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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Acide phosphoénolpyruvique</span></h1>
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<td colspan="2" class="entete defaut" style="background-color:#FFDEAD;color:black;">Acide phosphoénolpyruvique
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<td colspan="2" style="text-align:center;"><span class="skin-invert-image" typeof="mw:File"></span></td>
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<td colspan="2" style="text-align:center;">Structure de l'acide phosphoénolpyruvique</td>
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<th colspan="2" style="padding:4px; text-align:center; background-color:#FFDEAD; color:#000000">Identification</th></tr>
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<th scope="row"><a href="Nomenclature_de_l'UICPA" title="Nomenclature de l'UICPA">Nom UICPA</a>
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<td><small>Acide 2-phosphonooxyprop-2-ènoïque</small>
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<th scope="row"><a href="Num%C3%A9ro_CAS" title="Numéro CAS">N<sup>o</sup> CAS</a>
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<td><span class="reflink neverexpand"><span class="noarchive"><a class="external text" href="https://tools.wmflabs.org/magnustools/cas.php?cas=138-08-9&language=fr&title=Acide_phosphoénolpyruvique">138-08-9</a></span></span>
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<th scope="row"> N<sup>o</sup> <a href="Agence_europ%C3%A9enne_des_produits_chimiques" title="Agence européenne des produits chimiques">ECHA</a>
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<td><span class=""><span class="noarchive"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.004.830">100.004.830</a></span></span></td>
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<th scope="row"><a href="Num%C3%A9ro_CE" title="Numéro CE">N<sup>o</sup> CE</a>
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<td>205-312-2
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<th scope="row"><a href="PubChem" title="PubChem">PubChem</a>
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<td><span class=""><span class="noarchive"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/1005">1005</a></span></span>
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<th scope="row">ChEBI
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<td><span class=""><span class="noarchive"><a rel="nofollow" class="external text" href="http://www.ebi.ac.uk/chebi/searchId.do?chebiId=44897">44897</a></span></span>
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<th scope="row"><a href="Simplified_Molecular_Input_Line_Entry_System" title="Simplified Molecular Input Line Entry System">SMILES</a>
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<td><div class="NavFrame" title="[afficher]/[masquer]" style="border: none; padding: 0;"><div class="NavContent" style="display: none; text-align: left;">C=C(C(=O)O)OP(=O)(O)O <br><span class="reflink neverexpand"><a rel="nofollow" class="external text" href="http://pubchem.ncbi.nlm.nih.gov/search/?smarts=C%3DC%28C%28%3DO%29O%29OP%28%3DO%29%28O%29O">PubChem</a></span>, <span class="reflink neverexpand"><a rel="nofollow" class="external text" href="http://chemapps.stolaf.edu/jmol/jmol.php?title=&model=C%3DC%28C%28%3DO%29O%29OP%28%3DO%29%28O%29O">vue 3D</a></span></div></div>
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<th scope="row"><a href="International_Chemical_Identifier" title="International Chemical Identifier">InChI</a>
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<td><div class="NavFrame" title="[afficher]/[masquer]" style="border: none; padding: 0;"><div class="NavContent" style="display: none; text-align: left;"><b>InChI :</b> <span class="reflink neverexpand"><a rel="nofollow" class="external text" href="http://chemapps.stolaf.edu/jmol/jmol.php?title=&model=InChI%3D1%2FC3H5O6P%2Fc1-2%283%284%295%299-10%286%2C7%298%2Fh1H2%2C%28H%2C4%2C5%29%28H2%2C6%2C7%2C8%29%2Ff%2Fh4%2C6-7H">vue 3D</a></span> <br>InChI=1/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)/f/h4,6-7H <br><b>InChIKey :</b> <br>DTBNBXWJWCWCIK-HPEAKAIJCD <br><b>Std. InChI :</b> <span class="reflink neverexpand"><a rel="nofollow" class="external text" href="http://chemapps.stolaf.edu/jmol/jmol.php?title=&model=InChI%3D1S%2FC3H5O6P%2Fc1-2%283%284%295%299-10%286%2C7%298%2Fh1H2%2C%28H%2C4%2C5%29%28H2%2C6%2C7%2C8%29">vue 3D</a></span> <br>InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8) <br><b>Std. InChIKey :</b> <br>DTBNBXWJWCWCIK-UHFFFAOYSA-N</div></div>
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<th colspan="2" style="padding:4px; text-align:center; background-color:#FFDEAD; color:#000000">Propriétés chimiques</th></tr>
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<th scope="row"><a href="Formule_chimique" title="Formule chimique">Formule</a>
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<td><a href="Carbone" title="Carbone">C</a><sub>3</sub><a href="Hydrog%C3%A8ne" title="Hydrogène">H</a><sub>5</sub><a href="Oxyg%C3%A8ne" title="Oxygène">O</a><sub>6</sub><a href="Phosphore" title="Phosphore">P</a> <span class="page_h"><a href="C3H5O6P" class="mw-redirect" title="C3H5O6P"><small>[Isomères]</small></a></span><br>
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<th scope="row"><a href="Masse_molaire" title="Masse molaire">Masse molaire</a><sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</th>
<td>168,042 ± 0,004 6 <a href="Gramme" title="Gramme">g</a>/<a href="Mole_(unit%C3%A9)" title="Mole (unité)">mol</a> <br><small>C 21,44 %, H 3 %, O 57,13 %, P 18,43 %, </small>
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<td colspan="2"><hr style="height:2px; background-color:#FFDEAD;"></td></tr>
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<td colspan="2" style="text-align:center;">Unités du <a href="Syst%C3%A8me_international_d'unit%C3%A9s" title="Système international d'unités">SI</a> et <a href="Conditions_normales_de_temp%C3%A9rature_et_de_pression" title="Conditions normales de température et de pression"><abbr title="conditions normales de température et de pression">CNTP</abbr></a>, sauf indication contraire.</td>
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<p>L’<b>acide phosphoénolpyruvique</b> — ou <b>phosphoénolpyruvate</b> sous forme déprotonée, abrégée en <b>PEP</b> — est un <a href="Compos%C3%A9_organique" title="Composé organique">composé organique</a> important en <a href="Biochimie" title="Biochimie">biochimie</a>, en raison notamment de son <a href="Groupe_fonctionnel" title="Groupe fonctionnel">groupe</a> <a href="Phosphate" title="Phosphate">phosphate</a> à haut potentiel de transfert (<a href="Enthalpie_libre" title="Enthalpie libre">ΔG°'</a> = <span title="−0,641 548 eV ou −14 794,471 4 cal(th)/mol" style="cursor:help">−61,9</span> <abbr class="abbr" title="kilojoule par mole"><a href="Kilojoule" class="mw-redirect" title="Kilojoule">kJ</a> <a href="Mole_(unit%C3%A9)" title="Mole (unité)">mol</a><sup>−1</sup></abbr>, valeur la plus élevée trouvée chez les êtres vivants). Il intervient par conséquent comme <a href="M%C3%A9tabolite" title="Métabolite">métabolite</a> de la <a href="Glycolyse" title="Glycolyse">glycolyse</a> en relation avec la <a href="Cha%C3%AEne_respiratoire" title="Chaîne respiratoire">chaîne respiratoire</a>, fournissant l'énergie nécessaire à la <a href="Phosphorylation" title="Phosphorylation">phosphorylation</a> d'une molécule d'<a href="Ad%C3%A9nosine_diphosphate" title="Adénosine diphosphate">ADP</a> en <a href="Ad%C3%A9nosine_triphosphate" title="Adénosine triphosphate">ATP</a>. Il intervient également comme accepteur de <a href="Dioxyde_de_carbone" title="Dioxyde de carbone">C<sub></sub>O<sub>2</sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub></a> hydraté (HCO3-) chez les plantes au métabolisme <a href="Photosynth%C3%A8se" title="Photosynthèse">C4</a> ou <a href="M%C3%A9tabolisme_acide_crassulac%C3%A9en" title="Métabolisme acide crassulacéen">CAM</a>, pour former l'<a href="Acide_oxaloac%C3%A9tique" title="Acide oxaloacétique">oxaloacétate</a>, dans une réaction catalysée par la <a href="Phospho%C3%A9nolpyruvate_carboxylase" class="mw-redirect" title="Phosphoénolpyruvate carboxylase">phosphoénolpyruvate carboxylase</a>.
</p>
<div class="mw-heading mw-heading2"><h2 id="Rôle_dans_la_glycolyse"><span id="R.C3.B4le_dans_la_glycolyse"></span>Rôle dans la glycolyse</h2></div>
<dl><dd><table align="left">
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<td colspan="3" bgcolor="f0e0e0">'<i><b>Biosynthèse'</b></i>
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<td colspan="3" bgcolor="f0e0e0">'<i><b>Dégradation'</b></i>
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<td><span typeof="mw:File"></span>
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<td> <span class="mwe-math-element mwe-math-element-inline"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle \rightleftharpoons }">
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<annotation encoding="application/x-tex">{\displaystyle \rightleftharpoons }</annotation>
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</math></span><img src="./_assets_/eb734a37dd21ce173a46342d1cc64c92/1c37b981df851b9e54e489e017b1481e37d418f3.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.338ex; width:2.324ex; height:1.843ex;" alt="{\displaystyle \rightleftharpoons }" loading="lazy"></span> <a href="Eau" title="Eau">H<sub>2</sub>O<sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub><sub></sub></a> +
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</td>
<td><span typeof="mw:File"></span>
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<td> + <a href="Ad%C3%A9nosine_diphosphate" title="Adénosine diphosphate">ADP</a> + H<sup>+</sup> → <a href="Ad%C3%A9nosine_triphosphate" title="Adénosine triphosphate">ATP</a> +
</td>
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<td><a href="Acide_2-phosphoglyc%C3%A9rique" title="Acide 2-phosphoglycérique">2PG</a>
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<td>
</td>
<td>PEP
</td>
<td>
</td>
<td>PEP
</td>
<td>
</td>
<td><a href="Acide_pyruvique" title="Acide pyruvique">Pyruvate</a>
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<td colspan="3" bgcolor="ffffd0"><i><a href="%C3%89nolase" title="Énolase">Énolase</a> (phosphopyruvate hydratase)</i> – <small><b><a href="Nomenclature_EC" title="Nomenclature EC">EC</a> <span class="reflink neverexpand"><span class="noarchive"><a rel="nofollow" class="external text" href="http://www.expasy.org/enzyme/4.2.1.11"><span title="Lyases, Carbon-Oxygen Lyases, Hydro-Lyases, phosphopyruvate hydratase">4.2.1.11</span></a></span></span></b></small>
</td>
<td>
</td>
<td colspan="3" bgcolor="ffffd0"><i><a href="Pyruvate_kinase" class="mw-redirect" title="Pyruvate kinase">Pyruvate kinase</a></i> – <small><b><a href="Nomenclature_EC" title="Nomenclature EC">EC</a> <span class="reflink neverexpand"><span class="noarchive"><a rel="nofollow" class="external text" href="http://www.expasy.org/enzyme/2.7.1.40"><span title="Transferases, Transferring Phosphorus-Containing Groups, Phosphotransferases with an Alcohol Group as Acceptor, pyruvate kinase">2.7.1.40</span></a></span></span></b></small>
</td></tr></tbody></table><div class="clear" style="clear:left;"></div></dd></dl>
<div class="mw-heading mw-heading3"><h3 id="Biosynthèse"><span id="Biosynth.C3.A8se"></span>Biosynthèse</h3></div>
<p>Le <a href="Acide_2-phosphoglyc%C3%A9rique" title="Acide 2-phosphoglycérique">2-phospho-<small>D</small>-glycérate</a> (2PG) produit au cours de la glycolyse est <a href="R%C3%A9action_de_d%C3%A9shydratation" title="Réaction de déshydratation">déshydraté</a> par une <a href="Lyase" title="Lyase">lyase</a>, l’<i><a href="%C3%89nolase" title="Énolase">énolase</a></i> (ou <i>phosphopyruvate hydratase</i>), pour former le phosphoénolpyruvate (PEP). Un cation <a href="Magn%C3%A9sium" title="Magnésium">Mg<sup>2+</sup></a> est requis comme « <a href="Catalyseur" class="mw-redirect" title="Catalyseur">catalyseur</a> » de la <a href="R%C3%A9action_chimique" title="Réaction chimique">réaction</a> de déshydratation, tandis qu'un second Mg<sup>2+</sup> intervient avec un rôle « conformationnel » en coordination avec le <a href="Groupe_fonctionnel" title="Groupe fonctionnel">groupe</a> <a href="Carboxyle" title="Carboxyle">carboxyle</a> du 2PG.
</p>
<div class="mw-heading mw-heading3"><h3 id="Dégradation"><span id="D.C3.A9gradation"></span>Dégradation</h3></div>
<p>Le <a href="Groupe_fonctionnel" title="Groupe fonctionnel">groupe</a> <a href="Phosphate" title="Phosphate">phosphate</a> à haut potentiel de transfert (<a href="Enthalpie_libre" title="Enthalpie libre">ΔG°'</a> = <span title="−0,641 548 eV ou −14 794,471 4 cal(th)/mol" style="cursor:help">−61,9</span> <abbr class="abbr" title="kilojoule par mole"><a href="Kilojoule" class="mw-redirect" title="Kilojoule">kJ</a> <a href="Mole_(unit%C3%A9)" title="Mole (unité)">mol</a><sup>−1</sup></abbr>) du PEP permet la <a href="Phosphorylation" title="Phosphorylation">phosphorylation</a> d'une <a href="Mol%C3%A9cule" title="Molécule">molécule</a> d'<a href="Ad%C3%A9nosine_diphosphate" title="Adénosine diphosphate">ADP</a> en <a href="Ad%C3%A9nosine_triphosphate" title="Adénosine triphosphate">ATP</a> par la <i><a href="Pyruvate_kinase" class="mw-redirect" title="Pyruvate kinase">pyruvate kinase</a></i>. Un <a href="Cation" title="Cation">cation</a> <a href="Magn%C3%A9sium" title="Magnésium">Mg<sup>2+</sup></a> est nécessaire à cette réaction comme <a href="Cofacteur_(biochimie)" title="Cofacteur (biochimie)">cofacteur</a>.
</p>
<div class="mw-heading mw-heading2"><h2 id="Notes_et_références"><span id="Notes_et_r.C3.A9f.C3.A9rences"></span>Notes et références</h2></div>
<div class="references-small decimal" style=""><div class="mw-references-wrap"><ol class="references">
<li id="cite_note-1"><span class="mw-cite-backlink"><a href="#cite_ref-1">↑</a> </span><span class="reference-text">Masse molaire calculée d’après <span class="ouvrage">« <a rel="nofollow" class="external text" href="http://www.chem.qmul.ac.uk/iupac/AtWt/"><cite style="font-style:normal;"><span class="lang-en" lang="en">Atomic weights of the elements 2007</span></cite></a> », sur <span class="italique">www.chem.qmul.ac.uk</span></span>.</span>
</li>
</ol></div>
</div>
<div class="mw-heading mw-heading2"><h2 id="Voir_aussi">Voir aussi</h2></div>
<ul><li><a href="Transport_de_groupe_PEP" title="Transport de groupe PEP">Transport de groupe PEP</a></li></ul>
<div class="mw-heading mw-heading2"><h2 id="Liens_externes">Liens externes</h2></div>
<p class="mw-empty-elt">
</p>
<ul><li class="mw-empty-elt"></li>
<li><span class="liste-horizontale noarchive"><span class="wd_identifiers">Ressources relatives à la santé</span> : <ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/compound/inspect/CHEMBL1235228"><span class="lang-en" lang="en">ChEMBL</span></a></li> <li><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB01819"><span class="lang-en" lang="en">DrugBank</span></a></li> <li><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=4692"><span class="lang-en" lang="en">International Union of Pharmacology</span></a></li> </ul></span> </li>
<li><div class="liste-horizontale"><span class="wd_identifiers">Notice dans un dictionnaire ou une encyclopédie généraliste</span> : <ul><li><a rel="nofollow" class="external text" href="https://www.enciclopedia.cat/EC-GEC-0109975.xml"><i>Gran Enciclopèdia Catalana</i></a></li> </ul></div></li>
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