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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Formylglycin</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" style="text-align:center; font-size:80%;">Vereinfachte Strukturformel ohne Angabe der <a href="Stereochemie" title="Stereochemie">Stereochemie</a>
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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>Formylglycin
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<td>Andere Namen
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<ul><li>α-Formylglycin</li>
<li>3-Oxoalanin</li>
<li>(<i>RS</i>)-α-Formylglycin</li>
<li>(<i>RS</i>)-3-Oxoalanin</li>
<li>(<i>S</i>)-α-Formylglycin</li>
<li>(<i>S</i>)-3-Oxoalanin</li>
<li>(<i>R</i>)-α-Formylglycin</li>
<li>(<i>R</i>)-3-Oxoalanin</li></ul>
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<td><a href="Summenformel" title="Summenformel">Summenformel</a>
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<td>C<sub>3</sub>H<sub>5</sub>NO<sub>3</sub>
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Externe Identifikatoren/Datenbanken
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<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>
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<ul><li><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=5735-66-0">5735-66-0</a><span class="editoronly" style="display:none;"></span> (<a href="Racemat" title="Racemat">Racemat</a>)</li>
<li><span title="Untervorlage eingebunden: CASRN"></span><span class="KeinCASLink" title="CAS-Nummer ohne Common-Chemistry-Eintrag">205876-48-8</span><span class="editoronly" style="display:none;"></span> [(<i>S</i>)-Form]</li>
<li><span title="Untervorlage eingebunden: CASRN"></span><span class="KeinCASLink" title="CAS-Nummer ohne Common-Chemistry-Eintrag">2204271-37-2</span><span class="editoronly" style="display:none;"></span> [(<i>R</i>)-Form]</li></ul>
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<td><a href="PubChem" title="PubChem">PubChem</a>
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<td colspan="2"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/29">29</a>
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<td><a href="ChemSpider" title="ChemSpider">ChemSpider</a>
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<td colspan="2"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.28.html">28</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/Q27102573" class="extiw external" title="d:Q27102573">Q27102573</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>103,08 g·<a href="Mol" title="Mol">mol</a><sup>−1</sup>
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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><br><i>keine Einstufung verfügbar</i><sup id="cite_ref-NV_1-0" class="reference"><a href="#cite_note-NV-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).
</td></tr></tbody></table><p><span class="editoronly" style="display:none;"></span>
</p><p><b>Formylglycin (FGly)</b> oder auch <b>3-Oxoalanin</b> bzw. α-Formylglycin ist eine <a href="Nichtproteinogene_Aminos%C3%A4uren" title="Nichtproteinogene Aminosäuren">nichtproteinogene Aminosäure</a>. Sie kommt im <a href="Aktives_Zentrum" title="Aktives Zentrum">aktiven Zentrum</a> von einigen Enzymen, wie zum Beispiel <a href="Sulfatasen" title="Sulfatasen">Sulfatasen</a> vor. Formylglycin wird in <a href="Prokaryoten" title="Prokaryoten">Pro-</a> und <a href="Eukaryoten" title="Eukaryoten">Eukaryoten</a> durch das <a href="Formylglycin-generierendes_Enzym" title="Formylglycin-generierendes Enzym">Formylglycin-generierende Enzym</a> aus einem <a href="Cystein" title="Cystein">Cystein</a> synthetisiert.<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> In Prokaryoten existiert nebenbei das anaerobe Sulfatasenreifungsenzym AtsA bzw. AtsB.<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>Formylglycin kann ebenfalls in der Gentechnologie als <a href="Protein-Tag" title="Protein-Tag">Protein-Tag</a> genutzt werden.
</p><p>α-Formylglycin sollte nicht mit <i>N</i>-Formylglycin verwechselt werden.
</p>
<div class="mw-heading mw-heading2"><h2 id="Stereoisomerie">Stereoisomerie</h2></div>
<p>Formylglycin ist <a href="Chiralit%C3%A4t_(Chemie)" title="Chiralität (Chemie)">chiral</a>. Es gibt zwei Enantiomere:
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<table class="wikitable" style="text-align:center">
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<th colspan="2"><a href="Enantiomere" class="mw-redirect" title="Enantiomere">Enantiomere</a> von Formylglycin
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<td><span typeof="mw:File"></span><br>
</td>
<td><span typeof="mw:File"></span><br>
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<p>Das 1:1-Gemisch (Racemat) aus (<i>S</i>)-Form und (<i>R</i>)-Form wird (<i>RS</i>)-Formylglycin genannt.
</p>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-NV-1"><span class="mw-cite-backlink"><a href="#cite_ref-NV_1-0">↑</a></span> <span class="reference-text">Dieser Stoff wurde in Bezug auf seine Gefährlichkeit entweder noch nicht eingestuft oder eine verlässliche und zitierfähige Quelle hierzu wurde noch nicht gefunden.</span>
</li>
<li id="cite_note-2"><span class="mw-cite-backlink"><a href="#cite_ref-2">↑</a></span> <span class="reference-text">Maria Pia Cosma, Stefano Pepe, Ida Annunziata, Robert F. Newbold, Markus Grompe: <cite style="font-style:italic">The Multiple Sulfatase Deficiency Gene Encodes an Essential and Limiting Factor for the Activity of Sulfatases</cite>. In: <cite style="font-style:italic">Cell</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>113</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>4</span>, 16. Mai 2003, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>445–456</span>, <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/S0092-8674%2803%2900348-9">10.1016/S0092-8674(03)00348-9</a></span> (<a rel="nofollow" class="external text" href="https://www.cell.com/cell/abstract/S0092-8674%2803%2900348-9">cell.com</a> [abgerufen am 23. Januar 2020]).<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:Formylglycin&rft.atitle=The+Multiple+Sulfatase+Deficiency+Gene+Encodes+an+Essential+and+Limiting+Factor+for+the+Activity+of+Sulfatases&rft.au=Maria+Pia+Cosma%2C+Stefano+Pepe%2C+Ida+Annunziata%2C+...&rft.date=2003-05-16&rft.doi=10.1016%2FS0092-8674%2803%2900348-9&rft.genre=journal&rft.issue=4&rft.jtitle=Cell&rft.pages=445-456&rft.volume=113" style="display:none"> </span></span>
</li>
<li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text"><a href="UniProt" title="UniProt">UniProt</a> <a rel="nofollow" class="external text" href="https://www.uniprot.org/uniprotkb/Q9X758">Q9X758</a>: atsB - Anaerobic sulfatase-maturating enzyme - Klebsiella pneumoniae - atsB gene & protein (html), abgerufen am 13. Januar 2020</span>
</li>
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