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<li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Safety</span> </div> </a> <ul id="toc-Safety-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Pharmacology</span> </div> </a> <button aria-controls="toc-Pharmacology-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>Toggle Pharmacology subsection</span> </button> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> <li id="toc-Pharmacodynamics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacodynamics"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Pharmacodynamics</span> </div> </a> <ul id="toc-Pharmacodynamics-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism_in_humans" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metabolism_in_humans"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Metabolism in humans</span> </div> </a> <ul id="toc-Metabolism_in_humans-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Synthesis_in_nonhuman_organisms" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthesis_in_nonhuman_organisms"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Synthesis in nonhuman organisms</span> </div> </a> <ul id="toc-Synthesis_in_nonhuman_organisms-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Chemistry</span> </div> </a> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Notes" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Notes"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Notes</span> </div> </a> <ul id="toc-Notes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>External links</span> </div> </a> <ul id="toc-External_links-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="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <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="Toggle the table of contents" > <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">Toggle the table of contents</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">Leucine</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="Go to an article in another language. Available in 62 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-62" 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">62 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%84%D9%8A%D9%88%D8%B3%D9%8A%D9%86" title="ليوسين – Arabic" lang="ar" hreflang="ar" data-title="ليوسين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%84%D9%88%D8%B3%DB%8C%D9%86_(%D8%A7%D8%B3%DB%8C%D8%AF_%D8%A2%D9%85%DB%8C%D9%86%D9%87)" title="لوسین (اسید آمینه) – South Azerbaijani" lang="azb" hreflang="azb" data-title="لوسین (اسید آمینه)" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Leucin" title="Leucin – Minnan" lang="nan" hreflang="nan" data-title="Leucin" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9B%D0%B5%D0%B9%D1%86%D1%8B%D0%BD" title="Лейцын – Belarusian" lang="be" hreflang="be" data-title="Лейцын" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9B%D0%B5%D0%B2%D1%86%D0%B8%D0%BD" title="Левцин – Bulgarian" lang="bg" hreflang="bg" data-title="Левцин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Leucin" title="Leucin – Bosnian" lang="bs" hreflang="bs" data-title="Leucin" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Leucina" title="Leucina – Catalan" lang="ca" hreflang="ca" data-title="Leucina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Leucin" title="Leucin – Czech" lang="cs" hreflang="cs" data-title="Leucin" data-language-autonym="Čeština" data-language-local-name="Czech" 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/Leucin" title="Leucin – Danish" lang="da" hreflang="da" data-title="Leucin" data-language-autonym="Dansk" data-language-local-name="Danish" 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/Leucin" title="Leucin – German" lang="de" hreflang="de" data-title="Leucin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Leutsiin" title="Leutsiin – Estonian" lang="et" hreflang="et" data-title="Leutsiin" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9B%CE%B5%CF%85%CE%BA%CE%AF%CE%BD%CE%B7" title="Λευκίνη – Greek" lang="el" hreflang="el" data-title="Λευκίνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Leucina" title="Leucina – Spanish" lang="es" hreflang="es" data-title="Leucina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Le%C5%ADcino" title="Leŭcino – Esperanto" lang="eo" hreflang="eo" data-title="Leŭcino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Leuzina" title="Leuzina – Basque" lang="eu" hreflang="eu" data-title="Leuzina" data-language-autonym="Euskara" data-language-local-name="Basque" 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%84%D9%88%D8%B3%DB%8C%D9%86_(%D8%A7%D8%B3%DB%8C%D8%AF_%D8%A2%D9%85%DB%8C%D9%86%D9%87)" title="لوسین (اسید آمینه) – Persian" lang="fa" hreflang="fa" data-title="لوسین (اسید آمینه)" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Leucine" title="Leucine – French" lang="fr" hreflang="fr" data-title="Leucine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Leoic%C3%ADn" title="Leoicín – Irish" lang="ga" hreflang="ga" data-title="Leoicín" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Leucina" title="Leucina – Galician" lang="gl" hreflang="gl" data-title="Leucina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%A5%98%EC%8B%A0" title="류신 – Korean" lang="ko" hreflang="ko" data-title="류신" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%BC%D5%A5%D5%B5%D6%81%D5%AB%D5%B6" title="Լեյցին – Armenian" lang="hy" hreflang="hy" data-title="Լեյցին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B2%E0%A5%8D%E0%A4%AF%E0%A5%82%E0%A4%B8%E0%A4%BF%E0%A4%A8" title="ल्यूसिन – Hindi" lang="hi" hreflang="hi" data-title="ल्यूसिन" 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/Leucin" title="Leucin – Croatian" lang="hr" hreflang="hr" data-title="Leucin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Leusina" title="Leusina – Indonesian" lang="id" hreflang="id" data-title="Leusina" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Leucina" title="Leucina – Italian" lang="it" hreflang="it" data-title="Leucina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%9C%D7%90%D7%95%D7%A6%D7%99%D7%9F" title="לאוצין – Hebrew" lang="he" hreflang="he" data-title="לאוצין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/Leus%C3%AEn" title="Leusîn – Kurdish" lang="ku" hreflang="ku" data-title="Leusîn" data-language-autonym="Kurdî" data-language-local-name="Kurdish" class="interlanguage-link-target"><span>Kurdî</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Leucinum" title="Leucinum – Latin" lang="la" hreflang="la" data-title="Leucinum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Leic%C4%ABns" title="Leicīns – Latvian" lang="lv" hreflang="lv" data-title="Leicīns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Leucin" title="Leucin – Luxembourgish" lang="lb" hreflang="lb" data-title="Leucin" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" 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/Leucinas" title="Leucinas – Lithuanian" lang="lt" hreflang="lt" data-title="Leucinas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Leucin" title="Leucin – Hungarian" lang="hu" hreflang="hu" data-title="Leucin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9B%D0%B5%D1%83%D1%86%D0%B8%D0%BD" title="Леуцин – Macedonian" lang="mk" hreflang="mk" data-title="Леуцин" data-language-autonym="Македонски" data-language-local-name="Macedonian" 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/Leusina" title="Leusina – Malay" lang="ms" hreflang="ms" data-title="Leusina" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%9B%D0%B5%D0%B9%D1%86%D0%B8%D0%BD" title="Лейцин – Mongolian" lang="mn" hreflang="mn" data-title="Лейцин" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Leucine" title="Leucine – Dutch" lang="nl" hreflang="nl" data-title="Leucine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%AD%E3%82%A4%E3%82%B7%E3%83%B3" title="ロイシン – Japanese" lang="ja" hreflang="ja" data-title="ロイシン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Leucin" title="Leucin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Leucin" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Leusin" title="Leusin – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Leusin" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Leucina" title="Leucina – Occitan" lang="oc" hreflang="oc" data-title="Leucina" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Leytsin" title="Leytsin – Uzbek" lang="uz" hreflang="uz" data-title="Leytsin" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Leucyna" title="Leucyna – Polish" lang="pl" hreflang="pl" data-title="Leucyna" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Leucina" title="Leucina – Portuguese" lang="pt" hreflang="pt" data-title="Leucina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Leucin%C4%83" title="Leucină – Romanian" lang="ro" hreflang="ro" data-title="Leucină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9B%D0%B5%D0%B9%D1%86%D0%B8%D0%BD" title="Лейцин – Russian" lang="ru" hreflang="ru" data-title="Лейцин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-scn mw-list-item"><a href="https://scn.wikipedia.org/wiki/Liucina" title="Liucina – Sicilian" lang="scn" hreflang="scn" data-title="Liucina" data-language-autonym="Sicilianu" data-language-local-name="Sicilian" class="interlanguage-link-target"><span>Sicilianu</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Leuc%C3%ADn" title="Leucín – Slovak" lang="sk" hreflang="sk" data-title="Leucín" data-language-autonym="Slovenčina" data-language-local-name="Slovak" 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/Levcin" title="Levcin – Slovenian" lang="sl" hreflang="sl" data-title="Levcin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" 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/Leucin" title="Leucin – Serbian" lang="sr" hreflang="sr" data-title="Leucin" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Leucin" title="Leucin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Leucin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Leusin" title="Leusin – Sundanese" lang="su" hreflang="su" data-title="Leusin" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Leusiini" title="Leusiini – Finnish" lang="fi" hreflang="fi" data-title="Leusiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Leucin" title="Leucin – Swedish" lang="sv" hreflang="sv" data-title="Leucin" data-language-autonym="Svenska" data-language-local-name="Swedish" 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%B2%E0%AE%BF%E0%AE%AF%E0%AF%82%E0%AE%9A%E0%AE%BF%E0%AE%A9%E0%AF%8D" title="லியூசின் – Tamil" lang="ta" hreflang="ta" data-title="லியூசின்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%A5%E0%B8%B4%E0%B8%A7%E0%B8%8B%E0%B8%B5%E0%B8%99" title="ลิวซีน – Thai" lang="th" hreflang="th" data-title="ลิวซีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/L%C3%B6sin" title="Lösin – Turkish" lang="tr" hreflang="tr" data-title="Lösin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9B%D0%B5%D0%B9%D1%86%D0%B8%D0%BD" title="Лейцин – Ukrainian" lang="uk" hreflang="uk" data-title="Лейцин" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Leucin" title="Leucin – Vietnamese" lang="vi" hreflang="vi" data-title="Leucin" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-vls mw-list-item"><a href="https://vls.wikipedia.org/wiki/Leucine" title="Leucine – West Flemish" lang="vls" hreflang="vls" data-title="Leucine" data-language-autonym="West-Vlams" data-language-local-name="West Flemish" class="interlanguage-link-target"><span>West-Vlams</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E4%BA%AE%E6%B0%A8%E9%85%B8" title="亮氨酸 – Wu" lang="wuu" hreflang="wuu" data-title="亮氨酸" 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-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E4%BA%AE%E6%B0%A8%E9%85%B8" title="亮氨酸 – Cantonese" lang="yue" hreflang="yue" data-title="亮氨酸" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E4%BA%AE%E6%B0%A8%E9%85%B8" title="亮氨酸 – Chinese" lang="zh" hreflang="zh" data-title="亮氨酸" data-language-autonym="中文" data-language-local-name="Chinese" 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href="https://www.wikidata.org/wiki/Special:EntityPage/Q483745" title="Structured data on this page hosted by Wikidata [g]" accesskey="g"><span>Wikidata item</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="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <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">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><p> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> </p> <table class="infobox ib-chembox"> <caption>Leucine </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center skin-invert" typeof="mw:File"><a href="/wiki/File:L-Leucine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4d/L-Leucine.svg/220px-L-Leucine.svg.png" decoding="async" width="220" height="136" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4d/L-Leucine.svg/330px-L-Leucine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4d/L-Leucine.svg/440px-L-Leucine.svg.png 2x" data-file-width="255" data-file-height="158" /></a><figcaption></figcaption></figure><div style="text-align:center;"><a href="/wiki/Skeletal_formula" title="Skeletal formula">Skeletal formula</a> of <small>L</small>-leucine</div> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Leucine-from-xtal-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Leucine-from-xtal-3D-bs-17.png/110px-Leucine-from-xtal-3D-bs-17.png" decoding="async" width="110" height="135" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Leucine-from-xtal-3D-bs-17.png/165px-Leucine-from-xtal-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Leucine-from-xtal-3D-bs-17.png/220px-Leucine-from-xtal-3D-bs-17.png 2x" data-file-width="1888" data-file-height="2314" /></a><figcaption></figcaption></figure><div style="text-align:center"><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Ball-and-stick model</a><sup id="cite_ref-Binns_1-0" class="reference"><a href="#cite_note-Binns-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Leucine-from-xtal-3D-sf.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/81/Leucine-from-xtal-3D-sf.png/120px-Leucine-from-xtal-3D-sf.png" decoding="async" width="110" height="132" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/81/Leucine-from-xtal-3D-sf.png/250px-Leucine-from-xtal-3D-sf.png 1.5x" data-file-width="1912" data-file-height="2286" /></a><figcaption></figcaption></figure><div style="text-align:center"><a href="/wiki/Space-filling_model" title="Space-filling model">Space-filling model</a><sup id="cite_ref-Binns_1-1" class="reference"><a href="#cite_note-Binns-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Leucine</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">2-Amino-4-methylpentanoic acid</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=61-90-5">61-90-5</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28C%29C%5BC%40%40H%5D%28C%28%3DO%29O%29N">Interactive image</a></span></li><li><a href="/wiki/Zwitterion" title="Zwitterion">Zwitterion</a>: <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC%28C%29C%5BC%40%40H%5D%28C%28%3DO%29%5BO-%5D%29%5BNH3%2B%5D">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=15603">CHEBI:15603</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL291962">ChEMBL291962</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.5880.html">5880</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00149">DB00149</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.475">100.000.475</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q483745#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=3312">3312</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00030">D00030</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6106">6106</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/GMW67QNF9C">GMW67QNF9C</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID9023203">DTXSID9023203</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q483745#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: ROHFNLRQFUQHCH-YFKPBYRVSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: ROHFNLRQFUQHCH-YFKPBYRVBU</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">CC(C)C[C@@H](C(=O)O)N</div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;"><a href="/wiki/Zwitterion" title="Zwitterion">Zwitterion</a>: CC(C)C[C@@H](C(=O)[O-])[NH3+]</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>6</sub><span title="Hydrogen">H</span><sub>13</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002131175000000000♠"></span>131.175</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>2.36 (carboxyl), 9.60 (amino)<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> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−84.9·10<sup>−6</sup> cm<sup>3</sup>/mol </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Supplementary data page </th></tr> <tr> <td colspan="2" style="text-align:center"><a href="/wiki/Leucine_(data_page)" title="Leucine (data page)">Leucine (data page)</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Leucine-spin.gif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Leucine-spin.gif/220px-Leucine-spin.gif" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Leucine-spin.gif/330px-Leucine-spin.gif 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Leucine-spin.gif/440px-Leucine-spin.gif 2x" data-file-width="480" data-file-height="480" /></a><figcaption>Leucine ball and stick model spinning</figcaption></figure> <p><b>Leucine</b> (symbol <b>Leu</b> or <b>L</b>)<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> is an <a href="/wiki/Essential_amino_acid" title="Essential amino acid">essential amino acid</a> that is used in the <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a> of <a href="/wiki/Protein" title="Protein">proteins</a>. Leucine is an α-amino acid, meaning it contains an α-<a href="/wiki/Amino_group" class="mw-redirect" title="Amino group">amino group</a> (which is in the protonated −NH<sub>3</sub><sup>+</sup> form under biological conditions), an α-<a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid group</a> (which is in the deprotonated −COO<sup>−</sup> form under biological conditions), and a side chain <a href="/wiki/Isobutyl" class="mw-redirect" title="Isobutyl">isobutyl group</a>, making it a <a href="/wiki/Chemical_polarity" title="Chemical polarity">non-polar</a> <a href="/wiki/Aliphatic_compound" title="Aliphatic compound">aliphatic</a> amino acid. It is <a href="/wiki/Essential_amino_acid" title="Essential amino acid">essential</a> in humans, meaning the body cannot synthesize it; it must be obtained from the diet. Human dietary sources are foods that contain protein, such as meats, dairy products, soy products, and beans and other legumes. It is <a href="/wiki/Genetic_code" title="Genetic code">encoded</a> by the <a href="/wiki/Codon" class="mw-redirect" title="Codon">codons</a> UUA, UUG, CUU, CUC, CUA, and CUG. Leucine is named after the <a href="/wiki/Greek_language" title="Greek language">Greek</a> word for "white": <i>λευκός</i> (<i>leukós</i>, "white"), after its common appearance as a white powder, a property it shares with many other <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a>.<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><p>Like <a href="/wiki/Valine" title="Valine">valine</a> and <a href="/wiki/Isoleucine" title="Isoleucine">isoleucine</a>, leucine is a <a href="/wiki/Branched-chain_amino_acid" title="Branched-chain amino acid">branched-chain amino acid</a>. The primary <a href="/wiki/Metabolic_product" class="mw-redirect" title="Metabolic product">metabolic end products</a> of leucine metabolism are <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a> and <a href="/wiki/Acetoacetate" class="mw-redirect" title="Acetoacetate">acetoacetate</a>; consequently, it is one of the two exclusively <a href="/wiki/Ketogenic_amino_acid" title="Ketogenic amino acid">ketogenic amino acids</a>, with <a href="/wiki/Lysine" title="Lysine">lysine</a> being the other.<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> It is the most important ketogenic amino acid in humans.<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><p>Leucine and <a href="/wiki/%CE%92-hydroxy_%CE%B2-methylbutyric_acid" class="mw-redirect" title="Β-hydroxy β-methylbutyric acid">β-hydroxy β-methylbutyric acid</a>, a minor leucine <a href="/wiki/Metabolite" title="Metabolite">metabolite</a>, exhibit <a href="/wiki/Pharmacological_activity" class="mw-redirect" title="Pharmacological activity">pharmacological activity</a> in humans and have been demonstrated to promote <a href="/wiki/Protein_biosynthesis" title="Protein biosynthesis">protein biosynthesis</a> via the <a href="/wiki/Phosphorylation" title="Phosphorylation">phosphorylation</a> of the <a href="/wiki/Mechanistic_target_of_rapamycin" class="mw-redirect" title="Mechanistic target of rapamycin">mechanistic target of rapamycin</a> (mTOR).<sup id="cite_ref-Pimentel_2017_systematic_review_on_HMB_7-0" class="reference"><a href="#cite_note-Pimentel_2017_systematic_review_on_HMB-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Pharmacology_of_HMB-FA_in_humans_in_vivo_8-0" class="reference"><a href="#cite_note-Pharmacology_of_HMB-FA_in_humans_in_vivo-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Dietary_leucine">Dietary leucine</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Leucine&action=edit&section=1" title="Edit section: Dietary leucine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As a <a href="/wiki/Food_additive" title="Food additive">food additive</a>, L-leucine has <a href="/wiki/E_number" title="E number">E number</a> <b>E641</b> and is classified as a <a href="/wiki/Flavor_enhancer" class="mw-redirect" title="Flavor enhancer">flavor enhancer</a>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Requirements">Requirements</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Leucine&action=edit&section=2" title="Edit section: Requirements"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The Food and Nutrition Board (FNB) of the U.S. Institute of Medicine set Recommended Dietary Allowances (RDAs) for <a href="/wiki/Essential_amino_acid" title="Essential amino acid">essential amino acids</a> in 2002. For leucine, for adults 19 years and older, 42 mg/kg body weight/day.<sup id="cite_ref-DRItext_10-0" class="reference"><a href="#cite_note-DRItext-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Sources">Sources <span class="anchor" id="Dietary_sources"></span></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Leucine&action=edit&section=3" title="Edit section: Sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable sortable"> <caption>Food sources of leucine<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <th>Food </th> <th>g/100g </th></tr> <tr> <td><a href="/wiki/Whey_protein" title="Whey protein">Whey protein</a> concentrate, dry powder</td> <td>10.0–12.0 </td></tr> <tr> <td><a href="/wiki/Soy_protein" title="Soy protein">Soy protein</a> concentrate, dry powder</td> <td>7.5–8.5 </td></tr> <tr> <td><a href="/wiki/Pea_protein" title="Pea protein">Pea protein</a> concentrate, dry powder</td> <td>6.6 </td></tr> <tr> <td><a href="/wiki/Soybeans" class="mw-redirect" title="Soybeans">Soybeans</a>, mature seeds, roasted, salted</td> <td>2.87 </td></tr> <tr> <td><a href="/wiki/Hemp#Nutrition" title="Hemp">Hemp</a> seed, hulled</td> <td>2.16 </td></tr> <tr> <td><a href="/wiki/Beef" title="Beef">Beef</a>, round, top round, raw</td> <td>1.76 </td></tr> <tr> <td><a href="/wiki/Peanut" title="Peanut">Peanuts</a></td> <td>1.67 </td></tr> <tr> <td><a href="/wiki/Fish" title="Fish">Fish</a>, salmon, pink, raw</td> <td>1.62 </td></tr> <tr> <td><a href="/wiki/Wheat_germ" class="mw-redirect" title="Wheat germ">Wheat germ</a></td> <td>1.57 </td></tr> <tr> <td><a href="/wiki/Almonds" class="mw-redirect" title="Almonds">Almonds</a></td> <td>1.49 </td></tr> <tr> <td><a href="/wiki/Chicken" title="Chicken">Chicken</a>, broilers or fryers, thigh, raw</td> <td>1.48 </td></tr> <tr> <td><a href="/wiki/Chicken_egg" class="mw-redirect" title="Chicken egg">Chicken egg</a>, yolk, raw</td> <td>1.40 </td></tr> <tr> <td><a href="/wiki/Oat" title="Oat">Oats</a></td> <td>1.28 </td></tr> <tr> <td><a href="/wiki/Edamame" title="Edamame">Edamame</a> (soybeans, green, raw)</td> <td>0.93 </td></tr> <tr> <td>Beans, pinto, cooked</td> <td>0.78 </td></tr> <tr> <td><a href="/wiki/Lentils" class="mw-redirect" title="Lentils">Lentils</a>, cooked</td> <td>0.65 </td></tr> <tr> <td><a href="/wiki/Chickpea" title="Chickpea">Chickpea</a>, cooked</td> <td>0.63 </td></tr> <tr> <td><a href="/wiki/Maize" title="Maize">Corn</a>, yellow</td> <td>0.35 </td></tr> <tr> <td><a href="/wiki/Cow_milk" class="mw-redirect" title="Cow milk">Cow milk</a>, whole, 3.25% milk fat</td> <td>0.27 </td></tr> <tr> <td><a href="/wiki/Rice" title="Rice">Rice</a>, brown, medium-grain, cooked</td> <td>0.19 </td></tr> <tr> <td><a href="/wiki/Milk" title="Milk">Milk</a>, human, mature, fluid</td> <td>0.10 </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Health_effects">Health effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Leucine&action=edit&section=4" title="Edit section: Health effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As a <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a>, leucine has been found to slow the degradation of muscle tissue by increasing the synthesis of muscle proteins in aged rats.<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> However, results of comparative studies are conflicted. Long-term leucine supplementation does not increase muscle mass or strength in healthy elderly men.<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> More studies are needed, preferably ones based on an objective, random sample of society. Factors such as lifestyle choices, age, gender, diet, exercise, etc. must be factored into the analyses to isolate the effects of supplemental leucine as a stand-alone, or if taken with other <a href="/wiki/Branched-chain_amino_acid" title="Branched-chain amino acid">branched-chain amino acids</a> (BCAAs). Until then, dietary supplemental leucine cannot be associated as the prime reason for muscular growth or optimal maintenance for the entire population. </p><p>Both L-leucine and D-leucine protect mice against <a href="/wiki/Seizure" title="Seizure">epileptic seizures</a>.<sup id="cite_ref-pmid26054437_14-0" class="reference"><a href="#cite_note-pmid26054437-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> D-leucine also terminates seizures in mice after the onset of seizure activity, at least as effectively as diazepam and without sedative effects.<sup id="cite_ref-pmid26054437_14-1" class="reference"><a href="#cite_note-pmid26054437-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Decreased dietary intake of L-leucine lessens adiposity in mice.<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> High blood levels of leucine are associated with insulin resistance in humans, mice, and rodents.<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> This might be due to the effect of leucine to stimulate <a href="/wiki/MTOR" title="MTOR">mTOR</a> signaling.<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> Dietary restriction of leucine and the other BCAAs can reverse diet-induced obesity in wild-type mice by increasing energy expenditure, and can restrict fat mass gain of hyperphagic rats.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Leucine&action=edit&section=5" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Leucine toxicity, as seen in decompensated <a href="/wiki/Maple_syrup_urine_disease" title="Maple syrup urine disease">maple syrup urine disease</a>, causes delirium and neurologic compromise, and can be life-threatening.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>A high intake of leucine may cause or exacerbate symptoms of <a href="/wiki/Pellagra" title="Pellagra">pellagra</a> in people with low <a href="/wiki/Niacin_(substance)" class="mw-redirect" title="Niacin (substance)">niacin</a> status because it interferes with the conversion of <a href="/wiki/Tryptophan" title="Tryptophan">L-tryptophan</a> to niacin.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>Leucine at a dose exceeding 500 mg/kg/d was observed with <a href="/wiki/Hyperammonemia" title="Hyperammonemia">hyperammonemia</a>.<sup id="cite_ref-pmid22952178_22-0" class="reference"><a href="#cite_note-pmid22952178-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> As such, unofficially, a tolerable upper intake level (UL) for leucine in healthy adult men can be suggested at 500 mg/kg/d or 35 g/d under acute dietary conditions.<sup id="cite_ref-pmid22952178_22-1" class="reference"><a href="#cite_note-pmid22952178-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid27138628_23-0" class="reference"><a href="#cite_note-pmid27138628-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Leucine&action=edit&section=6" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Leucine&action=edit&section=7" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Leucine is a <a href="/wiki/Dietary" class="mw-redirect" title="Dietary">dietary</a> <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> with the capacity to directly stimulate <a href="/wiki/Myofibrillar" class="mw-redirect" title="Myofibrillar">myofibrillar</a> muscle <a href="/wiki/Protein_biosynthesis" title="Protein biosynthesis">protein synthesis</a>.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> This effect of leucine results from its role as an activator of the <a href="/wiki/Mechanistic_target_of_rapamycin" class="mw-redirect" title="Mechanistic target of rapamycin">mechanistic target of rapamycin</a> (mTOR),<sup id="cite_ref-Pharmacology_of_HMB-FA_in_humans_in_vivo_8-1" class="reference"><a href="#cite_note-Pharmacology_of_HMB-FA_in_humans_in_vivo-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> a <a href="/wiki/Serine-threonine_protein_kinase" class="mw-redirect" title="Serine-threonine protein kinase">serine-threonine protein kinase</a> that regulates <a href="/wiki/Protein_biosynthesis" title="Protein biosynthesis">protein biosynthesis</a> and <a href="/wiki/Cell_growth" title="Cell growth">cell growth</a>. The activation of mTOR by leucine is mediated through <a href="/wiki/Rag_GTPase" class="mw-redirect" title="Rag GTPase">Rag GTPases</a>,<sup id="cite_ref-pmid28963468_25-0" class="reference"><a href="#cite_note-pmid28963468-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid23361334_26-0" class="reference"><a href="#cite_note-pmid23361334-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid18497260_27-0" class="reference"><a href="#cite_note-pmid18497260-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> leucine <a href="/wiki/Ligand_binding" class="mw-redirect" title="Ligand binding">binding</a> to <a href="/wiki/Leucyl-tRNA_synthetase" title="Leucyl-tRNA synthetase">leucyl-tRNA synthetase</a>,<sup id="cite_ref-pmid28963468_25-1" class="reference"><a href="#cite_note-pmid28963468-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid23361334_26-1" class="reference"><a href="#cite_note-pmid23361334-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> leucine binding to <a href="/wiki/Sestrin_2" class="mw-redirect" title="Sestrin 2">sestrin 2</a>,<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> and possibly other mechanisms. </p> <div class="mw-heading mw-heading3"><h3 id="Metabolism_in_humans">Metabolism in humans</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Leucine&action=edit&section=8" title="Edit section: Metabolism in humans"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="skin-invert-image"> <table role="presentation" cellpadding="0" style="border-spacing:0; clear:right; float:right;"> <tbody><tr> <td><div class="thumb tright"> <div class="thumbinner" style="width:602px;"> <div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: light-dark(#F0F8FF,var(--background-color-neutral)); color:var(--color-base,light-dark(#202122,#eaecf0)); margin-bottom:3px;">Leucine metabolism in humans</div> <div class="skin-invert-image" style="position:relative; width:600px; height:436px; overflow:hidden; border:solid #ccc 1px; background-color:light-dark(white,transparent);"> <div style="left:0px; top:0px; width:600px; position:absolute"> <span typeof="mw:File"><a href="https://commons.wikimedia.org/wiki/File:HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg" title="commons:File:HMB biosynthesis and metabolism diagram - no labels.svg"><img alt="Diagram of leucine, HMB, and isovaleryl-CoA metabolism in humans" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg/600px-HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg.png" decoding="async" width="600" height="436" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg/900px-HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/03/HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg/1200px-HMB_biosynthesis_and_metabolism_diagram_-_no_labels.svg.png 2x" data-file-width="2126" data-file-height="1545" /></a></span> </div> <div style="text-align:center; font-size:12px; line-height:110%"> <div style="background-color:transparent; color:var(--color-base,#202122)"><div id="annotation_180x2" style="position:absolute; left:180px; top:2px; font-size:18px; font-size:18; line-height:20px;"><span style="background-color:transparent; color:inherit;"><span style="color:black;background:yellow"><b><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-Leucine</b></span></span></div> <div id="annotation_96x37" style="position:absolute; left:96px; top:37px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Branched-chain_amino_acid_aminotransferase" title="Branched-chain amino acid aminotransferase">Branched-chain amino<br />acid aminotransferase</a></span></div> <div id="annotation_240x30" style="position:absolute; left:240px; top:30px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/%CE%91-Ketoglutarate" class="mw-redirect" title="Α-Ketoglutarate">α-Ketoglutarate</a></span></div> <div id="annotation_243x61" style="position:absolute; left:243px; top:61px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">Glutamate</a></span></div> <div id="annotation_466x75" style="position:absolute; left:466px; top:75px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">Glutamate</a></span></div> <div id="annotation_383x30" style="position:absolute; left:383px; top:30px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Alanine" title="Alanine">Alanine</a></span></div> <div id="annotation_383x62" style="position:absolute; left:383px; top:62px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">Pyruvate</a></span></div> <div id="annotation_75x85" style="position:absolute; left:75px; top:85px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Skeletal_muscle" title="Skeletal muscle">Muscle</a>: <a href="/wiki/Alpha-Ketoisocaproic_acid" class="mw-redirect" title="Alpha-Ketoisocaproic acid">α-Ketoisocaproate</a> (α-KIC)</span></div> <div id="annotation_82x128" style="position:absolute; left:82px; top:128px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Liver" title="Liver">Liver</a>: <a href="/wiki/Alpha-Ketoisocaproic_acid" class="mw-redirect" title="Alpha-Ketoisocaproic acid">α-Ketoisocaproate</a> (α-KIC)</span></div> <div id="annotation_300x106" style="position:absolute; left:300px; top:106px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Branched-chain_%CE%B1-ketoacid_dehydrogenase" class="mw-redirect" title="Branched-chain α-ketoacid dehydrogenase">Branched-chain α-ketoacid<br />dehydrogenase</a> (<a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a>)</span></div> <div id="annotation_93x156" style="position:absolute; left:93px; top:156px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/4-Hydroxyphenylpyruvate_dioxygenase" title="4-Hydroxyphenylpyruvate dioxygenase">KIC-dioxygenase</a><br />(<a href="/wiki/Cytosol" title="Cytosol">cytosol</a>)</span></div> <div id="annotation_465x126" style="position:absolute; left:465px; top:126px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Isovaleryl-CoA" title="Isovaleryl-CoA">Isovaleryl-CoA</a></span></div> <div id="annotation_85x198" style="position:absolute; left:85px; top:198px; font-size:15px; font-size:15; line-height:17px;"><span style="background-color:; color:inherit;"><a href="/wiki/%CE%92-Hydroxy_%CE%B2-methylbutyric_acid" title="Β-Hydroxy β-methylbutyric acid"><b>β-Hydroxy<br />β-methylbutyrate</b></a><br />(<b>HMB</b>)</span></div> <div id="annotation_2x205" style="position:absolute; left:2px; top:205px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Excretion" title="Excretion">Excreted</a><br />in urine<br />(10–40%)</span></div> <p><br /> </p> <div id="annotation_239x217" style="position:absolute; left:239px; top:217px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Beta-Hydroxy_beta-methylbutyryl-CoA" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyryl-CoA">HMB-CoA</a></span></div> <div id="annotation_175x269" style="position:absolute; left:175px; top:269px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/HMG-CoA" title="HMG-CoA">β-Hydroxy β-methylglutaryl-CoA</a><br />(HMG-CoA)</span></div> <div id="annotation_445x208" style="position:absolute; left:445px; top:208px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Methylcrotonyl-CoA" title="Methylcrotonyl-CoA">β-Methylcrotonyl-CoA</a><br />(MC-CoA)</span></div> <div id="annotation_442x269" style="position:absolute; left:442px; top:269px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/3-Methylglutaconyl-CoA" title="3-Methylglutaconyl-CoA">β-Methylglutaconyl-CoA</a><br />(MG-CoA)</span></div> <div id="annotation_395x148" style="position:absolute; left:395px; top:148px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a></span></div> <div id="annotation_221x246" style="position:absolute; left:221px; top:246px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a></span></div> <div id="annotation_214x163" style="position:absolute; left:214px; top:163px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Oxygen" title="Oxygen">O<sub>2</sub></a></span></div> <div id="annotation_211x186" style="position:absolute; left:211px; top:186px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a></span></div> <div id="annotation_426x239" style="position:absolute; left:426px; top:239px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Properties_of_water" title="Properties of water">H<sub>2</sub>O</a></span></div> <div id="annotation_458x246" style="position:absolute; left:458px; top:246px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a></span></div> <div id="annotation_422x297" style="position:absolute; left:422px; top:297px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Properties_of_water" title="Properties of water">H<sub>2</sub>O</a></span></div> <div id="annotation_242x316" style="position:absolute; left:242px; top:316px; line-height:110%;"><span style="background-color:transparent; color:inherit;">(<a href="/wiki/Liver" title="Liver">liver</a>)<br /><a href="/wiki/HMG-CoA_lyase" class="mw-redirect" title="HMG-CoA lyase">HMG-CoA<br />lyase</a></span></div> <div id="annotation_314x208" style="position:absolute; left:314px; top:208px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Enoyl-CoA_hydratase" title="Enoyl-CoA hydratase">Enoyl-CoA hydratase</a></span></div> <div id="annotation_511x163" style="position:absolute; left:511px; top:163px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Isovaleryl-CoA_dehydrogenase" title="Isovaleryl-CoA dehydrogenase">Isovaleryl-CoA<br />dehydrogenase</a></span></div> <div id="annotation_511x238" style="position:absolute; left:511px; top:238px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Methylcrotonyl-CoA_carboxylase" title="Methylcrotonyl-CoA carboxylase">MC-CoA<br />carboxylase</a></span></div> <div id="annotation_376x254" style="position:absolute; left:376px; top:254px; font-size:12px; font-size:12; line-height:14px; text-align:center;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Methylglutaconyl-CoA_hydratase" title="Methylglutaconyl-CoA hydratase">MG-CoA<br />hydratase</a></span></div> <div id="annotation_59x316" style="position:absolute; left:59px; top:316px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/HMG-CoA_reductase" title="HMG-CoA reductase">HMG-CoA<br />reductase</a></span></div> <div id="annotation_410x331" style="position:absolute; left:410px; top:331px; font-size:12px; font-size:12; line-height:14px; text-align:right;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/HMG-CoA_synthase" class="mw-redirect" title="HMG-CoA synthase">HMG-CoA <br />synthase</a></span></div> <div id="annotation_205x387" style="position:absolute; left:205px; top:387px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/3-Hydroxybutyrate_dehydrogenase" title="3-Hydroxybutyrate dehydrogenase">β-Hydroxybutyrate<br />dehydrogenase</a></span></div> <div id="annotation_80x385" style="position:absolute; left:80px; top:385px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/File:Mevalonate_pathway.svg" title="File:Mevalonate pathway.svg">Mevalonate<br />pathway</a></span></div> <div id="annotation_389x385" style="position:absolute; left:389px; top:385px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Thiolase" title="Thiolase">Thiolase</a></span></div> <div id="annotation_274x236" style="position:absolute; left:274px; top:236px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;">Unknown<br />enzyme</span></div> <div id="annotation_152x420" style="position:absolute; left:152px; top:420px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:; color:inherit;"><a href="/wiki/Beta-Hydroxybutyric_acid" class="mw-redirect" title="Beta-Hydroxybutyric acid">β-Hydroxybutyrate</a></span></div> <div id="annotation_432x395" style="position:absolute; left:432px; top:395px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Acetoacetyl-CoA" title="Acetoacetyl-CoA">Acetoacetyl-CoA</a></span></div> <div id="annotation_328x395" style="position:absolute; left:328px; top:395px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">Acetyl-CoA</a></span></div> <div id="annotation_164x365" style="position:absolute; left:164px; top:365px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Acetoacetate" class="mw-redirect" title="Acetoacetate">Acetoacetate</a></span></div> <div id="annotation_44x365" style="position:absolute; left:44px; top:365px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Mevalonate" class="mw-redirect" title="Mevalonate">Mevalonate</a></span></div> <div id="annotation_43x420" style="position:absolute; left:43px; top:420px; font-size:13px; font-size:13; line-height:15px;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Cholesterol" title="Cholesterol">Cholesterol</a></span></div> <div id="annotation_206x209" style="position:absolute; left:206px; top:209px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>note 1<span class="cite-bracket">]</span></a></sup></span></div></div> </div> </div> <div class="thumbcaption" style="clear:left"><div style="float:left;margin-right:0.5em"><span typeof="mw:File"><span title="The image above contains clickable links"><img alt="The image above contains clickable links" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/20px-Interactive_icon.svg.png" decoding="async" width="18" height="27" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/40px-Interactive_icon.svg.png 1.5x" data-file-width="133" data-file-height="200" /></span></span></div>Human <a href="/wiki/Metabolic_pathway" title="Metabolic pathway">metabolic pathway</a> for <a href="/wiki/%CE%92-Hydroxy_%CE%B2-methylbutyric_acid" title="Β-Hydroxy β-methylbutyric acid">HMB</a> and <a href="/wiki/Isovaleryl-CoA" title="Isovaleryl-CoA">isovaleryl-CoA</a> relative to <span class="nowrap"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-leucine</span>.<sup id="cite_ref-ISSN_position_stand_2013_34-0" class="reference"><a href="#cite_note-ISSN_position_stand_2013-34"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HMB_athletic_performance-related_effects_2011_reviewb_35-0" class="reference"><a href="#cite_note-HMB_athletic_performance-related_effects_2011_reviewb-35"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Leucine_metabolism_36-0" class="reference"><a href="#cite_note-Leucine_metabolism-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Of the two major pathways, <span class="nowrap"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-leucine</span> is mostly metabolized into isovaleryl-CoA, while only about 5% is metabolized into HMB.<sup id="cite_ref-ISSN_position_stand_2013_34-1" class="reference"><a href="#cite_note-ISSN_position_stand_2013-34"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HMB_athletic_performance-related_effects_2011_reviewb_35-1" class="reference"><a href="#cite_note-HMB_athletic_performance-related_effects_2011_reviewb-35"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Leucine_metabolism_36-1" class="reference"><a href="#cite_note-Leucine_metabolism-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup></div> </div> </div> </td></tr></tbody></table> </div> <p><br /> Leucine metabolism occurs in many <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues in the human body</a>; however, most dietary leucine is metabolized within the <a href="/wiki/Liver" title="Liver">liver</a>, <a href="/wiki/Adipose_tissue" title="Adipose tissue">adipose tissue</a>, and <a href="/wiki/Muscle_tissue" class="mw-redirect" title="Muscle tissue">muscle tissue</a>.<sup id="cite_ref-pmid4855772_37-0" class="reference"><a href="#cite_note-pmid4855772-37"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> Adipose and muscle tissue use leucine in the formation of <a href="/wiki/Sterol" title="Sterol">sterols</a> and other compounds.<sup id="cite_ref-pmid4855772_37-1" class="reference"><a href="#cite_note-pmid4855772-37"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> Combined leucine use in these two tissues is seven times greater than in the liver.<sup id="cite_ref-pmid4855772_37-2" class="reference"><a href="#cite_note-pmid4855772-37"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p><p>In healthy individuals, approximately 60% of dietary <span class="nowrap"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-leucine</span> is metabolized after several hours, with roughly 5% (<span class="nowrap">2–10%</span> range) of dietary <span class="nowrap"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-leucine</span> being converted to <a href="/wiki/%CE%92-hydroxy_%CE%B2-methylbutyric_acid" class="mw-redirect" title="Β-hydroxy β-methylbutyric acid">β-hydroxy β-methylbutyric acid</a> (HMB).<sup id="cite_ref-HMB_athletic_performance-related_effects_2011_review_38-0" class="reference"><a href="#cite_note-HMB_athletic_performance-related_effects_2011_review-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Molecular_Aspects_of_Medicine_2016_review_39-0" class="reference"><a href="#cite_note-Molecular_Aspects_of_Medicine_2016_review-39"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Leucine_metabolism_36-2" class="reference"><a href="#cite_note-Leucine_metabolism-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Around 40% of dietary <span class="nowrap"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-leucine</span> is converted to <span class="nowrap">acetyl-CoA</span>, which is subsequently used in the synthesis of other compounds.<sup id="cite_ref-Leucine_metabolism_36-3" class="reference"><a href="#cite_note-Leucine_metabolism-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p><p>The vast majority of <span class="nowrap"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-leucine</span> metabolism is initially catalyzed by the <a href="/wiki/Branched-chain_amino_acid_aminotransferase" title="Branched-chain amino acid aminotransferase">branched-chain amino acid aminotransferase</a> enzyme, producing <span class="nowrap"><a href="/wiki/%CE%91-ketoisocaproate" class="mw-redirect" title="Α-ketoisocaproate">α-ketoisocaproate</a></span> (α-KIC).<sup id="cite_ref-HMB_athletic_performance-related_effects_2011_review_38-1" class="reference"><a href="#cite_note-HMB_athletic_performance-related_effects_2011_review-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Leucine_metabolism_36-4" class="reference"><a href="#cite_note-Leucine_metabolism-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> α-KIC is mostly metabolized by the <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondrial</a> enzyme <a href="/wiki/Branched-chain_alpha-keto_acid_dehydrogenase" class="mw-redirect" title="Branched-chain alpha-keto acid dehydrogenase">branched-chain <span class="nowrap">α-ketoacid</span> dehydrogenase</a>, which converts it to <a href="/wiki/Isovaleryl-CoA" title="Isovaleryl-CoA">isovaleryl-CoA</a>.<sup id="cite_ref-HMB_athletic_performance-related_effects_2011_review_38-2" class="reference"><a href="#cite_note-HMB_athletic_performance-related_effects_2011_review-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Leucine_metabolism_36-5" class="reference"><a href="#cite_note-Leucine_metabolism-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Isovaleryl-CoA is subsequently metabolized by <a href="/wiki/Isovaleryl-CoA_dehydrogenase" title="Isovaleryl-CoA dehydrogenase">isovaleryl-CoA dehydrogenase</a> and converted to <span class="nowrap">MC-CoA</span>, which is used in the synthesis of acetyl-CoA and other compounds.<sup id="cite_ref-Leucine_metabolism_36-6" class="reference"><a href="#cite_note-Leucine_metabolism-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> During <a href="/wiki/Biotin_deficiency" title="Biotin deficiency">biotin deficiency</a>, HMB can be synthesized from <span class="nowrap">MC-CoA</span> via <a href="/wiki/Enoyl-CoA_hydratase" title="Enoyl-CoA hydratase">enoyl-CoA hydratase</a> and an unknown <a href="/wiki/Thioesterase" title="Thioesterase">thioesterase</a> enzyme,<sup id="cite_ref-HMB-CoA_⇔_HMB_31-1" class="reference"><a href="#cite_note-HMB-CoA_⇔_HMB-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid21918059_32-1" class="reference"><a href="#cite_note-pmid21918059-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HMB-CoA_⇔_MC-CoA_40-0" class="reference"><a href="#cite_note-HMB-CoA_⇔_MC-CoA-40"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> which convert <span class="nowrap">MC-CoA</span> into <span class="nowrap">HMB-CoA</span> and <span class="nowrap">HMB-CoA</span> into HMB respectively.<sup id="cite_ref-pmid21918059_32-2" class="reference"><a href="#cite_note-pmid21918059-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> A relatively small amount of α-KIC is metabolized in the <a href="/wiki/Liver" title="Liver">liver</a> by the <a href="/wiki/Cytosol" title="Cytosol">cytosolic</a> enzyme <a href="/wiki/4-hydroxyphenylpyruvate_dioxygenase" class="mw-redirect" title="4-hydroxyphenylpyruvate dioxygenase">4-hydroxyphenylpyruvate dioxygenase</a> (KIC dioxygenase), which converts α-KIC to HMB.<sup id="cite_ref-HMB_athletic_performance-related_effects_2011_review_38-3" class="reference"><a href="#cite_note-HMB_athletic_performance-related_effects_2011_review-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Leucine_metabolism_36-7" class="reference"><a href="#cite_note-Leucine_metabolism-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KIC_dioxygenase_41-0" class="reference"><a href="#cite_note-KIC_dioxygenase-41"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> In healthy individuals, this minor pathway – which involves the conversion of <span class="nowrap"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-leucine</span> to α-KIC and then HMB – is the predominant route of HMB synthesis.<sup id="cite_ref-HMB_athletic_performance-related_effects_2011_review_38-4" class="reference"><a href="#cite_note-HMB_athletic_performance-related_effects_2011_review-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Leucine_metabolism_36-8" class="reference"><a href="#cite_note-Leucine_metabolism-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p><p>A small fraction of <span class="nowrap"><span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-leucine</span> metabolism – less than 5% in all tissues except the <a href="/wiki/Testes" class="mw-redirect" title="Testes">testes</a>, where it accounts for about 33% – is initially catalyzed by <a href="/wiki/Leucine_2,3-aminomutase" title="Leucine 2,3-aminomutase">leucine aminomutase</a>, producing <a href="/wiki/%CE%92-leucine" class="mw-redirect" title="Β-leucine">β-leucine</a>, which is subsequently metabolized into <span class="nowrap"><a href="/wiki/Beta-Ketoisocaproic_acid" class="mw-redirect" title="Beta-Ketoisocaproic acid">β-ketoisocaproate</a></span> (β-KIC), <a href="/w/index.php?title=%CE%92-ketoisocaproyl-CoA&action=edit&redlink=1" class="new" title="Β-ketoisocaproyl-CoA (page does not exist)">β-ketoisocaproyl-CoA</a>, and then acetyl-CoA by a series of uncharacterized enzymes.<sup id="cite_ref-Leucine_metabolism_36-9" class="reference"><a href="#cite_note-Leucine_metabolism-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BRENDA_leucine_metabolism_42-0" class="reference"><a href="#cite_note-BRENDA_leucine_metabolism-42"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>The metabolism of HMB is catalyzed by an uncharacterized enzyme which converts it to <a href="/wiki/%CE%92-hydroxy_%CE%B2-methylbutyryl-CoA" class="mw-redirect" title="Β-hydroxy β-methylbutyryl-CoA"><span class="nowrap">β-hydroxy</span> <span class="nowrap">β-methylbutyryl-CoA</span></a> (<span class="nowrap">HMB-CoA</span>).<sup id="cite_ref-HMB-CoA_⇔_HMB_31-2" class="reference"><a href="#cite_note-HMB-CoA_⇔_HMB-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Leucine_metabolism_36-10" class="reference"><a href="#cite_note-Leucine_metabolism-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> HMB-CoA is metabolized by either <a href="/wiki/Enoyl-CoA_hydratase" title="Enoyl-CoA hydratase">enoyl-CoA hydratase</a> or another uncharacterized enzyme, producing <a href="/wiki/%CE%92-methylcrotonyl-CoA" class="mw-redirect" title="Β-methylcrotonyl-CoA">β-methylcrotonyl-CoA</a> (<span class="nowrap">MC-CoA</span>) or <a href="/wiki/Hydroxymethylglutaryl-CoA" class="mw-redirect" title="Hydroxymethylglutaryl-CoA">hydroxymethylglutaryl-CoA</a> (<span class="nowrap">HMG-CoA</span>) respectively.<sup id="cite_ref-HMB_athletic_performance-related_effects_2011_review_38-5" class="reference"><a href="#cite_note-HMB_athletic_performance-related_effects_2011_review-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Leucine_metabolism_36-11" class="reference"><a href="#cite_note-Leucine_metabolism-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> <span class="nowrap">MC-CoA</span> is then converted by the enzyme <a href="/wiki/Methylcrotonyl-CoA_carboxylase" title="Methylcrotonyl-CoA carboxylase">methylcrotonyl-CoA carboxylase</a> to <a href="/wiki/Methylglutaconyl-CoA" class="mw-redirect" title="Methylglutaconyl-CoA">methylglutaconyl-CoA</a> (<span class="nowrap">MG-CoA</span>), which is subsequently converted to <span class="nowrap">HMG-CoA</span> by <a href="/wiki/Methylglutaconyl-CoA_hydratase" title="Methylglutaconyl-CoA hydratase">methylglutaconyl-CoA hydratase</a>.<sup id="cite_ref-HMB_athletic_performance-related_effects_2011_review_38-6" class="reference"><a href="#cite_note-HMB_athletic_performance-related_effects_2011_review-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Leucine_metabolism_36-12" class="reference"><a href="#cite_note-Leucine_metabolism-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BRENDA_leucine_metabolism_42-1" class="reference"><a href="#cite_note-BRENDA_leucine_metabolism-42"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> <span class="nowrap">HMG-CoA</span> is then cleaved into <span class="nowrap"><a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a></span> and <a href="/wiki/Acetoacetate" class="mw-redirect" title="Acetoacetate">acetoacetate</a> by <a href="/wiki/HMG-CoA_lyase" class="mw-redirect" title="HMG-CoA lyase"><span class="nowrap">HMG-CoA</span> lyase</a> or used in the production of cholesterol via the <a href="/wiki/Mevalonate_pathway" title="Mevalonate pathway">mevalonate pathway</a>.<sup id="cite_ref-HMB_athletic_performance-related_effects_2011_review_38-7" class="reference"><a href="#cite_note-HMB_athletic_performance-related_effects_2011_review-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Leucine_metabolism_36-13" class="reference"><a href="#cite_note-Leucine_metabolism-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis_in_nonhuman_organisms">Synthesis in nonhuman organisms</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Leucine&action=edit&section=9" title="Edit section: Synthesis in nonhuman organisms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Leucine is an essential amino acid in the diet of animals because they lack the complete enzyme pathway to synthesize it <i>de novo</i> from potential precursor compounds. Consequently, they must ingest it, usually as a component of proteins. Plants and microorganisms synthesize leucine from <a href="/wiki/Pyruvic_acid" title="Pyruvic acid">pyruvic acid</a> with a series of enzymes:<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p> <ul><li><a href="/wiki/Acetolactate_synthase" title="Acetolactate synthase">Acetolactate synthase</a></li> <li>Acetohydroxy acid isomero<a href="/wiki/Reductase" class="mw-redirect" title="Reductase">reductase</a></li> <li><a href="/wiki/Dihydroxyacid_dehydratase" class="mw-redirect" title="Dihydroxyacid dehydratase">Dihydroxyacid dehydratase</a></li> <li>α-Isopropylmalate <a href="/wiki/Synthase" title="Synthase">synthase</a></li> <li>α-Isopropylmalate <a href="/wiki/Isomerase" title="Isomerase">isomerase</a></li> <li>Leucine <a href="/wiki/Aminotransferase" class="mw-redirect" title="Aminotransferase">aminotransferase</a></li></ul> <p>Synthesis of the small, hydrophobic amino acid <a href="/wiki/Valine" title="Valine">valine</a> also includes the initial part of this pathway. </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Leucine&action=edit&section=10" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Betain-Leucin.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Betain-Leucin.png/350px-Betain-Leucin.png" decoding="async" width="350" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Betain-Leucin.png/525px-Betain-Leucin.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Betain-Leucin.png/700px-Betain-Leucin.png 2x" data-file-width="4138" data-file-height="1057" /></a><figcaption>(<i>S</i>)-Leucine (or <small>L</small>-leucine), left; (<i>R</i>)-leucine (or <small>D</small>-leucine), right, in zwitterionic form at neutral pH</figcaption></figure> <p>Leucine is a branched-chain amino acid (BCAA) since it possesses an <a href="/wiki/Aliphatic" class="mw-redirect" title="Aliphatic">aliphatic</a> side chain that is not linear. </p><p><a href="/wiki/Racemic" class="mw-redirect" title="Racemic">Racemic</a> leucine had been<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Manual_of_Style/Dates_and_numbers#Chronological_items" title="Wikipedia:Manual of Style/Dates and numbers"><span title="The time period mentioned near this tag is ambiguous. (October 2021)">when?</span></a></i>]</sup> subjected to circularly <a href="/wiki/Polarization_(waves)" title="Polarization (waves)">polarized</a> <a href="/wiki/Synchrotron_radiation" title="Synchrotron radiation">synchrotron radiation</a> to better understand the origin of biomolecular asymmetry. An enantiomeric enhancement of 2.6% had been induced, indicating a possible photochemical origin of biomolecules' <a href="/wiki/Homochirality" title="Homochirality">homochirality</a>.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Leucine&action=edit&section=11" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Leucines" title="Leucines">Leucines</a>, the isomers and derivatives of leucine</li> <li><a href="/wiki/Leucine_zipper" title="Leucine zipper">Leucine zipper</a>, a common motif in transcription factor proteins</li></ul> <div class="mw-heading mw-heading2"><h2 id="Notes">Notes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Leucine&action=edit&section=12" title="Edit section: Notes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-33">^</a></b></span> <span class="reference-text">This reaction is catalyzed by an unknown <a href="/wiki/Thioesterase" title="Thioesterase">thioesterase</a> enzyme.<sup id="cite_ref-HMB-CoA_⇔_HMB_31-0" class="reference"><a href="#cite_note-HMB-CoA_⇔_HMB-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid21918059_32-0" class="reference"><a href="#cite_note-pmid21918059-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Leucine&action=edit&section=13" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626" /><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-Binns-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Binns_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Binns_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFBinnsParsonsMcIntyre2016" class="citation journal cs1">Binns J, Parsons S, McIntyre GJ (December 2016). <a rel="nofollow" class="external text" href="https://www.pure.ed.ac.uk/ws/files/36568495/20170523_Parsons_Leucine_0410.pdf">"Accurate hydrogen parameters for the amino acid L-leucine"</a> <span class="cs1-format">(PDF)</span>. <i>Acta Crystallographica Section B</i>. <b>72</b> (Pt 6): <span class="nowrap">885–</span>92. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1107%2FS2052520616015699">10.1107/S2052520616015699</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/20.500.11820%2Fc784fdaf-aa3a-48e4-86a2-d0a0bd7fdb7a">20.500.11820/c784fdaf-aa3a-48e4-86a2-d0a0bd7fdb7a</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27910839">27910839</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:19288938">19288938</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Crystallographica+Section+B&rft.atitle=Accurate+hydrogen+parameters+for+the+amino+acid+L-leucine&rft.volume=72&rft.issue=Pt+6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E885-%3C%2Fspan%3E92&rft.date=2016-12&rft_id=info%3Ahdl%2F20.500.11820%2Fc784fdaf-aa3a-48e4-86a2-d0a0bd7fdb7a&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A19288938%23id-name%3DS2CID&rft_id=info%3Apmid%2F27910839&rft_id=info%3Adoi%2F10.1107%2FS2052520616015699&rft.aulast=Binns&rft.aufirst=J&rft.au=Parsons%2C+S&rft.au=McIntyre%2C+GJ&rft_id=https%3A%2F%2Fwww.pure.ed.ac.uk%2Fws%2Ffiles%2F36568495%2F20170523_Parsons_Leucine_0410.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text">Dawson, R.M.C., et al., <i>Data for Biochemical Research</i>, Oxford, Clarendon Press, 1959.</span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20081009023202/http://www.chem.qmul.ac.uk/iupac/AminoAcid/AA1n2.html">"Nomenclature and Symbolism for Amino Acids and Peptides"</a>. IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived from <a rel="nofollow" class="external text" href="http://www.chem.qmul.ac.uk/iupac/AminoAcid/AA1n2.html">the original</a> on 9 October 2008<span class="reference-accessdate">. Retrieved <span class="nowrap">5 March</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Nomenclature+and+Symbolism+for+Amino+Acids+and+Peptides&rft.pub=IUPAC-IUB+Joint+Commission+on+Biochemical+Nomenclature&rft.date=1983&rft_id=http%3A%2F%2Fwww.chem.qmul.ac.uk%2Fiupac%2FAminoAcid%2FAA1n2.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFleckPetrosyan2014" class="citation book cs1">Fleck, Michel; Petrosyan, Aram M. (2014). <a rel="nofollow" class="external text" href="https://link.springer.com/10.1007/978-3-319-06299-0"><i>Salts of Amino Acids: Crystallization, Structure and Properties</i></a>. Cham: Springer International Publishing. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-319-06299-0">10.1007/978-3-319-06299-0</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-319-06298-3" title="Special:BookSources/978-3-319-06298-3"><bdi>978-3-319-06298-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Salts+of+Amino+Acids%3A+Crystallization%2C+Structure+and+Properties&rft.place=Cham&rft.pub=Springer+International+Publishing&rft.date=2014&rft_id=info%3Adoi%2F10.1007%2F978-3-319-06299-0&rft.isbn=978-3-319-06298-3&rft.aulast=Fleck&rft.aufirst=Michel&rft.au=Petrosyan%2C+Aram+M.&rft_id=https%3A%2F%2Flink.springer.com%2F10.1007%2F978-3-319-06299-0&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFerrier2013" class="citation book cs1">Ferrier DR (2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=sSyMAwAAQBAJ&pg=PA266"><i>Biochemistry</i></a>. Lippincott Williams & Wilkins. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781451175622" title="Special:BookSources/9781451175622"><bdi>9781451175622</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Biochemistry&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2013&rft.isbn=9781451175622&rft.aulast=Ferrier&rft.aufirst=DR&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DsSyMAwAAQBAJ%26pg%3DPA266&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCynober2003" class="citation book cs1">Cynober LA (2003). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=X3DK4nWybaMC"><i>Metabolic & Therapeutic Aspects of Amino Acids in Clinical Nutrition</i></a> (2nd ed.). CRC Press. p. 101. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780203010266" title="Special:BookSources/9780203010266"><bdi>9780203010266</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Metabolic+%26+Therapeutic+Aspects+of+Amino+Acids+in+Clinical+Nutrition&rft.pages=101&rft.edition=2nd&rft.pub=CRC+Press&rft.date=2003&rft.isbn=9780203010266&rft.aulast=Cynober&rft.aufirst=LA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DX3DK4nWybaMC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-Pimentel_2017_systematic_review_on_HMB-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-Pimentel_2017_systematic_review_on_HMB_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSilvaBelozoMichelettiConrado2017" class="citation journal cs1">Silva VR, Belozo FL, Micheletti TO, Conrado M, Stout JR, Pimentel GD, Gonzalez AM (September 2017). "β-hydroxy-β-methylbutyrate free acid supplementation may improve recovery and muscle adaptations after resistance training: a systematic review". <i>Nutrition Research</i>. <b>45</b>: <span class="nowrap">1–</span>9. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.nutres.2017.07.008">10.1016/j.nutres.2017.07.008</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/11449%2F170023">11449/170023</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/29037326">29037326</a>. <q>HMB's mechanisms of action are generally considered to relate to its effect on both muscle protein synthesis and muscle protein breakdown (Figure 1) [2, 3]. HMB appears to stimulate muscle protein synthesis through an up-regulation of the mammalian/mechanistic target of rapamycin complex 1 (mTORC1), a signaling cascade involved in coordination of translation initiation of muscle protein synthesis [2, 4]. Additionally, HMB may have antagonistic effects on the ubiquitin–proteasome pathway, a system that degrades intracellular proteins [5, 6]. Evidence also suggests that HMB promotes myogenic proliferation, differentiation, and cell fusion [7]. ... Exogenous HMB-FA administration has shown to increase intramuscular anabolic signaling, stimulate muscle protein synthesis, and attenuate muscle protein breakdown in humans [2].</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nutrition+Research&rft.atitle=%CE%B2-hydroxy-%CE%B2-methylbutyrate+free+acid+supplementation+may+improve+recovery+and+muscle+adaptations+after+resistance+training%3A+a+systematic+review&rft.volume=45&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E9&rft.date=2017-09&rft_id=info%3Ahdl%2F11449%2F170023&rft_id=info%3Apmid%2F29037326&rft_id=info%3Adoi%2F10.1016%2Fj.nutres.2017.07.008&rft.aulast=Silva&rft.aufirst=VR&rft.au=Belozo%2C+FL&rft.au=Micheletti%2C+TO&rft.au=Conrado%2C+M&rft.au=Stout%2C+JR&rft.au=Pimentel%2C+GD&rft.au=Gonzalez%2C+AM&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-Pharmacology_of_HMB-FA_in_humans_in_vivo-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-Pharmacology_of_HMB-FA_in_humans_in_vivo_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Pharmacology_of_HMB-FA_in_humans_in_vivo_8-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWilkinsonHossainHillPhillips2013" class="citation journal cs1">Wilkinson DJ, Hossain T, Hill DS, Phillips BE, Crossland H, Williams J, et al. (June 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3690694">"Effects of leucine and its metabolite β-hydroxy-β-methylbutyrate on human skeletal muscle protein metabolism"</a>. <i>The Journal of Physiology</i>. <b>591</b> (11): <span class="nowrap">2911–</span>23. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1113%2Fjphysiol.2013.253203">10.1113/jphysiol.2013.253203</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3690694">3690694</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23551944">23551944</a>. <q>The stimulation of MPS through mTORc1-signalling following HMB exposure is in agreement with pre-clinical studies (Eley et al. 2008). ... Furthermore, there was clear divergence in the amplitude of phosphorylation for 4EBP1 (at Thr37/46 and Ser65/Thr70) and p70S6K (Thr389) in response to both Leu and HMB, with the latter showing more pronounced and sustained phosphorylation. ... Nonetheless, as the overall MPS response was similar, this cellular signalling distinction did not translate into statistically distinguishable anabolic effects in our primary outcome measure of MPS. ... Interestingly, although orally supplied HMB produced no increase in plasma insulin, it caused a depression in MPB (−57%). Normally, postprandial decreases in MPB (of ~50%) are attributed to the nitrogen-sparing effects of insulin since clamping insulin at post-absorptive concentrations (5 μU ml<sup>−1</sup>) while continuously infusing AAs (18 g h<sup>−1</sup>) did not suppress MPB (Greenhaff et al. 2008), which is why we chose not to measure MPB in the Leu group, due to an anticipated hyperinsulinaemia (Fig. 3C). Thus, HMB reduces MPB in a fashion similar to, but independent of, insulin. These findings are in-line with reports of the anti-catabolic effects of HMB suppressing MPB in pre-clinical models, via attenuating proteasomal-mediated proteolysis in response to LPS (Eley et al. 2008).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Physiology&rft.atitle=Effects+of+leucine+and+its+metabolite+%CE%B2-hydroxy-%CE%B2-methylbutyrate+on+human+skeletal+muscle+protein+metabolism&rft.volume=591&rft.issue=11&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2911-%3C%2Fspan%3E23&rft.date=2013-06&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3690694%23id-name%3DPMC&rft_id=info%3Apmid%2F23551944&rft_id=info%3Adoi%2F10.1113%2Fjphysiol.2013.253203&rft.aulast=Wilkinson&rft.aufirst=DJ&rft.au=Hossain%2C+T&rft.au=Hill%2C+DS&rft.au=Phillips%2C+BE&rft.au=Crossland%2C+H&rft.au=Williams%2C+J&rft.au=Loughna%2C+P&rft.au=Churchward-Venne%2C+TA&rft.au=Breen%2C+L&rft.au=Phillips%2C+SM&rft.au=Etheridge%2C+T&rft.au=Rathmacher%2C+JA&rft.au=Smith%2C+K&rft.au=Szewczyk%2C+NJ&rft.au=Atherton%2C+PJ&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3690694&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWinter2009" class="citation book cs1">Winter R (2009). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/isbn_9780307408921"><i>A consumer's dictionary of food additives</i></a></span> (7th ed.). New York: Three Rivers Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0307408921" title="Special:BookSources/978-0307408921"><bdi>978-0307408921</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=A+consumer%27s+dictionary+of+food+additives&rft.place=New+York&rft.edition=7th&rft.pub=Three+Rivers+Press&rft.date=2009&rft.isbn=978-0307408921&rft.aulast=Winter&rft.aufirst=R&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fisbn_9780307408921&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-DRItext-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-DRItext_10-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFInstitute_of_Medicine2002" class="citation book cs1"><a href="/wiki/Institute_of_Medicine" class="mw-redirect" title="Institute of Medicine">Institute of Medicine</a> (2002). <a rel="nofollow" class="external text" href="https://www.nap.edu/read/10490/chapter/12">"Protein and Amino Acids"</a>. <i>Dietary Reference Intakes for Energy, Carbohydrates, Fiber, Fat, Fatty Acids, Cholesterol, Protein, and Amino Acids</i>. Washington, DC: The National Academies Press. pp. <span class="nowrap">589–</span>768. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.17226%2F10490">10.17226/10490</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-309-08525-0" title="Special:BookSources/978-0-309-08525-0"><bdi>978-0-309-08525-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Protein+and+Amino+Acids&rft.btitle=Dietary+Reference+Intakes+for+Energy%2C+Carbohydrates%2C+Fiber%2C+Fat%2C+Fatty+Acids%2C+Cholesterol%2C+Protein%2C+and+Amino+Acids&rft.place=Washington%2C+DC&rft.pages=%3Cspan+class%3D%22nowrap%22%3E589-%3C%2Fspan%3E768&rft.pub=The+National+Academies+Press&rft.date=2002&rft_id=info%3Adoi%2F10.17226%2F10490&rft.isbn=978-0-309-08525-0&rft.au=Institute+of+Medicine&rft_id=https%3A%2F%2Fwww.nap.edu%2Fread%2F10490%2Fchapter%2F12&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20150303184216/http://www.nal.usda.gov/fnic/foodcomp/search/"><i>National Nutrient Database for Standard Reference</i></a>. U.S. Department of Agriculture. Archived from <a rel="nofollow" class="external text" href="https://www.nal.usda.gov/fnic/foodcomp/search/">the original</a> on 3 March 2015<span class="reference-accessdate">. Retrieved <span class="nowrap">16 September</span> 2009</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=National+Nutrient+Database+for+Standard+Reference&rft.pub=U.S.+Department+of+Agriculture&rft_id=http%3A%2F%2Fwww.nal.usda.gov%2Ffnic%2Ffoodcomp%2Fsearch%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCombaretDardevetRieuPouch2005" class="citation journal cs1">Combaret L, Dardevet D, Rieu I, Pouch MN, Béchet D, Taillandier D, et al. 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class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16195315">16195315</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Physiology&rft.atitle=A+leucine-supplemented+diet+restores+the+defective+postprandial+inhibition+of+proteasome-dependent+proteolysis+in+aged+rat+skeletal+muscle&rft.volume=569&rft.issue=Pt+2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E489-%3C%2Fspan%3E99&rft.date=2005-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1464228%23id-name%3DPMC&rft_id=info%3Apmid%2F16195315&rft_id=info%3Adoi%2F10.1113%2Fjphysiol.2005.098004&rft.aulast=Combaret&rft.aufirst=L&rft.au=Dardevet%2C+D&rft.au=Rieu%2C+I&rft.au=Pouch%2C+MN&rft.au=B%C3%A9chet%2C+D&rft.au=Taillandier%2C+D&rft.au=Grizard%2C+J&rft.au=Attaix%2C+D&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1464228&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFVerhoevenVanschoonbeekVerdijkKoopman2009" class="citation journal cs1">Verhoeven S, Vanschoonbeek K, Verdijk LB, Koopman R, Wodzig WK, Dendale P, van Loon LJ (May 2009). <a rel="nofollow" class="external text" href="https://doi.org/10.3945%2Fajcn.2008.26668">"Long-term leucine supplementation does not increase muscle mass or strength in healthy elderly men"</a>. <i>The American Journal of Clinical Nutrition</i>. <b>89</b> (5): <span class="nowrap">1468–</span>75. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3945%2Fajcn.2008.26668">10.3945/ajcn.2008.26668</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19321567">19321567</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+American+Journal+of+Clinical+Nutrition&rft.atitle=Long-term+leucine+supplementation+does+not+increase+muscle+mass+or+strength+in+healthy+elderly+men&rft.volume=89&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1468-%3C%2Fspan%3E75&rft.date=2009-05&rft_id=info%3Adoi%2F10.3945%2Fajcn.2008.26668&rft_id=info%3Apmid%2F19321567&rft.aulast=Verhoeven&rft.aufirst=S&rft.au=Vanschoonbeek%2C+K&rft.au=Verdijk%2C+LB&rft.au=Koopman%2C+R&rft.au=Wodzig%2C+WK&rft.au=Dendale%2C+P&rft.au=van+Loon%2C+LJ&rft_id=https%3A%2F%2Fdoi.org%2F10.3945%252Fajcn.2008.26668&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-pmid26054437-14"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid26054437_14-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid26054437_14-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHartmanSantosO'RiordanStafstrom2015" class="citation journal cs1">Hartman AL, Santos P, O'Riordan KJ, Stafstrom CE, Marie Hardwick J (October 2015). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4640989">"Potent anti-seizure effects of D-leucine"</a>. <i>Neurobiology of Disease</i>. <b>82</b>: <span class="nowrap">46–</span>53. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.nbd.2015.05.013">10.1016/j.nbd.2015.05.013</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a 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class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22952178">22952178</a>. <q>A significant increase in blood ammonia concentrations above normal values, plasma leucine concentrations, and urinary leucine excretion were observed with leucine intakes >500 mg · kg<sup>−1</sup> · d<sup>−1</sup>. The oxidation of l-[1-<sup>13</sup>C]-leucine expressed as label tracer oxidation in breath (F<sup>13</sup>CO<sub>2</sub>), leucine oxidation, and α-ketoisocaproic acid (KIC) oxidation led to different results: a plateau in F<sup>13</sup>CO<sub>2</sub> observed after 500 mg · kg<sup>−1</sup> · d<sup>−1</sup>, no clear plateau observed in leucine oxidation, and KIC oxidation appearing to plateau after 750 mg · kg<sup>−1</sup> · d<sup>−1</sup>. On the basis of plasma and urinary variables, the UL for leucine in healthy adult men can be suggested at 500 mg · kg<sup>−1</sup> · d<sup>−1</sup> or ~35 g/d as a cautious estimate under acute dietary conditions.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+American+Journal+of+Clinical+Nutrition&rft.atitle=Determination+of+the+tolerable+upper+intake+level+of+leucine+in+acute+dietary+studies+in+young+men&rft.volume=96&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E759-%3C%2Fspan%3E67&rft.date=2012-10&rft_id=info%3Adoi%2F10.3945%2Fajcn.111.024471&rft_id=info%3Apmid%2F22952178&rft.aulast=Elango&rft.aufirst=R&rft.au=Chapman%2C+K&rft.au=Rafii%2C+M&rft.au=Ball%2C+RO&rft.au=Pencharz%2C+PB&rft_id=https%3A%2F%2Fdoi.org%2F10.3945%252Fajcn.111.024471&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-pmid27138628-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid27138628_23-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRasmussenGilbertTurkiMadden2016" class="citation journal cs1">Rasmussen B, Gilbert E, Turki A, Madden K, Elango R (July 2016). 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(October 2014). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4223866">"The Sestrins interact with GATOR2 to negatively regulate the amino-acid-sensing pathway upstream of mTORC1"</a>. <i>Cell Reports</i>. <b>9</b> (1): <span class="nowrap">1–</span>8. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.celrep.2014.09.014">10.1016/j.celrep.2014.09.014</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4223866">4223866</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/25263562">25263562</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cell+Reports&rft.atitle=The+Sestrins+interact+with+GATOR2+to+negatively+regulate+the+amino-acid-sensing+pathway+upstream+of+mTORC1&rft.volume=9&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E8&rft.date=2014-10&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4223866%23id-name%3DPMC&rft_id=info%3Apmid%2F25263562&rft_id=info%3Adoi%2F10.1016%2Fj.celrep.2014.09.014&rft.aulast=Chantranupong&rft.aufirst=L&rft.au=Wolfson%2C+RL&rft.au=Orozco%2C+JM&rft.au=Saxton%2C+RA&rft.au=Scaria%2C+SM&rft.au=Bar-Peled%2C+L&rft.au=Spooner%2C+E&rft.au=Isasa%2C+M&rft.au=Gygi%2C+SP&rft.au=Sabatini%2C+DM&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4223866&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-HMB-CoA_⇔_HMB-31"><span class="mw-cite-backlink">^ <a href="#cite_ref-HMB-CoA_⇔_HMB_31-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-HMB-CoA_⇔_HMB_31-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-HMB-CoA_⇔_HMB_31-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.genome.jp/dbget-bin/www_bget?rn:R10759">"KEGG Reaction: R10759"</a>. <i>Kyoto Encyclopedia of Genes and Genomes</i>. Kanehisa Laboratories. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160701140720/http://www.genome.jp/dbget-bin/www_bget?rn:R10759">Archived</a> from the original on 1 July 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">24 June</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Kyoto+Encyclopedia+of+Genes+and+Genomes&rft.atitle=KEGG+Reaction%3A+R10759&rft_id=http%3A%2F%2Fwww.genome.jp%2Fdbget-bin%2Fwww_bget%3Frn%3AR10759&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-pmid21918059-32"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid21918059_32-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid21918059_32-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid21918059_32-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMockStrattonHorvathBogusiewicz2011" class="citation journal cs1">Mock DM, Stratton SL, Horvath TD, Bogusiewicz A, Matthews NI, Henrich CL, Dawson AM, Spencer HJ, Owen SN, Boysen G, Moran JH (November 2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3192457">"Urinary excretion of 3-hydroxyisovaleric acid and 3-hydroxyisovaleryl carnitine increases in response to a leucine challenge in marginally biotin-deficient humans"</a>. primary source. <i>The Journal of Nutrition</i>. <b>141</b> (11): <span class="nowrap">1925–</span>1930. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3945%2Fjn.111.146126">10.3945/jn.111.146126</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3192457">3192457</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21918059">21918059</a>. <q>Reduced activity of MCC impairs catalysis of an essential step in the mitochondrial catabolism of the BCAA leucine. Metabolic impairment diverts methylcrotonyl CoA to 3-hydroxyisovaleryl CoA in a reaction catalyzed by enoyl-CoA hydratase (22, 23). 3-Hydroxyisovaleryl CoA accumulation can inhibit cellular respiration either directly or via effects on the ratios of acyl CoA:free CoA if further metabolism and detoxification of 3-hydroxyisovaleryl CoA does not occur (22). The transfer to carnitine by 4 carnitine acyl-CoA transferases distributed in subcellular compartments likely serves as an important reservoir for acyl moieties (39–41). 3-Hydroxyisovaleryl CoA is likely detoxified by carnitine acetyltransferase producing 3HIA-carnitine, which is transported across the inner mitochondrial membrane (and hence effectively out of the mitochondria) via carnitine-acylcarnitine translocase (39). 3HIA-carnitine is thought to be either directly deacylated by a hydrolase to 3HIA or to undergo a second CoA exchange to again form 3-hydroxyisovaleryl CoA followed by release of 3HIA and free CoA by a thioesterase.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Nutrition&rft.atitle=Urinary+excretion+of+3-hydroxyisovaleric+acid+and+3-hydroxyisovaleryl+carnitine+increases+in+response+to+a+leucine+challenge+in+marginally+biotin-deficient+humans&rft.volume=141&rft.issue=11&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1925-%3C%2Fspan%3E1930&rft.date=2011-11&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3192457%23id-name%3DPMC&rft_id=info%3Apmid%2F21918059&rft_id=info%3Adoi%2F10.3945%2Fjn.111.146126&rft.aulast=Mock&rft.aufirst=DM&rft.au=Stratton%2C+SL&rft.au=Horvath%2C+TD&rft.au=Bogusiewicz%2C+A&rft.au=Matthews%2C+NI&rft.au=Henrich%2C+CL&rft.au=Dawson%2C+AM&rft.au=Spencer%2C+HJ&rft.au=Owen%2C+SN&rft.au=Boysen%2C+G&rft.au=Moran%2C+JH&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3192457&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-ISSN_position_stand_2013-34"><span class="mw-cite-backlink">^ <a href="#cite_ref-ISSN_position_stand_2013_34-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ISSN_position_stand_2013_34-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWilsonFitschenCampbellWilson2013" class="citation journal cs1">Wilson JM, Fitschen PJ, Campbell B, Wilson GJ, Zanchi N, Taylor L, Wilborn C, Kalman DS, Stout JR, Hoffman JR, Ziegenfuss TN, Lopez HL, Kreider RB, Smith-Ryan AE, Antonio J (February 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3568064">"International Society of Sports Nutrition Position Stand: beta-hydroxy-beta-methylbutyrate (HMB)"</a>. <i>Journal of the International Society of Sports Nutrition</i>. <b>10</b> (1): 6. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1186%2F1550-2783-10-6">10.1186/1550-2783-10-6</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3568064">3568064</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23374455">23374455</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+International+Society+of+Sports+Nutrition&rft.atitle=International+Society+of+Sports+Nutrition+Position+Stand%3A+beta-hydroxy-beta-methylbutyrate+%28HMB%29&rft.volume=10&rft.issue=1&rft.pages=6&rft.date=2013-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3568064%23id-name%3DPMC&rft_id=info%3Apmid%2F23374455&rft_id=info%3Adoi%2F10.1186%2F1550-2783-10-6&rft.aulast=Wilson&rft.aufirst=JM&rft.au=Fitschen%2C+PJ&rft.au=Campbell%2C+B&rft.au=Wilson%2C+GJ&rft.au=Zanchi%2C+N&rft.au=Taylor%2C+L&rft.au=Wilborn%2C+C&rft.au=Kalman%2C+DS&rft.au=Stout%2C+JR&rft.au=Hoffman%2C+JR&rft.au=Ziegenfuss%2C+TN&rft.au=Lopez%2C+HL&rft.au=Kreider%2C+RB&rft.au=Smith-Ryan%2C+AE&rft.au=Antonio%2C+J&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3568064&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-HMB_athletic_performance-related_effects_2011_reviewb-35"><span class="mw-cite-backlink">^ <a href="#cite_ref-HMB_athletic_performance-related_effects_2011_reviewb_35-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-HMB_athletic_performance-related_effects_2011_reviewb_35-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFZanchiGerlinger-RomeroGuimarães-Ferreirade_Siqueira_Filho2011" class="citation journal cs1">Zanchi NE, Gerlinger-Romero F, Guimarães-Ferreira L, de Siqueira Filho MA, Felitti V, Lira FS, Seelaender M, Lancha AH (April 2011). <a rel="nofollow" class="external text" href="https://repositorio.unal.edu.co/handle/unal/77957">"HMB supplementation: clinical and athletic performance-related effects and mechanisms of action"</a>. <i>Amino Acids</i>. <b>40</b> (4): <span class="nowrap">1015–</span>1025. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs00726-010-0678-0">10.1007/s00726-010-0678-0</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20607321">20607321</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:11120110">11120110</a>. <q>HMB is a metabolite of the amino acid leucine (Van Koverin and Nissen 1992), an essential amino acid. The first step in HMB metabolism is the reversible transamination of leucine to [α-KIC] that occurs mainly extrahepatically (Block and Buse 1990). Following this enzymatic reaction, [α-KIC] may follow one of two pathways. In the first, HMB is produced from [α-KIC] by the cytosolic enzyme KIC dioxygenase (Sabourin and Bieber 1983). The cytosolic dioxygenase has been characterized extensively and differs from the mitochondrial form in that the dioxygenase enzyme is a cytosolic enzyme, whereas the dehydrogenase enzyme is found exclusively in the mitochondrion (Sabourin and Bieber 1981, 1983). Importantly, this route of HMB formation is direct and completely dependent of liver KIC dioxygenase. Following this pathway, HMB in the cytosol is first converted to cytosolic β-hydroxy-β-methylglutaryl-CoA (HMG-CoA), which can then be directed for cholesterol synthesis (Rudney 1957) (Fig. 1). In fact, numerous biochemical studies have shown that HMB is a precursor of cholesterol (Zabin and Bloch 1951; Nissen et al. 2000).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Amino+Acids&rft.atitle=HMB+supplementation%3A+clinical+and+athletic+performance-related+effects+and+mechanisms+of+action&rft.volume=40&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1015-%3C%2Fspan%3E1025&rft.date=2011-04&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A11120110%23id-name%3DS2CID&rft_id=info%3Apmid%2F20607321&rft_id=info%3Adoi%2F10.1007%2Fs00726-010-0678-0&rft.aulast=Zanchi&rft.aufirst=NE&rft.au=Gerlinger-Romero%2C+F&rft.au=Guimar%C3%A3es-Ferreira%2C+L&rft.au=de+Siqueira+Filho%2C+MA&rft.au=Felitti%2C+V&rft.au=Lira%2C+FS&rft.au=Seelaender%2C+M&rft.au=Lancha%2C+AH&rft_id=https%3A%2F%2Frepositorio.unal.edu.co%2Fhandle%2Funal%2F77957&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-Leucine_metabolism-36"><span class="mw-cite-backlink">^ <a href="#cite_ref-Leucine_metabolism_36-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Leucine_metabolism_36-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Leucine_metabolism_36-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Leucine_metabolism_36-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Leucine_metabolism_36-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Leucine_metabolism_36-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Leucine_metabolism_36-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Leucine_metabolism_36-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Leucine_metabolism_36-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-Leucine_metabolism_36-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-Leucine_metabolism_36-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-Leucine_metabolism_36-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-Leucine_metabolism_36-12"><sup><i><b>m</b></i></sup></a> <a href="#cite_ref-Leucine_metabolism_36-13"><sup><i><b>n</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKohlmeier2015" class="citation book cs1">Kohlmeier M (May 2015). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=aTQTAAAAQBAJ&q=beta-hydroxy%20beta-methylbutyrate%20HMB&pg=PA387">"Leucine"</a>. <a rel="nofollow" class="external text" href="https://books.google.com/books?id=aTQTAAAAQBAJ"><i>Nutrient Metabolism: Structures, Functions, and Genes</i></a> (2nd ed.). Academic Press. pp. <span class="nowrap">385–</span>388. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-387784-0" title="Special:BookSources/978-0-12-387784-0"><bdi>978-0-12-387784-0</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180322000056/https://books.google.com/books?id=aTQTAAAAQBAJ&printsec=frontcover">Archived</a> from the original on 22 March 2018<span class="reference-accessdate">. Retrieved <span class="nowrap">6 June</span> 2016</span>. <q>Energy fuel: Eventually, most Leu is broken down, providing about 6.0kcal/g. About 60% of ingested Leu is oxidized within a few hours ... Ketogenesis: A significant proportion (40% of an ingested dose) is converted into acetyl-CoA and thereby contributes to the synthesis of ketones, steroids, fatty acids, and other compounds</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Leucine&rft.btitle=Nutrient+Metabolism%3A+Structures%2C+Functions%2C+and+Genes&rft.pages=%3Cspan+class%3D%22nowrap%22%3E385-%3C%2Fspan%3E388&rft.edition=2nd&rft.pub=Academic+Press&rft.date=2015-05&rft.isbn=978-0-12-387784-0&rft.aulast=Kohlmeier&rft.aufirst=M&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DaTQTAAAAQBAJ%26q%3Dbeta-hydroxy%2520beta-methylbutyrate%2520HMB%26pg%3DPA387&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span><br /><a rel="nofollow" class="external text" href="https://books.google.com/books?id=aTQTAAAAQBAJ&pg=PA386">Figure 8.57: Metabolism of <span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-leucine</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180322000056/https://books.google.com/books?id=aTQTAAAAQBAJ&pg=PA386">Archived</a> 22 March 2018 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></span> </li> <li id="cite_note-pmid4855772-37"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid4855772_37-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid4855772_37-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid4855772_37-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRosenthalAngelFarkas1974" class="citation journal cs1">Rosenthal J, Angel A, Farkas J (February 1974). "Metabolic fate of leucine: a significant sterol precursor in adipose tissue and muscle". <i>The American Journal of Physiology</i>. <b>226</b> (2): <span class="nowrap">411–</span>18. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1152%2Fajplegacy.1974.226.2.411">10.1152/ajplegacy.1974.226.2.411</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/4855772">4855772</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+American+Journal+of+Physiology&rft.atitle=Metabolic+fate+of+leucine%3A+a+significant+sterol+precursor+in+adipose+tissue+and+muscle&rft.volume=226&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E411-%3C%2Fspan%3E18&rft.date=1974-02&rft_id=info%3Adoi%2F10.1152%2Fajplegacy.1974.226.2.411&rft_id=info%3Apmid%2F4855772&rft.aulast=Rosenthal&rft.aufirst=J&rft.au=Angel%2C+A&rft.au=Farkas%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-HMB_athletic_performance-related_effects_2011_review-38"><span class="mw-cite-backlink">^ <a href="#cite_ref-HMB_athletic_performance-related_effects_2011_review_38-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-HMB_athletic_performance-related_effects_2011_review_38-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-HMB_athletic_performance-related_effects_2011_review_38-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-HMB_athletic_performance-related_effects_2011_review_38-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-HMB_athletic_performance-related_effects_2011_review_38-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-HMB_athletic_performance-related_effects_2011_review_38-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-HMB_athletic_performance-related_effects_2011_review_38-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-HMB_athletic_performance-related_effects_2011_review_38-7"><sup><i><b>h</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFZanchiGerlinger-RomeroGuimarães-Ferreirade_Siqueira_Filho2011" class="citation journal cs1">Zanchi NE, Gerlinger-Romero F, Guimarães-Ferreira L, de Siqueira Filho MA, Felitti V, Lira FS, Seelaender M, Lancha AH (April 2011). <a rel="nofollow" class="external text" href="https://repositorio.unal.edu.co/handle/unal/77957">"HMB supplementation: clinical and athletic performance-related effects and mechanisms of action"</a>. <i>Amino Acids</i>. <b>40</b> (4): <span class="nowrap">1015–</span>1025. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs00726-010-0678-0">10.1007/s00726-010-0678-0</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20607321">20607321</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:11120110">11120110</a>. <q>HMB is a metabolite of the amino acid leucine (Van Koverin and Nissen 1992), an essential amino acid. The first step in HMB metabolism is the reversible transamination of leucine to [α-KIC] that occurs mainly extrahepatically (Block and Buse 1990). Following this enzymatic reaction, [α-KIC] may follow one of two pathways. In the first, HMB is produced from [α-KIC] by the cytosolic enzyme KIC dioxygenase (Sabourin and Bieber 1983). The cytosolic dioxygenase has been characterized extensively and differs from the mitochondrial form in that the dioxygenase enzyme is a cytosolic enzyme, whereas the dehydrogenase enzyme is found exclusively in the mitochondrion (Sabourin and Bieber 1981, 1983). Importantly, this route of HMB formation is direct and completely dependent of liver KIC dioxygenase. Following this pathway, HMB in the cytosol is first converted to cytosolic β-hydroxy-β-methylglutaryl-CoA (HMG-CoA), which can then be directed for cholesterol synthesis (Rudney 1957) (Fig. 1). In fact, numerous biochemical studies have shown that HMB is a precursor of cholesterol (Zabin and Bloch 1951; Nissen et al. 2000).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Amino+Acids&rft.atitle=HMB+supplementation%3A+clinical+and+athletic+performance-related+effects+and+mechanisms+of+action&rft.volume=40&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1015-%3C%2Fspan%3E1025&rft.date=2011-04&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A11120110%23id-name%3DS2CID&rft_id=info%3Apmid%2F20607321&rft_id=info%3Adoi%2F10.1007%2Fs00726-010-0678-0&rft.aulast=Zanchi&rft.aufirst=NE&rft.au=Gerlinger-Romero%2C+F&rft.au=Guimar%C3%A3es-Ferreira%2C+L&rft.au=de+Siqueira+Filho%2C+MA&rft.au=Felitti%2C+V&rft.au=Lira%2C+FS&rft.au=Seelaender%2C+M&rft.au=Lancha%2C+AH&rft_id=https%3A%2F%2Frepositorio.unal.edu.co%2Fhandle%2Funal%2F77957&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-Molecular_Aspects_of_Medicine_2016_review-39"><span class="mw-cite-backlink"><b><a href="#cite_ref-Molecular_Aspects_of_Medicine_2016_review_39-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBriochePaganoPyChopard2016" class="citation journal cs1">Brioche T, Pagano AF, Py G, Chopard A (August 2016). <a rel="nofollow" class="external text" href="https://hal.archives-ouvertes.fr/hal-01837630/file/2016_Brioche_MAM_1.pdf">"Muscle wasting and aging: Experimental models, fatty infiltrations, and prevention"</a> <span class="cs1-format">(PDF)</span>. <i>Molecular Aspects of Medicine</i>. <b>50</b>: <span class="nowrap">56–</span>87. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.mam.2016.04.006">10.1016/j.mam.2016.04.006</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27106402">27106402</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:29717535">29717535</a>. <q>In conclusion, HMB treatment clearly appears to be a safe potent strategy against sarcopenia, and more generally against muscle wasting, because HMB improves muscle mass, muscle strength, and physical performance. It seems that HMB is able to act on three of the four major mechanisms involved in muscle deconditioning (protein turnover, apoptosis, and the regenerative process), whereas it is hypothesized to strongly affect the fourth (mitochondrial dynamics and functions). Moreover, HMB is inexpensive (~30– 50 US dollars per month at 3 g per day) and may prevent osteopenia (Bruckbauer and Zemel, 2013; Tatara, 2009; Tatara et al., 2007, 2008, 2012) and decrease cardiovascular risks (Nissen et al., 2000). For all these reasons, HMB should be routinely used in muscle-wasting conditions especially in aged people. ... 3 g of CaHMB taken three times a day (1 g each time) is the optimal posology, which allows for continual bioavailability of HMB in the body (Wilson et al., 2013)</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecular+Aspects+of+Medicine&rft.atitle=Muscle+wasting+and+aging%3A+Experimental+models%2C+fatty+infiltrations%2C+and+prevention&rft.volume=50&rft.pages=%3Cspan+class%3D%22nowrap%22%3E56-%3C%2Fspan%3E87&rft.date=2016-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A29717535%23id-name%3DS2CID&rft_id=info%3Apmid%2F27106402&rft_id=info%3Adoi%2F10.1016%2Fj.mam.2016.04.006&rft.aulast=Brioche&rft.aufirst=T&rft.au=Pagano%2C+AF&rft.au=Py%2C+G&rft.au=Chopard%2C+A&rft_id=https%3A%2F%2Fhal.archives-ouvertes.fr%2Fhal-01837630%2Ffile%2F2016_Brioche_MAM_1.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-HMB-CoA_⇔_MC-CoA-40"><span class="mw-cite-backlink"><b><a href="#cite_ref-HMB-CoA_⇔_MC-CoA_40-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.genome.jp/dbget-bin/www_bget?rn:R04137">"KEGG Reaction: R04137"</a>. <i>Kyoto Encyclopedia of Genes and Genomes</i>. Kanehisa Laboratories. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160701144143/http://www.genome.jp/dbget-bin/www_bget?rn:R04137">Archived</a> from the original on 1 July 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">24 June</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Kyoto+Encyclopedia+of+Genes+and+Genomes&rft.atitle=KEGG+Reaction%3A+R04137&rft_id=http%3A%2F%2Fwww.genome.jp%2Fdbget-bin%2Fwww_bget%3Frn%3AR04137&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-KIC_dioxygenase-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-KIC_dioxygenase_41-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.biocyc.org/META/NEW-IMAGE?type=REACTION&object=RXN-13640">"Homo sapiens: 4-hydroxyphenylpyruvate dioxygenase reaction"</a>. <i>MetaCyc</i>. SRI International. 20 August 2012<span class="reference-accessdate">. Retrieved <span class="nowrap">6 June</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=MetaCyc&rft.atitle=Homo+sapiens%3A+4-hydroxyphenylpyruvate+dioxygenase+reaction&rft.date=2012-08-20&rft_id=http%3A%2F%2Fwww.biocyc.org%2FMETA%2FNEW-IMAGE%3Ftype%3DREACTION%26object%3DRXN-13640&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-BRENDA_leucine_metabolism-42"><span class="mw-cite-backlink">^ <a href="#cite_ref-BRENDA_leucine_metabolism_42-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-BRENDA_leucine_metabolism_42-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20160817213425/http://www.brenda-enzymes.org/pathways/Maps/pathways/leucine_metabolism.svg">"Leucine metabolism"</a>. <i>BRENDA</i>. Technische Universität Braunschweig. Archived from <a rel="nofollow" class="external text" href="http://www.brenda-enzymes.org/pathways/Maps/pathways/leucine_metabolism.svg">the original</a> on 17 August 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">12 August</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=BRENDA&rft.atitle=Leucine+metabolism&rft_id=http%3A%2F%2Fwww.brenda-enzymes.org%2Fpathways%2FMaps%2Fpathways%2Fleucine_metabolism.svg&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-43">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLehningerNelsonCox2000" class="citation book cs1">Lehninger AL, Nelson DL, Cox MM (2000). <i>Lehninger principles of biochemistry</i> (3rd ed.). New York: Worth Publishers. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-57259-153-0" title="Special:BookSources/978-1-57259-153-0"><bdi>978-1-57259-153-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Lehninger+principles+of+biochemistry.&rft.place=New+York&rft.edition=3rd&rft.pub=Worth+Publishers&rft.date=2000&rft.isbn=978-1-57259-153-0&rft.aulast=Lehninger&rft.aufirst=AL&rft.au=Nelson%2C+DL&rft.au=Cox%2C+MM&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALeucine" class="Z3988"></span></span> </li> <li id="cite_note-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-44">^</a></b></span> <span class="reference-text"><a href="/wiki/Uwe_Meierhenrich" title="Uwe Meierhenrich">Meierhenrich</a>: <i>Amino acids and the asymmetry of life</i>, Springer-Verlag, 2008, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-76885-2" title="Special:BookSources/978-3-540-76885-2">978-3-540-76885-2</a>.</span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Leucine&action=edit&section=14" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20170506172105/http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/AminoAcid/Leu.html">Leucine Biosynthesis</a> at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> (archived 2017-05-06)</li></ul> <div class="navbox-styles"><style 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.navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /></div><div role="navigation" class="navbox" aria-labelledby="Encoded_(proteinogenic)_amino_acids563" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="3"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Proteinogenic_amino_acids" title="Template:Proteinogenic amino acids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Proteinogenic_amino_acids" title="Template talk:Proteinogenic amino acids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Proteinogenic_amino_acids" title="Special:EditPage/Template:Proteinogenic amino acids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Encoded_(proteinogenic)_amino_acids563" style="font-size:114%;margin:0 4em"><a href="/wiki/Proteinogenic_amino_acid" title="Proteinogenic amino acid">Encoded (proteinogenic) amino acids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">General topics</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Protein" title="Protein">Protein</a></li> <li><a href="/wiki/Peptide" title="Peptide">Peptide</a></li> <li><a href="/wiki/Genetic_code" title="Genetic code">Genetic code</a></li></ul> </div></td><td class="noviewer navbox-image" rowspan="2" style="width:1px;padding:0 0 0 2px"><div><figure typeof="mw:File/Thumb"><a href="/wiki/File:L-amino_acid_any.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/L-amino_acid_any.png/120px-L-amino_acid_any.png" decoding="async" width="100" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/L-amino_acid_any.png/250px-L-amino_acid_any.png 1.5x" data-file-width="728" data-file-height="640" /></a><figcaption>Unspecified L-amino acid</figcaption></figure></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">By properties</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aliphatic_compound" title="Aliphatic compound">Aliphatic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Branched-chain_amino_acid" title="Branched-chain amino acid">Branched-chain amino acids</a> (<a href="/wiki/Valine" title="Valine">Valine</a></li> <li><a href="/wiki/Isoleucine" title="Isoleucine">Isoleucine</a></li> <li><a class="mw-selflink selflink">Leucine</a>)</li> <li><a href="/wiki/Methionine" title="Methionine">Methionine</a></li> <li><a href="/wiki/Alanine" title="Alanine">Alanine</a></li> <li><a href="/wiki/Proline" title="Proline">Proline</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aromatic_amino_acid" title="Aromatic amino acid">Aromatic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Histidine" title="Histidine">Histidine</a></li> <li><a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chemical_polarity" title="Chemical polarity">Polar</a>, uncharged</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Asparagine" title="Asparagine">Asparagine</a></li> <li><a href="/wiki/Glutamine" title="Glutamine">Glutamine</a></li> <li><a href="/wiki/Serine" title="Serine">Serine</a></li> <li><a href="/wiki/Threonine" title="Threonine">Threonine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Positive charge (p<i>K</i><sub>a</sub>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Lysine" title="Lysine">Lysine</a> (≈10.8)</li> <li><a href="/wiki/Arginine" title="Arginine">Arginine</a> (≈12.5)</li> <li><a href="/wiki/Histidine" title="Histidine">Histidine</a> (≈6.1)</li> <li><a href="/wiki/Pyrrolysine" title="Pyrrolysine">Pyrrolysine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Negative charge (p<i>K</i><sub>a</sub>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aspartic_acid" title="Aspartic acid">Aspartic acid</a> (≈3.9)</li> <li><a href="/wiki/Glutamic_acid" title="Glutamic acid">Glutamic acid</a> (≈4.1)</li> <li><a href="/wiki/Selenocysteine" title="Selenocysteine">Selenocysteine</a> (≈5.4)</li> <li><a href="/wiki/Cysteine" title="Cysteine">Cysteine</a> (≈8.3)</li> <li><a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a> (≈10.1)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="3"><div><div class="hlist" style="font-size:88%;"> <ul><li><b><a href="/wiki/Amino_acids" class="mw-redirect" title="Amino acids">Amino acids</a> types</b>: <a href="/wiki/Template:Encoded_amino_acids" class="mw-redirect" title="Template:Encoded amino acids">Encoded (proteins)</a></li> <li><a href="/wiki/Essential_amino_acids" class="mw-redirect" title="Essential amino acids">Essential</a></li> <li><a href="/wiki/Template:Non-proteinogenic_amino_acids" title="Template:Non-proteinogenic amino acids">Non-proteinogenic</a></li> <li><a href="/wiki/Ketogenic_amino_acids" class="mw-redirect" title="Ketogenic amino acids">Ketogenic</a></li> <li><a href="/wiki/Glucogenic_amino_acids" class="mw-redirect" title="Glucogenic amino acids">Glucogenic</a></li> <li><a href="/wiki/Secondary_amino_acid" title="Secondary amino acid">Secondary amino</a></li> <li><a href="/wiki/Imino_acid" title="Imino acid">Imino acids</a></li> <li><a href="/wiki/D-amino_acids" class="mw-redirect" title="D-amino acids">D-amino acids</a></li> <li><a href="/wiki/Dehydroamino_acid" title="Dehydroamino acid">Dehydroamino acids</a></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Amino_acid_metabolism_metabolic_intermediates153" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Amino_acid_metabolism_intermediates" title="Template:Amino acid metabolism intermediates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Amino_acid_metabolism_intermediates" title="Template talk:Amino acid metabolism intermediates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Amino_acid_metabolism_intermediates" title="Special:EditPage/Template:Amino acid metabolism intermediates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Amino_acid_metabolism_metabolic_intermediates153" style="font-size:114%;margin:0 4em"><a href="/wiki/Amino_acid" title="Amino acid">Amino acid</a> <a href="/wiki/Amino_acid_synthesis" title="Amino acid synthesis">metabolism</a> <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ketogenic_amino_acid" title="Ketogenic amino acid">K</a>→<a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lysine" title="Lysine">lysine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Saccharopine" title="Saccharopine">Saccharopine</a></li> <li><a href="/wiki/Allysine" title="Allysine">Allysine</a></li> <li><a href="/wiki/Alpha-Aminoadipic_acid" class="mw-redirect" title="Alpha-Aminoadipic acid">α-Aminoadipic acid</a></li> <li><a href="/wiki/2-Oxoadipic_acid" title="2-Oxoadipic acid">2-Oxoadipic acid</a></li> <li><a href="/wiki/Glutaryl-CoA" title="Glutaryl-CoA">Glutaryl-CoA</a></li> <li><a href="/wiki/Glutaconyl-CoA" title="Glutaconyl-CoA">Glutaconyl-CoA</a></li> <li><a href="/wiki/Crotonyl-CoA" title="Crotonyl-CoA">Crotonyl-CoA</a></li> <li><a href="/wiki/Beta-Hydroxybutyryl-CoA" class="mw-redirect" title="Beta-Hydroxybutyryl-CoA">β-Hydroxybutyryl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">leucine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Beta-Hydroxy_beta-methylbutyric_acid" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyric acid">β-Hydroxy β-methylbutyric acid</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyryl-CoA" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyryl-CoA">β-Hydroxy β-methylbutyryl-CoA</a></li> <li><a href="/wiki/Isovaleryl-CoA" title="Isovaleryl-CoA">Isovaleryl-CoA</a></li> <li><a href="/wiki/Alpha-Ketoisocaproic_acid" class="mw-redirect" title="Alpha-Ketoisocaproic acid">α-Ketoisocaproic acid</a></li> <li><a href="/wiki/Beta-Ketoisocaproic_acid" class="mw-redirect" title="Beta-Ketoisocaproic acid">β-Ketoisocaproic acid</a></li> <li><a href="/w/index.php?title=Beta-Ketoisocaproyl-CoA&action=edit&redlink=1" class="new" title="Beta-Ketoisocaproyl-CoA (page does not exist)">β-Ketoisocaproyl-CoA</a></li> <li><a href="/wiki/%CE%92-Leucine" title="Β-Leucine">β-Leucine</a></li> <li><a href="/wiki/Methylcrotonyl-CoA" title="Methylcrotonyl-CoA">β-Methylcrotonyl-CoA</a></li> <li><a href="/wiki/%CE%92-Methylglutaconyl-CoA" class="mw-redirect" title="Β-Methylglutaconyl-CoA">β-Methylglutaconyl-CoA</a></li> <li><a href="/wiki/HMG-CoA" title="HMG-CoA">β-Hydroxy β-methylglutaryl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a>→<a href="/wiki/Alanine" title="Alanine">alanine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/N%27-Formylkynurenine" title="N'-Formylkynurenine"><i>N</i>′-Formylkynurenine</a></li> <li><a href="/wiki/Kynurenine" title="Kynurenine">Kynurenine</a></li> <li><a href="/wiki/Anthranilic_acid" title="Anthranilic acid">Anthranilic acid</a></li> <li><a href="/wiki/3-Hydroxykynurenine" title="3-Hydroxykynurenine">3-Hydroxykynurenine</a></li> <li><a href="/wiki/3-Hydroxyanthranilic_acid" title="3-Hydroxyanthranilic acid">3-Hydroxyanthranilic acid</a></li> <li><a href="/wiki/2-Amino-3-carboxymuconic_semialdehyde" title="2-Amino-3-carboxymuconic semialdehyde">2-Amino-3-carboxymuconic semialdehyde</a></li> <li><a href="/wiki/2-Aminomuconic_semialdehyde" title="2-Aminomuconic semialdehyde">2-Aminomuconic semialdehyde</a></li> <li><a href="/wiki/2-Aminomuconic_acid" title="2-Aminomuconic acid">2-Aminomuconic acid</a></li> <li><a href="/wiki/Glutaryl-CoA" title="Glutaryl-CoA">Glutaryl-CoA</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glucogenic_amino_acid" title="Glucogenic amino acid">G</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a>→ <br /><a href="/wiki/Citrate" class="mw-redirect" title="Citrate">citrate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="glycine→serine→31" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glycine" title="Glycine">glycine</a>→<br /><a href="/wiki/Serine" title="Serine">serine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Phosphoglyceric_acid" title="3-Phosphoglyceric acid">3-Phosphoglyceric acid</a></li></ul> <ul><li><a href="/wiki/Glycine" title="Glycine">glycine</a>→<a href="/wiki/Creatine" title="Creatine">creatine</a>: <a href="/wiki/Glycocyamine" title="Glycocyamine">Glycocyamine</a></li> <li><a href="/wiki/Phosphocreatine" title="Phosphocreatine">Phosphocreatine</a></li> <li><a href="/wiki/Creatinine" title="Creatinine">Creatinine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a>→<br /><a href="/wiki/Alpha-Ketoglutaric_acid" class="mw-redirect" title="Alpha-Ketoglutaric acid">α-ketoglutarate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Histidine" title="Histidine">histidine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Urocanic_acid" title="Urocanic acid">Urocanic acid</a></li> <li><a href="/wiki/Imidazol-4-one-5-propionic_acid" title="Imidazol-4-one-5-propionic acid">Imidazol-4-one-5-propionic acid</a></li> <li><a href="/wiki/Formiminoglutamic_acid" title="Formiminoglutamic acid">Formiminoglutamic acid</a></li> <li><a href="/wiki/Glutamate-1-semialdehyde" title="Glutamate-1-semialdehyde">Glutamate-1-semialdehyde</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Proline" title="Proline">proline</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Pyrroline-5-carboxylic_acid" title="1-Pyrroline-5-carboxylic acid">1-Pyrroline-5-carboxylic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arginine" title="Arginine">arginine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Agmatine" title="Agmatine">Agmatine</a></li> <li><a href="/wiki/Ornithine" title="Ornithine">Ornithine</a></li> <li><a href="/wiki/Citrulline" title="Citrulline">Citrulline</a></li> <li><a href="/wiki/Cadaverine" title="Cadaverine">Cadaverine</a></li> <li><a href="/wiki/Putrescine" title="Putrescine">Putrescine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cysteine" title="Cysteine">cysteine</a>+<a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a>→<a href="/wiki/Glutathione" title="Glutathione">glutathione</a>: <a href="/wiki/Gamma-Glutamylcysteine" class="mw-redirect" title="Gamma-Glutamylcysteine">γ-Glutamylcysteine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">propionyl-CoA</a>→<br /><a href="/wiki/Succinyl-CoA" title="Succinyl-CoA">succinyl-CoA</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Valine" title="Valine">valine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alpha-Ketoisovaleric_acid" class="mw-redirect" title="Alpha-Ketoisovaleric acid">α-Ketoisovaleric acid</a></li> <li><a href="/wiki/Isobutyryl-CoA" title="Isobutyryl-CoA">Isobutyryl-CoA</a></li> <li><a href="/wiki/Methacrylyl-CoA" title="Methacrylyl-CoA">Methacrylyl-CoA</a></li> <li><a href="/wiki/3-Hydroxyisobutyryl-CoA" title="3-Hydroxyisobutyryl-CoA">3-Hydroxyisobutyryl-CoA</a></li> <li><a href="/wiki/3-Hydroxyisobutyric_acid" title="3-Hydroxyisobutyric acid">3-Hydroxyisobutyric acid</a></li> <li><a href="/wiki/2-Methyl-3-oxopropanoic_acid" class="mw-redirect" title="2-Methyl-3-oxopropanoic acid">2-Methyl-3-oxopropanoic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isoleucine" title="Isoleucine">isoleucine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2,3-Dihydroxy-3-methylpentanoic_acid" title="2,3-Dihydroxy-3-methylpentanoic acid">2,3-Dihydroxy-3-methylpentanoic acid</a></li> <li><a href="/wiki/2-Methylbutyryl-CoA" title="2-Methylbutyryl-CoA">2-Methylbutyryl-CoA</a></li> <li><a href="/wiki/Tiglyl-CoA" title="Tiglyl-CoA">Tiglyl-CoA</a></li> <li><a href="/wiki/2-Methylacetoacetyl-CoA" title="2-Methylacetoacetyl-CoA">2-Methylacetoacetyl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Methionine" title="Methionine">methionine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Methionine#Generation_of_homocysteine" title="Methionine">generation of homocysteine</a>:</i> <a href="/wiki/S-Adenosyl_methionine" title="S-Adenosyl methionine"><i>S</i>-Adenosyl methionine</a></li> <li><a href="/wiki/S-Adenosyl-L-homocysteine" title="S-Adenosyl-L-homocysteine"><i>S</i>-Adenosyl-<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-homocysteine</a></li> <li><a href="/wiki/Homocysteine" title="Homocysteine">Homocysteine</a></li></ul> <ul><li><i><a href="/wiki/Methionine#Conversion_to_cysteine" title="Methionine">conversion to cysteine</a>:</i> <a href="/wiki/Cystathionine" title="Cystathionine">Cystathionine</a></li> <li><a href="/wiki/Alpha-Ketobutyric_acid" class="mw-redirect" title="Alpha-Ketobutyric acid">α-Ketobutyric acid</a> + <a href="/wiki/Cysteine" title="Cysteine">Cysteine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Threonine" title="Threonine">threonine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alpha-Ketobutyric_acid" class="mw-redirect" title="Alpha-Ketobutyric acid">α-Ketobutyric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">propionyl-CoA</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylmalonyl-CoA" title="Methylmalonyl-CoA">Methylmalonyl-CoA</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Fumarate" class="mw-redirect" title="Fumarate">fumarate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a>→<a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Hydroxyphenylpyruvic_acid" title="4-Hydroxyphenylpyruvic acid">4-Hydroxyphenylpyruvic acid</a></li> <li><a href="/wiki/Homogentisic_acid" title="Homogentisic acid">Homogentisic acid</a></li> <li><a href="/wiki/4-Maleylacetoacetic_acid" title="4-Maleylacetoacetic acid">4-Maleylacetoacetic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Oxaloacetate" class="mw-redirect" title="Oxaloacetate">oxaloacetate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>see <a href="/wiki/Urea_cycle" title="Urea cycle">urea cycle</a></i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a 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