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rootpage-Prolina skin-vector-2022 action-view"><a class="mw-jump-link" href="#bodyContent">Vai al contenuto</a> <div class="vector-header-container"> <header class="vector-header mw-header"> <div class="vector-header-start"> <nav class="vector-main-menu-landmark" aria-label="Sito"> <div id="vector-main-menu-dropdown" class="vector-dropdown vector-main-menu-dropdown vector-button-flush-left vector-button-flush-right" > <input type="checkbox" id="vector-main-menu-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-main-menu-dropdown" class="vector-dropdown-checkbox " aria-label="Menu principale" > <label id="vector-main-menu-dropdown-label" for="vector-main-menu-dropdown-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-menu mw-ui-icon-wikimedia-menu"></span> <span class="vector-dropdown-label-text">Menu principale</span> </label> <div class="vector-dropdown-content"> <div id="vector-main-menu-unpinned-container" class="vector-unpinned-container"> <div id="vector-main-menu" class="vector-main-menu vector-pinnable-element"> <div class="vector-pinnable-header vector-main-menu-pinnable-header vector-pinnable-header-unpinned" data-feature-name="main-menu-pinned" data-pinnable-element-id="vector-main-menu" data-pinned-container-id="vector-main-menu-pinned-container" data-unpinned-container-id="vector-main-menu-unpinned-container" > <div class="vector-pinnable-header-label">Menu principale</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-main-menu.pin">sposta nella barra laterale</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-main-menu.unpin">nascondi</button> </div> <div id="p-navigation" class="vector-menu mw-portlet mw-portlet-navigation" > <div class="vector-menu-heading"> Navigazione </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-mainpage-description" class="mw-list-item"><a href="/wiki/Pagina_principale" title="Visita la pagina principale [z]" accesskey="z"><span>Pagina principale</span></a></li><li id="n-recentchanges" class="mw-list-item"><a href="/wiki/Speciale:UltimeModifiche" title="Elenco delle ultime modifiche del sito [r]" accesskey="r"><span>Ultime modifiche</span></a></li><li id="n-randompage" class="mw-list-item"><a href="/wiki/Speciale:PaginaCasuale" title="Mostra una pagina a caso [x]" accesskey="x"><span>Una voce a caso</span></a></li><li id="n-nearby-pages-title" class="mw-list-item"><a href="/wiki/Speciale:NelleVicinanze"><span>Nelle vicinanze</span></a></li><li id="n-vetrina" class="mw-list-item"><a href="/wiki/Wikipedia:Vetrina"><span>Vetrina</span></a></li><li id="n-help" class="mw-list-item"><a href="/wiki/Aiuto:Aiuto" title="Pagine di aiuto"><span>Aiuto</span></a></li><li id="n-Sportello-informazioni" class="mw-list-item"><a href="/wiki/Aiuto:Sportello_informazioni"><span>Sportello informazioni</span></a></li> </ul> </div> </div> <div id="p-Comunità" class="vector-menu mw-portlet mw-portlet-Comunità" > <div class="vector-menu-heading"> Comunità </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-portal" class="mw-list-item"><a href="/wiki/Portale:Comunit%C3%A0" title="Descrizione del progetto, cosa puoi fare, dove trovare le cose"><span>Portale Comunità</span></a></li><li id="n-villagepump" class="mw-list-item"><a href="/wiki/Wikipedia:Bar"><span>Bar</span></a></li><li id="n-wikipediano" class="mw-list-item"><a href="/wiki/Wikipedia:Wikipediano"><span>Il Wikipediano</span></a></li><li id="n-contactpage" class="mw-list-item"><a href="/wiki/Wikipedia:Contatti"><span>Contatti</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> <a href="/wiki/Pagina_principale" class="mw-logo"> <img class="mw-logo-icon" src="/static/images/icons/wikipedia.png" alt="" aria-hidden="true" height="50" width="50"> <span class="mw-logo-container skin-invert"> <img class="mw-logo-wordmark" alt="Wikipedia" src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" style="width: 7.5em; height: 1.125em;"> <img class="mw-logo-tagline" alt="L'enciclopedia libera" src="/static/images/mobile/copyright/wikipedia-tagline-it.svg" width="120" height="13" style="width: 7.5em; height: 0.8125em;"> </span> </a> </div> <div class="vector-header-end"> <div id="p-search" role="search" class="vector-search-box-vue vector-search-box-collapses vector-search-box-show-thumbnail vector-search-box-auto-expand-width vector-search-box"> <a href="/wiki/Speciale:Ricerca" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only search-toggle" title="Cerca in 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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-appearance mw-ui-icon-wikimedia-appearance"></span> <span class="vector-dropdown-label-text">Aspetto</span> </label> <div class="vector-dropdown-content"> <div id="vector-appearance-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <div id="p-vector-user-menu-notifications" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-overflow" class="vector-menu mw-portlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="//donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_it.wikipedia.org&uselang=it" class=""><span>Fai una donazione</span></a> </li> <li id="pt-createaccount-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Speciale:CreaUtenza&returnto=Prolina" title="Si consiglia di registrarsi e di effettuare l'accesso, anche se non è obbligatorio" class=""><span>registrati</span></a> </li> <li id="pt-login-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Speciale:Entra&returnto=Prolina" title="Si consiglia di effettuare l'accesso, anche se non è obbligatorio [o]" accesskey="o" class=""><span>entra</span></a> </li> </ul> </div> </div> </div> <div id="vector-user-links-dropdown" class="vector-dropdown vector-user-menu vector-button-flush-right vector-user-menu-logged-out" title="Altre opzioni" > <input type="checkbox" id="vector-user-links-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-user-links-dropdown" class="vector-dropdown-checkbox " aria-label="Strumenti personali" > <label id="vector-user-links-dropdown-label" for="vector-user-links-dropdown-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-ellipsis mw-ui-icon-wikimedia-ellipsis"></span> <span class="vector-dropdown-label-text">Strumenti personali</span> </label> <div class="vector-dropdown-content"> <div id="p-personal" class="vector-menu mw-portlet mw-portlet-personal user-links-collapsible-item" title="Menu utente" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport" class="user-links-collapsible-item mw-list-item"><a href="//donate.wikimedia.org/wiki/Special:FundraiserRedirector?utm_source=donate&utm_medium=sidebar&utm_campaign=C13_it.wikipedia.org&uselang=it"><span>Fai una donazione</span></a></li><li id="pt-createaccount" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Speciale:CreaUtenza&returnto=Prolina" title="Si consiglia di registrarsi e di effettuare l'accesso, anche se non è obbligatorio"><span class="vector-icon mw-ui-icon-userAdd mw-ui-icon-wikimedia-userAdd"></span> <span>registrati</span></a></li><li id="pt-login" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Speciale:Entra&returnto=Prolina" title="Si consiglia di effettuare l'accesso, anche se non è obbligatorio [o]" accesskey="o"><span class="vector-icon mw-ui-icon-logIn mw-ui-icon-wikimedia-logIn"></span> <span>entra</span></a></li> </ul> </div> </div> <div id="p-user-menu-anon-editor" class="vector-menu mw-portlet mw-portlet-user-menu-anon-editor" > <div class="vector-menu-heading"> Pagine per utenti anonimi <a href="/wiki/Aiuto:Benvenuto" aria-label="Ulteriori informazioni sulla contribuzione"><span>ulteriori informazioni</span></a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Speciale:MieiContributi" title="Un elenco delle modifiche fatte da questo indirizzo IP [y]" accesskey="y"><span>contributi</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Speciale:MieDiscussioni" title="Discussioni sulle modifiche fatte da questo indirizzo IP [n]" accesskey="n"><span>discussioni</span></a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="Sito"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="Indice" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">Indice</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">sposta nella barra laterale</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">nascondi</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">Inizio</div> </a> </li> <li id="toc-Storia_ed_etimologia" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Storia_ed_etimologia"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Storia ed etimologia</span> </div> </a> <ul id="toc-Storia_ed_etimologia-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biosintesi" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biosintesi"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Biosintesi</span> </div> </a> <button aria-controls="toc-Biosintesi-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Attiva/disattiva la sottosezione Biosintesi</span> </button> <ul id="toc-Biosintesi-sublist" class="vector-toc-list"> <li id="toc-La_biosintesi_nelle_piante" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#La_biosintesi_nelle_piante"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>La biosintesi nelle piante</span> </div> </a> <ul id="toc-La_biosintesi_nelle_piante-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-La_biosintesi_negli_animali" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#La_biosintesi_negli_animali"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>La biosintesi negli animali</span> </div> </a> <ul id="toc-La_biosintesi_negli_animali-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-La_prolina_nelle_proteine" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#La_prolina_nelle_proteine"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>La prolina nelle proteine</span> </div> </a> <ul id="toc-La_prolina_nelle_proteine-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Usi" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Usi"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Usi</span> </div> </a> <ul id="toc-Usi-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Derivati" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Derivati"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Derivati</span> </div> </a> <ul id="toc-Derivati-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-Bibliografia" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Bibliografia"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Bibliografia</span> </div> </a> <ul id="toc-Bibliografia-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> <li id="toc-Collegamenti_esterni" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Collegamenti_esterni"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Collegamenti esterni</span> </div> </a> <ul id="toc-Collegamenti_esterni-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" > <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">Prolina</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 58 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-58" 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">58 lingue</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/%D8%A8%D8%B1%D9%88%D9%84%D9%8A%D9%86" title="برولين - arabo" lang="ar" hreflang="ar" data-title="برولين" data-language-autonym="العربية" data-language-local-name="arabo" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Prolin" title="Prolin - azerbaigiano" lang="az" hreflang="az" data-title="Prolin" data-language-autonym="Azərbaycanca" data-language-local-name="azerbaigiano" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%BE%D8%B1%D9%88%D9%84%DB%8C%D9%86" title="پرولین - South Azerbaijani" lang="azb" hreflang="azb" data-title="پرولین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9F%D1%80%D0%BE%D0%BB%D0%B8%D0%BD" title="Пролин - bulgaro" lang="bg" hreflang="bg" data-title="Пролин" data-language-autonym="Български" data-language-local-name="bulgaro" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AA%E0%A7%8D%E0%A6%B0%E0%A7%8B%E0%A6%B2%E0%A6%BF%E0%A6%A8" title="প্রোলিন - bengalese" lang="bn" hreflang="bn" data-title="প্রোলিন" data-language-autonym="বাংলা" data-language-local-name="bengalese" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Prolin" title="Prolin - bosniaco" lang="bs" hreflang="bs" data-title="Prolin" 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/Prolina" title="Prolina - catalano" lang="ca" hreflang="ca" data-title="Prolina" 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/Prolin" title="Prolin - ceco" lang="cs" hreflang="cs" data-title="Prolin" 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/Prolin" title="Prolin - danese" lang="da" hreflang="da" data-title="Prolin" 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/Prolin" title="Prolin - tedesco" lang="de" hreflang="de" data-title="Prolin" 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%A0%CF%81%CE%BF%CE%BB%CE%AF%CE%BD%CE%B7" title="Προλίνη - greco" lang="el" hreflang="el" data-title="Προλίνη" 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/Proline" title="Proline - inglese" lang="en" hreflang="en" data-title="Proline" 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/Prolino" title="Prolino - esperanto" lang="eo" hreflang="eo" data-title="Prolino" 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/Prolina" title="Prolina - spagnolo" lang="es" hreflang="es" data-title="Prolina" data-language-autonym="Español" data-language-local-name="spagnolo" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-et badge-Q17437798 badge-goodarticle mw-list-item" title="voce di qualità"><a href="https://et.wikipedia.org/wiki/Proliin" title="Proliin - estone" lang="et" hreflang="et" data-title="Proliin" 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/Prolina" title="Prolina - basco" lang="eu" hreflang="eu" data-title="Prolina" 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/%D9%BE%D8%B1%D9%88%D9%84%DB%8C%D9%86" title="پرولین - persiano" lang="fa" hreflang="fa" data-title="پرولین" 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/Proliini" title="Proliini - finlandese" lang="fi" hreflang="fi" data-title="Proliini" 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/Proline" title="Proline - francese" lang="fr" hreflang="fr" data-title="Proline" 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/Prolina" title="Prolina - galiziano" lang="gl" hreflang="gl" data-title="Prolina" 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%A4%D7%A8%D7%95%D7%9C%D7%99%D7%9F" title="פרולין - ebraico" lang="he" hreflang="he" data-title="פרולין" data-language-autonym="עברית" data-language-local-name="ebraico" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AA%E0%A5%8D%E0%A4%B0%E0%A5%8B%E0%A4%B2%E0%A4%BF%E0%A4%A8" title="प्रोलिन - hindi" lang="hi" hreflang="hi" data-title="प्रोलिन" data-language-autonym="हिन्दी" data-language-local-name="hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Prolin" title="Prolin - croato" lang="hr" hreflang="hr" data-title="Prolin" data-language-autonym="Hrvatski" data-language-local-name="croato" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Prolin" title="Prolin - ungherese" lang="hu" hreflang="hu" data-title="Prolin" data-language-autonym="Magyar" data-language-local-name="ungherese" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8A%D6%80%D5%B8%D5%AC%D5%AB%D5%B6" title="Պրոլին - armeno" lang="hy" hreflang="hy" data-title="Պրոլին" data-language-autonym="Հայերեն" data-language-local-name="armeno" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Prolina" title="Prolina - indonesiano" lang="id" hreflang="id" data-title="Prolina" 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-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%97%E3%83%AD%E3%83%AA%E3%83%B3" title="プロリン - giapponese" lang="ja" hreflang="ja" data-title="プロリン" 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-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9F%D1%80%D0%BE%D0%BB%D0%B8%D0%BD" title="Пролин - kazako" lang="kk" hreflang="kk" data-title="Пролин" data-language-autonym="Қазақша" data-language-local-name="kazako" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%94%84%EB%A1%A4%EB%A6%B0" title="프롤린 - coreano" lang="ko" hreflang="ko" data-title="프롤린" data-language-autonym="한국어" data-language-local-name="coreano" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/Prol%C3%AEn" title="Prolîn - curdo" lang="ku" hreflang="ku" data-title="Prolîn" data-language-autonym="Kurdî" data-language-local-name="curdo" class="interlanguage-link-target"><span>Kurdî</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Prolin" title="Prolin - lussemburghese" lang="lb" hreflang="lb" data-title="Prolin" data-language-autonym="Lëtzebuergesch" data-language-local-name="lussemburghese" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Prolinas" title="Prolinas - lituano" lang="lt" hreflang="lt" data-title="Prolinas" data-language-autonym="Lietuvių" data-language-local-name="lituano" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Prol%C4%ABns" title="Prolīns - lettone" lang="lv" hreflang="lv" data-title="Prolīns" data-language-autonym="Latviešu" data-language-local-name="lettone" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9F%D1%80%D0%BE%D0%BB%D0%B8%D0%BD" title="Пролин - macedone" lang="mk" hreflang="mk" data-title="Пролин" data-language-autonym="Македонски" data-language-local-name="macedone" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Prolina" title="Prolina - malese" lang="ms" hreflang="ms" data-title="Prolina" 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/Proline" title="Proline - olandese" lang="nl" hreflang="nl" data-title="Proline" data-language-autonym="Nederlands" data-language-local-name="olandese" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Prolin" title="Prolin - norvegese nynorsk" lang="nn" hreflang="nn" data-title="Prolin" data-language-autonym="Norsk nynorsk" data-language-local-name="norvegese nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Prolin" title="Prolin - norvegese bokmål" lang="nb" hreflang="nb" data-title="Prolin" 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-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Prolina" title="Prolina - occitano" lang="oc" hreflang="oc" data-title="Prolina" data-language-autonym="Occitan" data-language-local-name="occitano" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Prolina" title="Prolina - polacco" lang="pl" hreflang="pl" data-title="Prolina" 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/Prolina" title="Prolina - portoghese" lang="pt" hreflang="pt" data-title="Prolina" 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/Prolin%C4%83" title="Prolină - rumeno" lang="ro" hreflang="ro" data-title="Prolină" 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%9F%D1%80%D0%BE%D0%BB%D0%B8%D0%BD" title="Пролин - russo" lang="ru" hreflang="ru" data-title="Пролин" 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/Prolin" title="Prolin - serbo-croato" lang="sh" hreflang="sh" data-title="Prolin" 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-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Prol%C3%ADn" title="Prolín - slovacco" lang="sk" hreflang="sk" data-title="Prolín" 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/Prolin" title="Prolin - sloveno" lang="sl" hreflang="sl" data-title="Prolin" 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%9F%D1%80%D0%BE%D0%BB%D0%B8%D0%BD" title="Пролин - serbo" lang="sr" hreflang="sr" data-title="Пролин" 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-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Prolin" title="Prolin - sundanese" lang="su" hreflang="su" data-title="Prolin" data-language-autonym="Sunda" data-language-local-name="sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Prolin" title="Prolin - svedese" lang="sv" hreflang="sv" data-title="Prolin" data-language-autonym="Svenska" data-language-local-name="svedese" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AA%E0%AF%81%E0%AE%B0%E0%AF%8B%E0%AE%B2%E0%AE%BF%E0%AE%A9%E0%AF%8D" title="புரோலின் - tamil" lang="ta" hreflang="ta" data-title="புரோலின்" data-language-autonym="தமிழ்" data-language-local-name="tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Prolin" title="Prolin - turco" lang="tr" hreflang="tr" data-title="Prolin" 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%9F%D1%80%D0%BE%D0%BB%D1%96%D0%BD" title="Пролін - ucraino" lang="uk" hreflang="uk" data-title="Пролін" data-language-autonym="Українська" data-language-local-name="ucraino" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Prolin" title="Prolin - uzbeco" lang="uz" hreflang="uz" data-title="Prolin" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="uzbeco" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Prolin" title="Prolin - vietnamita" lang="vi" hreflang="vi" data-title="Prolin" data-language-autonym="Tiếng Việt" data-language-local-name="vietnamita" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%84%AF%E6%B0%A8%E9%85%B8" title="脯氨酸 - wu" lang="wuu" hreflang="wuu" data-title="脯氨酸" data-language-autonym="吴语" data-language-local-name="wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%84%AF%E6%B0%A8%E9%85%B8" title="脯氨酸 - cinese" lang="zh" hreflang="zh" data-title="脯氨酸" data-language-autonym="中文" data-language-local-name="cinese" class="interlanguage-link-target"><span>中文</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Prolin" title="Prolin - min nan" lang="nan" hreflang="nan" data-title="Prolin" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="min nan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E8%84%AF%E6%B0%A8%E9%85%B8" title="脯氨酸 - cantonese" lang="yue" hreflang="yue" data-title="脯氨酸" data-language-autonym="粵語" data-language-local-name="cantonese" class="interlanguage-link-target"><span>粵語</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/Q484583#sitelinks-wikipedia" title="Modifica collegamenti interlinguistici" class="wbc-editpage">Modifica collegamenti</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="Namespace"> <div 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cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">Strumenti</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-tools-unpinned-container" class="vector-unpinned-container"> <div id="vector-page-tools" class="vector-page-tools vector-pinnable-element"> <div class="vector-pinnable-header vector-page-tools-pinnable-header vector-pinnable-header-unpinned" data-feature-name="page-tools-pinned" data-pinnable-element-id="vector-page-tools" data-pinned-container-id="vector-page-tools-pinned-container" data-unpinned-container-id="vector-page-tools-unpinned-container" > <div class="vector-pinnable-header-label">Strumenti</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-page-tools.pin">sposta nella barra laterale</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-page-tools.unpin">nascondi</button> </div> <div id="p-cactions" class="vector-menu mw-portlet mw-portlet-cactions emptyPortlet vector-has-collapsible-items" title="Altre opzioni" > <div class="vector-menu-heading"> Azioni </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-more-view" class="selected vector-more-collapsible-item mw-list-item"><a href="/wiki/Prolina"><span>Leggi</span></a></li><li id="ca-more-ve-edit" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Prolina&veaction=edit" title="Modifica questa pagina [v]" accesskey="v"><span>Modifica</span></a></li><li id="ca-more-edit" class="collapsible vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Prolina&action=edit" title="Modifica il wikitesto di questa pagina [e]" accesskey="e"><span>Modifica wikitesto</span></a></li><li id="ca-more-history" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Prolina&action=history"><span>Cronologia</span></a></li> </ul> </div> </div> <div id="p-tb" class="vector-menu mw-portlet mw-portlet-tb" > <div class="vector-menu-heading"> Generale </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="t-whatlinkshere" class="mw-list-item"><a href="/wiki/Speciale:PuntanoQui/Prolina" title="Elenco di tutte le pagine che sono collegate a questa [j]" accesskey="j"><span>Puntano qui</span></a></li><li id="t-recentchangeslinked" class="mw-list-item"><a href="/wiki/Speciale:ModificheCorrelate/Prolina" rel="nofollow" title="Elenco delle ultime modifiche alle pagine collegate a questa [k]" accesskey="k"><span>Modifiche correlate</span></a></li><li id="t-specialpages" class="mw-list-item"><a href="/wiki/Speciale:PagineSpeciali" title="Elenco di tutte le pagine speciali [q]" accesskey="q"><span>Pagine speciali</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Prolina&oldid=142161010" title="Collegamento permanente a questa versione di questa pagina"><span>Link permanente</span></a></li><li id="t-info" class="mw-list-item"><a href="/w/index.php?title=Prolina&action=info" title="Ulteriori informazioni su questa pagina"><span>Informazioni pagina</span></a></li><li id="t-cite" class="mw-list-item"><a href="/w/index.php?title=Speciale:Cita&page=Prolina&id=142161010&wpFormIdentifier=titleform" title="Informazioni su come citare questa pagina"><span>Cita questa voce</span></a></li><li id="t-urlshortener" class="mw-list-item"><a href="/w/index.php?title=Speciale:UrlShortener&url=https%3A%2F%2Fit.wikipedia.org%2Fwiki%2FProlina"><span>Ottieni URL breve</span></a></li><li id="t-urlshortener-qrcode" class="mw-list-item"><a href="/w/index.php?title=Speciale:QrCode&url=https%3A%2F%2Fit.wikipedia.org%2Fwiki%2FProlina"><span>Scarica codice QR</span></a></li> </ul> </div> </div> <div id="p-coll-print_export" class="vector-menu mw-portlet mw-portlet-coll-print_export" > <div class="vector-menu-heading"> Stampa/esporta </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="coll-create_a_book" class="mw-list-item"><a href="/w/index.php?title=Speciale:Libro&bookcmd=book_creator&referer=Prolina"><span>Crea un libro</span></a></li><li id="coll-download-as-rl" class="mw-list-item"><a href="/w/index.php?title=Speciale:DownloadAsPdf&page=Prolina&action=show-download-screen"><span>Scarica come PDF</span></a></li><li id="t-print" class="mw-list-item"><a href="/w/index.php?title=Prolina&printable=yes" title="Versione stampabile di questa pagina [p]" accesskey="p"><span>Versione stampabile</span></a></li> </ul> </div> </div> <div id="p-wikibase-otherprojects" class="vector-menu mw-portlet mw-portlet-wikibase-otherprojects" > <div class="vector-menu-heading"> In altri progetti </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="wb-otherproject-link wb-otherproject-commons mw-list-item"><a href="https://commons.wikimedia.org/wiki/Category:Proline" hreflang="en"><span>Wikimedia Commons</span></a></li><li id="t-wikibase" class="wb-otherproject-link wb-otherproject-wikibase-dataitem mw-list-item"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q484583" title="Collegamento all'elemento connesso dell'archivio dati [g]" accesskey="g"><span>Elemento Wikidata</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Strumenti pagine"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Aspetto"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" 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">Aspetto</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">sposta nella barra laterale</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">nascondi</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">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"><table class="infobox sinottico" summary="Tabella sinottica che riassume i principali dati del soggetto" style="width:300px;"><tbody><tr class="sinottico_testata"><th colspan="2" style="background-color:#AADDFF;">Prolina</th></tr><tr><td class="sinottico_testo_centrale" colspan="2"><figure class="mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:(S)-Proline.png" class="mw-file-description" title="formula di struttura"><img alt="formula di struttura" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/%28S%29-Proline.png/130px-%28S%29-Proline.png" decoding="async" width="130" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/%28S%29-Proline.png/195px-%28S%29-Proline.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/%28S%29-Proline.png/260px-%28S%29-Proline.png 2x" data-file-width="1098" data-file-height="743" /></a><figcaption>formula di struttura</figcaption></figure> </td></tr><tr class="sinottico_divisione"><th colspan="2" style="background-color:#DDEEFF;">Nome <a href="/wiki/Unione_internazionale_di_chimica_pura_e_applicata" title="Unione internazionale di chimica pura e applicata">IUPAC</a></th></tr><tr><td class="sinottico_testo_centrale" colspan="2">L-prolina </td></tr><tr class="sinottico_divisione"><th colspan="2" style="background-color:#DDEEFF;">Abbreviazioni</th></tr><tr><td class="sinottico_testo_centrale" colspan="2"><b>P</b><br /><b>Pro</b> </td></tr><tr class="sinottico_divisione"><th colspan="2" style="background-color:#DDEEFF;">Nomi alternativi</th></tr><tr><td class="sinottico_testo_centrale" colspan="2">acido 2(<i>S</i>)-pirrolidincarbossilico </td></tr><tr class="sinottico_divisione"><th colspan="2" style="background-color:#AAEEFF;">Caratteristiche generali</th></tr><tr><th><a href="/wiki/Formula_bruta" title="Formula bruta">Formula bruta</a> o <a href="/wiki/Formula_molecolare" title="Formula molecolare">molecolare</a></th><td>C<sub>5</sub>H<sub>9</sub>NO<sub>2</sub> </td></tr><tr><th><a href="/wiki/Massa_molecolare" title="Massa molecolare">Massa molecolare</a> (<a href="/wiki/Unit%C3%A0_di_massa_atomica" title="Unità di massa atomica">u</a>)</th><td>115,13 </td></tr><tr><th><a href="/wiki/Colore" title="Colore">Aspetto</a></th><td>solido cristallino bianco </td></tr><tr><th><a href="/wiki/Numero_CAS" title="Numero CAS">Numero CAS</a></th><td><span class="reflink plainlinksneverexpand"><span class="noarchive"><a class="external text" href="https://iw.toolforge.org/magnustools/cas.php?language=it&cas=147-85-3">147-85-3</a></span></span> </td></tr><tr><th><a href="/wiki/Numero_EINECS" title="Numero EINECS">Numero EINECS</a></th><td>210-189-3 </td></tr><tr><th><a href="/wiki/PubChem" title="PubChem">PubChem</a></th><td><a rel="nofollow" class="external text" href="http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=614">614</a> e <a rel="nofollow" class="external text" href="http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=25246272">25246272</a> </td></tr><tr><th><a href="/wiki/SMILES" title="SMILES">SMILES</a></th><td><div style="word-break: break-all;"><code style="background-color:transparent; border:none">C1CC(NC1)C(=O)O</code></div> </td></tr><tr class="sinottico_divisione"><th colspan="2" style="background-color:#AAEEFF;">Proprietà chimico-fisiche</th></tr><tr><th><a href="/wiki/Costante_di_dissociazione_acida" title="Costante di dissociazione acida">Costante di dissociazione acida</a> a 293 K</th><td>pK<sub>1</sub>: 1,95<br /> <p>pK<sub>2</sub>: 10,64 </p> </td></tr><tr><th><a href="/wiki/Punto_isoelettrico" title="Punto isoelettrico">Punto isoelettrico</a></th><td>6,30 </td></tr><tr><th><a href="/wiki/Solubilit%C3%A0" title="Solubilità">Solubilità</a> in <a href="/wiki/Acqua" title="Acqua">acqua</a></th><td>1500 g/l a 293 K </td></tr><tr><th><a href="/wiki/Temperatura_di_fusione" class="mw-redirect" title="Temperatura di fusione">Temperatura di fusione</a></th><td>220 °C (493 K) con decomposizione </td></tr><tr class="sinottico_divisione"><th colspan="2" style="background-color:#AAEEFF;">Proprietà termochimiche</th></tr><tr><th><a href="/wiki/Entalpia_standard_di_formazione" title="Entalpia standard di formazione">Δ<sub>f</sub>H<sup>0</sup></a> (kJ·mol<sup>−1</sup>)</th><td>−515,2 </td></tr><tr class="sinottico_divisione"><th colspan="2" style="background-color:#AAEEFF;">Indicazioni di sicurezza</th></tr><tr><th><a href="/wiki/Frasi_H" class="mw-redirect" title="Frasi H">Frasi H</a></th><td>--- </td></tr><tr><th><a href="/wiki/Consigli_P" title="Consigli P">Consigli P</a></th><td>---<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> </td></tr><tr><td class="sinottico_piede2 noprint nomobile metadata" colspan="2"><a href="https://www.wikidata.org/wiki/Q484583" class="extiw" title="d:Q484583"><span title="Modifica i dati della voce Prolina su Wikidata">Modifica dati su Wikidata</span></a><b> ·</b> <a href="/wiki/Template:Composto_chimico/man" title="Template:Composto chimico/man"><span title="Manuale del template Composto chimico">Manuale</span></a></td></tr></tbody></table> <p>La <b>prolina</b> (simbolo <b>Pro</b> o <b>P</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> è un <a href="/wiki/Amminoacido" title="Amminoacido">amminoacido</a> <a href="/wiki/Apolare" class="mw-redirect" title="Apolare">apolare</a>. È una molecola <a href="/wiki/Chiralit%C3%A0_(chimica)" title="Chiralità (chimica)">chirale</a>. </p><p>Il gruppo laterale è costituito da un anello che non si adatta in una struttura secondaria ordinata, ciò le regala la capacità di formare "cerniere" all'interno di un polipeptide, tendendo ad interromperne la linearità. </p><p>A pH fisiologico in ambiente acquoso si trova in forma <a href="/wiki/Zwitterione" title="Zwitterione">zwitterionica</a>. </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Proline01.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/1/1f/Proline01.png" decoding="async" width="98" height="92" class="mw-file-element" data-file-width="98" data-file-height="92" /></a><figcaption>Forma zwitterionica della Prolina</figcaption></figure> <p>La prolina è uno dei venti amminoacidi usati nelle cellule per la biosintesi di <a href="/wiki/Proteine" title="Proteine">proteine</a>. La prolina è una <a href="/wiki/Molecola" title="Molecola">molecola</a> chirale: possiede un unico centro chirale sul carbonio 2 e quindi due enantiomeri, L e D. L’enatiomero che si trova nelle proteine è la L-prolina. </p><p>Come tutti gli amminoacidi contiene un <a href="/wiki/Acidi_carbossilici" title="Acidi carbossilici">gruppo carbossilico</a> e un gruppo amminico in α al carbonio carbossilico. La prolina è però l’unico tra di essi la cui funzione amminica non è primaria ma secondaria: la catena laterale, costituita da un anello pirrolidinico, si chiude sull’atomo di azoto. Per via della catena laterale alifatica, la prolina è classificata come un amminoacido alifatico apolare. Non è considerata un amminoacido essenziale per il corpo umano, in quanto è sintetizzabile a partire dalla <a href="/wiki/Glutammina" title="Glutammina">glutammina</a> o dal <a href="/wiki/Acido_glutammico" title="Acido glutammico">glutammato</a>.<sup id="cite_ref-:0_3-0" class="reference"><a href="#cite_note-:0-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>La miscela racemica della prolina può essere ottenuta in laboratorio a partire da acrilonitrile e malonato di etile (vedi figura). </p><p>Un metodo che prevede la reazione di un estere della prolina con fosgene, seguita da idrogenazione e idrolisi, porta alla formazione di L-Prolina.<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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Storia_ed_etimologia">Storia ed etimologia</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prolina&veaction=edit&section=1" title="Modifica la sezione Storia ed etimologia" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Prolina&action=edit&section=1" title="Edit section's source code: Storia ed etimologia"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>La prolina venne isolata per la prima volta nel 1900 da Richard Willstatter durante lo studio della N-metilprolina. La reazione di sintesi prevede la reazione del sale sodico del dietilmalonato con l’1,3-dibromopropano. </p><p>L’anno seguente avvenne la pubblicazione della sintesi dell’amminoacido a partire dal’estere propilmalonico della ftalammide ad opera di Emil Fisher.<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>Il nome Prolina deriva dalla pirrolidina, uno dei suoi costituenti.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Biosintesi">Biosintesi</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prolina&veaction=edit&section=2" title="Modifica la sezione Biosintesi" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Prolina&action=edit&section=2" title="Edit section's source code: Biosintesi"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:DL-Proline_synth.png" class="mw-file-description"><img alt="Sintesi da laboratorio della prolina" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/DL-Proline_synth.png/220px-DL-Proline_synth.png" decoding="async" width="220" height="112" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/DL-Proline_synth.png/330px-DL-Proline_synth.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c2/DL-Proline_synth.png/440px-DL-Proline_synth.png 2x" data-file-width="2266" data-file-height="1153" /></a><figcaption>Sintesi da laboratorio della prolina</figcaption></figure> <p>Il processo di biosintesi della prolina è noto sia per le cellule vegetali sia per quelle animali. I processi sono simili. </p> <div class="mw-heading mw-heading3"><h3 id="La_biosintesi_nelle_piante">La biosintesi nelle piante</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prolina&veaction=edit&section=3" title="Modifica la sezione La biosintesi nelle piante" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Prolina&action=edit&section=3" title="Edit section's source code: La biosintesi nelle piante"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nelle piante, la prolina viene sintetizzata principalmente a partire dal glutammato.<sup id="cite_ref-:1_7-0" class="reference"><a href="#cite_note-:1-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Il glutammato viene ridotto a glutammato-semialdeide dall’enzima pirrolin-5-carbossilato sintetasi, in presenza di NADPH e ATP. La glutammato-semialdeide si converte spontaneamente in pirrolin-5-carbossilato (P5C). L’enzima P5C reduttasi, in presenza di NADPH, riduce la P5C in prolina.<sup id="cite_ref-:1_7-1" class="reference"><a href="#cite_note-:1-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Si ritiene che queste reazioni, che fanno parte del metabolismo della prolina, avvengano principalmente nel citosol. </p><p>I processi che costituiscono il catabolismo della prolina (si ritiene avvengano nei mitocondri) sono le reazioni inverse a quelle della sua sintesi. Gli enzimi prolin-deidrogenasi o prolin-ossidasi ossidano la prolina a P5C, in presenza di FAD<sup>+</sup>, e successivamente l’enzima P5C deidrogenasi converte la P5C in glutammato.<sup id="cite_ref-:1_7-2" class="reference"><a href="#cite_note-:1-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>La prevalenza dei processi di biosintesi o degradazione della prolina nei vegetali è regolata dalla luce e dallo stress subito. Infatti in letteratura è stato riportato che in presenza di luce e in situazioni come la disidratazione i processi di degradazione vengono repressi, portando a un accumulo di prolina.<sup id="cite_ref-:1_7-3" class="reference"><a href="#cite_note-:1-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Ciò può essere attribuito al fatto che la prolina svolge diverse funzioni all’interno delle cellule: innanzitutto è un antiossidante, in quanto funge da <i>quencher</i> per l’ossigeno di singoletto; inoltre, la biosintesi della prolina è un processo ossidativo che richiede la presenza di NADPH, e questo contribuisce a mantenere il bilancio redox della cellula, proteggendo i centri fotosintetici.<sup id="cite_ref-:1_7-4" class="reference"><a href="#cite_note-:1-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> L'amminoacido è inoltre parte dell'attività di sviluppo di tessuti generativi, come nel polline.<sup id="cite_ref-dx.doi.org_8-0" class="reference"><a href="#cite_note-dx.doi.org-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="La_biosintesi_negli_animali">La biosintesi negli animali</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prolina&veaction=edit&section=4" title="Modifica la sezione La biosintesi negli animali" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Prolina&action=edit&section=4" title="Edit section's source code: La biosintesi negli animali"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nei mammiferi la biosintesi di prolina è localizzata per la maggior parte nell’intestino, poiché vi si trovano gli enzimi necessari alla sintesi.<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> La glutammina viene idrolizzata a glutammato dall’enzima glutamminasi. Il glutammato viene convertito in glutammato-semialdeide dalla P5C sintasi. Quest'ultimo ciclizza spontaneamente a P5C, il quale viene poi ridotto a prolina. La degradazione della prolina segue il processo inverso. </p><p>Per via dell’esistenza di questi processi di biosintesi, la prolina non è considerata un amminoacido essenziale per l’uomo, almeno per quanto riguarda individui adulti in salute.<sup id="cite_ref-:0_3-1" class="reference"><a href="#cite_note-:0-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Prolina e idrossiprolina, un derivato, sono però i principali costituenti, insieme alla glicina, del collagene: circa il 20% dei residui sono costituiti da questi due amminoacidi. Il collagene è una proteina strutturale che si trova nella pelle, nelle ossa, nei tendini, nella cartilagine e nei vasi sanguigni. Essa rappresenta, negli esseri umani, un terzo delle proteine totali, ed è quindi la proteina più abbondante.<sup id="cite_ref-:2_10-0" class="reference"><a href="#cite_note-:2-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Si trova inoltre in grandi quantità nelle proteine del latte.<sup id="cite_ref-:0_3-2" class="reference"><a href="#cite_note-:0-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Si ritiene quindi che la prolina possa essere utile all’organismo durante la crescita o nei casi di danneggiamento dei tessuti.<sup id="cite_ref-:0_3-3" class="reference"><a href="#cite_note-:0-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>L’enantiomero L della prolina agisce da debole antagonista per il recettore della glicina, per il recettore dell’NMDA (N-metil-D-aspartato) e per quello del glutammato ionotropico (non-NMDA). Sembra inoltre essere una potenziale eccitotossina endogena.<sup id="cite_ref-dx.doi.org_8-1" class="reference"><a href="#cite_note-dx.doi.org-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="La_prolina_nelle_proteine">La prolina nelle proteine</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prolina&veaction=edit&section=5" title="Modifica la sezione La prolina nelle proteine" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Prolina&action=edit&section=5" title="Edit section's source code: La prolina nelle proteine"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>La distintiva struttura ciclica della catena laterale della prolina le conferisce alcune proprietà particolari rispetto agli altri amminoacidi. Innanzitutto, la prolina ha una maggiore rigidità conformazionale, in quanto l’angolo diedro φ è bloccato e assume valori intorno a -65°. Inoltre, quando la prolina si trova come residuo in un legame peptidico, il suo atomo di azoto non è legato ad alcun atomo di idrogeno, e ciò significa che non può agire come donatore di legame a idrogeno. Essa però è un ottimo accettore per i legami a idrogeno, grazie al fatto che la catena laterale alifatica è elettron-donatrice.<sup id="cite_ref-:3_11-0" class="reference"><a href="#cite_note-:3-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup>La prolina grazie alle sue proprietà può svolgere nelle proteine funzioni sia strutturali che di riconoscimento. </p><p>La prolina agisce da perturbatore in elementi di struttura secondaria ordinati come α-eliche e <i>β-sheet</i>. Essa si trova comunemente come residuo iniziale in un’α-elica, nei <i>loop</i>, e nei filamenti di margine dei <i>β-sheet</i>. Interviene inoltre nella formazione dei <i>β-turn</i> (le svolte nei <i>β-sheet</i>).<sup id="cite_ref-:3_11-1" class="reference"><a href="#cite_note-:3-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Un altro importante ruolo strutturale è quello che la prolina e l’idrossiprolina ricoprono nel <a href="/wiki/Collagene" title="Collagene">collagene</a>. Gli elementi strutturali principali del collagene sono catene polipeptidiche costituite da unità ripetute di tre amminoacidi, XaaYaaGly. Gly è un residuo di glicina; X e Y possono essere qualsiasi altro amminoacido, ma si tratta per la maggior parte di residui di Pro o idrossiprolina. Esse hanno una conformazione a elica, come quella della poliprolina, un tipo di polipeptide formato solo da prolina. Tre di queste catene, parallele e tenute insieme da legami a H, si intrecciano formando una tripla elica destrorsa, che costituisce la molecola del collagene.<sup id="cite_ref-:2_10-1" class="reference"><a href="#cite_note-:2-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> L’idrossilazione della prolina da parte della prolina-idrossilasi (o l’aggiunta di altri sostituenti elettron-attrattori) aumenta significativamente la stabilità conformazionale del collagene.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> L’idrossilazione della prolina è per cui un processo biochimico essenziale per il mantenimento del tessuto connettivo. Alcune patologie, come ad esempio lo scorbuto, possono derivare da un difetto nell’idrossilazione, causata da mutazioni dell’enzima prolina-idrossilasi o da una mancanza del cofattore, l’ascorbato o vitamina C. </p><p>La prolina si può trovare anche in molte proteine nelle cosiddette <i>proline-rich regions</i>, ossia parti specifiche di una proteina ricche in residui di prolina. Queste regioni possono essere composte da ripetizioni di brevi gruppi di amminoacidi del tipo XP o XPY, oppure da sequenze più lunghe e variabili.<sup id="cite_ref-:3_11-2" class="reference"><a href="#cite_note-:3-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> La loro funzione è principalmente quella di rendere possibile il legame con altre molecole, oppure le interazioni tra proteine diverse, agendo da sito di legame.<sup id="cite_ref-:3_11-3" class="reference"><a href="#cite_note-:3-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> È infatti noto che, in diverse proteine, esistono dei domini in grado di riconoscere le <i>proline-rich regions</i>,<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> e ciò consente di avere dei siti di legame specifici. Le proteine così assemblate possono poi svolgere diverse funzioni, ad esempio di regolazione o di trasduzione di segnali. </p><p>La <i>trasduzione del segnale intracellulare</i> si serve spesso di proteine che possiedono domini dove le concentrazioni di prolina sono discrete (<i>poly-proline stretches</i>), ma più abbondanti rispetto alla sequenza proteica integrale. Questi domini ricchi di prolina, ad alfa elica, fungono da ligandi per delle "tasche" molecolari che furono identificate inizialmente in alcune protein <a href="/w/index.php?title=Tirosina_chinasi&action=edit&redlink=1" class="new" title="Tirosina chinasi (la pagina non esiste)">tirosina chinasi</a> citoplasmatiche, come il <a href="/wiki/Oncogene#Proto-oncogeni" title="Oncogene">proto-oncogene</a> c-Src o la tirosina chinasi linfocitaria Ltk. Si chiamano <i>domini SH3 (Src Homology number 3)</i> e una volta legati queste sequenze di poli-prolina, inducono una modificazione conformazionale delle proteine in cui sono contenuti. Come risultato, es. la tirosina chinasi può attivarsi o rallentare la sua funzione. Anche la chinasi attivata dai fosfoinositidi (PI-3K) possiede due domini SH3 in grado di legare diversi tipi di sequenze di poli-prolina. </p> <div class="mw-heading mw-heading2"><h2 id="Usi">Usi</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prolina&veaction=edit&section=6" title="Modifica la sezione Usi" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Prolina&action=edit&section=6" title="Edit section's source code: Usi"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>La prolina e i suoi derivati sono spesso utilizzati come catalizzatori chirali in sintesi asimmetriche<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup>: si vedano ad esempio la riduzione di CBS e la condensazione aldolica. </p><p>Nella birrificazione, nella vinificazione e nella produzione di succhi frutta l’utilizzo di proteine ricche in prolina aumenta la torbidità grazie alle reazioni che avvengono con i <a href="/wiki/Polifenoli" title="Polifenoli">polifenoli</a>. Si è constatato inoltre che l’analisi delle interazioni fenoli-proteine può essere di grande aiuto nella misura dell’indice di torbidità.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>La L-prolina agisce inoltre da osmoprotettore, soprattutto in caso di stress osmotici, ed è quindi utilizzata in ambiti farmacologici e biotecnologici. </p><p>L’amminoacido viene inoltre utilizzato come integratore nel terreno di coltura sul quale vengono fatti crescere tessuti vegetali. La prolina infatti può aumentare la crescita in quanto aiuta la pianta a tollerare lo stress dell’ambiente di coltura. </p> <div class="mw-heading mw-heading2"><h2 id="Derivati">Derivati</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prolina&veaction=edit&section=7" title="Modifica la sezione Derivati" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Prolina&action=edit&section=7" title="Edit section's source code: Derivati"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/4-mercaptoprolina" title="4-mercaptoprolina">4-mercaptoprolina</a>, tramite addizione di un gruppo solfidrile.</li> <li><a href="/wiki/1-metilprolina" title="1-metilprolina">1-metilprolina</a></li> <li><a href="/wiki/Idrossiprolina" title="Idrossiprolina">Idrossiprolina</a>, è la forma ossidrilata della prolina.</li></ul> <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=Prolina&veaction=edit&section=8" 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=Prolina&action=edit&section=8" 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 mw-references-columns"><ol class="references"> <li id="cite_note-1"><a href="#cite_ref-1"><b>^</b></a> <span class="reference-text">scheda della prolina su <a rel="nofollow" class="external autonumber" href="http://www.merckmillipore.com/INTERSHOP/web/WFS/Merck-IT-Site/it_IT/-/EUR/ProcessMSDS-Start;pgid=eDZMKfaY4rtSRpEoBJhgbI720000UjzLrWcv;sid=4ItiDhLQZdR1Dk7A9xpyhvyFWQ2gUSrxMZdZvPAI_RxAJJq-OEniwsSyp6RobJq45XVMF8GmI7abplci-02ry778girmBxHt3TWKhE443A5qlBirO1JrLeEu7zAaFH_O5vnbiNCPaOW6zNHtGSNodckJ?PlainSKU=MDA_CHEM-107434&Origin=PDP">[1]</a></span> </li> <li id="cite_note-2"><a href="#cite_ref-2"><b>^</b></a> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal"> IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN), <a rel="nofollow" class="external text" href="https://web.archive.org/web/20190127074726/http://bip.cnrs-mrs.fr/bip10/AA-EJB.pdf"><span style="font-style:italic;">Nomenclature and Symbolism for Amino Acids and Peptides</span></a> (<span style="font-weight: bolder; font-size:80%"><abbr title="documento in formato PDF">PDF</abbr></span>), in <span style="font-style:italic;">Eur. J. Biochem.</span>, vol. 138, 1984, pp. 9-37. <small>URL consultato il 12 dicembre 2018</small> <small>(archiviato dall'<abbr title="http://bip.cnrs-mrs.fr/bip10/AA-EJB.pdf">url originale</abbr> il 27 gennaio 2019)</small>.</cite></span> </li> <li id="cite_note-:0-3"><span class="mw-cite-backlink"><b>^</b> <sup><i><a href="#cite_ref-:0_3-0">a</a></i></sup> <sup><i><a href="#cite_ref-:0_3-1">b</a></i></sup> <sup><i><a href="#cite_ref-:0_3-2">c</a></i></sup> <sup><i><a href="#cite_ref-:0_3-3">d</a></i></sup></span> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal">(<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>) Guoyao Wu, Fuller W. Bazer e Robert C. Burghardt, <a rel="nofollow" class="external text" href="https://oadoi.org/10.1007/s00726-010-0715-z"><span style="font-style:italic;">Proline and hydroxyproline metabolism: implications for animal and human nutrition</span></a>, in <span style="font-style:italic;">Amino Acids</span>, vol. 40, n. 4, 10 agosto 2010, pp. 1053–1063, <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%2Fs00726-010-0715-z">10.1007/s00726-010-0715-z</a>. <small>URL consultato il 10 novembre 2018</small>.</cite></span> </li> <li id="cite_note-4"><a href="#cite_ref-4"><b>^</b></a> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal"> Drauz et al., <span style="font-style:italic;">Amino Acids. 7.la A Novel Synthetic Route to L-Proline</span>, in <span style="font-style:italic;">J. Org. Chem.</span>, n. 51, 1986, pp. 3494-3498.</cite></span> </li> <li id="cite_note-5"><a href="#cite_ref-5"><b>^</b></a> <span class="reference-text"><cite class="citation web" style="font-style:normal">(<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>) Vladimir Sevin, <a rel="nofollow" class="external text" href="http://www.aminoacidsguide.com/Pro.html"><span style="font-style:italic;">Proline - nonessential amino acid - structure, properties, function, benefits</span></a>, su <span style="font-style:italic;">aminoacidsguide.com</span>. <small>URL consultato il 12 dicembre 2018</small>.</cite></span> </li> <li id="cite_note-6"><a href="#cite_ref-6"><b>^</b></a> <span class="reference-text"><cite class="citation web" style="font-style:normal"> <a rel="nofollow" class="external text" href="https://www.yourdictionary.com/proline"><span style="font-style:italic;">Proline dictionary definition | proline defined</span></a>, su <span style="font-style:italic;">yourdictionary.com</span>. <small>URL consultato il 12 dicembre 2018</small>.</cite></span> </li> <li id="cite_note-:1-7"><span class="mw-cite-backlink"><b>^</b> <sup><i><a href="#cite_ref-:1_7-0">a</a></i></sup> <sup><i><a href="#cite_ref-:1_7-1">b</a></i></sup> <sup><i><a href="#cite_ref-:1_7-2">c</a></i></sup> <sup><i><a href="#cite_ref-:1_7-3">d</a></i></sup> <sup><i><a href="#cite_ref-:1_7-4">e</a></i></sup></span> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal"> László Szabados e Arnould Savouré, <a rel="nofollow" class="external text" href="https://oadoi.org/10.1016/j.tplants.2009.11.009"><span style="font-style:italic;">Proline: a multifunctional amino acid</span></a>, in <span style="font-style:italic;">Trends in Plant Science</span>, vol. 15, n. 2, 2010-02, pp. 89–97, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1016%2Fj.tplants.2009.11.009">10.1016/j.tplants.2009.11.009</a>. <small>URL consultato il 10 novembre 2018</small>.</cite></span> </li> <li id="cite_note-dx.doi.org-8"><span class="mw-cite-backlink"><b>^</b> <sup><i><a href="#cite_ref-dx.doi.org_8-0">a</a></i></sup> <sup><i><a href="#cite_ref-dx.doi.org_8-1">b</a></i></sup></span> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal"> Nathalie Verbruggen e Christian Hermans, <a rel="nofollow" class="external text" href="https://dx.doi.org/10.1007/s00726-008-0061-6"><span style="font-style:italic;">Proline accumulation in plants: a review</span></a>, in <span style="font-style:italic;">Amino Acids</span>, vol. 35, n. 4, 1º aprile 2008, pp. 753–759, <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%2Fs00726-008-0061-6">10.1007/s00726-008-0061-6</a>. <small>URL consultato il 10 novembre 2018</small>.</cite></span> </li> <li id="cite_note-9"><a href="#cite_ref-9"><b>^</b></a> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal">(<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>) Malcolm Watford, <a rel="nofollow" class="external text" href="https://academic.oup.com/jn/article/138/10/2003S/4670096"><span style="font-style:italic;">Glutamine Metabolism and Function in Relation to Proline Synthesis and the Safety of Glutamine and Proline Supplementation</span></a>, in <span style="font-style:italic;">The Journal of Nutrition</span>, vol. 138, n. 10, 1º ottobre 2008, pp. 2003S–2007S, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1093%2Fjn%2F138.10.2003s">10.1093/jn/138.10.2003s</a>. <small>URL consultato il 10 novembre 2018</small>.</cite></span> </li> <li id="cite_note-:2-10"><span class="mw-cite-backlink"><b>^</b> <sup><i><a href="#cite_ref-:2_10-0">a</a></i></sup> <sup><i><a href="#cite_ref-:2_10-1">b</a></i></sup></span> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal">(<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>) Matthew D. 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Raines, <a rel="nofollow" class="external text" href="https://www.annualreviews.org/doi/10.1146/annurev.biochem.77.032207.120833"><span style="font-style:italic;">Collagen Structure and Stability</span></a>, in <span style="font-style:italic;">Annual Review of Biochemistry</span>, vol. 78, n. 1, 2009-06, pp. 929–958, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1146%2Fannurev.biochem.77.032207.120833">10.1146/annurev.biochem.77.032207.120833</a>. <small>URL consultato il 10 novembre 2018</small>.</cite></span> </li> <li id="cite_note-:3-11"><span class="mw-cite-backlink"><b>^</b> <sup><i><a href="#cite_ref-:3_11-0">a</a></i></sup> <sup><i><a href="#cite_ref-:3_11-1">b</a></i></sup> <sup><i><a href="#cite_ref-:3_11-2">c</a></i></sup> <sup><i><a href="#cite_ref-:3_11-3">d</a></i></sup></span> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal"> M P Williamson, <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1137821/"><span style="font-style:italic;">The structure and function of proline-rich regions in proteins.</span></a>, in <span style="font-style:italic;">Biochemical Journal</span>, vol. 297, Pt 2, 15 gennaio 1994, pp. 249–260. <small>URL consultato il 10 novembre 2018</small>.</cite></span> </li> <li id="cite_note-12"><a href="#cite_ref-12"><b>^</b></a> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal">(<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>) T. Reid Alderson, Jung Ho Lee e Cyril Charlier, <a rel="nofollow" class="external text" href="https://onlinelibrary.wiley.com/doi/full/10.1002/cbic.201700548"><span style="font-style:italic;">Propensity for cis -Proline Formation in Unfolded Proteins</span></a>, in <span style="font-style:italic;">ChemBioChem</span>, vol. 19, n. 1, 16 novembre 2017, pp. 37–42, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1002%2Fcbic.201700548">10.1002/cbic.201700548</a>. <small>URL consultato il 10 novembre 2018</small>.</cite></span> </li> <li id="cite_note-13"><a href="#cite_ref-13"><b>^</b></a> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal">(<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>) Ali Zarrinpar, Roby P. Bhattacharyya e Wendell A. Lim, <a rel="nofollow" class="external text" href="http://stke.sciencemag.org/content/2003/179/re8"><span style="font-style:italic;">The Structure and Function of Proline Recognition Domains</span></a>, in <span style="font-style:italic;">Sci. STKE</span>, vol. 2003, n. 179, 22 aprile 2003, pp. re8–re8, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1126%2Fstke.2003.179.re8">10.1126/stke.2003.179.re8</a>. <small>URL consultato il 10 novembre 2018</small>.</cite></span> </li> <li id="cite_note-14"><a href="#cite_ref-14"><b>^</b></a> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal">(<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>) Benjamin List, Richard A. Lerner e Carlos F. Barbas, <a rel="nofollow" class="external text" href="https://pubs.acs.org/doi/abs/10.1021/ja994280y"><span style="font-style:italic;">Proline-Catalyzed Direct Asymmetric Aldol Reactions</span></a>, in <span style="font-style:italic;">Journal of the American Chemical Society</span>, vol. 122, n. 10, 2000-03, pp. 2395–2396, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1021%2Fja994280y">10.1021/ja994280y</a>. <small>URL consultato il 16 novembre 2018</small>.</cite></span> </li> <li id="cite_note-15"><a href="#cite_ref-15"><b>^</b></a> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal"> Benjamin List, <a rel="nofollow" class="external text" href="https://oadoi.org/10.1016/s0040-4020(02)00516-1"><span style="font-style:italic;">Proline-catalyzed asymmetric reactions</span></a>, in <span style="font-style:italic;">Tetrahedron</span>, vol. 58, n. 28, 2002-07, pp. 5573–5590, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1016%2Fs0040-4020%2802%2900516-1">10.1016/s0040-4020(02)00516-1</a>. <small>URL consultato il 16 novembre 2018</small>.</cite></span> </li> <li id="cite_note-16"><a href="#cite_ref-16"><b>^</b></a> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal"> Arianna Bassan, Weibiao Zou e Efraim Reyes, <a rel="nofollow" class="external text" href="https://dx.doi.org/10.1002/ange.200502388"><span style="font-style:italic;">The Origin of Stereoselectivity in Primary Amino Acid Catalyzed Intermolecular Aldol Reactions</span></a>, in <span style="font-style:italic;">Angewandte Chemie</span>, vol. 117, n. 43, 4 novembre 2005, pp. 7190–7194, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1002%2Fange.200502388">10.1002/ange.200502388</a>. <small>URL consultato il 16 novembre 2018</small>.</cite></span> </li> <li id="cite_note-17"><a href="#cite_ref-17"><b>^</b></a> <span class="reference-text"><cite class="citation web" style="font-style:normal"> <a rel="nofollow" class="external text" href="http://blogs.cornell.edu/siebert/index/haze/"><span style="font-style:italic;">Cornell Universuty</span></a>, su <span style="font-style:italic;">blogs.cornell.edu</span>.</cite></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Bibliografia">Bibliografia</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prolina&veaction=edit&section=9" title="Modifica la sezione Bibliografia" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Prolina&action=edit&section=9" title="Edit section's source code: Bibliografia"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>David L. Nelson e Michael M. Cox, <i>I principi di biochimica del Lehninger</i>, quarta edizione, Ed. Zanichelli, 2006</li> <li>David A. Frank, <i>Signal transduction in cancer</i>, Kluwer Academic Publishers New York, Boston, Dordrecht, London, Moscow, 2004</li> <li>J. Behre, R. Voigt, I. Althöfer, S. Schuster: <i>On the evolutionary significance of the size and planarity of the proline ring</i>. Naturwissenschaften 99 (2012) 789-799.</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=Prolina&veaction=edit&section=10" 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=Prolina&action=edit&section=10" 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/prolina" class="extiw" title="wikt:prolina">Wikizionario</a></li> <li class="" title=""><span class="plainlinks" title="commons:Category:Proline"><a class="external text" href="https://commons.wikimedia.org/wiki/Category:Proline?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" width="18" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Wiktionary_small.svg/27px-Wiktionary_small.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Wiktionary_small.svg/36px-Wiktionary_small.svg.png 2x" data-file-width="350" data-file-height="350" /></a></span> <a href="https://it.wiktionary.org/wiki/" class="extiw" title="wikt:">Wikizionario</a> contiene il lemma di dizionario «<b><a href="https://it.wiktionary.org/wiki/prolina" class="extiw" title="wikt:prolina">prolina</a></b>»</li> <li><span typeof="mw:File"><a href="https://commons.wikimedia.org/wiki/?uselang=it" title="Collabora a Wikimedia Commons"><img alt="Collabora a Wikimedia Commons" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png" decoding="async" width="18" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Commons-logo.svg/27px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Commons-logo.svg/36px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></a></span> <span class="plainlinks"><a class="external text" href="https://commons.wikimedia.org/wiki/?uselang=it">Wikimedia Commons</a></span> contiene immagini o altri file su <b><span class="plainlinks"><a class="external text" href="https://commons.wikimedia.org/wiki/Category:Proline?uselang=it">prolina</a></span></b></li></ul> <div class="mw-heading mw-heading2"><h2 id="Collegamenti_esterni">Collegamenti esterni</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prolina&veaction=edit&section=11" title="Modifica la sezione Collegamenti esterni" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Prolina&action=edit&section=11" title="Edit section's source code: Collegamenti esterni"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li class="mw-empty-elt"></li> <li><cite id="CITEREFBritannica.com" class="citation web" style="font-style:normal">(<span style="font-weight:bolder; font-size:80%"><abbr title="inglese">EN</abbr></span>) <a rel="nofollow" class="external text" href="https://www.britannica.com/science/proline"><span style="font-style:italic;">proline</span></a>, su <span style="font-style:italic;"><a href="/wiki/Enciclopedia_Britannica" title="Enciclopedia Britannica">Enciclopedia Britannica</a></span>, Encyclopædia Britannica, Inc.</cite> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q484583#P1417" title="Modifica su Wikidata"><img alt="Modifica su Wikidata" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Blue_pencil.svg/10px-Blue_pencil.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Blue_pencil.svg/15px-Blue_pencil.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/73/Blue_pencil.svg/20px-Blue_pencil.svg.png 2x" data-file-width="600" data-file-height="600" /></a></span></li></ul> <style data-mw-deduplicate="TemplateStyles:r141815314">.mw-parser-output .navbox{border:1px solid #aaa;clear:both;margin:auto;padding:2px;width:100%}.mw-parser-output .navbox th{padding-left:1em;padding-right:1em;text-align:center}.mw-parser-output .navbox>tbody>tr:first-child>th{background:#ccf;font-size:90%;width:100%;color:var(--color-base,black)}.mw-parser-output .navbox_navbar{float:left;margin:0;padding:0 10px 0 0;text-align:left;width:6em}.mw-parser-output .navbox_title{font-size:110%}.mw-parser-output .navbox_abovebelow{background:#ddf;font-size:90%;font-weight:normal}.mw-parser-output .navbox_group{background:#ddf;font-size:90%;padding:0 10px;white-space:nowrap}.mw-parser-output .navbox_list{font-size:90%;width:100%}.mw-parser-output .navbox_list a{white-space:nowrap}html:not(.vector-feature-night-mode-enabled) .mw-parser-output .navbox_odd{background:#fdfdfd;color:var(--color-base,black)}html:not(.vector-feature-night-mode-enabled) .mw-parser-output .navbox_even{background:#f7f7f7;color:var(--color-base,black)}.mw-parser-output .navbox a.mw-selflink{color:var(--color-base,black)}.mw-parser-output .navbox_center{text-align:center}.mw-parser-output .navbox .navbox_image{padding-left:7px;vertical-align:middle;width:0}.mw-parser-output .navbox+.navbox{margin-top:-1px}.mw-parser-output .navbox .mw-collapsible-toggle{font-weight:normal;text-align:right;width:7em}body.skin--responsive .mw-parser-output .navbox_image img{max-width:none!important}.mw-parser-output .subnavbox{margin:-3px;width:100%}.mw-parser-output .subnavbox_group{background:#e6e6ff;padding:0 10px}@media screen{html.skin-theme-clientpref-night .mw-parser-output .navbox>tbody>tr:first-child>th{background:var(--background-color-interactive)!important}html.skin-theme-clientpref-night .mw-parser-output .navbox th{color:var(--color-base)!important}html.skin-theme-clientpref-night .mw-parser-output .navbox_abovebelow,html.skin-theme-clientpref-night .mw-parser-output .navbox_group{background:var(--background-color-interactive-subtle)!important}html.skin-theme-clientpref-night .mw-parser-output .subnavbox_group{background:var(--background-color-neutral-subtle)!important}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .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-Amminoacidi"><tbody><tr><th colspan="2"><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:Amminoacidi" title="Template:Amminoacidi"><span title="Vai alla pagina del template">V</span></a> · <a href="/w/index.php?title=Discussioni_template:Amminoacidi&action=edit&redlink=1" class="new" title="Discussioni template:Amminoacidi (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:Amminoacidi&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/Amminoacidi" class="mw-redirect" title="Amminoacidi">Amminoacidi</a></span></th></tr><tr><th colspan="1" class="navbox_group"><a href="/wiki/Amminoacidi_proteinogenici" title="Amminoacidi proteinogenici">Proteinogenici</a></th><td colspan="1" class="navbox_list navbox_odd"><table class="subnavbox"><tbody><tr><th class="subnavbox_group" style="width:125px">Amminoacidi L-α</th><td colspan="1"><a href="/wiki/Acido_aspartico" title="Acido aspartico">Acido L-aspartico</a><b> ·</b> <a href="/wiki/Acido_glutammico" title="Acido glutammico">Acido L-glutammico</a><b> ·</b> L-<a href="/wiki/Alanina" title="Alanina">Alanina</a><b> ·</b> L-<a href="/wiki/Arginina" title="Arginina">Arginina</a><b> ·</b> L-<a href="/wiki/Asparagina" title="Asparagina">Asparagina</a><b> ·</b> L-<a href="/wiki/Cisteina" title="Cisteina">Cisteina</a><b> ·</b> L-<a href="/wiki/Fenilalanina" title="Fenilalanina">Fenilalanina</a><b> ·</b> <a href="/wiki/Glicina" title="Glicina">Glicina</a><b> ·</b> L-<a href="/wiki/Glutammina" title="Glutammina">Glutammina</a><b> ·</b> L-<a href="/wiki/Isoleucina" title="Isoleucina">Isoleucina</a><b> ·</b> L-<a href="/wiki/Istidina" title="Istidina">Istidina</a><b> ·</b> L-<a href="/wiki/Leucina" title="Leucina">Leucina</a><b> ·</b> L-<a href="/wiki/Lisina" title="Lisina">Lisina</a><b> ·</b> L-<a href="/wiki/Metionina" title="Metionina">Metionina</a><b> ·</b> L-<a href="/wiki/Pirrolisina" title="Pirrolisina">Pirrolisina</a><b> ·</b> L-<a class="mw-selflink selflink">Prolina</a><b> ·</b> L-<a href="/wiki/Selenocisteina" title="Selenocisteina">Selenocisteina</a><b> ·</b> L-<a href="/wiki/Serina_(chimica)" title="Serina (chimica)">Serina</a><b> ·</b> L-<a href="/wiki/Tirosina" title="Tirosina">Tirosina</a><b> ·</b> L-<a href="/wiki/Treonina" title="Treonina">Treonina</a><b> ·</b> L-<a href="/wiki/Triptofano" title="Triptofano">Triptofano</a><b> ·</b> L-<a href="/wiki/Valina" title="Valina">Valina</a></td></tr></tbody></table></td></tr><tr><th colspan="1" class="navbox_group"><a href="/wiki/Amminoacidi_non_proteinogenici" title="Amminoacidi non proteinogenici">Non proteinogenici</a></th><td colspan="1" class="navbox_list navbox_even"><table class="subnavbox"><tbody><tr><th class="subnavbox_group" style="width:125px">Amminoacidi D-α</th><td colspan="1"><a href="/wiki/Acido_aspartico" title="Acido aspartico">Acido D-aspartico</a><b> ·</b> <a href="/wiki/Acido_glutammico" title="Acido glutammico">Acido D-glutammico</a><b> ·</b> D-<a href="/wiki/Alanina" title="Alanina">Alanina</a><b> ·</b> D-<a href="/wiki/Arginina" title="Arginina">Arginina</a><b> ·</b> D-<a href="/wiki/Asparagina" title="Asparagina">Asparagina</a><b> ·</b> D-<a href="/wiki/Cisteina" title="Cisteina">Cisteina</a><b> ·</b> D-<a href="/wiki/Fenilalanina" title="Fenilalanina">Fenilalanina</a><b> ·</b> D-<a href="/wiki/Glutammina" title="Glutammina">Glutammina</a><b> ·</b> D-<a href="/wiki/Isoleucina" title="Isoleucina">Isoleucina</a><b> ·</b> D-<a href="/wiki/Istidina" title="Istidina">Istidina</a><b> ·</b> D-<a href="/wiki/Leucina" title="Leucina">Leucina</a><b> ·</b> D-<a href="/wiki/Lisina" title="Lisina">Lisina</a><b> ·</b> D-<a href="/wiki/Metionina" title="Metionina">Metionina</a><b> ·</b> D-<a href="/wiki/Pirrolisina" title="Pirrolisina">Pirrolisina</a><b> ·</b> D-<a class="mw-selflink selflink">Prolina</a><b> ·</b> D-<a href="/wiki/Selenocisteina" title="Selenocisteina">Selenocisteina</a><b> ·</b> D-<a href="/wiki/Serina_(chimica)" title="Serina (chimica)">Serina</a><b> ·</b> D-<a href="/wiki/Tirosina" title="Tirosina">Tirosina</a><b> ·</b> D-<a href="/wiki/Treonina" title="Treonina">Treonina</a><b> ·</b> D-<a href="/wiki/Triptofano" title="Triptofano">Triptofano</a><b> ·</b> D-<a href="/wiki/Valina" title="Valina">Valina</a><b> ·</b> <a href="/wiki/Alliina" title="Alliina">Alliina</a><b> ·</b> <a href="/w/index.php?title=Isoalliina&action=edit&redlink=1" class="new" title="Isoalliina (la pagina non esiste)">Isoalliina</a></td></tr><tr><th class="subnavbox_group" style="width:125px">Amminoacidi L-α</th><td colspan="1"><a href="/w/index.php?title=S-metilcisteina&action=edit&redlink=1" class="new" title="S-metilcisteina (la pagina non esiste)">S-metilcisteina</a><b> ·</b> <a href="/w/index.php?title=L-terzleucina&action=edit&redlink=1" class="new" title="L-terzleucina (la pagina non esiste)">L-terzleucina</a></td></tr><tr><th class="subnavbox_group" style="width:125px">Amminoacidi α senza stereocentri</th><td colspan="1"><a href="/w/index.php?title=Acido_2-amminoisobutirrico&action=edit&redlink=1" class="new" title="Acido 2-amminoisobutirrico (la pagina non esiste)">Acido 2-amminoisobutirrico</a><b> ·</b> <a href="/w/index.php?title=Acido_2-amminomuconico&action=edit&redlink=1" class="new" title="Acido 2-amminomuconico (la pagina non esiste)">Acido 2-amminomuconico</a><b> ·</b> <a href="/w/index.php?title=Deidroalanina&action=edit&redlink=1" class="new" title="Deidroalanina (la pagina non esiste)">Deidroalanina</a></td></tr><tr><th class="subnavbox_group" style="width:125px">Amminoacidi α con uno stereocentro</th><td colspan="1"><a href="/wiki/5-idrossitriptofano" title="5-idrossitriptofano">5-idrossitriptofano</a><b> ·</b> <a href="/wiki/Acido_%CE%B1-amminobutirrico" title="Acido α-amminobutirrico">Acido α-amminobutirrico</a><b> ·</b> <a href="/w/index.php?title=Acido_carbossiglutammico&action=edit&redlink=1" class="new" title="Acido carbossiglutammico (la pagina non esiste)">Acido carbossiglutammico</a><b> ·</b> <a href="/wiki/Acido_ibotenico" title="Acido ibotenico">Acido ibotenico</a><b> ·</b> <a href="/w/index.php?title=Acido_quisqualico&action=edit&redlink=1" class="new" title="Acido quisqualico (la pagina non esiste)">Acido quisqualico</a><b> ·</b> <a href="/wiki/Canavanina" title="Canavanina">Canavanina</a><b> ·</b> <a href="/wiki/Citrullina" title="Citrullina">Citrullina</a><b> ·</b> <a href="/wiki/Ipoglicina" title="Ipoglicina">Ipoglicina</a><b> ·</b> <a href="/wiki/Levodopa" class="mw-redirect" title="Levodopa">Levodopa</a><b> ·</b> <a href="/w/index.php?title=Norleucina&action=edit&redlink=1" class="new" title="Norleucina (la pagina non esiste)">Norleucina</a><b> ·</b> <a href="/wiki/Norvalina" title="Norvalina">Norvalina</a><b> ·</b> <a href="/wiki/Omocisteina" title="Omocisteina">Omocisteina</a><b> ·</b> <a href="/wiki/Ornitina" title="Ornitina">Ornitina</a><b> ·</b> <a href="/wiki/Penicillamina" title="Penicillamina">Penicillamina</a><b> ·</b> <a href="/wiki/Tiroxina" title="Tiroxina">Tiroxina</a></td></tr><tr><th class="subnavbox_group" style="width:125px">Amminoacidi α con più stereocentri</th><td colspan="1"><a href="/w/index.php?title=Acido_diaminopimelico&action=edit&redlink=1" class="new" title="Acido diaminopimelico (la pagina non esiste)">Acido diaminopimelico</a><b> ·</b> <a href="/wiki/Cistationina" title="Cistationina">Cistationina</a><b> ·</b> <a href="/wiki/Cistina" title="Cistina">Cistina</a><b> ·</b> <a href="/w/index.php?title=Lantionina&action=edit&redlink=1" class="new" title="Lantionina (la pagina non esiste)">Lantionina</a><b> ·</b> <a href="/w/index.php?title=Metillantionina&action=edit&redlink=1" class="new" title="Metillantionina (la pagina non esiste)">Metillantionina</a></td></tr><tr><th class="subnavbox_group" style="width:125px">Amminoacidi α non-ammine primarie</th><td colspan="1"><a href="/wiki/Acido_N-metil-D-aspartico" title="Acido N-metil-D-aspartico">Acido N-metil-D-aspartico</a><b> ·</b> <a href="/w/index.php?title=Acido_N-metil-L-aspartico&action=edit&redlink=1" class="new" title="Acido N-metil-L-aspartico (la pagina non esiste)">Acido N-metil-L-aspartico</a><b> ·</b> <a href="/wiki/Acido_pipecolico" title="Acido pipecolico">Acido pipecolico</a><b> ·</b> <a href="/wiki/Carnitina" title="Carnitina">Carnitina</a><b> ·</b> <a href="/w/index.php?title=Cicloalliina&action=edit&redlink=1" class="new" title="Cicloalliina (la pagina non esiste)">Cicloalliina</a><b> ·</b> <a href="/wiki/Idrossiprolina" title="Idrossiprolina">Idrossiprolina</a><b> ·</b> <a href="/wiki/Sarcosina" title="Sarcosina">Sarcosina</a></td></tr><tr><th class="subnavbox_group" style="width:125px">Amminoacidi non-α</th><td colspan="1"><a href="/wiki/%CE%92-alanina" title="Β-alanina">β-alanina</a><b> ·</b> <a href="/w/index.php?title=%CE%92-leucina&action=edit&redlink=1" class="new" title="Β-leucina (la pagina non esiste)">β-leucina</a><b> ·</b> <a href="/wiki/Acido_%CE%B2-amminobutirrico" title="Acido β-amminobutirrico">Acido β-amminobutirrico</a><b> ·</b> <a href="/wiki/Acido_%CE%B3-amminobutirrico" title="Acido γ-amminobutirrico">Acido γ-amminobutirrico</a><b> ·</b> <a href="/wiki/Acido_2-amminobenzoico" class="mw-redirect" title="Acido 2-amminobenzoico">Acido 2-amminobenzoico</a><b> ·</b> <a href="/wiki/Acido_3-amminobenzoico" title="Acido 3-amminobenzoico">Acido 3-amminobenzoico</a><b> ·</b> <a href="/wiki/Acido_4-amminobenzoico" title="Acido 4-amminobenzoico">Acido 4-amminobenzoico</a><b> ·</b> <a href="/w/index.php?title=Acido_3-amminolevulinico&action=edit&redlink=1" class="new" title="Acido 3-amminolevulinico (la pagina non esiste)">Acido 3-amminolevulinico</a><b> ·</b> <a href="/wiki/Acido_5-amminolevulinico" title="Acido 5-amminolevulinico">Acido 5-amminolevulinico</a><b> ·</b> <a href="/wiki/Baclofene" title="Baclofene">Baclofene</a><b> ·</b> <a href="/wiki/Pregabalin" title="Pregabalin">Pregabalin</a></td></tr></tbody></table></td></tr></tbody></table> <div class="noprint" style="width:100%; padding: 3px 0; display: flex; flex-wrap: wrap; row-gap: 4px; column-gap: 8px; box-sizing: border-box;"><div style="flex-grow: 1"><style data-mw-deduplicate="TemplateStyles:r140555418">.mw-parser-output .itwiki-template-occhiello{width:100%;line-height:25px;border:1px solid #CCF;background-color:#F0EEFF;box-sizing:border-box}.mw-parser-output .itwiki-template-occhiello-progetto{background-color:#FAFAFA}@media screen{html.skin-theme-clientpref-night .mw-parser-output .itwiki-template-occhiello{background-color:#202122;border-color:#54595D}html.skin-theme-clientpref-night .mw-parser-output .itwiki-template-occhiello-progetto{background-color:#282929}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .itwiki-template-occhiello{background-color:#202122;border-color:#54595D}html.skin-theme-clientpref-os .mw-parser-output .itwiki-template-occhiello-progetto{background-color:#282929}}</style><div class="itwiki-template-occhiello"><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Gnome-applications-science.svg" class="mw-file-description" title="Chimica"><img alt=" " src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Gnome-applications-science.svg/25px-Gnome-applications-science.svg.png" decoding="async" width="25" height="25" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Gnome-applications-science.svg/38px-Gnome-applications-science.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Gnome-applications-science.svg/50px-Gnome-applications-science.svg.png 2x" data-file-width="48" data-file-height="48" /></a></span> <b><a href="/wiki/Portale:Chimica" title="Portale:Chimica">Portale Chimica</a></b>: il portale della scienza della composizione, delle proprietà e delle trasformazioni della materia</div></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="">Estratto da "<a dir="ltr" href="https://it.wikipedia.org/w/index.php?title=Prolina&oldid=142161010">https://it.wikipedia.org/w/index.php?title=Prolina&oldid=142161010</a>"</div></div> <div id="catlinks" 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