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Available in 30 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-30" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">30 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%85%D8%B5%D8%A7%D9%88%D8%BA_%D8%B5%D9%86%D9%88%D9%8A" title="مصاوغ صنوي – Arabic" lang="ar" hreflang="ar" data-title="مصاوغ صنوي" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%95%D0%BF%D0%B8%D0%BC%D0%B5%D1%80" title="Епимер – Bulgarian" lang="bg" hreflang="bg" data-title="Епимер" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Epimer" title="Epimer – Bosnian" lang="bs" hreflang="bs" data-title="Epimer" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Ep%C3%ADmer" title="Epímer – Catalan" lang="ca" hreflang="ca" data-title="Epímer" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Epimer" title="Epimer – Czech" lang="cs" hreflang="cs" data-title="Epimer" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Epimer" title="Epimer – German" lang="de" hreflang="de" data-title="Epimer" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%95%CF%80%CE%B9%CE%BC%CE%B5%CF%81%CE%AD%CF%82" title="Επιμερές – Greek" lang="el" hreflang="el" data-title="Επιμερές" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Ep%C3%ADmero" title="Epímero – Spanish" lang="es" hreflang="es" data-title="Epímero" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/%C3%89pim%C3%A8re" title="Épimère – French" lang="fr" hreflang="fr" data-title="Épimère" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Ep%C3%ADmero" title="Epímero – Galician" lang="gl" hreflang="gl" data-title="Epímero" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%97%90%ED%94%BC%EB%A8%B8" title="에피머 – Korean" lang="ko" hreflang="ko" data-title="에피머" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Epimer" title="Epimer – Indonesian" lang="id" hreflang="id" data-title="Epimer" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Epimero" title="Epimero – Italian" lang="it" hreflang="it" data-title="Epimero" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%A4%D7%99%D7%9E%D7%A8" title="אפימר – Hebrew" lang="he" hreflang="he" data-title="אפימר" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Epimer" title="Epimer – Hungarian" lang="hu" hreflang="hu" data-title="Epimer" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Epimer" title="Epimer – Malay" lang="ms" hreflang="ms" data-title="Epimer" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Epimeer" title="Epimeer – Dutch" lang="nl" hreflang="nl" data-title="Epimeer" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%A8%E3%83%94%E3%83%9E%E3%83%BC" title="エピマー – Japanese" lang="ja" hreflang="ja" data-title="エピマー" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Epimery" title="Epimery – Polish" lang="pl" hreflang="pl" data-title="Epimery" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Ep%C3%ADmero" title="Epímero – Portuguese" lang="pt" hreflang="pt" data-title="Epímero" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Epimer" title="Epimer – Romanian" lang="ro" hreflang="ro" data-title="Epimer" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%AD%D0%BF%D0%B8%D0%BC%D0%B5%D1%80" title="Эпимер – Russian" lang="ru" hreflang="ru" data-title="Эпимер" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Epim%C3%A9r" title="Epimér – Slovak" lang="sk" hreflang="sk" data-title="Epimér" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Epimer" title="Epimer – Serbian" lang="sr" hreflang="sr" data-title="Epimer" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Epimer" title="Epimer – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Epimer" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Epimeeri" title="Epimeeri – Finnish" lang="fi" hreflang="fi" data-title="Epimeeri" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Epimer" title="Epimer – Swedish" lang="sv" hreflang="sv" data-title="Epimer" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Epimer" title="Epimer – Turkish" lang="tr" hreflang="tr" data-title="Epimer" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%95%D0%BF%D1%96%D0%BC%D0%B5%D1%80%D0%B8" title="Епімери – Ukrainian" lang="uk" hreflang="uk" data-title="Епімери" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%B7%AE%E5%90%91%E5%BC%82%E6%9E%84%E4%BD%93" title="差向异构体 – Chinese" lang="zh" hreflang="zh" data-title="差向异构体" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q926272#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul 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class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">One of a pair of diastereomers</div> <p>In <a href="/wiki/Stereochemistry" title="Stereochemistry">stereochemistry</a>, an <b>epimer</b> is one of a pair of <a href="/wiki/Diastereomer" title="Diastereomer">diastereomers</a>.<sup id="cite_ref-Clayden_1-0" class="reference"><a href="#cite_note-Clayden-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The two epimers have opposite <a href="/wiki/Absolute_configuration" title="Absolute configuration">configuration</a> at only one <a href="/wiki/Stereogenic_center" class="mw-redirect" title="Stereogenic center">stereogenic center</a> out of at least two.<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> All other stereogenic centers in the molecules are the same in each. <b>Epimerization</b> is the interconversion of one epimer to the other epimer. </p><p><a href="/wiki/Doxorubicin" title="Doxorubicin">Doxorubicin</a> and <a href="/wiki/Epirubicin" title="Epirubicin">epirubicin</a> are two epimers that are used as drugs. </p> <table class="wikitable" style="margin: 1em auto 1em auto"> <tbody><tr> <td><span typeof="mw:File"><a href="/wiki/File:Doxorubicin%E2%80%93epirubicin_comparison.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Doxorubicin%E2%80%93epirubicin_comparison.svg/456px-Doxorubicin%E2%80%93epirubicin_comparison.svg.png" decoding="async" width="456" height="145" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/13/Doxorubicin%E2%80%93epirubicin_comparison.svg/684px-Doxorubicin%E2%80%93epirubicin_comparison.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/13/Doxorubicin%E2%80%93epirubicin_comparison.svg/912px-Doxorubicin%E2%80%93epirubicin_comparison.svg.png 2x" data-file-width="1700" data-file-height="540" /></a></span> </td></tr> <tr align="center"> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">Doxorubicin–epirubicin comparison</div> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Examples">Examples</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Epimer&action=edit&section=1" title="Edit section: Examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The stereoisomers β-<small>D</small>-<a href="/wiki/Glucopyranose" class="mw-redirect" title="Glucopyranose">glucopyranose</a> and β-<small>D</small>-<a href="/wiki/Mannose" title="Mannose">mannopyranose</a> are epimers because they differ only in the stereochemistry at the C-2 position. The hydroxy group in β-D-glucopyranose is equatorial (in the "plane" of the ring), while in β-D-mannopyranose the C-2 hydroxy group is <a href="/wiki/Cyclohexane_conformation#Chair_conformation" title="Cyclohexane conformation">axial</a> (up from the "plane" of the ring). These two molecules are epimers but, because they are not mirror images of each other, are not <a href="/wiki/Enantiomer" title="Enantiomer">enantiomers</a>. (Enantiomers have the same name, but differ in <b><small>D</small></b> and <b><small>L</small></b> classification.) They are also not sugar <a href="/wiki/Anomer" title="Anomer">anomers</a>, since it is not the <a href="/wiki/Anomeric_carbon" class="mw-redirect" title="Anomeric carbon">anomeric carbon</a> involved in the stereochemistry. Similarly, β-<small>D</small>-glucopyranose and β-<small>D</small>-<a href="/wiki/Galactose" title="Galactose">galactopyranose</a> are epimers that differ at the C-4 position, with the former being equatorial and the latter being axial. </p> <table class="wikitable" style="margin: 1em auto 1em auto"> <tbody><tr> <td><span typeof="mw:File"><a href="/wiki/File:Beta-D-glucopyranose.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/Beta-D-glucopyranose.svg/200px-Beta-D-glucopyranose.svg.png" decoding="async" width="200" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/Beta-D-glucopyranose.svg/300px-Beta-D-glucopyranose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/07/Beta-D-glucopyranose.svg/400px-Beta-D-glucopyranose.svg.png 2x" data-file-width="156" data-file-height="115" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Beta-D-mannopyranose.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Beta-D-mannopyranose.svg/200px-Beta-D-mannopyranose.svg.png" decoding="async" width="200" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Beta-D-mannopyranose.svg/300px-Beta-D-mannopyranose.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/eb/Beta-D-mannopyranose.svg/400px-Beta-D-mannopyranose.svg.png 2x" data-file-width="156" data-file-height="93" /></a></span> </td></tr> <tr align="center"> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">β-<small>D</small>-glucopyranose </div></td> <td> <div class="center" style="width:auto; margin-left:auto; margin-right:auto;">β-<small>D</small>-mannopyranose </div> </td></tr></tbody></table> <p><br /> In the case that the difference is the -OH groups on C-1, the anomeric carbon, such as in the case of α-<small>D</small>-glucopyranose and β-<small>D</small>-glucopyranose, the molecules are both epimers and anomers (as indicated by the <b>α</b> and <b>β</b> designation).<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> <table class="wikitable" style="margin: 1em auto 1em auto"> <tbody><tr> <td><span typeof="mw:File"><a href="/wiki/File:Alpha-D-glucopyranose-2D-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Alpha-D-glucopyranose-2D-skeletal.svg/220px-Alpha-D-glucopyranose-2D-skeletal.svg.png" decoding="async" width="220" height="157" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Alpha-D-glucopyranose-2D-skeletal.svg/330px-Alpha-D-glucopyranose-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Alpha-D-glucopyranose-2D-skeletal.svg/440px-Alpha-D-glucopyranose-2D-skeletal.svg.png 2x" data-file-width="136" data-file-height="97" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Beta-D-glucopyranose-2D-skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Beta-D-glucopyranose-2D-skeletal.svg/220px-Beta-D-glucopyranose-2D-skeletal.svg.png" decoding="async" width="220" height="128" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Beta-D-glucopyranose-2D-skeletal.svg/330px-Beta-D-glucopyranose-2D-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5e/Beta-D-glucopyranose-2D-skeletal.svg/440px-Beta-D-glucopyranose-2D-skeletal.svg.png 2x" data-file-width="149" data-file-height="87" /></a></span> </td></tr> <tr align="center"> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">α-<small>D</small>-glucopyranose</div></td> <td> <div class="center" style="width:auto; margin-left:auto; margin-right:auto;">β-<small>D</small>-glucopyranose</div> </td></tr></tbody></table> <p><br /> Other closely related compounds are <a href="/wiki/Epi-inositol" class="mw-redirect" title="Epi-inositol"><i>epi</i>-inositol</a> and <a href="/wiki/Inositol" title="Inositol">inositol</a> and <a href="/wiki/Lipoxin" title="Lipoxin">lipoxin</a> and <a href="/w/index.php?title=Epilipoxin&action=edit&redlink=1" class="new" title="Epilipoxin (page does not exist)">epilipoxin</a>. </p> <table class="wikitable" style="margin: 1em auto 1em auto"> <tbody><tr> <td><span typeof="mw:File"><a href="/wiki/File:Epi-inositol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Epi-inositol.svg/156px-Epi-inositol.svg.png" decoding="async" width="156" height="156" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Epi-inositol.svg/234px-Epi-inositol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e7/Epi-inositol.svg/312px-Epi-inositol.svg.png 2x" data-file-width="200" data-file-height="200" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Myo-inositol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Myo-inositol.svg/156px-Myo-inositol.svg.png" decoding="async" width="156" height="156" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Myo-inositol.svg/234px-Myo-inositol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Myo-inositol.svg/312px-Myo-inositol.svg.png 2x" data-file-width="200" data-file-height="200" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:Lipoxin_B4.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Lipoxin_B4.svg/200px-Lipoxin_B4.svg.png" decoding="async" width="200" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Lipoxin_B4.svg/300px-Lipoxin_B4.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ae/Lipoxin_B4.svg/400px-Lipoxin_B4.svg.png 2x" data-file-width="520" data-file-height="349" /></a></span></td> <td><span typeof="mw:File"><a href="/wiki/File:15-epi-lipoxin_B4.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/15-epi-lipoxin_B4.svg/200px-15-epi-lipoxin_B4.svg.png" decoding="async" width="200" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/15-epi-lipoxin_B4.svg/300px-15-epi-lipoxin_B4.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a0/15-epi-lipoxin_B4.svg/400px-15-epi-lipoxin_B4.svg.png 2x" data-file-width="520" data-file-height="349" /></a></span> </td></tr> <tr align="center"> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;"><i>epi</i>-inositol</div> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">Inositol</div> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">Lipoxin</div> </td> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">Epilipoxin</div> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Epimerization">Epimerization</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Epimer&action=edit&section=2" title="Edit section: Epimerization"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Epimerization is a chemical process where an epimer is converted to its diastereomeric counterpart.<sup id="cite_ref-Clayden_1-1" class="reference"><a href="#cite_note-Clayden-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> It can happen in <a href="/wiki/Condensed_tannins_depolymerization" class="mw-redirect" title="Condensed tannins depolymerization">condensed tannins depolymerization</a> reactions. Epimerization can be spontaneous (generally a slow process), or catalysed by enzymes, e.g. the epimerization between the sugars <a href="/wiki/N-acetylglucosamine" class="mw-redirect" title="N-acetylglucosamine"><i>N</i>-acetylglucosamine</a> and <a href="/wiki/N-acetylmannosamine" class="mw-redirect" title="N-acetylmannosamine"><i>N</i>-acetylmannosamine</a>, which is catalysed by <a href="/wiki/RENBP" title="RENBP">renin-binding protein</a>. </p><p>The penultimate step in Zhang & Trudell's classic <a href="/wiki/Epibatidine" title="Epibatidine">epibatidine</a> synthesis is an example of epimerization.<sup id="cite_ref-ZhangTrudell1996_4-0" class="reference"><a href="#cite_note-ZhangTrudell1996-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Pharmaceutical examples include epimerization of the <a href="/wiki/Diastereomer#Erythro_/_threo" title="Diastereomer">erythro isomers</a> of <a href="/wiki/Methylphenidate" title="Methylphenidate">methylphenidate</a> to the pharmacologically preferred and lower-energy threo isomers, and undesired <i>in vivo</i> epimerization of <a href="/wiki/Tesofensine" title="Tesofensine">tesofensine</a> to <a href="/wiki/Brasofensine" title="Brasofensine">brasofensine</a>. </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Epimer&action=edit&section=3" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-Clayden-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Clayden_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Clayden_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFClaydenGreevesWarren2012" class="citation book cs1"><a href="/wiki/Jonathan_Clayden" title="Jonathan Clayden">Clayden, Jonathan</a>; Greeves, Nick; <a href="/wiki/Stuart_Warren" title="Stuart Warren">Warren, Stuart</a> (2012). <i>Organic Chemistry</i> (2nd ed.). Oxford University Press. p. 1112.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Organic+Chemistry&rft.pages=1112&rft.edition=2nd&rft.pub=Oxford+University+Press&rft.date=2012&rft.aulast=Clayden&rft.aufirst=Jonathan&rft.au=Greeves%2C+Nick&rft.au=Warren%2C+Stuart&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpimer" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><a href="/wiki/International_Union_of_Pure_and_Applied_Chemistry" title="International Union of Pure and Applied Chemistry">IUPAC</a>, <i><a href="/wiki/IUPAC_books#Gold_Book" class="mw-redirect" title="IUPAC books">Compendium of Chemical Terminology</a></i>, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "<a rel="nofollow" class="external text" href="https://goldbook.iupac.org/terms/view/E02167.html">Epimers</a>". <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fgoldbook.E02167">10.1351/goldbook.E02167</a></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.biotopics.co.uk/as/glucose2.html">Structure of the glucose molecule</a></span> </li> <li id="cite_note-ZhangTrudell1996-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-ZhangTrudell1996_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZhangTrudell1996" class="citation journal cs1">Zhang, Chunming; Trudell, Mark L. (1996). "A Short and Efficient Total Synthesis of (±)-Epibatidine". <i>The Journal of Organic Chemistry</i>. <b>61</b> (20): 7189–7191. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo9608681">10.1021/jo9608681</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0022-3263">0022-3263</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11667626">11667626</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=A+Short+and+Efficient+Total+Synthesis+of+%28%C2%B1%29-Epibatidine&rft.volume=61&rft.issue=20&rft.pages=7189-7191&rft.date=1996&rft.issn=0022-3263&rft_id=info%3Apmid%2F11667626&rft_id=info%3Adoi%2F10.1021%2Fjo9608681&rft.aulast=Zhang&rft.aufirst=Chunming&rft.au=Trudell%2C+Mark+L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEpimer" class="Z3988"></span></span> </li> </ol></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Epimer&oldid=1186846738">https://en.wikipedia.org/w/index.php?title=Epimer&oldid=1186846738</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Category</a>: <ul><li><a href="/wiki/Category:Stereochemistry" title="Category:Stereochemistry">Stereochemistry</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_is_different_from_Wikidata" title="Category:Short description is different from Wikidata">Short description is different from Wikidata</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 25 November 2023, at 21:38<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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