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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Digitoxose</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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<td colspan="2" style="text-align:center; font-size:80%;"><small>D</small>-Digitoxose (links) und <small>L</small>-Digitoxose (rechts)
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<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
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<tr>
<td style="width:33%;">Name
</td>
<td>Digitoxose
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<ul><li>2,6-Didesoxyaltrose</li>
<li>(3<i>S</i>,4<i>R</i>,5<i>R</i>)-3,4,5-Trihydroxyhexanal</li>
<li> (<a href="Symbol-Nomenklatur_f%C3%BCr_Glykane" title="Symbol-Nomenklatur für Glykane">SNFG</a>-Symbol)</li></ul>
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<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>6</sub>H<sub>12</sub>O<sub>4</sub>
</td></tr>
<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=527-52-6">527-52-6</a><span class="editoronly" style="display:none;"></span><small>(D(+)-Form)</small></li>
<li><span title="Untervorlage eingebunden: CASRN"></span><span class="KeinCASLink" title="CAS-Nummer ohne Common-Chemistry-Eintrag">75044-73-4</span><span class="editoronly" style="display:none;"></span><small>(L(−)-Form)</small></li></ul>
</td>
<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="EG-Nummer" title="EG-Nummer">EG-Nummer</a>
</td>
<td colspan="2">208-416-6
</td></tr>
<tr>
<td><a href="Europ%C3%A4ische_Chemikalienagentur" title="Europäische Chemikalienagentur">ECHA</a>-InfoCard
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.echa.europa.eu/de/substance-information/-/substanceinfo/100.007.652">100.007.652</a>
</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/94168">94168</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.84984.html">84984</a>
</td></tr>
<tr>
<td style="border-right:1px solid #a2a9b1;"><a href="Wikidata" title="Wikidata">Wikidata</a>
</td>
<td colspan="2"><a href="https://www.wikidata.org/wiki/Q27114041" class="extiw external" title="d:Q27114041">Q27114041</a>
</td></tr></tbody></table>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Eigenschaften
</th></tr>
<tr>
<td><a href="Molare_Masse" title="Molare Masse">Molare Masse</a>
</td>
<td>148,16 g·<a href="Mol" title="Mol">mol</a><sup>−1</sup>
</td></tr>
<tr>
<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<ul><li>112 °C <small>(D(+)-Form)</small><sup id="cite_ref-Roempp_1-0" class="reference"><a href="#cite_note-Roempp-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></li>
<li>112–114 °C <small>(L(−)-Form)</small><sup id="cite_ref-Roempp_1-1" class="reference"><a href="#cite_note-Roempp-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></li></ul>
</td></tr>
<tr>
<td><a href="L%C3%B6slichkeit" title="Löslichkeit">Löslichkeit</a>
</td>
<td>
<p>leicht löslich in Wasser, löslich in Aceton und Ethanol, unlöslich in Diethylether<sup id="cite_ref-Roempp_1-2" class="reference"><a href="#cite_note-Roempp-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Sicherheitshinweise
</th></tr>
<tr>
<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><br><i>keine Einstufung verfügbar</i><sup id="cite_ref-NV_2-0" class="reference"><a href="#cite_note-NV-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</td></tr></tbody></table>
</td></tr>
<tr>
<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>Digitoxose</b> (kurz: <b>Dig</b>, auch <b>2,6-Didesoxyaltrose</b>) ist eine <a href="Hexosen" title="Hexosen">Hexose</a>, die in diversen <a href="Glycoside" title="Glycoside">glycosidischen</a> <a href="Naturstoff" title="Naturstoff">Naturstoffen</a> vorkommt.
</p>
<div class="mw-heading mw-heading2"><h2 id="Vorkommen">Vorkommen</h2></div>
<p>In <a href="Herzglykoside" title="Herzglykoside">Herzglycosiden</a> aus <i><a href="Fingerh%C3%BCte" title="Fingerhüte">Digitalis</a></i> (z. B. <a href="Digitoxin" title="Digitoxin">Digitoxin</a> und <a href="Digoxin" title="Digoxin">Digoxin</a>) kommt <small>L</small>-Digitoxose vor.<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><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> In bakteriellen <a href="Sekund%C3%A4rmetaboliten" title="Sekundärmetaboliten">Sekundärmetaboliten</a> kommen die <small>D</small>- und die <small>L</small>-Form vor.<sup id="cite_ref-:0_5-0" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Zu den bakteriellen Naturstoffen, die Digitoxose enthalten, gehören z. B. Kijanimicin<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> aus <i>Actinomadura kijaniata</i>, die Jadomycine aus <i><a href="Streptomyces" title="Streptomyces">Streptomyces</a></i> und die Habarimicine aus <i>Microbiospora</i>.<sup id="cite_ref-:0_5-1" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><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> Die Saccharomicine sind <a href="Antibiotikum" title="Antibiotikum">antibiotisch</a> wirksame Heptadecaglycoside, die ebenfalls Digitoxose enthalten.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Biosynthese">Biosynthese</h2></div>
<p><a href="Glucose" title="Glucose">Glucose</a> ist ein Vorläufer der in Herzglycosiden vorkommenden Digitoxose.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Verwandte_Verbindungen">Verwandte Verbindungen</h2></div>
<p>Es existieren vier Enantiomerenpaare der 2,6-Didesoxyhexosen. Die anderen drei sind <a href="Oliose" title="Oliose">Oliose</a>, <a href="Olivose" title="Olivose">Olivose</a> und <a href="Boivinose" title="Boivinose">Boivinose</a>.
</p>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-Roempp-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Roempp_1-0">a</a></sup> <sup><a href="#cite_ref-Roempp_1-1">b</a></sup> <sup><a href="#cite_ref-Roempp_1-2">c</a></sup></span> <span class="reference-text">Eintrag zu <a rel="nofollow" class="external text" href="https://roempp.thieme.de/lexicon/RD-04-01496"><i>Digitoxose</i></a>. In: <i><a href="R%C3%B6mpp_Online" class="mw-redirect" title="Römpp Online">Römpp Online</a>.</i> Georg Thieme Verlag, abgerufen am 9. Juli 2023.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-NV-2"><span class="mw-cite-backlink"><a href="#cite_ref-NV_2-0">↑</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-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text">Donald G. Barceloux: <i>FOXGLOVE (DIGITALIS PURPUREA L.): History and Toxicity.</i> In: <i>CliniCians.</i> 13.</span>
</li>
<li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text">J. Colin Mizia, Mohammed U. Syed, Clay S. Bennett: <cite style="font-style:italic">Synthesis of the α-Linked Digitoxose Trisaccharide Fragment of Kijanimicin: An Unexpected Application of Glycosyl Sulfonates</cite>. In: <cite style="font-style:italic"><a href="Organic_Letters" title="Organic Letters">Organic Letters</a></cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>24</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>2</span>, 21. Januar 2022, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>731–735</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/10.1021/acs.orglett.1c04190">10.1021/acs.orglett.1c04190</a></span>.<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:Digitoxose&rft.atitle=Synthesis+of+the+%CE%B1-Linked+Digitoxose+Trisaccharide+Fragment+of+Kijanimicin%3A+An+Unexpected+Application+of+Glycosyl+Sulfonates&rft.au=J.+Colin+Mizia%2C+Mohammed+U.+Syed%2C+Clay+S.+Bennett&rft.date=2022-01-21&rft.doi=10.1021%2Facs.orglett.1c04190&rft.genre=journal&rft.issue=2&rft.jtitle=Organic+Letters&rft.pages=731-735&rft.volume=24" style="display:none"> </span></span>
</li>
<li id="cite_note-:0-5"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-:0_5-0">a</a></sup> <sup><a href="#cite_ref-:0_5-1">b</a></sup></span> <span class="reference-text">Hua Zhang, Jess A. White-Phillip, Charles E. Melançon, Hyung-jin Kwon, Wei-luen Yu, Hung-wen Liu: <cite style="font-style:italic">Elucidation of the Kijanimicin Gene Cluster: Insights into the Biosynthesis of Spirotetronate Antibiotics and Nitrosugars</cite>. In: <cite style="font-style:italic"><a href="Journal_of_the_American_Chemical_Society" title="Journal of the American Chemical Society">Journal of the American Chemical Society</a></cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>129</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>47</span>, 28. November 2007, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>14670–14683</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/10.1021/ja0744854">10.1021/ja0744854</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/17985890?dopt=Abstract">PMID 17985890</a>, <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2515274/">PMC 2515274</a> (freier Volltext).<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:Digitoxose&rft.atitle=Elucidation+of+the+Kijanimicin+Gene+Cluster%3A+Insights+into+the+Biosynthesis+of+Spirotetronate+Antibiotics+and+Nitrosugars&rft.au=Hua+Zhang%2C+Jess+A.+White-Phillip%2C+Charles+E.+Melan%C3%A7on%2C+...&rft.date=2007-11-28&rft.doi=10.1021%2Fja0744854&rft.genre=journal&rft.issue=47&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.pages=14670-14683&rft.pmc=2515274&rft.pmid=17985890&rft.volume=129" style="display:none"> </span></span>
</li>
<li id="cite_note-6"><span class="mw-cite-backlink"><a href="#cite_ref-6">↑</a></span> <span class="reference-text">Externe Identifikatoren von bzw. Datenbank-Links zu <span style="font-style:italic">Kijanimicin</span>: <a href="CAS-Nummer" title="CAS-Nummer">CAS-Nr.</a>: <span class="wikidata-content">78798-08-0</span><span style="display:none;"></span>, <a href="PubChem" title="PubChem">PubChem</a>: <span class="wikidata-content"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/54685752">54685752</a></span><span style="display:none;"></span>, <a href="ChemSpider" title="ChemSpider">ChemSpider</a>: <a rel="nofollow" class="external text" href="http://www.chemspider.com/Chemical-Structure.29272074.html"><span class="wikidata-content">29272074</span></a><span style="display:none;"></span>, <a href="Wikidata" title="Wikidata">Wikidata</a>: <a href="https://www.wikidata.org/wiki/Q119361987" class="extiw external" title="d:Q119361987">Q119361987</a>.<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-7"><span class="mw-cite-backlink"><a href="#cite_ref-7">↑</a></span> <span class="reference-text">Sherif I. Elshahawi, Khaled A. Shaaban, Madan K. Kharel, Jon S. Thorson: <cite style="font-style:italic">A comprehensive review of glycosylated bacterial natural products</cite>. In: <cite style="font-style:italic"><a href="Chemical_Society_Reviews" title="Chemical Society Reviews">Chemical Society Reviews</a></cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>44</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>21</span>, 2015, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>7591–7697</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/10.1039/C4CS00426D">10.1039/C4CS00426D</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/25735878?dopt=Abstract">PMID 25735878</a>, <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4560691/">PMC 4560691</a> (freier Volltext).<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:Digitoxose&rft.atitle=A+comprehensive+review+of+glycosylated+bacterial+natural+products&rft.au=Sherif+I.+Elshahawi%2C+Khaled+A.+Shaaban%2C+Madan+K.+Kharel%2C+...&rft.date=2015&rft.doi=10.1039%2FC4CS00426D&rft.genre=journal&rft.issue=21&rft.jtitle=Chemical+Society+Reviews&rft.pages=7591-7697&rft.pmc=4560691&rft.pmid=25735878&rft.volume=44" style="display:none"> </span></span>
</li>
<li id="cite_note-8"><span class="mw-cite-backlink"><a href="#cite_ref-8">↑</a></span> <span class="reference-text">Fangming Kong, Ning Zhao, Marshall M. Siegel, Kasia Janota, Joseph S. Ashcroft, Frank E. Koehn, Donald B. Borders, Guy T. Carter: <cite style="font-style:italic">Saccharomicins, Novel Heptadecaglycoside Antibiotics Effective against Multidrug-Resistant Bacteria</cite>. In: <cite style="font-style:italic"><a href="Journal_of_the_American_Chemical_Society" title="Journal of the American Chemical Society">Journal of the American Chemical Society</a></cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>120</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>51</span>, 1. Dezember 1998, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>13301–13311</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/10.1021/ja981641l">10.1021/ja981641l</a></span>.<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:Digitoxose&rft.atitle=Saccharomicins%2C+Novel+Heptadecaglycoside+Antibiotics+Effective+against+Multidrug-Resistant+Bacteria&rft.au=Fangming+Kong%2C+Ning+Zhao%2C+Marshall+M.+Siegel%2C+...&rft.date=1998-12-01&rft.doi=10.1021%2Fja981641l&rft.genre=journal&rft.issue=51&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.pages=13301-13311&rft.volume=120" style="display:none"> </span></span>
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<li id="cite_note-9"><span class="mw-cite-backlink"><a href="#cite_ref-9">↑</a></span> <span class="reference-text">G. Franz, W.Z. Hassid: <cite style="font-style:italic">Biosynthesis of digitoxose and glucose in the purpurea glycosides of Digitalis purpurea</cite>. In: <cite style="font-style:italic"><a href="Phytochemistry" title="Phytochemistry">Phytochemistry</a></cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>6</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>6</span>, Januar 1967, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>841–844</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/S0031-9422%2800%2986030-6">10.1016/S0031-9422(00)86030-6</a></span>.<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:Digitoxose&rft.atitle=Biosynthesis+of+digitoxose+and+glucose+in+the+purpurea+glycosides+of+Digitalis+purpurea&rft.au=G.+Franz%2C+W.Z.+Hassid&rft.date=1967-01&rft.doi=10.1016%2FS0031-9422%2800%2986030-6&rft.genre=journal&rft.issue=6&rft.jtitle=Phytochemistry&rft.pages=841-844&rft.volume=6" style="display:none"> </span></span>
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