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vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Separazione"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Separazione</span> </div> </a> <ul id="toc-Separazione-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Origine" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Origine"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Origine</span> </div> </a> <ul id="toc-Origine-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Note" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Note"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Note</span> </div> </a> <ul id="toc-Note-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Voci_correlate" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Voci_correlate"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Voci correlate</span> </div> </a> <ul id="toc-Voci_correlate-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Altri_progetti" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Altri_progetti"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Altri progetti</span> </div> </a> <ul id="toc-Altri_progetti-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Indice" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Indice" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Mostra/Nascondi l'indice" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Mostra/Nascondi l'indice</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Enantiomero</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Vai a una voce in un'altra lingua. Disponibile in 39 lingue" > <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-39" 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">39 lingue</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Enantiomeer" title="Enantiomeer - afrikaans" lang="af" hreflang="af" data-title="Enantiomeer" data-language-autonym="Afrikaans" data-language-local-name="afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><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_%D9%85%D8%B1%D8%A2%D8%AA%D9%8A" title="مصاوغ مرآتي - arabo" lang="ar" hreflang="ar" data-title="مصاوغ مرآتي" data-language-autonym="العربية" data-language-local-name="arabo" 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%BD%D0%B0%D0%BD%D1%82%D0%B8%D0%BE%D0%BC%D0%B5%D1%80" title="Енантиомер - bulgaro" lang="bg" hreflang="bg" data-title="Енантиомер" data-language-autonym="Български" data-language-local-name="bulgaro" 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/Enantiomer" title="Enantiomer - bosniaco" lang="bs" hreflang="bs" data-title="Enantiomer" data-language-autonym="Bosanski" data-language-local-name="bosniaco" 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/Enanti%C3%B2mer" title="Enantiòmer - catalano" lang="ca" hreflang="ca" data-title="Enantiòmer" data-language-autonym="Català" data-language-local-name="catalano" 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/Enantiomer" title="Enantiomer - ceco" lang="cs" hreflang="cs" data-title="Enantiomer" data-language-autonym="Čeština" data-language-local-name="ceco" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Enantiomer" title="Enantiomer - danese" lang="da" hreflang="da" data-title="Enantiomer" data-language-autonym="Dansk" data-language-local-name="danese" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Enantiomer" title="Enantiomer - tedesco" lang="de" hreflang="de" data-title="Enantiomer" data-language-autonym="Deutsch" data-language-local-name="tedesco" 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%CE%BD%CE%B1%CE%BD%CF%84%CE%B9%CE%BF%CE%BC%CE%B5%CF%81%CE%AD%CF%82" title="Εναντιομερές - greco" lang="el" hreflang="el" data-title="Εναντιομερές" data-language-autonym="Ελληνικά" data-language-local-name="greco" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Enantiomer" title="Enantiomer - inglese" lang="en" hreflang="en" data-title="Enantiomer" data-language-autonym="English" data-language-local-name="inglese" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Enantiomero" title="Enantiomero - esperanto" lang="eo" hreflang="eo" data-title="Enantiomero" data-language-autonym="Esperanto" data-language-local-name="esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Enanti%C3%B3mero" title="Enantiómero - spagnolo" lang="es" hreflang="es" data-title="Enantiómero" data-language-autonym="Español" data-language-local-name="spagnolo" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Enantiomeer" title="Enantiomeer - estone" lang="et" hreflang="et" data-title="Enantiomeer" data-language-autonym="Eesti" data-language-local-name="estone" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Enantiomero" title="Enantiomero - basco" lang="eu" hreflang="eu" data-title="Enantiomero" data-language-autonym="Euskara" data-language-local-name="basco" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D9%86%D8%A7%D9%86%D8%AA%DB%8C%D9%88%D9%85%D8%B1" title="انانتیومر - persiano" lang="fa" hreflang="fa" data-title="انانتیومر" data-language-autonym="فارسی" data-language-local-name="persiano" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Enantiomeeri" title="Enantiomeeri - finlandese" lang="fi" hreflang="fi" data-title="Enantiomeeri" data-language-autonym="Suomi" data-language-local-name="finlandese" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/%C3%89nantiom%C3%A9rie" title="Énantiomérie - francese" lang="fr" hreflang="fr" data-title="Énantiomérie" data-language-autonym="Français" data-language-local-name="francese" 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/Enanti%C3%B3mero" title="Enantiómero - galiziano" lang="gl" hreflang="gl" data-title="Enantiómero" data-language-autonym="Galego" data-language-local-name="galiziano" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%A0%D7%A0%D7%98%D7%99%D7%95%D7%9E%D7%A8" title="אננטיומר - ebraico" lang="he" hreflang="he" data-title="אננטיומר" data-language-autonym="עברית" data-language-local-name="ebraico" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Enantiomer" title="Enantiomer - croato" lang="hr" hreflang="hr" data-title="Enantiomer" data-language-autonym="Hrvatski" data-language-local-name="croato" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Enantiomer" title="Enantiomer - indonesiano" lang="id" hreflang="id" data-title="Enantiomer" data-language-autonym="Bahasa Indonesia" data-language-local-name="indonesiano" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Handhverfa" title="Handhverfa - islandese" lang="is" hreflang="is" data-title="Handhverfa" data-language-autonym="Íslenska" data-language-local-name="islandese" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E5%85%89%E5%AD%A6%E7%95%B0%E6%80%A7%E4%BD%93" title="光学異性体 - giapponese" lang="ja" hreflang="ja" data-title="光学異性体" data-language-autonym="日本語" data-language-local-name="giapponese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EA%B4%91%ED%95%99_%EC%9D%B4%EC%84%B1%EC%A7%88%EC%B2%B4" title="광학 이성질체 - coreano" lang="ko" hreflang="ko" data-title="광학 이성질체" data-language-autonym="한국어" data-language-local-name="coreano" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Enantiomer" title="Enantiomer - malese" lang="ms" hreflang="ms" data-title="Enantiomer" data-language-autonym="Bahasa Melayu" data-language-local-name="malese" 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/Optische_isomerie" title="Optische isomerie - olandese" lang="nl" hreflang="nl" data-title="Optische isomerie" data-language-autonym="Nederlands" data-language-local-name="olandese" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Enantiomer" title="Enantiomer - norvegese bokmål" lang="nb" hreflang="nb" data-title="Enantiomer" data-language-autonym="Norsk bokmål" data-language-local-name="norvegese bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Enancjomery" title="Enancjomery - polacco" lang="pl" hreflang="pl" data-title="Enancjomery" data-language-autonym="Polski" data-language-local-name="polacco" 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/Enanti%C3%B4mero" title="Enantiômero - portoghese" lang="pt" hreflang="pt" data-title="Enantiômero" data-language-autonym="Português" data-language-local-name="portoghese" 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/Enantiomer" title="Enantiomer - rumeno" lang="ro" hreflang="ro" data-title="Enantiomer" data-language-autonym="Română" data-language-local-name="rumeno" 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%BD%D0%B0%D0%BD%D1%82%D0%B8%D0%BE%D0%BC%D0%B5%D1%80%D1%8B" title="Энантиомеры - russo" lang="ru" hreflang="ru" data-title="Энантиомеры" data-language-autonym="Русский" data-language-local-name="russo" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Enantiomer" title="Enantiomer - serbo-croato" lang="sh" hreflang="sh" data-title="Enantiomer" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="serbo-croato" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Enantiomer" title="Enantiomer - Simple English" lang="en-simple" hreflang="en-simple" data-title="Enantiomer" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Enantiom%C3%A9r" title="Enantiomér - slovacco" lang="sk" hreflang="sk" data-title="Enantiomér" data-language-autonym="Slovenčina" data-language-local-name="slovacco" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Enantiomer" title="Enantiomer - sloveno" lang="sl" hreflang="sl" data-title="Enantiomer" data-language-autonym="Slovenščina" data-language-local-name="sloveno" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%95%D0%BD%D0%B0%D0%BD%D1%82%D0%B8%D0%BE%D0%BC%D0%B5%D1%80" title="Енантиомер - serbo" lang="sr" hreflang="sr" data-title="Енантиомер" data-language-autonym="Српски / srpski" data-language-local-name="serbo" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Enantiyomer" title="Enantiyomer - turco" lang="tr" hreflang="tr" data-title="Enantiyomer" data-language-autonym="Türkçe" data-language-local-name="turco" 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%BD%D0%B0%D0%BD%D1%82%D1%96%D0%BE%D0%BC%D0%B5%D1%80%D0%B8" title="Енантіомери - ucraino" lang="uk" hreflang="uk" data-title="Енантіомери" data-language-autonym="Українська" data-language-local-name="ucraino" 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%AF%B9%E6%98%A0%E5%BC%82%E6%9E%84" title="对映异构 - cinese" lang="zh" hreflang="zh" data-title="对映异构" data-language-autonym="中文" data-language-local-name="cinese" 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/Q494483#sitelinks-wikipedia" title="Modifica 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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">Da Wikipedia, l'enciclopedia libera.</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="it" dir="ltr"><figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Chiralit%C3%A0_acido_lattico_enantiomeri.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Chiralit%C3%A0_acido_lattico_enantiomeri.png/350px-Chiralit%C3%A0_acido_lattico_enantiomeri.png" decoding="async" width="350" height="195" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Chiralit%C3%A0_acido_lattico_enantiomeri.png/525px-Chiralit%C3%A0_acido_lattico_enantiomeri.png 1.5x, //upload.wikimedia.org/wikipedia/commons/0/0e/Chiralit%C3%A0_acido_lattico_enantiomeri.png 2x" data-file-width="569" data-file-height="317" /></a><figcaption>Modelli molecolari dei due enantiomeri dell'<a href="/wiki/Acido_lattico" title="Acido lattico">acido lattico</a></figcaption></figure> <p>Sono detti <b>enantiomeri</b> le <a href="/wiki/Entit%C3%A0_molecolare" title="Entità molecolare">entità molecolari</a> che sono immagini speculari ciascuna dell'altra e non sovrapponibili.<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> I termini <b>isomeri ottici</b><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> e <b>antipodi ottici</b><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> sono <a href="/wiki/Sinonimia" title="Sinonimia">sinonimi</a>, ancorché deprecati. </p><p>Le molecole che manifestano questa <a href="/wiki/Isomeria" title="Isomeria">isomeria</a> sono dette <a href="/wiki/Chiralit%C3%A0_(chimica)" title="Chiralità (chimica)">chirali</a> (dal <a href="/wiki/Greco_antico" class="mw-redirect" title="Greco antico">greco</a> <i>χείρ</i>, khéir, «mano»);<b><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></b> la chiralità è la proprietà delle molecole non sovrapponibili alla propria immagine speculare. Queste molecole non posseggono né piani di simmetria né centri di inversione né assi S<sub>n</sub> superiori. </p><p>Un elemento stereogenico in una molecola è un atomo o un gruppo di atomi che conferisce alla molecola la capacità di esistere in due forme non sovrapponibili tra loro, note come enantiomeri. Questo avviene quando l'elemento stereogenico è legato a quattro sostituenti diversi. </p><p>Tuttavia, è importante notare che la presenza di un elemento stereogenico non garantisce automaticamente che la molecola sia chirale. Ad esempio, se una molecola ha più di un atomo di carbonio tetraedrico con tutti e quattro i sostituenti diversi, potrebbe avere più di un elemento stereogenico, ma potrebbe ancora essere simmetrica rispetto alla sua immagine riflessa e quindi non essere chirale. </p><p>Un esempio macroscopico di chiralità può essere rappresentato dalle due mani di una persona o dalle due scarpe di un unico paio: ogni mano, o ogni scarpa, rappresenta un enantiomero. </p><p>Una miscela 1:1 di due enantiomeri viene detta <i><a href="/wiki/Racemo_(chimica)" title="Racemo (chimica)">racemo</a></i> e rappresentata con i simboli (RS), (<i>dl</i>) o (±). I singoli enantiomeri sono invece rappresentati con (R) o (S), (<i>d</i>) o (<i>l</i>), (+) o (–).<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>All'interno di una miscela racemica l'eutomero è l'isomero più attivo, nel senso dell'azione desiderata e ricercata. Il distomero è invece l'enantiomero meno attivo.<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> Il rapporto eudismico è il rapporto di potenza tra l'eutomero e il distomero. Un alto valore del rapporto eudismico sta a significare un'interazione altamente specifica. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Etimologia">Etimologia</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantiomero&veaction=edit&section=1" title="Modifica la sezione Etimologia" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Enantiomero&action=edit&section=1" title="Edit section's source code: Etimologia"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Il termine enantiomero<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> deriva dal <a href="/wiki/Lingua_greca_antica" title="Lingua greca antica">greco</a> ed è composto da <i>ἐναντίος</i> (enantíos), che vuol dire "contrapposto, opposto",<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> e da <i>μέρος</i> (meros), che vuol dire genericamente "parte, porzione"<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> e che in questo contesto può ben riferirsi a "molecola"; quindi il senso complessivo è quello di "molecola opposta" (nei riguardi della chiralità): l'enantiomero di una data molecola chirale ha chiralità opposta. </p> <div class="mw-heading mw-heading2"><h2 id="Proprietà_e_reattività"><span id="Propriet.C3.A0_e_reattivit.C3.A0"></span>Proprietà e reattività</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantiomero&veaction=edit&section=2" title="Modifica la sezione Proprietà e reattività" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Enantiomero&action=edit&section=2" title="Edit section's source code: Proprietà e reattività"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Due molecole enantiomere l'una dell'altra possiedono proprietà fisiche di valore uguale, tranne per una: la capacità di ruotare il <a href="/wiki/Piano_(geometria)" title="Piano (geometria)">piano</a> della <a href="/wiki/Polarizzazione_della_radiazione_elettromagnetica" title="Polarizzazione della radiazione elettromagnetica">luce polarizzata</a>. Questa capacità, definita <a href="/wiki/Potere_rotatorio" title="Potere rotatorio">potere rotatorio</a>, è uguale in <a href="/wiki/Valore_assoluto" title="Valore assoluto">valore assoluto</a>, ma opposta di <a href="/wiki/Segno_(matematica)" title="Segno (matematica)">segno</a> per ognuno dei due enantiomeri. </p><p>Due molecole enantiomere l'una dell'altra manifestano anche la stessa reattività chimica in ambiente achirale o chirale racemico; ben diversa può invece essere la loro reattività nei confronti di un enantiomero di un'altra coppia. </p> <dl><dd><code>(RS)-A* + X (non chirale) → (R)-A*X (50%) + (S)-A*X (50%)</code></dd></dl> <dl><dd><code>(RS)-A* + (R)-B* (chirale) → (R,R)-A*B* (>50%) + (S,R)-A*B* (<50%)</code></dd></dl> <dl><dd><small>L'asterisco indica che la specie è chirale, le indicazioni R e S sono arbitrarie.</small></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Separazione">Separazione</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantiomero&veaction=edit&section=3" title="Modifica la sezione Separazione" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Enantiomero&action=edit&section=3" title="Edit section's source code: Separazione"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Una fonte di enantiomeri puri di composti chirali sono le sostanze naturali da cui possono essere estratti, purificati e opportunamente modificati tramite reazioni che non alterino la configurazione stereochimica della molecola. Per quanto riguarda la sintesi di enantiomeri puri, occorre tener presente che le reazioni tra composti achirali producono sempre <i>racemi</i>. </p><p>Il processo attraverso cui da un racemo sono separati i due enantiomeri puri viene detto <i>risoluzione</i>. La risoluzione di un racemo può essere eseguita per via chimica. Ci sono due possibilità: la <b>risoluzione classica</b> e la <b>risoluzione cinetica</b>. Nella prima si esegue una reazione stechiometrica con un substrato enantiomericamente puro a dare un addotto che contiene entrambi i substrati: </p> <dl><dd><code>(RS)-A* + (R)-B* (chirale) → (R,R)-A*B* + (S,R)-A*B* </code></dd></dl> <p>I due prodotti della reazione qui sopra non sono enantiomeri, ma <a href="/wiki/Diastereoisomero" title="Diastereoisomero">diastereoisomeri</a> e posseggono proprietà chimico-fisiche diverse: ad esempio diversa <a href="/wiki/Solubilit%C3%A0" title="Solubilità">solubilità</a> nei <a href="/wiki/Solvente" title="Solvente">solventi</a> per cui possono quindi essere separati per <a href="/wiki/Cristallizzazione_frazionata" title="Cristallizzazione frazionata">cristallizzazione frazionata</a> oppure diversa forma fisica (uno dei due diastereoisomeri può essere un liquido e l'altro un solido cristallino). Dopo averli separati viene eseguita una reazione che ripristina i composti iniziali, che saranno quindi enantiomeri puri: </p> <dl><dd><code>(R,R)-A*B* → (R)-A* + (R)-B* </code></dd> <dd><code>(S,R)-A*B* → (S)-A* + (R)-B* </code></dd></dl> <p>Nella <b>risoluzione cinetica</b> si sfrutta invece la diversa velocità di reazione dei due enantiomeri con un reattivo stechiometrico o molto più spesso un catalizzatore, ad esempio un enzima, enantiomericamente puro. In questo caso in genere il reattivo enantiomericamente puro non è incorporato nei prodotti. Grazie alla diversa velocità di reazione uno dei due enantiomeri, per esempio l'(R), reagirà più lentamente. Quindi, arrestando al momento opportuno la reazione, il substrato non reagito sarà arricchito nell'enantiomero (R) e il prodotto sarà arricchito nell'enantiomero (S). Trattandosi di due sostanze del tutto diverse, la loro separazione sarà facile. </p><p>Un secondo metodo di separazione (fisico) di due enantiomeri è la <a href="/wiki/Cromatografia" title="Cromatografia">cromatografia</a> su fase stazionaria chirale: i due enantiomeri interagiscono diversamente con la fase stazionaria chirale della colonna e pertanto percorrono la colonna in tempi differenti. </p><p>Un terzo metodo di risoluzione è quello enzimatico. Gli <a href="/wiki/Enzima" title="Enzima">enzimi</a> sono chirali quindi interagiscono con i due enantiomeri in modo diverso e spesso reagiscono con uno solo dei due enantiomeri; ciò si traduce nella diversa <a href="/wiki/Velocit%C3%A0_di_reazione" title="Velocità di reazione">velocità di reazione</a> che sarà elevata per uno e molto bassa o praticamente nulla per l'altro. </p> <div class="mw-heading mw-heading2"><h2 id="Origine">Origine</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantiomero&veaction=edit&section=4" title="Modifica la sezione Origine" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Enantiomero&action=edit&section=4" title="Edit section's source code: Origine"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Sulle cause per cui nel mondo vivente le sostanze chirali sono generalmente presenti in forma enantiomerica si hanno solo ipotesi. La più accreditata vuole che l'enantiomeria sia stata originata dalla <a href="/wiki/Luce_polarizzata" class="mw-redirect" title="Luce polarizzata">luce polarizzata</a> circolarmente emessa da alcune formazioni stellari. Nella <a href="/wiki/Nebulosa_di_Orione" title="Nebulosa di Orione">nebulosa di Orione</a> è stata scoperta una forte sorgente di luce polarizzata circolarmente, e nel <a href="/wiki/Murchison_(meteorite)" title="Murchison (meteorite)">meteorite di Murchinson</a> del 1969 in Australia si è riscontrato un eccesso di L-aminoacidi e ciò dimostrerebbe che l'asimmetria chirale era presente prima della vita sulla Terra.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Note">Note</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantiomero&veaction=edit&section=5" title="Modifica la sezione Note" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Enantiomero&action=edit&section=5" title="Edit section's source code: Note"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-1"><a href="#cite_ref-1"><b>^</b></a> <span class="reference-text">(<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>) <a rel="nofollow" class="external text" href="http://goldbook.iupac.org/E02069.html">Enantiomer</a>, definizione <a href="/wiki/Unione_internazionale_di_chimica_pura_e_applicata" title="Unione internazionale di chimica pura e applicata">IUPAC</a> <a rel="nofollow" class="external text" href="http://goldbook.iupac.org/index.html">Gold Book</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20100124150119/http://goldbook.iupac.org/index.html">Archiviato</a> il 24 gennaio 2010 in <a href="/wiki/Internet_Archive" title="Internet Archive">Internet Archive</a>.</span> </li> <li id="cite_note-2"><a href="#cite_ref-2"><b>^</b></a> <span class="reference-text">(<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>) <a rel="nofollow" class="external text" href="http://goldbook.iupac.org/O04308.html">Optical isomers</a>, definizione <a href="/wiki/Unione_internazionale_di_chimica_pura_e_applicata" title="Unione internazionale di chimica pura e applicata">IUPAC</a> <a rel="nofollow" class="external text" href="http://goldbook.iupac.org/index.html">Gold Book</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20100124150119/http://goldbook.iupac.org/index.html">Archiviato</a> il 24 gennaio 2010 in <a href="/wiki/Internet_Archive" title="Internet Archive">Internet Archive</a>.</span> </li> <li id="cite_note-3"><a href="#cite_ref-3"><b>^</b></a> <span class="reference-text">(<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>) <a rel="nofollow" class="external text" href="http://goldbook.iupac.org/O04304.html">Optical antipodes</a>, definizione <a href="/wiki/Unione_internazionale_di_chimica_pura_e_applicata" title="Unione internazionale di chimica pura e applicata">IUPAC</a> <a rel="nofollow" class="external text" href="http://goldbook.iupac.org/index.html">Gold Book</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20100124150119/http://goldbook.iupac.org/index.html">Archiviato</a> il 24 gennaio 2010 in <a href="/wiki/Internet_Archive" title="Internet Archive">Internet Archive</a>.</span> </li> <li id="cite_note-4"><a href="#cite_ref-4"><b>^</b></a> <span class="reference-text"><cite class="citation web" style="font-style:normal"> <a rel="nofollow" class="external text" href="https://www.grecoantico.com/dizionario-greco-antico.php?parola=%CF%87%CE%B5%CE%AF%CF%81"><span style="font-style:italic;">DIZIONARIO GRECO ANTICO - Greco antico - Italiano</span></a>, su <span style="font-style:italic;">www.grecoantico.com</span>. <small>URL consultato il 19 marzo 2024</small>.</cite></span> </li> <li id="cite_note-5"><a href="#cite_ref-5"><b>^</b></a> <span class="reference-text">Per le regole di assegnazione dei prefissi R- e S-, si veda la sezione "Nomenclatura" della voce <a href="/wiki/Stereoisomero" title="Stereoisomero">Stereoisomero</a>.</span> </li> <li id="cite_note-6"><a href="#cite_ref-6"><b>^</b></a> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal"> E. J. Ariëns, <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6092093/?dopt=Abstract"><span style="font-style:italic;">Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology</span></a>, in <span style="font-style:italic;">European Journal of Clinical Pharmacology</span>, vol. 26, n. 6, 1984, pp. 663-668, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1007%2FBF00541922">10.1007/BF00541922</a>. <small>URL consultato il 4 novembre 2022</small>.</cite></span> </li> <li id="cite_note-7"><a href="#cite_ref-7"><b>^</b></a> <span class="reference-text"><cite class="citation web" style="font-style:normal"> <a rel="nofollow" class="external text" href="https://www.treccani.it/enciclopedia/enantiomero_(Dizionario-delle-Scienze-Fisiche)/,%20https://www.treccani.it/enciclopedia/enantiomero_(Dizionario-delle-Scienze-Fisiche)/"><span style="font-style:italic;">enantiomero - Treccani</span></a>, su <span style="font-style:italic;">Treccani</span>. <small>URL consultato il 23 marzo 2024</small>.</cite></span> </li> <li id="cite_note-8"><a href="#cite_ref-8"><b>^</b></a> <span class="reference-text"><cite class="citation web" style="font-style:normal"> <a rel="nofollow" class="external text" href="https://www.grecoantico.com/dizionario-greco-antico.php?lemma=ENANTIOS100"><span style="font-style:italic;">DIZIONARIO GRECO ANTICO - Greco antico - Italiano</span></a>, su <span style="font-style:italic;">www.grecoantico.com</span>. <small>URL consultato il 23 marzo 2024</small>.</cite></span> </li> <li id="cite_note-9"><a href="#cite_ref-9"><b>^</b></a> <span class="reference-text"><cite class="citation web" style="font-style:normal"> <a rel="nofollow" class="external text" href="https://www.grecoantico.com/dizionario-greco-antico.php?parola=meros"><span style="font-style:italic;">DIZIONARIO GRECO ANTICO - Greco antico - Italiano</span></a>, su <span style="font-style:italic;">www.grecoantico.com</span>. <small>URL consultato il 23 marzo 2024</small>.</cite></span> </li> <li id="cite_note-10"><a href="#cite_ref-10"><b>^</b></a> <span class="reference-text"><i>Chemistry in Britain</i>, ottobre 1998, 18</span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Voci_correlate">Voci correlate</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantiomero&veaction=edit&section=6" title="Modifica la sezione Voci correlate" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Enantiomero&action=edit&section=6" title="Edit section's source code: Voci correlate"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Isomeria" title="Isomeria">Isomeria</a></li> <li><a href="/wiki/Stereoisomero" title="Stereoisomero">Stereoisomero</a></li> <li><a href="/wiki/Stereochimica" title="Stereochimica">Stereochimica</a></li> <li><a href="/wiki/Elemento_stereogenico" title="Elemento stereogenico">Elemento stereogenico</a></li> <li><a href="/wiki/Prochiralit%C3%A0" title="Prochiralità">Prochiralità</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Altri_progetti">Altri progetti</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Enantiomero&veaction=edit&section=7" title="Modifica la sezione Altri progetti" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Enantiomero&action=edit&section=7" title="Edit section's source code: Altri progetti"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <div id="interProject" class="toccolours" style="display: none; clear: both; margin-top: 2em"><p id="sisterProjects" style="background-color: #efefef; color: black; font-weight: bold; margin: 0"><span>Altri progetti</span></p><ul title="Collegamenti verso gli altri progetti Wikimedia"> <li class="" title=""><a href="https://it.wiktionary.org/wiki/enantiomero" class="extiw" title="wikt:enantiomero">Wikizionario</a></li> <li class="" title=""><span class="plainlinks" title="commons:Category:Enantiomers"><a class="external text" href="https://commons.wikimedia.org/wiki/Category:Enantiomers?uselang=it">Wikimedia Commons</a></span></li></ul></div> <ul><li><span typeof="mw:File"><a href="https://it.wiktionary.org/wiki/" title="Collabora a Wikizionario"><img alt="Collabora a Wikizionario" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Wiktionary_small.svg/18px-Wiktionary_small.svg.png" decoding="async" 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.navbox>tbody>tr:first-child>th{background:var(--background-color-interactive)!important}html.skin-theme-clientpref-os .mw-parser-output .navbox th{color:var(--color-base)!important}html.skin-theme-clientpref-os .mw-parser-output .navbox_abovebelow,html.skin-theme-clientpref-os .mw-parser-output .navbox_group{background:var(--background-color-interactive-subtle)!important}html.skin-theme-clientpref-os .mw-parser-output .subnavbox_group{background:var(--background-color-neutral-subtle)!important}}</style><table class="navbox mw-collapsible mw-collapsed noprint metadata" id="navbox-Stereochimica"><tbody><tr><th colspan="3"><div class="navbox_navbar"><div class="noprint plainlinks" style="background-color:transparent; padding:0; font-size:xx-small; color:var(--color-base, #000000); white-space:nowrap;"><a href="/wiki/Template:Stereochimica" title="Template:Stereochimica"><span title="Vai alla pagina del template">V</span></a> · <a href="/w/index.php?title=Discussioni_template:Stereochimica&action=edit&redlink=1" class="new" title="Discussioni template:Stereochimica (la pagina non esiste)"><span title="Discuti del template">D</span></a> · <a class="external text" href="https://it.wikipedia.org/w/index.php?title=Template:Stereochimica&action=edit"><span title="Modifica il template. Usa l'anteprima prima di salvare">M</span></a></div></div><span class="navbox_title"><a href="/wiki/Stereochimica" title="Stereochimica">Stereochimica</a></span></th></tr><tr><th colspan="1" class="navbox_group"><a href="/wiki/Isomeria" title="Isomeria">Isomeria</a></th><td colspan="1" class="navbox_list navbox_odd"><a href="/wiki/Stereoisomero" title="Stereoisomero">Stereoisomero</a><b> ·</b> <a class="mw-selflink selflink">Enantiomero</a><b> ·</b> <a href="/wiki/Diastereoisomero" title="Diastereoisomero">Diastereoisomero</a><b> ·</b> <a href="/wiki/Epimero" title="Epimero">Epimero</a><b> ·</b> <a href="/wiki/Composto_meso" title="Composto meso">Composto meso</a></td><td rowspan="5" class="navbox_image"><span typeof="mw:File"><a href="/wiki/File:Chirality_with_hands.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Chirality_with_hands.svg/175px-Chirality_with_hands.svg.png" decoding="async" width="175" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Chirality_with_hands.svg/263px-Chirality_with_hands.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e8/Chirality_with_hands.svg/350px-Chirality_with_hands.svg.png 2x" data-file-width="765" data-file-height="519" /></a></span></td></tr><tr><th colspan="1" class="navbox_group"><a href="/wiki/Chiralit%C3%A0_(chimica)" title="Chiralità (chimica)">Chiralità</a></th><td colspan="1" class="navbox_list navbox_even"><a href="/wiki/Elemento_stereogenico" title="Elemento stereogenico">Elemento stereogenico</a><b> ·</b> <a href="/w/index.php?title=Chiralit%C3%A0_planare&action=edit&redlink=1" class="new" title="Chiralità planare (la pagina non esiste)">Chiralità planare</a><b> ·</b> <a href="/w/index.php?title=Ligando_chirale&action=edit&redlink=1" class="new" title="Ligando chirale (la pagina non esiste)">Ligando chirale</a><b> ·</b> <a href="/w/index.php?title=Chiralit%C3%A0_assiale&action=edit&redlink=1" class="new" title="Chiralità assiale (la pagina non esiste)">Chiralità assiale</a><b> ·</b> <a href="/wiki/Chiralit%C3%A0_inerente" title="Chiralità inerente">Chiralità inerente</a><b> ·</b> <a href="/wiki/Prochiralit%C3%A0" title="Prochiralità">Prochiralità</a><b> ·</b> <a href="/wiki/Omochiralit%C3%A0" title="Omochiralità">Omochiralità</a><b> ·</b> <a href="/wiki/Racemo_(chimica)" title="Racemo (chimica)">Racemo</a><b> ·</b> <a href="/wiki/Anomeria" title="Anomeria">Anomeria</a> <b> ·</b></td></tr><tr><th colspan="1" class="navbox_group">Sintesi</th><td colspan="1" class="navbox_list navbox_odd"><a href="/wiki/Stereospecificit%C3%A0" title="Stereospecificità">Stereospecificità</a><b> ·</b> <a href="/wiki/Stereoselettivit%C3%A0" title="Stereoselettività">Stereoselettività</a><b> ·</b> <a href="/wiki/Eccesso_enantiomerico" title="Eccesso enantiomerico">Eccesso enantiomerico</a><b> ·</b> <a href="/w/index.php?title=Eccesso_diastereoisomerico&action=edit&redlink=1" class="new" title="Eccesso diastereoisomerico (la pagina non esiste)">Eccesso diastereoisomerico</a></td></tr><tr><th colspan="1" class="navbox_group">Analisi</th><td colspan="1" class="navbox_list navbox_even"><a href="/wiki/Potere_rotatorio" title="Potere rotatorio">Potere rotatorio</a><b> ·</b> <a href="/w/index.php?title=Risoluzione_chirale&action=edit&redlink=1" class="new" title="Risoluzione chirale (la pagina non esiste)">Risoluzione chirale</a><b> ·</b> <a href="/wiki/Dicroismo_circolare" title="Dicroismo circolare">Dicroismo circolare</a></td></tr><tr><th colspan="1" class="navbox_group">Reazioni</th><td colspan="1" class="navbox_list navbox_odd"><a href="/wiki/Sintesi_asimmetrica" title="Sintesi asimmetrica">Sintesi asimmetrica</a><b> ·</b> <a href="/wiki/Ausiliario_chirale" title="Ausiliario chirale">Ausiliario chirale</a><b> ·</b> <a href="/wiki/Organocatalisi" title="Organocatalisi">Organocatalisi</a><b> ·</b> <a href="/wiki/Biocatalisi" title="Biocatalisi">Biocatalisi</a></td></tr></tbody></table> <div class="noprint" style="width:100%; 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