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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Geranylpyrophosphat</span></h1>
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<div id="mw-content-text" class="mw-body-content mw-content-ltr" lang="de" dir="ltr"><div class="mw-content-ltr mw-parser-output" lang="de" dir="ltr"><table class="wikitable infobox float-right" id="Vorlage_Infobox_Chemikalie" style="font-size:90%; margin-top:0; width:350px;" summary="Infobox Chemikalie">
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Strukturformel
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<td colspan="2" class="hintergrundfarbe-basis skin-invert-image" style="text-align:center;"><span typeof="mw:File"></span>
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
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<td style="width:33%;">Name
</td>
<td>Geranylpyrophosphat
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>Geranyl-PP</li>
<li>GPP</li>
<li>Geranyldiphosphat</li></ul>
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<td><a href="Summenformel" title="Summenformel">Summenformel</a>
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<td>
<ul><li>C<sub>10</sub>H<sub>17</sub>O<sub>7</sub>P<sub>2</sub><sup>3−</sup></li>
<li>C<sub>10</sub>H<sub>20</sub>O<sub>7</sub>P<sub>2</sub> (protoniert)</li></ul>
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<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Externe Identifikatoren/Datenbanken
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<tr>
<td colspan="2" style="padding:0;">
<table class="mw-collapsible mw-collapsed wikitable" data-expandtext="+" data-collapsetext="−" style="border-top:none; margin:-1px; width:calc(100% + 2px);">
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<td style="width:33%;"><a href="CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a>
</td>
<td>
<ul><li><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=763-10-0">763-10-0</a><span class="editoronly" style="display:none;"></span></li>
<li><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=21141-43-5">21141-43-5</a><span class="editoronly" style="display:none;"></span> (Lithium-Salz)</li></ul>
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<td style="background:#FFDEAD; color:#202122; border-top:1px solid #FFDEAD; padding:0.2em 0; vertical-align:bottom; width:5%;">
</td></tr>
<tr>
<td><a href="PubChem" title="PubChem">PubChem</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/445995">445995</a>
</td></tr>
<tr>
<td><a href="ChemSpider" title="ChemSpider">ChemSpider</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.393471.html">393471</a>
</td></tr>
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<td><a href="DrugBank" title="DrugBank">DrugBank</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB02552">DB02552</a>
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<td style="border-right:1px solid #a2a9b1;"><a href="Wikidata" title="Wikidata">Wikidata</a>
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<td colspan="2"><a href="https://www.wikidata.org/wiki/Q418125" class="extiw external" title="d:Q418125">Q418125</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>314,21 g·mol<sup>−1</sup>
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Sicherheitshinweise
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<td colspan="2">
<table cellspacing="0" cellpadding="2" style="width:100%;">
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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_1-0" class="reference"><a href="#cite_note-Sigma-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
<table class="hintergrundfarbe-neutral" style="text-align:center; margin-left:auto; margin-right:auto; display:flex; justify-content:center;">
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<td><i>keine GHS-Piktogramme</i>
</td></tr></tbody></table>
<p>
</p>
</td></tr>
<tr>
<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>
</td>
<td style="border-top:1px #A7A7A7 dashed;">H: <span title="Untervorlage eingebunden: H-Sätze"></span><i>keine H-Sätze</i>
</td></tr>
<tr>
<td style="border-top:1px #A7A7A7 dashed;">P: <span title="Untervorlage eingebunden: P-Sätze"></span><i>keine P-Sätze</i>
</td></tr>
</tbody></table>
</td></tr>
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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).
</td></tr></tbody></table><p><span class="editoronly" style="display:none;"></span>
</p><p><b>Geranylpyrophosphat</b> (kurz <b>Geranyl-PP</b> oder auch <b>GPP</b>) ist ein <a href="Biomolek%C3%BCl" class="mw-redirect" title="Biomolekül">Biomolekül</a>, welches als Baustein in der <a href="Terpen" class="mw-redirect" title="Terpen">Terpenbiosynthese</a> zu finden ist. Chemisch gesehen ist es ein <a href="Ester" title="Ester">Ester</a> aus <a href="Geraniol" title="Geraniol">Geraniol</a> (einem <a href="Alkohole" title="Alkohole">Alkohol</a> mit zwei zusätzlichen C=C-<a href="Doppelbindung" title="Doppelbindung">Doppelbindungen</a>) und der <a href="Diphosphors%C3%A4ure" title="Diphosphorsäure">Diphosphorsäure</a>.
</p><p>Es entsteht biosynthetisch durch eine Kopf-zu-Schwanz-Kondensation (<a href="Nukleophile_Substitution" title="Nukleophile Substitution">nukleophile Substitution</a>) aus den beiden <a href="Isopren" title="Isopren">Isopreneinheiten</a> <a href="Isopentenylpyrophosphat" title="Isopentenylpyrophosphat">Isopentenylpyrophosphat</a> und <a href="Dimethylallylpyrophosphat" title="Dimethylallylpyrophosphat">Dimethylallylpyrophosphat</a>, mithilfe einer Prenyltransferase (Dimethylallyl-<i>trans</i>-Transferase).<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>
</p>
<p>Das Geranylpyrophosphat ist die Ausgangsverbindung einiger Tausend pflanzlicher Mono<a href="Terpene" title="Terpene">terpene</a>, die vor allen Dingen als Duftstoffe (ätherische Öle) und Pharmaka (etwa <a href="Limonen" title="Limonen">Limonen</a>) Verwendung finden.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</p><p>So werden beispielsweise <a href="%CE%91-Pinen" class="mw-redirect" title="Α-Pinen">α-Pinen</a> und <a href="%CE%92-Pinen" class="mw-redirect" title="Β-Pinen">β-Pinen</a> aus Geranylpyrophosphat durch Cyclisierung von Linaloylpyrophosphat synthetisiert, mit anschließender Umlagerung eines Wasserstoffatoms.
</p><p>
</p><p>Beim Menschen dient Geranylpyrophosphat zur Synthese von <a href="Squalen" title="Squalen">Squalen</a>, einem wichtigen Vorläufer für die <a href="Cholesterin" title="Cholesterin">Cholesterinsynthese</a>.
</p>
<div class="mw-heading mw-heading2"><h2 id="Literatur">Literatur</h2></div>
<ul><li>Albert L. Lehninger: <i>Biochemie</i>, 2. Auflage, Weinheim 1983, ISBN 3-527-25688-1, S. 561.</li></ul>
<div class="mw-heading mw-heading2"><h2 id="Weblinks">Weblinks</h2></div>
<div class="sisterproject" style="margin:0.1em 0 0 0;"><div class="noresize noviewer" style="display:inline-block; line-height:10px; min-width:1.6em; text-align:center;" aria-hidden="true" role="presentation"><span class="mw-default-size" typeof="mw:File"><span title="Commons"></span></span></div><b><span class=""><a class="external text" href="https://commons.wikimedia.org/wiki/Category:Geranyl_pyrophosphate?uselang=de"><span lang="en">Commons</span>: Geranylpyrophosphat</a></span></b> – Sammlung von Bildern, Videos und Audiodateien</div>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-Sigma-1"><span class="mw-cite-backlink"><a href="#cite_ref-Sigma_1-0">↑</a></span> <span class="reference-text">Datenblatt <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/catalog/product/SIGMA/76532">Geranyl pyrophosphate lithium salt</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 24. Juli 2018 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/SIGMA/76532?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">Voet & Voet, <i>Biochemistry</i> (second edition), Wiley & Son’s, S. 696.</span>
</li>
<li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text">Susan C. Trapp, Rodney B. Croteau: <i>Genomic Organization of Plant Terpene Synthases and Molecular Evolutionary Implications</i>; Genetics, 2001, 158: 811–832; <a rel="nofollow" class="external free" href="https://www.genetics.org/content/158/2/811">https://www.genetics.org/content/158/2/811</a>; <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/11404343?dopt=Abstract">PMID 11404343</a>.</span>
</li>
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