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id="toc-Nutritional_value-sublist" class="vector-toc-list"> <li id="toc-Dietary_sources" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dietary_sources"> <div class="vector-toc-text"> 3.1 Dietary sources </div> </a> <ul id="toc-Dietary_sources-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Biological_roles" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biological_roles"> <div class="vector-toc-text"> 4 Biological roles </div> </a> <button aria-controls="toc-Biological_roles-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Biological roles subsection </button> <ul id="toc-Biological_roles-sublist" class="vector-toc-list"> <li id="toc-Disputed_roles" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Disputed_roles"> <div class="vector-toc-text"> 4.1 Disputed roles </div> </a> <ul id="toc-Disputed_roles-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Roles_in_disease" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Roles_in_disease"> <div class="vector-toc-text"> 5 Roles in disease </div> </a> <ul id="toc-Roles_in_disease-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Use_of_lysine_in_animal_feed" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Use_of_lysine_in_animal_feed"> <div class="vector-toc-text"> 6 Use of lysine in animal feed </div> </a> <ul id="toc-Use_of_lysine_in_animal_feed-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-In_popular_culture" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#In_popular_culture"> <div class="vector-toc-text"> 7 In popular culture </div> </a> <ul id="toc-In_popular_culture-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"> 8 References </div> </a> <ul id="toc-References-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" > <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" > Toggle the table of contents </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">Lysine</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 56 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-56" aria-hidden="true" > 56 languages </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%D8%A7%D9%8A%D8%B3%D9%8A%D9%86" title="لايسين – Arabic" lang="ar" hreflang="ar" data-title="لايسين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%84%DB%8C%D8%B2%DB%8C%D9%86" title="لیزین – South Azerbaijani" lang="azb" hreflang="azb" data-title="لیزین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B2%E0%A6%BE%E0%A6%87%E0%A6%B8%E0%A6%BF%E0%A6%A8" title="লাইসিন – Bangla" lang="bn" hreflang="bn" data-title="লাইসিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target">বাংলা</a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Lysin" title="Lysin – Minnan" lang="nan" hreflang="nan" data-title="Lysin" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target">閩南語 / Bân-lâm-gú</a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9B%D0%B8%D0%B7%D0%B8%D0%BD" title="Лизин – Bulgarian" lang="bg" hreflang="bg" data-title="Лизин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target">Български</a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Lisina" title="Lisina – Catalan" lang="ca" hreflang="ca" data-title="Lisina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target">Català</a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Lysin" title="Lysin – Czech" lang="cs" hreflang="cs" data-title="Lysin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target">Čeština</a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Lysin" title="Lysin – German" lang="de" hreflang="de" data-title="Lysin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/L%C3%BCsiin" title="Lüsiin – Estonian" lang="et" hreflang="et" data-title="Lüsiin" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target">Eesti</a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9B%CF%85%CF%83%CE%AF%CE%BD%CE%B7" title="Λυσίνη – Greek" lang="el" hreflang="el" data-title="Λυσίνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target">Ελληνικά</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Lisina" title="Lisina – Spanish" lang="es" hreflang="es" data-title="Lisina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Lizino" title="Lizino – Esperanto" lang="eo" hreflang="eo" data-title="Lizino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target">Esperanto</a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Lisina" title="Lisina – Basque" lang="eu" hreflang="eu" data-title="Lisina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target">Euskara</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%84%DB%8C%D8%B2%DB%8C%D9%86" title="لیزین – Persian" lang="fa" hreflang="fa" data-title="لیزین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Lysine" title="Lysine – French" lang="fr" hreflang="fr" data-title="Lysine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Lisina" title="Lisina – Galician" lang="gl" hreflang="gl" data-title="Lisina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target">Galego</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%9D%BC%EC%9D%B4%EC%8B%A0" title="라이신 – Korean" lang="ko" hreflang="ko" data-title="라이신" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%BC%D5%AB%D5%A6%D5%AB%D5%B6" title="Լիզին – Armenian" lang="hy" hreflang="hy" data-title="Լիզին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target">Հայերեն</a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Lizin" title="Lizin – Croatian" lang="hr" hreflang="hr" data-title="Lizin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target">Hrvatski</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Lisin" title="Lisin – Indonesian" lang="id" hreflang="id" data-title="Lisin" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Lisina" title="Lisina – Italian" lang="it" hreflang="it" data-title="Lisina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%9C%D7%99%D7%96%D7%99%D7%9F" title="ליזין – Hebrew" lang="he" hreflang="he" data-title="ליזין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target">עברית</a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%9A%E1%83%98%E1%83%96%E1%83%98%E1%83%9C%E1%83%98" title="ლიზინი – Georgian" lang="ka" hreflang="ka" data-title="ლიზინი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target">ქართული</a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9B%D0%B8%D0%B7%D0%B8%D0%BD" title="Лизин – Kazakh" lang="kk" hreflang="kk" data-title="Лизин" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target">Қазақша</a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9B%D0%B8%D0%B7%D0%B8%D0%BD" title="Лизин – Kyrgyz" lang="ky" hreflang="ky" data-title="Лизин" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target">Кыргызча</a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Liz%C4%ABns" title="Lizīns – Latvian" lang="lv" hreflang="lv" data-title="Lizīns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target">Latviešu</a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Lysin" title="Lysin – Luxembourgish" lang="lb" hreflang="lb" data-title="Lysin" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target">Lëtzebuergesch</a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Lizinas" title="Lizinas – Lithuanian" lang="lt" hreflang="lt" data-title="Lizinas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target">Lietuvių</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Lizin" title="Lizin – Hungarian" lang="hu" hreflang="hu" data-title="Lizin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target">Magyar</a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9B%D0%B8%D0%B7%D0%B8%D0%BD" title="Лизин – Macedonian" lang="mk" hreflang="mk" data-title="Лизин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target">Македонски</a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Lisina" title="Lisina – Malay" lang="ms" hreflang="ms" data-title="Lisina" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target">Bahasa Melayu</a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%9B%D0%B8%D0%B7%D0%B8%D0%BD" title="Лизин – Mongolian" lang="mn" hreflang="mn" data-title="Лизин" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target">Монгол</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Lysine" title="Lysine – Dutch" lang="nl" hreflang="nl" data-title="Lysine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%AA%E3%82%B7%E3%83%B3" title="リシン – Japanese" lang="ja" hreflang="ja" data-title="リシン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Lysin" title="Lysin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Lysin" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target">Norsk bokmål</a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Lysin" title="Lysin – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Lysin" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target">Norsk nynorsk</a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Lisina" title="Lisina – Occitan" lang="oc" hreflang="oc" data-title="Lisina" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target">Occitan</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Lizyna" title="Lizyna – Polish" lang="pl" hreflang="pl" data-title="Lizyna" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Lisina" title="Lisina – Portuguese" lang="pt" hreflang="pt" data-title="Lisina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Lizin%C4%83" title="Lizină – Romanian" lang="ro" hreflang="ro" data-title="Lizină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target">Română</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9B%D0%B8%D0%B7%D0%B8%D0%BD" title="Лизин – Russian" lang="ru" hreflang="ru" data-title="Лизин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Lyz%C3%ADn" title="Lyzín – Slovak" lang="sk" hreflang="sk" data-title="Lyzín" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target">Slovenčina</a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Lizin" title="Lizin – Slovenian" lang="sl" hreflang="sl" data-title="Lizin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target">Slovenščina</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Lizin" title="Lizin – Serbian" lang="sr" hreflang="sr" data-title="Lizin" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Lizin" title="Lizin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Lizin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Lisin" title="Lisin – Sundanese" lang="su" hreflang="su" data-title="Lisin" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target">Sunda</a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Lysiini" title="Lysiini – Finnish" lang="fi" hreflang="fi" data-title="Lysiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target">Suomi</a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Lysin" title="Lysin – Swedish" lang="sv" hreflang="sv" data-title="Lysin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target">Svenska</a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%B2%E0%AF%88%E0%AE%9A%E0%AE%BF%E0%AE%A9%E0%AF%8D" title="லைசின் – Tamil" lang="ta" hreflang="ta" data-title="லைசின்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target">தமிழ்</a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%84%E0%B8%A5%E0%B8%8B%E0%B8%B5%E0%B8%99" title="ไลซีน – Thai" lang="th" hreflang="th" data-title="ไลซีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target">ไทย</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Lizin" title="Lizin – Turkish" lang="tr" hreflang="tr" data-title="Lizin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9B%D1%96%D0%B7%D0%B8%D0%BD" title="Лізин – Ukrainian" lang="uk" hreflang="uk" data-title="Лізин" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target">Українська</a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Lysin" title="Lysin – Vietnamese" lang="vi" hreflang="vi" data-title="Lysin" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target">Tiếng Việt</a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%B5%96%E6%B0%A8%E9%85%B8" title="赖氨酸 – Wu" lang="wuu" hreflang="wuu" data-title="赖氨酸" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target">吴语</a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E8%B3%B4%E6%B0%A8%E9%85%B8" title="賴氨酸 – Cantonese" lang="yue" hreflang="yue" data-title="賴氨酸" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target">粵語</a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%9B%A2%E8%83%BA%E9%85%B8" title="離胺酸 – Chinese" lang="zh" hreflang="zh" data-title="離胺酸" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target">中文</a></li> </ul> <div class="after-portlet after-portlet-lang"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q178430#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> 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class="mw-parser-output"><a href="https://doi.org/10.15347/WJS/2018.004" title="This article has been published in the peer-reviewed journal WikiJournal of Science (2018). Click to view the published version." rel="nofollow"><img alt="This article has been published in the peer-reviewed journal WikiJournal of Science (2018). Click to view the published version." src="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Journal_Icon.svg/20px-Journal_Icon.svg.png" decoding="async" width="20" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Journal_Icon.svg/30px-Journal_Icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/63/Journal_Icon.svg/40px-Journal_Icon.svg.png 2x" data-file-width="525" data-file-height="479" /></a></div></div> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Amino acid</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Lysin" title="Lysin">lysin</a> or <a href="/wiki/Leucine" title="Leucine">leucine</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.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%}</style> <table class="infobox ib-chembox"> <caption>Lysine </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><a href="/wiki/File:L-Lysin_-_L-Lysine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/L-Lysin_-_L-Lysine.svg/220px-L-Lysin_-_L-Lysine.svg.png" decoding="async" width="220" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/L-Lysin_-_L-Lysine.svg/330px-L-Lysin_-_L-Lysine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/88/L-Lysin_-_L-Lysine.svg/440px-L-Lysin_-_L-Lysine.svg.png 2x" data-file-width="300" data-file-height="121" /></a> <div style="text-align:center;"><a href="/wiki/Skeletal_formula" title="Skeletal formula">Skeletal formula</a> of L-lysine</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:Lysine-from-xtal-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Lysine-from-xtal-3D-bs-17.png/100px-Lysine-from-xtal-3D-bs-17.png" decoding="async" width="100" height="180" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Lysine-from-xtal-3D-bs-17.png/150px-Lysine-from-xtal-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/66/Lysine-from-xtal-3D-bs-17.png/200px-Lysine-from-xtal-3D-bs-17.png 2x" data-file-width="1243" data-file-height="2237" /></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><a href="#cite_note-Williams-1">[1]</a></div> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Lysine-from-xtal-3D-sf.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Lysine-from-xtal-3D-sf.png/120px-Lysine-from-xtal-3D-sf.png" decoding="async" width="120" height="184" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Lysine-from-xtal-3D-sf.png/180px-Lysine-from-xtal-3D-sf.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0e/Lysine-from-xtal-3D-sf.png/240px-Lysine-from-xtal-3D-sf.png 2x" data-file-width="1497" data-file-height="2291" /></a><figcaption></figcaption></figure><div style="text-align:center"><a href="/wiki/Space-filling_model" title="Space-filling model">Space-filling model</a><a href="#cite_note-Williams-1">[1]</a></div> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC names</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">L-lysine D-lysine</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;">(2S)-2,6-Diaminohexanoic acid (L-lysine) (2R)-2,6-Diaminohexanoic acid (D-lysine)</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Lysine, D-lysine, L-lysine, LYS, h-Lys-OH</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; 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><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=70-54-2">70-54-2</a> DL <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" />Y</li><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=56-87-1">56-87-1</a> L <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" />Y</li><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=923-27-3">923-27-3</a> D <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" />Y</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><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%28CCN%29C%5BC%40%40H%5D%28C%28%3DO%29O%29N">Interactive image</a></li><li><a href="/wiki/Zwitterion" title="Zwitterion">Zwitterion</a>: <a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%28CC%5BNH3%2B%5D%29C%5BC%40%40H%5D%28C%28%3DO%29%5BO-%5D%29N">Interactive image</a></li><li>Protonated zwitterion: <a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%28CC%5BNH3%2B%5D%29C%5BC%40%40H%5D%28C%28%3DO%29%5BO-%5D%29%5BNH3%2B%5D">Interactive image</a></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><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=25094">CHEBI:25094</a> <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" />Y</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><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL28328">ChEMBL28328</a> <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" />Y</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><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.843.html">843</a> <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" />Y</li><li><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.5747.html">5747</a> L <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" />Y</li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.673">100.000.673</a> <a href="https://www.wikidata.org/wiki/Q178430#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> </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><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=724">724</a></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><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C16440">C16440</a> <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" />Y</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><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/866">866</a></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><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/AI4RT59273">AI4RT59273</a> DL <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" />Y</li><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/K3Z4F929H6">K3Z4F929H6</a> L <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" />Y</li><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/3HQ6U6424Q">3HQ6U6424Q</a> D <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" />Y</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> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID90859004">DTXSID90859004</a> <a href="https://www.wikidata.org/wiki/Q178430#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></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; background:transparent;"><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/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10) <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" />Y</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: KDXKERNSBIXSRK-UHFFFAOYSA-N <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" />Y</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/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: KDXKERNSBIXSRK-UHFFFAOYAY</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; background:transparent;"><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%;">C(CCN)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>: C(CC[NH3+])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%;">Protonated zwitterion: C(CC[NH3+])C[C@@H](C(=O)[O-])[NH3+]</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; 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>C6H14N2O2 </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>146.190 g·mol−1 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>1.5 kg/L </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_B05" title="ATC code B05">B05XB03</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=B05XB03">WHO</a>) </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Supplementary data page </th></tr> <tr> <td colspan="2" style="text-align:center"><a href="/wiki/Lysine_(data_page)" title="Lysine (data page)">Lysine (data page)</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; 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> Lysine (symbol Lys or K)<a href="#cite_note-2">[2]</a> is an <a href="/wiki/%CE%91-amino_acid" class="mw-redirect" title="Α-amino acid">α-amino acid</a> that is a <a href="/wiki/Biosynthesis" title="Biosynthesis">precursor</a> to many <a href="/wiki/Proteins" class="mw-redirect" title="Proteins">proteins</a>. Lysine contains an α-amino group (which is in the <a href="/wiki/Protonation" title="Protonation">protonated</a> <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style>−NH+3 form when the lysine is dissolved in water at <a href="/wiki/Physiological_pH" class="mw-redirect" title="Physiological pH">physiological pH</a>), an α-carboxylic acid group (which is in the deprotonated <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">−COO− form when the lysine is dissolved in water at physiological pH), and a side chain <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">(CH2)4NH2 (which is partially protonated when the lysine is dissolved in water at physiological pH), and so it is classified as a <a href="/wiki/Base_(chemistry)" title="Base (chemistry)">basic</a>, charged (in water at physiological pH), <a href="/wiki/Aliphatic_compound" title="Aliphatic compound">aliphatic</a> amino acid. It is encoded by the <a href="/wiki/Codon" class="mw-redirect" title="Codon">codons</a> AAA and AAG. Like almost all other amino acids, the α-carbon is <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chiral</a> and lysine may refer to either <a href="/wiki/Enantiomer" title="Enantiomer">enantiomer</a> or a <a href="/wiki/Racemic_mixture" title="Racemic mixture">racemic mixture</a> of both. For the purpose of this article, lysine will refer to the biologically active enantiomer L-lysine, where the α-carbon is in the S configuration. The human body cannot synthesize lysine. It is <a href="/wiki/Essential_amino_acid" title="Essential amino acid">essential in humans</a> and must therefore be obtained from the diet. In organisms that synthesise lysine, two main <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthetic pathways</a> exist, the <a href="/wiki/Diaminopimelate_pathway" class="mw-redirect" title="Diaminopimelate pathway">diaminopimelate</a> and <a href="/wiki/Alpha-aminoadipate_pathway" class="mw-redirect" title="Alpha-aminoadipate pathway">α-aminoadipate</a> pathways, which employ distinct <a href="/wiki/Enzymes" class="mw-redirect" title="Enzymes">enzymes</a> and <a href="/wiki/Substrate_(chemistry)" title="Substrate (chemistry)">substrates</a> and are found in diverse organisms. Lysine <a href="/wiki/Catabolism" title="Catabolism">catabolism</a> occurs through one of several pathways, the most common of which is the <a href="/wiki/Saccharopine_pathway" class="mw-redirect" title="Saccharopine pathway">saccharopine pathway</a>. Lysine plays several roles in humans, most importantly <a href="/wiki/Proteinogenesis" class="mw-redirect" title="Proteinogenesis">proteinogenesis</a>, but also in the crosslinking of <a href="/wiki/Collagen" title="Collagen">collagen</a> polypeptides, uptake of essential mineral nutrients, and in the production of <a href="/wiki/Carnitine" title="Carnitine">carnitine</a>, which is key in <a href="/wiki/Fatty_acid_metabolism" title="Fatty acid metabolism">fatty acid metabolism</a>. Lysine is also often involved in <a href="/wiki/Histone_modification" class="mw-redirect" title="Histone modification">histone modifications</a>, and thus, impacts the <a href="/wiki/Epigenome" title="Epigenome">epigenome</a>. The ε-amino group often participates in hydrogen bonding and as a general base in <a href="/wiki/Catalysis" title="Catalysis">catalysis</a>. The ε-<a href="/wiki/Ammonium" title="Ammonium">ammonium</a> group (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">−NH+3) is attached to the fourth carbon from the α-carbon, which is attached to the <a href="/wiki/Carboxyl" class="mw-redirect" title="Carboxyl">carboxyl</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410">−COOH) group.<a href="#cite_note-3">[3]</a> Due to its importance in several biological processes, a lack of lysine can lead to several disease states including defective connective tissues, impaired fatty acid metabolism, anaemia, and systemic protein-energy deficiency. In contrast, an overabundance of lysine, caused by ineffective catabolism, can cause severe <a href="/wiki/Neurological_disorder" title="Neurological disorder">neurological disorders</a>. Lysine was first isolated by the German biological chemist Ferdinand Heinrich Edmund Drechsel in 1889 from hydrolysis of the protein <a href="/wiki/Casein" title="Casein">casein</a>,<a href="#cite_note-4">[4]</a> and thus named it Lysin, from <a href="/wiki/Greek_language" title="Greek language">Greek</a> λύσις (lysis) 'loosening'.<a href="#cite_note-5">[5]</a><a href="#cite_note-6">[6]</a> In 1902, the German chemists <a href="/wiki/Hermann_Emil_Fischer" class="mw-redirect" title="Hermann Emil Fischer">Emil Fischer</a> and <a href="/wiki/Fritz_Weigert" title="Fritz Weigert">Fritz Weigert</a> determined lysine's chemical structure by synthesizing it.<a href="#cite_note-7">[7]</a> The one-letter symbol K was assigned to lysine for being alphabetically nearest, with L being assigned to the structurally simpler leucine, and M to methionine.<a href="#cite_note-:1-8">[8]</a> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2>[<a href="/w/index.php?title=Lysine&action=edit&section=1" title="Edit section: Biosynthesis">edit</a>]</div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:AAA_DAP_pathways.tif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/AAA_DAP_pathways.tif/lossless-page1-220px-AAA_DAP_pathways.tif.png" decoding="async" width="220" height="293" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8f/AAA_DAP_pathways.tif/lossless-page1-330px-AAA_DAP_pathways.tif.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8f/AAA_DAP_pathways.tif/lossless-page1-440px-AAA_DAP_pathways.tif.png 2x" data-file-width="517" data-file-height="689" /></a><figcaption>Lysine biosynthesis pathways. Two pathways are responsible for the de novo biosynthesis of L-lysine, namely the (A) diaminopimelate pathway and (B) α‑aminoadipate pathway.</figcaption></figure> Two pathways have been identified in nature for the synthesis of lysine. The <a href="/wiki/Diaminopimelate" class="mw-redirect" title="Diaminopimelate">diaminopimelate</a> (DAP) pathway belongs to the <a href="/wiki/Aspartic_acid" title="Aspartic acid">aspartate</a> derived biosynthetic family, which is also involved in the synthesis of <a href="/wiki/Threonine" title="Threonine">threonine</a>, <a href="/wiki/Methionine" title="Methionine">methionine</a> and <a href="/wiki/Isoleucine" title="Isoleucine">isoleucine</a>,<a href="#cite_note-Hudson_2005-9">[9]</a><a href="#cite_note-Velasco_2002-10">[10]</a> whereas the <a href="/wiki/%CE%91-aminoadipate" class="mw-redirect" title="Α-aminoadipate">α-aminoadipate</a> (AAA) pathway is part of the <a href="/wiki/Glutamic_acid" title="Glutamic acid">glutamate</a> biosynthetic family.<a href="#cite_note-Miyazaki_2004-11">[11]</a><a href="#cite_note-Xu_2006-12">[12]</a> <div class="mw-heading mw-heading3"><h3 id="DAP_pathway">DAP pathway</h3>[<a href="/w/index.php?title=Lysine&action=edit&section=2" title="Edit section: DAP pathway">edit</a>]</div> The DAP pathway is found in both <a href="/wiki/Prokaryote" title="Prokaryote">prokaryotes</a> and plants and begins with the <a href="/wiki/Dihydrodipicolinate_synthase" title="Dihydrodipicolinate synthase">dihydrodipicolinate synthase</a> (DHDPS) (E.C 4.3.3.7) <a href="/wiki/Catalysis" title="Catalysis">catalysed</a> <a href="/wiki/Condensation_reaction" title="Condensation reaction">condensation reaction</a> between the aspartate derived, L-aspartate semialdehyde, and <a href="/wiki/Pyruvic_acid" title="Pyruvic acid">pyruvate</a> to form (4S)-4-hydroxy-2,3,4,5-tetrahydro-(2S)-dipicolinic acid (HTPA).<a href="#cite_note-Atkinson_2013-13">[13]</a><a href="#cite_note-Griffin_2012-14">[14]</a><a href="#cite_note-Soares_da_Costa_2010-15">[15]</a><a href="#cite_note-Soares_da_Costa_2015-16">[16]</a><a href="#cite_note-17">[17]</a> The product is then <a href="/wiki/Redox" title="Redox">reduced</a> by <a href="/wiki/4-hydroxy-tetrahydrodipicolinate_reductase" title="4-hydroxy-tetrahydrodipicolinate reductase">dihydrodipicolinate reductase (DHDPR)</a> (E.C 1.3.1.26), with <a href="/wiki/Nicotinamide_adenine_dinucleotide_phosphate" title="Nicotinamide adenine dinucleotide phosphate">NAD(P)H</a> as a proton donor, to yield 2,3,4,5-tetrahydrodipicolinate (THDP).<a href="#cite_note-18">[18]</a> From this point on, four pathway variations have been found, namely the acetylase, aminotransferase, dehydrogenase, and succinylase pathways.<a href="#cite_note-Hudson_2005-9">[9]</a><a href="#cite_note-19">[19]</a> Both the acetylase and succinylase variant pathways use four <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> catalysed steps, the aminotransferase pathway uses two enzymes, and the dehydrogenase pathway uses a single enzyme.<a href="#cite_note-20">[20]</a> These four variant pathways converge at the formation of the penultimate product, meso‑diaminopimelate, which is subsequently enzymatically <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylated</a> in an irreversible reaction catalysed by <a href="/wiki/Diaminopimelate_decarboxylase" title="Diaminopimelate decarboxylase">diaminopimelate decarboxylase (DAPDC)</a> (E.C 4.1.1.20) to produce L-lysine.<a href="#cite_note-21">[21]</a><a href="#cite_note-Soares_da_Costa_2016-22">[22]</a> The DAP pathway is regulated at multiple levels, including upstream at the enzymes involved in aspartate processing as well as at the initial DHDPS catalysed condensation step.<a href="#cite_note-Soares_da_Costa_2016-22">[22]</a><a href="#cite_note-Jander_2009-23">[23]</a> Lysine imparts a strong <a href="/wiki/Negative_feedback" title="Negative feedback">negative feedback</a> loop on these enzymes and, subsequently, regulates the entire pathway.<a href="#cite_note-Jander_2009-23">[23]</a> <div class="mw-heading mw-heading3"><h3 id="AAA_pathway">AAA pathway</h3>[<a href="/w/index.php?title=Lysine&action=edit&section=3" title="Edit section: AAA pathway">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/%CE%91-Aminoadipate_pathway" title="Α-Aminoadipate pathway">α-Aminoadipate pathway</a></div> The AAA pathway involves the condensation of <a href="/wiki/Alpha-Ketoglutaric_acid" class="mw-redirect" title="Alpha-Ketoglutaric acid">α-ketoglutarate</a> and <a href="/wiki/Acetyl-CoA" title="Acetyl-CoA">acetyl-CoA</a> via the intermediate AAA for the synthesis of L-lysine. This pathway has been shown to be present in several <a href="/wiki/Yeast" title="Yeast">yeast</a> species, as well as protists and higher fungi.<a href="#cite_note-Xu_2006-12">[12]</a><a href="#cite_note-24">[24]</a><a href="#cite_note-25">[25]</a><a href="#cite_note-26">[26]</a><a href="#cite_note-27">[27]</a><a href="#cite_note-28">[28]</a><a href="#cite_note-29">[29]</a> It has also been reported that an alternative variant of the AAA route has been found in <a href="/wiki/Thermus_thermophilus" title="Thermus thermophilus">Thermus thermophilus</a> and <a href="/wiki/Pyrococcus_horikoshii" title="Pyrococcus horikoshii">Pyrococcus horikoshii</a>, which could indicate that this pathway is more widely spread in prokaryotes than originally proposed.<a href="#cite_note-30">[30]</a><a href="#cite_note-31">[31]</a><a href="#cite_note-Nishida_1999-32">[32]</a> The first and <a href="/wiki/Rate-determining_step" title="Rate-determining step">rate-limiting step</a> in the AAA pathway is the condensation reaction between acetyl-CoA and α‑ketoglutarate catalysed by <a href="/wiki/Homocitrate_synthase" title="Homocitrate synthase">homocitrate-synthase (HCS)</a> (E.C 2.3.3.14) to give the intermediate homocitryl‑CoA, which is <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysed</a> by the same enzyme to produce <a href="/wiki/Homocitric_acid" title="Homocitric acid">homocitrate</a>.<a href="#cite_note-Nishida_2000-33">[33]</a> Homocitrate is enzymatically <a href="/wiki/Dehydration_reaction" title="Dehydration reaction">dehydrated</a> by <a href="/wiki/Homoaconitate_hydratase" title="Homoaconitate hydratase">homoaconitase (HAc)</a> (E.C 4.2.1.36) to yield <a href="/wiki/Homoaconitic_acid" title="Homoaconitic acid">cis-homoaconitate</a>.<a href="#cite_note-34">[34]</a> HAc then catalyses a second reaction in which cis-homoaconitate undergoes <a href="/wiki/Hydration_reaction" title="Hydration reaction">rehydration</a> to produce <a href="/wiki/Homoisocitric_acid" title="Homoisocitric acid">homoisocitrate</a>.<a href="#cite_note-Xu_2006-12">[12]</a> The resulting product undergoes an <a href="/wiki/Redox" title="Redox">oxidative</a> decarboxylation by <a href="/wiki/Homoisocitrate_dehydrogenase" title="Homoisocitrate dehydrogenase">homoisocitrate dehydrogenase (HIDH)</a> (E.C 1.1.1.87) to yield α‑ketoadipate.<a href="#cite_note-Xu_2006-12">[12]</a> AAA is then formed via a <a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">pyridoxal 5′-phosphate (PLP)</a>-dependent <a href="/wiki/Transaminase" title="Transaminase">aminotransferase</a> <a href="/wiki/2-aminoadipate_transaminase" title="2-aminoadipate transaminase">(PLP-AT)</a> (E.C 2.6.1.39), using glutamate as the amino donor.<a href="#cite_note-Nishida_2000-33">[33]</a> From this point on, the AAA pathway varies with [something is missing here ? -> at the very least, section header! ] on the kingdom. In fungi, AAA is reduced to α‑aminoadipate-semialdehyde via AAA reductase (E.C 1.2.1.95) in a unique process involving both <a href="/wiki/Adenylylation" title="Adenylylation">adenylation</a> and reduction that is activated by a <a href="/wiki/Holo-(acyl-carrier-protein)_synthase" title="Holo-(acyl-carrier-protein) synthase">phosphopantetheinyl transferase</a> (E.C 2.7.8.7).<a href="#cite_note-Xu_2006-12">[12]</a> Once the semialdehyde is formed, <a href="/wiki/Saccharopine" title="Saccharopine">saccharopine</a> <a href="/wiki/Saccharopine_dehydrogenase_(NADP%2B,_L-glutamate-forming)" title="Saccharopine dehydrogenase (NADP+, L-glutamate-forming)">reductase</a> (E.C 1.5.1.10) catalyses a condensation reaction with glutamate and NAD(P)H, as a proton donor, and the <a href="/wiki/Imine" title="Imine">imine</a> is reduced to produce the penultimate product, saccharopine.<a href="#cite_note-Nishida_1999-32">[32]</a> The final step of the pathway in fungi involves the <a href="/wiki/Saccharopine_dehydrogenase_(NADP%2B,_L-lysine-forming)" title="Saccharopine dehydrogenase (NADP+, L-lysine-forming)">saccharopine dehydrogenase (SDH)</a> (E.C 1.5.1.8) catalysed oxidative <a href="/wiki/Deamination" title="Deamination">deamination</a> of saccharopine, resulting in L-lysine.<a href="#cite_note-Xu_2006-12">[12]</a> In a variant AAA pathway found in some prokaryotes, AAA is first converted to N‑acetyl-α-aminoadipate, which is <a href="/wiki/Phosphorylation" title="Phosphorylation">phosphorylated</a> and then reductively <a href="/wiki/Dephosphorylation" title="Dephosphorylation">dephosphorylated</a> to the ε-aldehyde.<a href="#cite_note-Nishida_1999-32">[32]</a><a href="#cite_note-Nishida_2000-33">[33]</a> The aldehyde is then <a href="/wiki/Transamination" title="Transamination">transaminated</a> to N‑acetyllysine, which is deacetylated to give L-lysine.<a href="#cite_note-Nishida_1999-32">[32]</a><a href="#cite_note-Nishida_2000-33">[33]</a> However, the enzymes involved in this variant pathway need further validation. <div class="mw-heading mw-heading2"><h2 id="Catabolism">Catabolism</h2>[<a href="/w/index.php?title=Lysine&action=edit&section=4" title="Edit section: Catabolism">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Saccharopine_Pathway_Final.tiff" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Saccharopine_Pathway_Final.tiff/lossy-page1-180px-Saccharopine_Pathway_Final.tiff.jpg" decoding="async" width="180" height="461" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Saccharopine_Pathway_Final.tiff/lossy-page1-270px-Saccharopine_Pathway_Final.tiff.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bb/Saccharopine_Pathway_Final.tiff/lossy-page1-360px-Saccharopine_Pathway_Final.tiff.jpg 2x" data-file-width="1181" data-file-height="3027" /></a><figcaption>Saccharopine lysine catabolism pathway. The saccharopine pathway is the most prominent pathway for the catabolism of lysine.</figcaption></figure> As with all amino acids, <a href="/wiki/Catabolism" title="Catabolism">catabolism</a> of lysine is initiated from the uptake of dietary lysine or from the breakdown of <a href="/wiki/Intracellular" class="mw-redirect" title="Intracellular">intracellular</a> protein. Catabolism is also used as a means to control the intracellular concentration of free lysine and maintain a <a href="/wiki/Steady_state" title="Steady state">steady-state</a> to prevent the toxic effects of excessive free lysine.<a href="#cite_note-Zhu_2004-35">[35]</a> There are several pathways involved in lysine catabolism but the most commonly used is the saccharopine pathway, which primarily takes place in the <a href="/wiki/Liver" title="Liver">liver</a> (and equivalent organs) in animals, specifically within the <a href="/wiki/Mitochondrion" title="Mitochondrion">mitochondria</a>.<a href="#cite_note-Tomé_2007-36">[36]</a><a href="#cite_note-Zhu_2004-35">[35]</a><a href="#cite_note-37">[37]</a><a href="#cite_note-38">[38]</a> This is the reverse of the previously described AAA pathway.<a href="#cite_note-Tomé_2007-36">[36]</a><a href="#cite_note-39">[39]</a> In animals and plants, the first two steps of the saccharopine pathway are catalysed by the bifunctional enzyme, <a href="/wiki/Alpha-aminoadipic_semialdehyde_synthase,_mitochondrial" class="mw-redirect" title="Alpha-aminoadipic semialdehyde synthase, mitochondrial">α-aminoadipic semialdehyde synthase (AASS)</a>, which possess both lysine-ketoglutarate reductase (LKR) (E.C 1.5.1.8) and SDH activities, whereas in other organisms, such as bacteria and fungi, both of these enzymes are encoded by separate <a href="/wiki/Gene" title="Gene">genes</a>.<a href="#cite_note-40">[40]</a><a href="#cite_note-41">[41]</a> The first step involves the LKR catalysed reduction of L-lysine in the presence of α-ketoglutarate to produce saccharopine, with NAD(P)H acting as a proton donor.<a href="#cite_note-Kiyota_2015-42">[42]</a> Saccharopine then undergoes a dehydration reaction, catalysed by SDH in the presence of <a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NAD+</a>, to produce AAS and glutamate.<a href="#cite_note-43">[43]</a> <a href="/wiki/L-aminoadipate-semialdehyde_dehydrogenase" title="L-aminoadipate-semialdehyde dehydrogenase">AAS dehydrogenase (AASD)</a> (E.C 1.2.1.31) then further dehydrates the molecule into AAA.<a href="#cite_note-Kiyota_2015-42">[42]</a> Subsequently, PLP-AT catalyses the reverse reaction to that of the AAA biosynthesis pathway, resulting in AAA being converted to α-ketoadipate. The product, α‑ketoadipate, is decarboxylated in the presence of NAD+ and coenzyme A to yield glutaryl-CoA, however the enzyme involved in this is yet to be fully elucidated.<a href="#cite_note-Danhauser_2012-44">[44]</a><a href="#cite_note-45">[45]</a> Some evidence suggests that the 2-oxoadipate dehydrogenase complex (OADHc), which is structurally homologous to the E1 subunit of the <a href="/wiki/Oxoglutarate_dehydrogenase_complex" title="Oxoglutarate dehydrogenase complex">oxoglutarate dehydrogenase complex (OGDHc)</a> (E.C 1.2.4.2), is responsible for the decarboxylation reaction.<a href="#cite_note-Danhauser_2012-44">[44]</a><a href="#cite_note-46">[46]</a> Finally, glutaryl-CoA is oxidatively decarboxylated to crotonyl-CoA by <a href="/wiki/Glutaryl-CoA_dehydrogenase" title="Glutaryl-CoA dehydrogenase">glutaryl-CoA dehydrogenase</a> (E.C 1.3.8.6), which goes on to be further processed through multiple enzymatic steps to yield acetyl-CoA; an essential carbon <a href="/wiki/Metabolite" title="Metabolite">metabolite</a> involved in the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">tricarboxylic acid cycle (TCA)</a>.<a href="#cite_note-Kiyota_2015-42">[42]</a><a href="#cite_note-47">[47]</a><a href="#cite_note-48">[48]</a><a href="#cite_note-49">[49]</a> <div class="mw-heading mw-heading2"><h2 id="Nutritional_value">Nutritional value</h2>[<a href="/w/index.php?title=Lysine&action=edit&section=5" title="Edit section: Nutritional value">edit</a>]</div> Lysine is an essential amino acid in humans.<a href="#cite_note-Nelson_2013-50">[50]</a> The human daily nutritional requirement varies from ~60 mg/kg in infancy to ~30 mg/kg in adults.<a href="#cite_note-Tomé_2007-36">[36]</a> This requirement is commonly met in a <a href="/wiki/Western_world" title="Western world">western society</a> with the intake of <a href="#Dietary_sources">lysine from meat and vegetable sources</a> well in excess of the recommended requirement.<a href="#cite_note-Tomé_2007-36">[36]</a> In vegetarian diets, the intake of lysine is less due to the limited quantity of lysine in <a href="/wiki/Cereal" title="Cereal">cereal crops</a> compared to meat sources.<a href="#cite_note-Tomé_2007-36">[36]</a> Given the limiting concentration of lysine in cereal crops, it has long been speculated that the content of lysine can be increased through <a href="/wiki/Genetic_engineering" title="Genetic engineering">genetic modification</a> practices.<a href="#cite_note-Galili_2013-51">[51]</a><a href="#cite_note-Wang_2017-52">[52]</a> Often these practices have involved the intentional dysregulation of the DAP pathway by means of introducing lysine feedback-insensitive <a href="/wiki/Sequence_homology#Orthology" title="Sequence homology">orthologues</a> of the DHDPS enzyme.<a href="#cite_note-Galili_2013-51">[51]</a><a href="#cite_note-Wang_2017-52">[52]</a> These methods have met limited success likely due to the <a href="/wiki/Toxicity" title="Toxicity">toxic</a> side effects of increased free lysine and indirect effects on the TCA cycle.<a href="#cite_note-53">[53]</a> Plants accumulate lysine and other amino acids in the form of seed <a href="/wiki/Storage_protein" title="Storage protein">storage proteins</a>, found within the seeds of the plant, and this represents the edible component of cereal crops.<a href="#cite_note-54">[54]</a> This highlights the need to not only increase free lysine, but also direct lysine towards the synthesis of stable seed storage proteins, and subsequently, increase the nutritional value of the consumable component of crops.<a href="#cite_note-55">[55]</a><a href="#cite_note-Shewry_2007-56">[56]</a> While genetic modification practices have met limited success, more traditional <a href="/wiki/Selective_breeding" title="Selective breeding">selective breeding</a> techniques have allowed for the isolation of "<a href="/wiki/Quality_Protein_Maize" title="Quality Protein Maize">Quality Protein Maize</a>", which has significantly increased levels of lysine and <a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a>, also an essential amino acid. This increase in lysine content is attributed to an opaque-2 mutation that reduced the <a href="/wiki/Transcription_(biology)" title="Transcription (biology)">transcription</a> of lysine-lacking <a href="/wiki/Zein" title="Zein">zein</a>-related seed storage proteins and, as a result, increased the abundance of other proteins that are rich in lysine.<a href="#cite_note-Shewry_2007-56">[56]</a><a href="#cite_note-57">[57]</a> Commonly, to overcome the limiting abundance of lysine in <a href="/wiki/Livestock" title="Livestock">livestock</a> feed, industrially produced lysine is added.<a href="#cite_note-Kircher_2001-58">[58]</a><a href="#cite_note-59">[59]</a> The industrial process includes the <a href="/wiki/Fermentation" title="Fermentation">fermentative</a> culturing of <a href="/wiki/Corynebacterium_glutamicum" title="Corynebacterium glutamicum">Corynebacterium glutamicum</a> and the subsequent purification of lysine.<a href="#cite_note-Kircher_2001-58">[58]</a> <div class="mw-heading mw-heading3"><h3 id="Dietary_sources">Dietary sources</h3>[<a href="/w/index.php?title=Lysine&action=edit&section=6" title="Edit section: Dietary sources">edit</a>]</div> Good sources of lysine are high-protein foods such as eggs, meat (specifically red meat, lamb, pork, and poultry), <a href="/wiki/Soy_protein" title="Soy protein">soy</a>, beans and peas, cheese (particularly Parmesan), and certain fish (such as <a href="/wiki/Cod" title="Cod">cod</a> and <a href="/wiki/Sardine" title="Sardine">sardines</a>).<a href="#cite_note-60">[60]</a> Lysine is the <a href="/wiki/Essential_amino_acid#Protein_quality" title="Essential amino acid">limiting amino acid</a> (the essential amino acid found in the smallest quantity in the particular foodstuff) in most <a href="/wiki/Cereal_grain" class="mw-redirect" title="Cereal grain">cereal grains</a>, but is plentiful in most <a href="/wiki/Pulse_(legume)" class="mw-redirect" title="Pulse (legume)">pulses</a> (legumes).<a href="#cite_note-VRYoung-61">[61]</a> Beans contain the lysine that <a href="/wiki/Maize" title="Maize">maize</a> lacks, and in the human archeological record beans and maize often appear together, as in the <a href="/wiki/Three_Sisters_(agriculture)" title="Three Sisters (agriculture)">Three Sisters</a>: beans, maize, and squash.<a href="#cite_note-62">[62]</a> A food is considered to have sufficient lysine if it has at least 51 mg of lysine per gram of protein (so that the protein is 5.1% lysine).<a href="#cite_note-63">[63]</a> L-lysine HCl is used as a <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a>, providing 80.03% L-lysine.<a href="#cite_note-DSBI-64">[64]</a> As such, 1 g of L-lysine is contained in 1.25 g of L-lysine HCl. <div class="mw-heading mw-heading2"><h2 id="Biological_roles">Biological roles</h2>[<a href="/w/index.php?title=Lysine&action=edit&section=7" title="Edit section: Biological roles">edit</a>]</div> The most common role for lysine is proteinogenesis. Lysine frequently plays an important role in <a href="/wiki/Protein_structure" title="Protein structure">protein structure</a>. Since its side chain contains a positively charged group on one end and a long <a href="/wiki/Hydrophobe" title="Hydrophobe">hydrophobic</a> carbon tail close to the backbone, lysine is considered somewhat <a href="/wiki/Amphiphile" title="Amphiphile">amphipathic</a>. For this reason, lysine can be found buried as well as more commonly in solvent channels and on the exterior of proteins, where it can interact with the aqueous environment.<a href="#cite_note-Betts_2003-65">[65]</a> Lysine can also contribute to protein stability as its ε-amino group often participates in <a href="/wiki/Hydrogen_bond" title="Hydrogen bond">hydrogen bonding</a>, <a href="/wiki/Salt_bridge_(protein_and_supramolecular)" title="Salt bridge (protein and supramolecular)">salt bridges</a> and <a href="/wiki/Covalent_bond" title="Covalent bond">covalent</a> interactions to form a <a href="/wiki/Schiff_base" title="Schiff base">Schiff base</a>.<a href="#cite_note-Betts_2003-65">[65]</a><a href="#cite_note-66">[66]</a><a href="#cite_note-67">[67]</a><a href="#cite_note-68">[68]</a> A second major role of lysine is in <a href="/wiki/Epigenetics" title="Epigenetics">epigenetic</a> regulation by means of <a href="/wiki/Histone" title="Histone">histone</a> <a href="/wiki/Histone#Histone_modification" title="Histone">modification</a>.<a href="#cite_note-Dambacher_2010-69">[69]</a><a href="#cite_note-70">[70]</a> There are several types of covalent histone modifications, which commonly involve lysine residues found in the protruding tail of histones. Modifications often include the addition or removal of an <a href="/wiki/Acetylation" title="Acetylation">acetyl (−CH3CO)</a> forming <a href="/wiki/Acetyllysine" title="Acetyllysine">acetyllysine</a> or reverting to lysine, up to three <a href="/wiki/Methylation" title="Methylation">methyl (−CH3)</a>, <a href="/wiki/Ubiquitin#Ubiquitylation" title="Ubiquitin">ubiquitin</a> or a <a href="/wiki/SUMO_protein" title="SUMO protein">sumo protein</a> group.<a href="#cite_note-Dambacher_2010-69">[69]</a><a href="#cite_note-71">[71]</a><a href="#cite_note-72">[72]</a><a href="#cite_note-73">[73]</a><a href="#cite_note-74">[74]</a> The various modifications have downstream effects on <a href="/wiki/Regulation_of_gene_expression" title="Regulation of gene expression">gene regulation</a>, in which genes can be activated or repressed. Lysine has also been implicated to play a key role in other biological processes including; structural proteins of <a href="/wiki/Connective_tissue" title="Connective tissue">connective tissues</a>, <a href="/wiki/Calcium" title="Calcium">calcium</a> <a href="/wiki/Homeostasis" title="Homeostasis">homeostasis</a>, and <a href="/wiki/Fatty_acid_metabolism" title="Fatty acid metabolism">fatty acid metabolism</a>.<a href="#cite_note-Shoulders_2009-75">[75]</a><a href="#cite_note-Civitelli_1992-76">[76]</a><a href="#cite_note-Vaz_2002-77">[77]</a> Lysine has been shown to be involved in the <a href="/wiki/Cross-link" title="Cross-link">crosslinking</a> between the three <a href="/wiki/Alpha_helix" title="Alpha helix">helical polypeptides</a> in <a href="/wiki/Collagen" title="Collagen">collagen</a>, resulting in its stability and tensile strength.<a href="#cite_note-Shoulders_2009-75">[75]</a><a href="#cite_note-78">[78]</a> This mechanism is akin to the role of lysine in <a href="/wiki/Bacterial_cell_structure#Cell_wall" title="Bacterial cell structure">bacterial cell walls</a>, in which lysine (and meso-diaminopimelate) are critical to the formation of crosslinks, and therefore, stability of the cell wall.<a href="#cite_note-79">[79]</a> This concept has previously been explored as a means to circumvent the unwanted release of potentially <a href="/wiki/Pathogen#Bacteria" title="Pathogen">pathogenic</a> genetically modified bacteria. It was proposed that an <a href="/wiki/Auxotrophy" title="Auxotrophy">auxotrophic</a> strain of <a href="/wiki/Escherichia_coli" title="Escherichia coli">Escherichia coli</a> (X1776) could be used for all genetic modification practices, as the strain is unable to survive without the supplementation of DAP, and thus, cannot live outside of a laboratory environment.<a href="#cite_note-80">[80]</a> Lysine has also been proposed to be involved in calcium intestinal absorption and renal retention, and thus, may play a role in <a href="/wiki/Calcium_metabolism" title="Calcium metabolism">calcium homeostasis</a>.<a href="#cite_note-Civitelli_1992-76">[76]</a> Finally, lysine has been shown to be a precursor for <a href="/wiki/Carnitine" title="Carnitine">carnitine</a>, which transports fatty acids to the <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a>, where they can be oxidised for the release of energy.<a href="#cite_note-Vaz_2002-77">[77]</a><a href="#cite_note-Rudman_1977-81">[81]</a> Carnitine is synthesised from <a href="/wiki/Methyllysine" title="Methyllysine">trimethyllysine</a>, which is a product of the degradation of certain proteins, as such lysine must first be incorporated into proteins and be methylated prior to being converted to carnitine.<a href="#cite_note-Vaz_2002-77">[77]</a> However, in mammals the primary source of carnitine is through dietary sources, rather than through lysine conversion.<a href="#cite_note-Vaz_2002-77">[77]</a> In <a href="/wiki/Opsins" class="mw-redirect" title="Opsins">opsins</a> like <a href="/wiki/Rhodopsin" title="Rhodopsin">rhodopsin</a> and the visual opsins (encoded by the genes <a href="/wiki/OPN1SW" title="OPN1SW">OPN1SW</a>, <a href="/wiki/OPN1MW" title="OPN1MW">OPN1MW</a>, and <a href="/wiki/OPN1LW" title="OPN1LW">OPN1LW</a>), <a href="/wiki/Retinaldehyde" class="mw-redirect" title="Retinaldehyde">retinaldehyde</a> forms a <a href="/wiki/Schiff_base" title="Schiff base">Schiff base</a> with a conserved lysine residue, and interaction of light with the <a href="/wiki/Retinylidene" class="mw-redirect" title="Retinylidene">retinylidene</a> group causes signal transduction in <a href="/wiki/Color_vision" title="Color vision">color vision</a> (See <a href="/wiki/Visual_cycle" title="Visual cycle">visual cycle</a> for details). <div class="mw-heading mw-heading3"><h3 id="Disputed_roles">Disputed roles</h3>[<a href="/w/index.php?title=Lysine&action=edit&section=8" title="Edit section: Disputed roles">edit</a>]</div> There has been a long discussion that lysine, when administered intravenously or orally, can significantly increase the release of <a href="/wiki/Growth_hormone" title="Growth hormone">growth hormones</a>.<a href="#cite_note-Chromiak_2002-82">[82]</a> This has led to athletes using lysine as a means of promoting muscle growth while training, however, no significant evidence to support this application of lysine has been found to date.<a href="#cite_note-Chromiak_2002-82">[82]</a><a href="#cite_note-83">[83]</a> Because <a href="/wiki/Herpes_simplex_virus" title="Herpes simplex virus">herpes simplex virus</a> (HSV) proteins are richer in arginine and poorer in lysine than the cells they infect, lysine supplements have been tried as a treatment. Since the two amino acids are taken up in the intestine, reclaimed in the kidney, and moved into cells by the same <a href="/wiki/Amino_acid_transporter" title="Amino acid transporter">amino acid transporters</a>, an abundance of lysine would, in theory, limit the amount of arginine available for viral replication.<a href="#cite_note-pmid16813459-84">[84]</a> Clinical studies do not provide good evidence for effectiveness as a <a href="/wiki/Preventive_healthcare" title="Preventive healthcare">prophylactic</a> or in the treatment for HSV outbreaks.<a href="#cite_note-pmid11225166-85">[85]</a><a href="#cite_note-86">[86]</a> In response to product claims that lysine could improve immune responses to HSV, a review by the <a href="/wiki/European_Food_Safety_Authority" title="European Food Safety Authority">European Food Safety Authority</a> found no evidence of a cause–effect relationship. The same review, published in 2011, found no evidence to support claims that lysine could lower cholesterol, increase appetite, contribute to protein synthesis in any role other than as an ordinary nutrient, or increase calcium absorption or retention.<a href="#cite_note-87">[87]</a> <div class="mw-heading mw-heading2"><h2 id="Roles_in_disease">Roles in disease</h2>[<a href="/w/index.php?title=Lysine&action=edit&section=9" title="Edit section: Roles in disease">edit</a>]</div> Diseases related to lysine are a result of the downstream processing of lysine, i.e. the incorporation into proteins or modification into alternative biomolecules. The role of lysine in collagen has been outlined above, however, a lack of lysine and <a href="/wiki/Hydroxylysine" title="Hydroxylysine">hydroxylysine</a> involved in the crosslinking of collagen peptides has been linked to a disease state of the connective tissue.<a href="#cite_note-88">[88]</a> As carnitine is a key lysine-derived metabolite involved in fatty acid metabolism, a substandard diet lacking sufficient carnitine and lysine can lead to decreased carnitine levels, which can have significant cascading effects on an individual's health.<a href="#cite_note-Rudman_1977-81">[81]</a><a href="#cite_note-89">[89]</a> Lysine has also been shown to play a role in <a href="/wiki/Anemia" title="Anemia">anaemia</a>, as lysine is suspected to have an effect on the uptake of <a href="/wiki/Iron" title="Iron">iron</a> and, subsequently, the concentration of <a href="/wiki/Ferritin" title="Ferritin">ferritin</a> in <a href="/wiki/Blood_plasma" title="Blood plasma">blood plasma</a>.<a href="#cite_note-Rushton_2002-90">[90]</a> However, the exact mechanism of action is yet to be elucidated.<a href="#cite_note-Rushton_2002-90">[90]</a> Most commonly, lysine deficiency is seen in non-western societies and manifests as <a href="/wiki/Protein%E2%80%93energy_malnutrition" title="Protein–energy malnutrition">protein-energy malnutrition</a>, which has profound and systemic effects on the health of the individual.<a href="#cite_note-91">[91]</a><a href="#cite_note-92">[92]</a> There is also a <a href="/wiki/Heredity" title="Heredity">hereditary</a> genetic disease that involves <a href="/wiki/Mutation" title="Mutation">mutations</a> in the enzymes responsible for lysine catabolism, namely the bifunctional AASS enzyme of the saccharopine pathway.<a href="#cite_note-Houten_2013-93">[93]</a> Due to a lack of lysine catabolism, the amino acid accumulates in plasma and patients develop <a href="/wiki/Hyperlysinemia" title="Hyperlysinemia">hyperlysinaemia</a>, which can present as asymptomatic to severe <a href="/wiki/Neurological_disorder" title="Neurological disorder">neurological disabilities</a>, including <a href="/wiki/Epilepsy" title="Epilepsy">epilepsy</a>, <a href="/wiki/Ataxia" title="Ataxia">ataxia</a>, <a href="/wiki/Spasticity" title="Spasticity">spasticity</a>, and <a href="/wiki/Psychomotor_retardation" title="Psychomotor retardation">psychomotor impairment</a>.<a href="#cite_note-Houten_2013-93">[93]</a><a href="#cite_note-94">[94]</a> The clinical significance of hyperlysinemia is the subject of debate in the field with some studies finding no correlation between physical or mental disabilities and hyperlysinemia.<a href="#cite_note-95">[95]</a> In addition to this, mutations in genes related to lysine metabolism have been implicated in several disease states, including <a href="/wiki/Pyridoxine-dependent_epilepsy" title="Pyridoxine-dependent epilepsy">pyridoxine-dependent epilepsia</a> (<a href="/wiki/ALDH7A1" title="ALDH7A1">ALDH7A1 gene</a>), <a href="/wiki/Alpha-aminoadipic_and_alpha-ketoadipic_aciduria" title="Alpha-aminoadipic and alpha-ketoadipic aciduria">α-ketoadipic and α-aminoadipic aciduria</a> (<a href="/wiki/DHTKD1" title="DHTKD1">DHTKD1 gene</a>), and <a href="/wiki/Glutaric_aciduria_type_1" title="Glutaric aciduria type 1">glutaric aciduria type 1</a> (<a href="/wiki/Glutaryl-CoA_dehydrogenase" title="Glutaryl-CoA dehydrogenase">GCDH gene</a>).<a href="#cite_note-Danhauser_2012-44">[44]</a><a href="#cite_note-96">[96]</a><a href="#cite_note-97">[97]</a><a href="#cite_note-98">[98]</a><a href="#cite_note-99">[99]</a> Hyperlysinuria is marked by high amounts of lysine in the urine.<a href="#cite_note-100">[100]</a> It is often due to a <a href="/wiki/Metabolic_disease" class="mw-redirect" title="Metabolic disease">metabolic disease</a> in which a <a href="/wiki/Protein" title="Protein">protein</a> involved in the breakdown of lysine is non functional due to a genetic mutation.<a href="#cite_note-Book06-101">[101]</a> It may also occur due to a failure of <a href="/wiki/Renal" class="mw-redirect" title="Renal">renal</a> tubular transport.<a href="#cite_note-Book06-101">[101]</a> <div class="mw-heading mw-heading2"><h2 id="Use_of_lysine_in_animal_feed">Use of lysine in animal feed</h2>[<a href="/w/index.php?title=Lysine&action=edit&section=10" title="Edit section: Use of lysine in animal feed">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:L-lysine_for_cats.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/L-lysine_for_cats.jpg/220px-L-lysine_for_cats.jpg" decoding="async" width="220" height="235" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/L-lysine_for_cats.jpg/330px-L-lysine_for_cats.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/69/L-lysine_for_cats.jpg/440px-L-lysine_for_cats.jpg 2x" data-file-width="1932" data-file-height="2061" /></a><figcaption>Lysine sold as a supplement for cats</figcaption></figure> Lysine production for animal feed is a major global industry, reaching in 2009 almost 700,000 tons for a market value of over €1.22 billion.<a href="#cite_note-lysineanimalfeed1-102">[102]</a> Lysine is an important additive to animal feed because it is a limiting amino acid when optimizing the growth of certain animals such as pigs and chickens for the production of meat. Lysine supplementation allows for the use of lower-cost plant protein (maize, for instance, rather than <a href="/wiki/Soy" class="mw-redirect" title="Soy">soy</a>) while maintaining high growth rates, and limiting the pollution from nitrogen excretion.<a href="#cite_note-lysineanimalfeed-103">[103]</a> In turn, however, phosphate pollution is a major environmental cost when corn is used as feed for poultry and swine.<a href="#cite_note-104">[104]</a> Lysine is industrially produced by microbial fermentation, from a base mainly of sugar. Genetic engineering research is actively pursuing bacterial strains to improve the efficiency of production and allow lysine to be made from other substrates.<a href="#cite_note-lysineanimalfeed1-102">[102]</a> The most common bacteria used is <a href="/wiki/Corynebacterium_glutamicum" title="Corynebacterium glutamicum">Corynebacterium glutamicum</a> specially mutagenized or gene-engineered to produce lysine, but analogous strains of <a href="/wiki/Escherichia_coli" title="Escherichia coli">Escherichia coli</a> are also employed. <div class="mw-heading mw-heading2"><h2 id="In_popular_culture">In popular culture</h2>[<a href="/w/index.php?title=Lysine&action=edit&section=11" title="Edit section: In popular culture">edit</a>]</div> The 1993 film <a href="/wiki/Jurassic_Park_(film)" title="Jurassic Park (film)">Jurassic Park</a>, which is based on the 1990 novel <a href="/wiki/Jurassic_Park_(novel)" title="Jurassic Park (novel)">Jurassic Park</a> by <a href="/wiki/Michael_Crichton" title="Michael Crichton">Michael Crichton</a>, features <a href="/wiki/Dinosaur" title="Dinosaur">dinosaurs</a> that were <a href="/wiki/Genetic_engineering" title="Genetic engineering">genetically altered</a> so that they could not produce lysine, an example of engineered <a href="/wiki/Auxotrophy" title="Auxotrophy">auxotrophy</a>.<a href="#cite_note-105">[105]</a> This was known as the "lysine contingency" and was supposed to prevent the <a href="/wiki/Cloning" title="Cloning">cloned</a> dinosaurs from surviving outside the park, forcing them to depend on lysine supplements provided by the park's veterinary staff. In reality, no animal can produce lysine; it is an <a href="/wiki/Essential_amino_acid" title="Essential amino acid">essential amino acid</a>.<a href="#cite_note-106">[106]</a> In 1996, lysine became the focus of a <a href="/wiki/Lysine_price-fixing_conspiracy" title="Lysine price-fixing conspiracy">price-fixing case</a>, the largest in United States history. The <a href="/wiki/Archer_Daniels_Midland_Company" class="mw-redirect" title="Archer Daniels Midland Company">Archer Daniels Midland Company</a> paid a fine of US$100 million, and three of its executives were convicted and served prison time. Also found guilty in the price-fixing case were two Japanese firms (<a href="/wiki/Ajinomoto" title="Ajinomoto">Ajinomoto</a>, Kyowa Hakko) and a South Korean firm (Sewon).<a href="#cite_note-107">[107]</a> Secret video recordings of the conspirators fixing lysine's price can be found online or by requesting the video from the <a href="/wiki/U.S._Department_of_Justice" class="mw-redirect" title="U.S. Department of Justice">U.S. Department of Justice</a>, Antitrust Division. This case gave the basis for the book <a href="/wiki/The_Informant_(book)" title="The Informant (book)">The Informant: A True Story</a>,<a href="#cite_note-108">[108]</a> and the movie <a href="/wiki/The_Informant!" title="The Informant!">The Informant!</a>. <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Lysine&action=edit&section=12" title="Edit section: References">edit</a>]</div> <a href="/wiki/File:Open_Access_logo_PLoS_transparent.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Open_Access_logo_PLoS_transparent.svg/9px-Open_Access_logo_PLoS_transparent.svg.png" decoding="async" width="9" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Open_Access_logo_PLoS_transparent.svg/14px-Open_Access_logo_PLoS_transparent.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/Open_Access_logo_PLoS_transparent.svg/18px-Open_Access_logo_PLoS_transparent.svg.png 2x" data-file-width="640" data-file-height="1000" /></a> This article was adapted from the following source under a <a rel="nofollow" class="external text" href="https://creativecommons.org/licenses/by/4.0/">CC BY 4.0</a> license (<a class="external text" href="https://en.wikipedia.org/w/index.php?title=Lysine&action=history&date-range-to=2018-06-10">2018</a>) (<a class="external text" href="https://en.wikiversity.org/wiki/talk:WikiJournal_of_Science/Lysine:_biosynthesis,_catabolism_and_roles">reviewer reports</a>): <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 class="citation journal cs1">Cody J Hall; Tatiana P. Soares da Costa (1 June 2018). <a class="external text" href="https://upload.wikimedia.org/wikiversity/en/8/88/Lysine_biosynthesis%2C_catabolism_and_roles.pdf">"Lysine: biosynthesis, catabolism and roles"</a> (PDF). WikiJournal of Science. 1 (1): 4. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15347%2FWJS%2F2018.004">10.15347/WJS/2018.004</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2470-6345">2470-6345</a>. <a href="/wiki/WDQ_(identifier)" class="mw-redirect" title="WDQ (identifier)">Wikidata</a> <a href="https://www.wikidata.org/wiki/Q55120301" class="extiw" title="d:Q55120301">Q55120301</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=WikiJournal+of+Science&rft.atitle=Lysine%3A+biosynthesis%2C+catabolism+and+roles&rft.volume=1&rft.issue=1&rft.pages=4&rft.date=2018-06-01&rft_id=info%3Adoi%2F10.15347%2FWJS%2F2018.004&rft.issn=2470-6345&rft.au=Cody+J+Hall&rft.au=Tatiana+P.+Soares+da+Costa&rft_id=https%3A%2F%2Fupload.wikimedia.org%2Fwikiversity%2Fen%2F8%2F88%2FLysine_biosynthesis%252C_catabolism_and_roles.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALysine" class="Z3988"> <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 mw-references-columns"><ol class="references"> <li id="cite_note-Williams-1">^ <a href="#cite_ref-Williams_1-0">a</a> <a href="#cite_ref-Williams_1-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWilliamsHughesHarris2015" class="citation journal cs1">Williams, P. A.; Hughes, C. E.; Harris, K. D. M (2015). "L-Lysine: Exploiting Powder X-ray Diffraction to Complete the Set of Crystal Structures of the 20 Directly Encoded Proteinogenic Amino Acids". <a href="/wiki/Angewandte_Chemie_International_Edition" class="mw-redirect" title="Angewandte Chemie International Edition">Angew. Chem. Int. Ed.</a> 54 (13): 3973–3977. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.201411520">10.1002/anie.201411520</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/25651303">25651303</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angew.+Chem.+Int.+Ed.&rft.atitle=L-Lysine%3A+Exploiting+Powder+X-ray+Diffraction+to+Complete+the+Set+of+Crystal+Structures+of+the+20+Directly+Encoded+Proteinogenic+Amino+Acids&rft.volume=54&rft.issue=13&rft.pages=3973-3977&rft.date=2015&rft_id=info%3Adoi%2F10.1002%2Fanie.201411520&rft_id=info%3Apmid%2F25651303&rft.aulast=Williams&rft.aufirst=P.+A.&rft.au=Hughes%2C+C.+E.&rft.au=Harris%2C+K.+D.+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALysine" class="Z3988"> </li> <li id="cite_note-2"><a href="#cite_ref-2">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1153490">"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). Nomenclature and symbolism for amino acids and peptides. Recommendations 1983"</a>. Biochemical Journal. 219 (2): 345–373. 15 April 1984. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1042%2Fbj2190345">10.1042/bj2190345</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1153490">1153490</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/6743224">6743224</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochemical+Journal&rft.atitle=IUPAC-IUB+Joint+Commission+on+Biochemical+Nomenclature+%28JCBN%29.+Nomenclature+and+symbolism+for+amino+acids+and+peptides.+Recommendations+1983&rft.volume=219&rft.issue=2&rft.pages=345-373&rft.date=1984-04-15&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1153490%23id-name%3DPMC&rft_id=info%3Apmid%2F6743224&rft_id=info%3Adoi%2F10.1042%2Fbj2190345&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1153490&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALysine" class="Z3988"> </li> <li id="cite_note-3"><a href="#cite_ref-3">^</a> <a rel="nofollow" class="external text" href="http://www.biology.arizona.edu/biochemistry/problem_sets/aa/Lysine.html">Lysine.</a> The Biology Project, Department of Biochemistry and Molecular Biophysics, University of Arizona. </li> <li id="cite_note-4"><a href="#cite_ref-4">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDrechsel1889" class="citation journal cs1 cs1-prop-foreign-lang-source">Drechsel E (1889). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=osu.32435060196680;view=1up;seq=441">"Zur Kenntniss der Spaltungsprodukte des Caseïns"</a> [[Contribution] to [our] knowledge of the cleavage products of casein]. Journal für Praktische Chemie. 2nd series (in German). 39: 425–429. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fprac.18890390135">10.1002/prac.18890390135</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+f%C3%BCr+Praktische+Chemie&rft.atitle=Zur+Kenntniss+der+Spaltungsprodukte+des+Case%C3%AFns&rft.volume=39&rft.pages=425-429&rft.date=1889&rft_id=info%3Adoi%2F10.1002%2Fprac.18890390135&rft.aulast=Drechsel&rft.aufirst=E&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dosu.32435060196680%3Bview%3D1up%3Bseq%3D441&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALysine" class="Z3988"> On p. 428, Drechsel presented an empirical formula for the chloroplatinate salt of lysine – C8H16N2O2Cl2·PtCl4 + H2O – but he later admitted that this formula was wrong because the salt's crystals contained ethanol instead of water. See: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDrechsel1891" class="citation journal cs1 cs1-prop-foreign-lang-source">Drechsel E (1891). "Der Abbau der Eiweissstoffe" [The disassembly of proteins]. Archiv für Anatomie und Physiologie (in German): 248–278;</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Archiv+f%C3%BCr+Anatomie+und+Physiologie&rft.atitle=Der+Abbau+der+Eiweissstoffe&rft.pages=248-278&rft.date=1891&rft.aulast=Drechsel&rft.aufirst=E&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALysine" class="Z3988"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDrechsel1877" class="citation web cs1 cs1-prop-foreign-lang-source">Drechsel E (1877). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=coo.31924056294253;view=1up;seq=268">"Zur Kenntniss der Spaltungsproducte des Caseïns"</a> [Contribution] to [our] knowledge of the cleavage products of casein] (in German). pp. 254–260. <q>From p. 256:] " … die darin enthaltene Base hat die Formel C6H14N2O2. Der anfängliche Irrthum ist dadurch veranlasst worden, dass das Chloroplatinat nicht, wie angenommen ward, Krystallwasser, sondern Krystallalkohol enthält, … " ( … the base [that's] contained therein has the [empirical] formula C6H14N2O2. The initial error was caused by the chloroplatinate containing not water in the crystal (as was assumed), but ethanol … )</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Zur+Kenntniss+der+Spaltungsproducte+des+Case%C3%AFns&rft.pages=254-260&rft.date=1877&rft.aulast=Drechsel&rft.aufirst=E&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dcoo.31924056294253%3Bview%3D1up%3Bseq%3D268&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALysine" class="Z3988"> </li> <li id="cite_note-5"><a href="#cite_ref-5">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVickerySchmidt1931" class="citation journal cs1">Vickery, Hubert Bradford.; Schmidt, Carl L. A. (1 October 1931). <a rel="nofollow" class="external text" href="https://pubs.acs.org/doi/abs/10.1021/cr60033a001">"The History of the Discovery of the Amino Acids"</a>. Chemical Reviews. 9 (2): 169–318. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fcr60033a001">10.1021/cr60033a001</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0009-2665">0009-2665</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Reviews&rft.atitle=The+History+of+the+Discovery+of+the+Amino+Acids.&rft.volume=9&rft.issue=2&rft.pages=169-318&rft.date=1931-10-01&rft_id=info%3Adoi%2F10.1021%2Fcr60033a001&rft.issn=0009-2665&rft.aulast=Vickery&rft.aufirst=Hubert+Bradford.&rft.au=Schmidt%2C+Carl+L.+A.&rft_id=https%3A%2F%2Fpubs.acs.org%2Fdoi%2Fabs%2F10.1021%2Fcr60033a001&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALysine" class="Z3988"> </li> <li id="cite_note-6"><a href="#cite_ref-6">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDrechsel1891" class="citation journal cs1 cs1-prop-foreign-lang-source">Drechsel E (1891). "Der Abbau der Eiweissstoffe" [The disassembly of proteins]. Archiv für Anatomie und Physiologie (in German): 248–278.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Archiv+f%C3%BCr+Anatomie+und+Physiologie&rft.atitle=Der+Abbau+der+Eiweissstoffe&rft.pages=248-278&rft.date=1891&rft.aulast=Drechsel&rft.aufirst=E&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALysine" class="Z3988">; <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFischer1891" class="citation journal cs1 cs1-prop-foreign-lang-source">Fischer E (1891). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=coo.31924056294253;view=1up;seq=281">"Ueber neue Spaltungsproducte des Leimes"</a> [On new cleavage products of gelatin]. Archiv für Anatomie und Physiologie (in German): 465–469. <q>From p. 469:] " … die Base C6H14N2O2, welche mit dem Namen Lysin bezeichnet werden mag, … " ( … the base C6H14N2O2, which may be designated with the name "lysine", … ) [Note: Ernst Fischer was a graduate student of Drechsel.]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Archiv+f%C3%BCr+Anatomie+und+Physiologie&rft.atitle=Ueber+neue+Spaltungsproducte+des+Leimes&rft.pages=465-469&rft.date=1891&rft.aulast=Fischer&rft.aufirst=Ernst&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dcoo.31924056294253%3Bview%3D1up%3Bseq%3D281&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALysine" class="Z3988"> </li> <li id="cite_note-7"><a href="#cite_ref-7">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFischerWeigert1902" class="citation journal cs1 cs1-prop-foreign-lang-source">Fischer E, Weigert F (1902). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=hvd.cl1i27;view=1up;seq=1240">"Synthese der α,ε – Diaminocapronsäure (Inactives Lysin)"</a> [Synthesis of α,ε-diaminohexanoic acid ([optically] inactive lysine)]. 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Global Price Fixing (2nd ed.). Heidelberg: Springer-Verlag. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-78669-6" title="Special:BookSources/978-3-540-78669-6"><bdi>978-3-540-78669-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Global+Price+Fixing&rft.place=Heidelberg&rft.edition=2nd&rft.pub=Springer-Verlag&rft.date=2008&rft.isbn=978-3-540-78669-6&rft.aulast=Connor&rft.aufirst=JM&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALysine" class="Z3988"> </li> <li id="cite_note-108"><a href="#cite_ref-108">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFEichenwald2000" class="citation book cs1">Eichenwald K (2000). <a rel="nofollow" class="external text" href="https://archive.org/details/informanttruest00eich">The Informant: a true story</a>. New York: Broadway Books. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7679-0326-4" title="Special:BookSources/978-0-7679-0326-4"><bdi>978-0-7679-0326-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Informant%3A+a+true+story&rft.place=New+York&rft.pub=Broadway+Books&rft.date=2000&rft.isbn=978-0-7679-0326-4&rft.aulast=Eichenwald&rft.aufirst=Kurt&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Finformanttruest00eich&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALysine" class="Z3988"> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output 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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_acids" 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><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/182px-L-amino_acid_any.png" decoding="async" width="182" height="160" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0e/L-amino_acid_any.png/273px-L-amino_acid_any.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0e/L-amino_acid_any.png/364px-L-amino_acid_any.png 2x" data-file-width="728" data-file-height="640" /></a></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 href="/wiki/Leucine" title="Leucine">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 (pKa)</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 class="mw-selflink selflink">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 (pKa)</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><a href="/wiki/Amino_acids" class="mw-redirect" title="Amino acids">Amino acids</a> types: <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_intermediates" 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_intermediates" 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 class="mw-selflink selflink">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 href="/wiki/Leucine" title="Leucine">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">N′-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>→ <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→" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glycine" title="Glycine">glycine</a>→ <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>→ <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>→ <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><a href="/wiki/Methionine#Generation_of_homocysteine" title="Methionine">generation of homocysteine</a>: <a href="/wiki/S-Adenosyl_methionine" title="S-Adenosyl methionine">S-Adenosyl methionine</a></li> <li><a href="/wiki/S-Adenosyl-L-homocysteine" title="S-Adenosyl-L-homocysteine">S-Adenosyl-L-homocysteine</a></li> <li><a href="/wiki/Homocysteine" title="Homocysteine">Homocysteine</a></li></ul> <ul><li><a href="/wiki/Methionine#Conversion_to_cysteine" title="Methionine">conversion to cysteine</a>: <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>see <a href="/wiki/Urea_cycle" title="Urea cycle">urea cycle</a></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 href="/wiki/Cysteine_metabolism" title="Cysteine metabolism">Cysteine metabolism</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/Cysteine_sulfinic_acid" title="Cysteine sulfinic acid">Cysteine sulfinic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" 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