p><p><b>HCTU</b> (2-(6-Chlor-1<i>H</i>-benzotriazol-1-yl)-1,1,3,3-tetramethylaminium-hexafluorophosphat) ist ein <a href="Kopplungsreagenz" class="mw-redirect" title="Kopplungsreagenz">Kopplungsreagenz</a>, welches in der <a href="Peptidsynthese" title="Peptidsynthese">Peptidsynthese</a> zur Erzeugung von <a href="Peptid" title="Peptid">Peptiden</a> verwendet wird.

</p><p>Die Kopplung von aktivierten <a href="Aminos%C3%A4uren" title="Aminosäuren">Aminosäuren</a> mit Peptiden unter Verwendung von HCTU als Hilfreagenz verläuft racemisierungsarm und innerhalb von zwei Minuten.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DOI10.1016/S0040-4039%2800%2999616-3_3-0" class="reference"><a href="#cite_note-DOI10.1016/S0040-4039%252800%252999616-3-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>

</p><p>Die Verbindung ist thermisch instabil und kann sich stark exotherm zersetzen. Eine <a href="Dynamische_Differenzkalorimetrie" title="Dynamische Differenzkalorimetrie">DSC-Messung</a> zeigt ab 149 °C eine Zersetzungsreaktion mit einer spezifischen <a href="Reaktionsenthalpie" title="Reaktionsenthalpie">Reaktionsenthalpie</a> von −845 J·g<sup>−1</sup> bzw. −350 kJ·mol<sup>−1</sup>.<sup id="cite_ref-Sperry_4-0" class="reference"><a href="#cite_note-Sperry-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>

</p><p>Alternative Kopplungsreagenzien sind z. B. <a href="HATU" title="HATU">HATU</a>, <a href="HBTU" title="HBTU">HBTU</a>,<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> <a href="TBTU" class="mw-redirect" title="TBTU">TBTU</a>, <a href="COMU" title="COMU">COMU</a>,<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> <a href="TOMBU" title="TOMBU">TOMBU</a> und <a href="COMBU" title="COMBU">COMBU</a>.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup>

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<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>

<li id="cite_note-Sigma-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Sigma_1-0">a</a></sup> <sup><a href="#cite_ref-Sigma_1-1">b</a></sup> <sup><a href="#cite_ref-Sigma_1-2">c</a></sup> <sup><a href="#cite_ref-Sigma_1-3">d</a></sup></span> <span class="reference-text">Datenblatt <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/catalog/product/SIAL/04936">O-(6-Chlorobenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate ≥98.0% (HPLC)</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 19. Mai 2017 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/SIAL/04936?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>

</li>

<li id="cite_note-2"><span class="mw-cite-backlink"><a href="#cite_ref-2">↑</a></span> <span class="reference-text">C. A. Chantell, M. A. Onaiyekan, M. Menakuru: <i>Fast conventional Fmoc solid-phase peptide synthesis: a comparative study of different activators.</i> In: <i><a href="Journal_of_Peptide_Science" title="Journal of Peptide Science">Journal of Peptide Science</a>.</i> Band 18, Nummer 2, Februar 2012, S. 88–91, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1002/psc.1419">10.1002/psc.1419</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/22147296?dopt=Abstract">PMID 22147296</a>.</span>

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<li id="cite_note-DOI10.1016/S0040-4039%2800%2999616-3-3"><span class="mw-cite-backlink"><a href="#cite_ref-DOI10.1016/S0040-4039%252800%252999616-3_3-0">↑</a></span> <span class="reference-text">Reinhard Knorr, Arnold Trzeciak, Willi Bannwarth, Dieter Gillessen: <i>New coupling reagents in peptide chemistry.</i> In: <i><a href="Tetrahedron_Letters" title="Tetrahedron Letters">Tetrahedron Letters</a>.</i> 30, 1989, S. 1927, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1016/S0040-4039%2800%2999616-3">10.1016/S0040-4039(00)99616-3</a></span>.</span>

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<li id="cite_note-Sperry-4"><span class="mw-cite-backlink"><a href="#cite_ref-Sperry_4-0">↑</a></span> <span class="reference-text">J. B. Sperry, C. J. Minteer, JingYa Tao, R. Johnson, R. Duzguner, M. Hawksworth, S. Oke, P. F. Richardson, R. Barnhart, D. R. Bill, R. A. Giusto, J. D. Weaver: <i>Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing.</i> In: <i><a href="Organic_Process_Research_%26_Development" title="Organic Process Research & Development">Organic Process Research & Development</a>.</i> Band 22, 2020, S. 1262–1275, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1021/acs.oprd.8b00193">10.1021/acs.oprd.8b00193</a></span>.</span>

</li>

<li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text">C. U. Hjørringgaard, A. Brust, P. F. Alewood: <i>Evaluation of COMU as a coupling reagent for in situ neutralization Boc solid phase peptide synthesis.</i> In: <i>Journal of Peptide Science.</i> Band 18, Nummer 3, März 2012, S. 199–207, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1002/psc.1438">10.1002/psc.1438</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/22252935?dopt=Abstract">PMID 22252935</a>.</span>

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<li id="cite_note-6"><span class="mw-cite-backlink"><a href="#cite_ref-6">↑</a></span> <span class="reference-text">R. Subirós-Funosas, L. Nieto-Rodriguez, K. J. Jensen, F. Albericio: <i>COMU: scope and limitations of the latest innovation in peptide acyl transfer reagents.</i> In: <i>Journal of Peptide Science.</i> Band 19, Nummer 7, Juli 2013, S. 408–414, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.1002/psc.2517">10.1002/psc.2517</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/23712932?dopt=Abstract">PMID 23712932</a>.</span>

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<li id="cite_note-7"><span class="mw-cite-backlink"><a href="#cite_ref-7">↑</a></span> <span class="reference-text">Y. E. Jad, S. N. Khattab, B. G. de la Torre, T. Govender, H. G. Kruger, A. El-Faham, F. Albericio: <i>TOMBU and COMBU as Novel Uronium-type peptide coupling reagents derived from Oxyma-B.</i> In: <i>Molecules.</i> Band 19, Nummer 11, 2014, S. 18953–18965, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.3390/molecules191118953">10.3390/molecules191118953</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/25412042?dopt=Abstract">PMID 25412042</a>.</span>

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Dieser Artikel wurde von <a class="external text" title="Zuletzt bearbeitet am 2023-06-16" href="https://de.wikipedia.org/wiki/?title=HCTU&oldid=234657257">Wikipedia</a> herausgegeben. Der Text ist unter <a class="external text" href="https://creativecommons.org/licenses/by-sa/4.0/deed.de">Creative Commons Attribution-Share Alike 4.0</a> verfügbar, sofern nicht anders angegeben. Für die Mediendateien können zusätzliche Bedingungen gelten.

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