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class="vector-toc-numb">2</span> <span>Dietary sources</span> </div> </a> <ul id="toc-Dietary_sources-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Industrial_sources" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Industrial_sources"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Industrial sources</span> </div> </a> <ul id="toc-Industrial_sources-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biological_functions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biological_functions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Biological functions</span> </div> </a> <button aria-controls="toc-Biological_functions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Biological functions subsection</span> </button> <ul id="toc-Biological_functions-sublist" class="vector-toc-list"> <li id="toc-Precursor_to_the_antioxidant_glutathione" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Precursor_to_the_antioxidant_glutathione"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Precursor to the antioxidant glutathione</span> </div> </a> <ul id="toc-Precursor_to_the_antioxidant_glutathione-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Precursor_to_iron-sulfur_clusters" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Precursor_to_iron-sulfur_clusters"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Precursor to iron-sulfur clusters</span> </div> </a> <ul id="toc-Precursor_to_iron-sulfur_clusters-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metal_ion_binding" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metal_ion_binding"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Metal ion binding</span> </div> </a> <ul id="toc-Metal_ion_binding-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Roles_in_protein_structure" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Roles_in_protein_structure"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Roles in protein structure</span> </div> </a> <ul id="toc-Roles_in_protein_structure-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Evolutionary_role_of_cysteine" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Evolutionary_role_of_cysteine"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Evolutionary role of cysteine</span> </div> </a> <ul id="toc-Evolutionary_role_of_cysteine-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Applications</span> </div> </a> <button aria-controls="toc-Applications-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Applications subsection</span> </button> <ul id="toc-Applications-sublist" class="vector-toc-list"> <li id="toc-Reducing_toxic_effects_of_alcohol" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reducing_toxic_effects_of_alcohol"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Reducing toxic effects of alcohol</span> </div> </a> <ul id="toc-Reducing_toxic_effects_of_alcohol-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-N-Acetylcysteine" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#N-Acetylcysteine"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span><i>N</i>-Acetylcysteine</span> </div> </a> <ul id="toc-N-Acetylcysteine-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Sheep" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Sheep"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3</span> <span>Sheep</span> </div> </a> <ul id="toc-Sheep-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Chemical_reactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemical_reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Chemical reactions</span> </div> </a> <ul id="toc-Chemical_reactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Safety" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Safety"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Safety</span> </div> </a> <ul id="toc-Safety-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">13</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">14</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Cysteine</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 58 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-58" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">58 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%B3%D9%8A%D8%B3%D8%AA%D8%A6%D9%8A%D9%86" title="سيستئين – Arabic" lang="ar" hreflang="ar" data-title="سيستئين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%B3%DB%8C%D8%B3%D8%AA%D8%A6%DB%8C%D9%86" title="سیستئین – South Azerbaijani" lang="azb" hreflang="azb" data-title="سیستئین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Cystein" title="Cystein – Minnan" lang="nan" hreflang="nan" data-title="Cystein" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A6%D1%8B%D1%81%D1%82%D1%8D%D1%96%D0%BD" title="Цыстэін – Belarusian" lang="be" hreflang="be" data-title="Цыстэін" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-be-x-old mw-list-item"><a href="https://be-tarask.wikipedia.org/wiki/%D0%A6%D1%8B%D1%81%D1%82%D1%8D%D1%96%D0%BD" title="Цыстэін – Belarusian (Taraškievica orthography)" lang="be-tarask" hreflang="be-tarask" data-title="Цыстэін" data-language-autonym="Беларуская (тарашкевіца)" data-language-local-name="Belarusian (Taraškievica orthography)" class="interlanguage-link-target"><span>Беларуская (тарашкевіца)</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A6%D0%B8%D1%81%D1%82%D0%B5%D0%B8%D0%BD" title="Цистеин – Bulgarian" lang="bg" hreflang="bg" data-title="Цистеин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Cistein" title="Cistein – Bosnian" lang="bs" hreflang="bs" data-title="Cistein" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Ciste%C3%AFna" title="Cisteïna – Catalan" lang="ca" hreflang="ca" data-title="Cisteïna" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Cystein" title="Cystein – Czech" lang="cs" hreflang="cs" data-title="Cystein" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Cystein" title="Cystein – Danish" lang="da" hreflang="da" data-title="Cystein" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Cystein" title="Cystein – German" lang="de" hreflang="de" data-title="Cystein" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Ts%C3%BCsteiin" title="Tsüsteiin – Estonian" lang="et" hreflang="et" data-title="Tsüsteiin" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9A%CF%85%CF%83%CF%84%CE%B5%CE%90%CE%BD%CE%B7" title="Κυστεΐνη – Greek" lang="el" hreflang="el" data-title="Κυστεΐνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Ciste%C3%ADna" title="Cisteína – Spanish" lang="es" hreflang="es" data-title="Cisteína" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Cisteino" title="Cisteino – Esperanto" lang="eo" hreflang="eo" data-title="Cisteino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Zisteina" title="Zisteina – Basque" lang="eu" hreflang="eu" data-title="Zisteina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%DB%8C%D8%B3%D8%AA%D8%A6%DB%8C%D9%86" title="سیستئین – Persian" lang="fa" hreflang="fa" data-title="سیستئین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Cyst%C3%A9ine" title="Cystéine – French" lang="fr" hreflang="fr" data-title="Cystéine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Ciste%C3%ADna" title="Cisteína – Galician" lang="gl" hreflang="gl" data-title="Cisteína" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%8B%9C%EC%8A%A4%ED%85%8C%EC%9D%B8" title="시스테인 – Korean" lang="ko" hreflang="ko" data-title="시스테인" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%91%D5%AB%D5%BD%D5%BF%D5%A5%D5%AB%D5%B6" title="Ցիստեին – Armenian" lang="hy" hreflang="hy" data-title="Ցիստեին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Cistein" title="Cistein – Croatian" lang="hr" hreflang="hr" data-title="Cistein" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Sisteina" title="Sisteina – Indonesian" lang="id" hreflang="id" data-title="Sisteina" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Cisteina" title="Cisteina – Italian" lang="it" hreflang="it" data-title="Cisteina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A6%D7%99%D7%A1%D7%98%D7%90%D7%99%D7%9F" title="ציסטאין – Hebrew" lang="he" hreflang="he" data-title="ציסטאין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/S%C3%AEste%C3%AEn" title="Sîsteîn – Kurdish" lang="ku" hreflang="ku" data-title="Sîsteîn" data-language-autonym="Kurdî" data-language-local-name="Kurdish" class="interlanguage-link-target"><span>Kurdî</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Cysteinum" title="Cysteinum – Latin" lang="la" hreflang="la" data-title="Cysteinum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Ciste%C4%ABns" title="Cisteīns – Latvian" lang="lv" hreflang="lv" data-title="Cisteīns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Cystein" title="Cystein – Luxembourgish" lang="lb" hreflang="lb" data-title="Cystein" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Cisteinas" title="Cisteinas – Lithuanian" lang="lt" hreflang="lt" data-title="Cisteinas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Cisztein" title="Cisztein – Hungarian" lang="hu" hreflang="hu" data-title="Cisztein" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A6%D0%B8%D1%81%D1%82%D0%B5%D0%B8%D0%BD" title="Цистеин – Macedonian" lang="mk" hreflang="mk" data-title="Цистеин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Sisteina" title="Sisteina – Malay" lang="ms" hreflang="ms" data-title="Sisteina" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cyste%C3%AFne" title="Cysteïne – Dutch" lang="nl" hreflang="nl" data-title="Cysteïne" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B7%E3%82%B9%E3%83%86%E3%82%A4%E3%83%B3" title="システイン – Japanese" lang="ja" hreflang="ja" data-title="システイン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Cystein" title="Cystein – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Cystein" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Cystein" title="Cystein – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Cystein" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Ciste%C3%AFna" title="Cisteïna – Occitan" lang="oc" hreflang="oc" data-title="Cisteïna" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Cysteina" title="Cysteina – Polish" lang="pl" hreflang="pl" data-title="Cysteina" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Ciste%C3%ADna" title="Cisteína – Portuguese" lang="pt" hreflang="pt" data-title="Cisteína" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Cistein%C4%83" title="Cisteină – Romanian" lang="ro" hreflang="ro" data-title="Cisteină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A6%D0%B8%D1%81%D1%82%D0%B5%D0%B8%D0%BD" title="Цистеин – Russian" lang="ru" hreflang="ru" data-title="Цистеин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Cysteine" title="Cysteine – Simple English" lang="en-simple" hreflang="en-simple" data-title="Cysteine" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Cyste%C3%ADn" title="Cysteín – Slovak" lang="sk" hreflang="sk" data-title="Cysteín" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Cistein" title="Cistein – Slovenian" lang="sl" hreflang="sl" data-title="Cistein" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Cistein" title="Cistein – Serbian" lang="sr" hreflang="sr" data-title="Cistein" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a 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dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Proteinogenic 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/Cytosine" title="Cytosine">cytosine</a>, <a href="/wiki/Cystine" title="Cystine">cystine</a>, <a href="/wiki/Cytisine" title="Cytisine">cytisine</a>, <a href="/wiki/Cytidine" title="Cytidine">cytidine</a>, or <a href="/wiki/Sistine" class="mw-redirect" title="Sistine">Sistine</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">"Cys" redirects here. For other uses, see <a href="/wiki/Cys_(disambiguation)" class="mw-redirect mw-disambig" title="Cys (disambiguation)">Cys (disambiguation)</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><style data-mw-deduplicate="TemplateStyles:r920966791">.mw-parser-output span.smallcaps{font-variant:small-caps}.mw-parser-output span.smallcaps-smaller{font-size:85%}</style><span class="smallcaps">l</span>-Cysteine </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:L-Cystein_-_L-Cysteine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/L-Cystein_-_L-Cysteine.svg/220px-L-Cystein_-_L-Cysteine.svg.png" decoding="async" width="220" height="144" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1a/L-Cystein_-_L-Cysteine.svg/330px-L-Cystein_-_L-Cysteine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1a/L-Cystein_-_L-Cysteine.svg/440px-L-Cystein_-_L-Cysteine.svg.png 2x" data-file-width="185" data-file-height="121" /></a></span><br /><div style="text-align:center;"><a href="/wiki/Skeletal_formula" title="Skeletal formula">Skeletal formula</a> of <small>L</small>-cysteine</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:Cysteine-from-xtal-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Cysteine-from-xtal-3D-bs-17.png/110px-Cysteine-from-xtal-3D-bs-17.png" decoding="async" width="110" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Cysteine-from-xtal-3D-bs-17.png/165px-Cysteine-from-xtal-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Cysteine-from-xtal-3D-bs-17.png/220px-Cysteine-from-xtal-3D-bs-17.png 2x" data-file-width="2000" data-file-height="1834" /></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></div> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:L-cysteine-from-xtal-Mercury-3D-sf.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2d/L-cysteine-from-xtal-Mercury-3D-sf.png/110px-L-cysteine-from-xtal-Mercury-3D-sf.png" decoding="async" width="110" height="107" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2d/L-cysteine-from-xtal-Mercury-3D-sf.png/165px-L-cysteine-from-xtal-Mercury-3D-sf.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2d/L-cysteine-from-xtal-Mercury-3D-sf.png/220px-L-cysteine-from-xtal-Mercury-3D-sf.png 2x" data-file-width="2000" data-file-height="1946" /></a><figcaption></figcaption></figure><div style="text-align:center"><a href="/wiki/Space-filling_model" title="Space-filling model">Space-filling model</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 name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Cysteine</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;"><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>2-Amino-3-sulfhydrylpropanoic acid</li></ul></div></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><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=52-90-4">52-90-4</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=52-89-1">52-89-1</a></span> (hydrochloride)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=921-01-7">921-01-7</a></span> D-cysteine</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%28%5BC%40%40H%5D%28C%28%3DO%29O%29N%29S">Interactive image</a></span></li><li><a href="/wiki/Zwitterion" title="Zwitterion">Zwitterion</a>: <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%28%5BC%40%40H%5D%28C%28%3DO%29%5BO-%5D%29%5BNH3%2B%5D%29S">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td>Abbreviations </td> <td><b>Cys</b>, <b>C</b> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=15356">CHEBI:15356</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL54943">ChEMBL54943</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.574.html">574</a></span> (Racemic)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.5653.html">5653</a></span> (<small>L</small>-form)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.145">100.000.145</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q186474#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>200-158-2</li></ul></div> </td></tr> <tr> <td><a href="/wiki/E_number" title="E number"><span title="E number (food additive code)">E number</span></a> </td> <td>E920 <a href="/wiki/E_number#E900–E999" title="E number">(glazing agents, ...)</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><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=4782">4782</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00026">D00026</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5862">5862</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/K848JZ4886">K848JZ4886</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/A9U1687S1S">A9U1687S1S</a></span> (hydrochloride)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID8022876">DTXSID8022876</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q186474#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; 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/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: XUJNEKJLAYXESH-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: XUJNEKJLAYXESH-REOHCLBHBU</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/C3H7NO2S/c4-2(1-7)3(5)6/h2,7H,1,4H2,(H,5,6)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: XUJNEKJLAYXESH-UHFFFAOYAC</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([C@@H](C(=O)O)N)S</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([C@@H](C(=O)[O-])[NH3+])S</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>3</sub><span title="Hydrogen">H</span><sub>7</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span><sub>2</sub><span title="Sulfur">S</span> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002121150000000000♠"></span>121.15</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>white crystals or powder </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>240 °C (464 °F; 513 K) decomposes </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>277g/L (at 25 °C)<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>1.5g/100g ethanol 19 °C <sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>1.71 (<a href="/wiki/Conjugate_acid" class="mw-redirect" title="Conjugate acid">conjugate acid</a>), 8.33 (<a href="/wiki/Thiol" title="Thiol">thiol</a>), 10.78<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Specific_rotation" title="Specific rotation">Chiral rotation</a> ([α]<sub>D</sub>)</div> </td> <td>+9.4° (H<sub>2</sub>O, <i>c</i> = 1.3) </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/Cysteine_(data_page)" title="Cysteine (data page)">Cysteine (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 style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=443554430&page2=Cysteine">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></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> <p><b>Cysteine</b> (symbol <b>Cys</b> or <b>C</b>;<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> <span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="'s' in 'sigh'">s</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'s' in 'sigh'">s</span><span title="'t' in 'tie'">t</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span>)<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> is a semiessential<sup id="cite_ref-microbial_7-0" class="reference"><a href="#cite_note-microbial-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Proteinogenic_amino_acid" title="Proteinogenic amino acid">proteinogenic amino acid</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">formula</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><span class="chemf nowrap">HOOC−CH(−NH<sub class="template-chem2-sub">2</sub>)−CH<sub class="template-chem2-sub">2</sub>−SH</span>. The <a href="/wiki/Thiol" title="Thiol">thiol</a> side chain in cysteine often participates in <a href="/wiki/Enzymatic" class="mw-redirect" title="Enzymatic">enzymatic</a> reactions as a <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a>. Cysteine is chiral, but both <small>D</small> and <small>L</small>-cysteine are found in nature. <small>L</small>‑Cysteine is a protein monomer in all biota, and <small>D</small>-cysteine acts as a signaling molecule in mammalian nervous systems.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Cysteine is named after its discovery in urine, which comes from the urinary bladder or cyst, from <a href="/wiki/Greek_language" title="Greek language">Greek</a> κύστη <i>kýsti</i>, "bladder".<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>The thiol is susceptible to oxidation to give the <a href="/wiki/Disulfide_bond" class="mw-redirect" title="Disulfide bond">disulfide</a> derivative <a href="/wiki/Cystine" title="Cystine">cystine</a>, which serves an important structural role in many <a href="/wiki/Protein" title="Protein">proteins</a>. In this case, the symbol <b>Cyx</b> is sometimes used.<sup id="cite_ref-:0_10-0" class="reference"><a href="#cite_note-:0-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_11-0" class="reference"><a href="#cite_note-:1-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> The deprotonated form can generally be described by the symbol <b>Cym</b> as well.<sup id="cite_ref-:1_11-1" class="reference"><a href="#cite_note-:1-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:02_12-0" class="reference"><a href="#cite_note-:02-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>When used as a food additive, cysteine has the <a href="/wiki/E_number" title="E number">E number</a> E920. </p><p>Cysteine is <a href="/wiki/Genetic_code" title="Genetic code">encoded</a> by the <a href="/wiki/Codon" class="mw-redirect" title="Codon">codons</a> UGU and UGC. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=1" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Like other amino acids (not as a residue of a protein), cysteine exists as a <a href="/wiki/Zwitterion" title="Zwitterion">zwitterion</a>. Cysteine has <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span> <a href="/wiki/Dextrorotation_and_levorotation" class="mw-redirect" title="Dextrorotation and levorotation">chirality</a> in the older <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>/<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span> notation based on homology to <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">d</span>- and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-glyceraldehyde. In the newer <i>R</i>/<i>S</i> system of designating chirality, based on the atomic numbers of atoms near the asymmetric carbon, cysteine (and selenocysteine) have <i>R</i> chirality, because of the presence of sulfur (or selenium) as a second neighbor to the asymmetric carbon atom. The remaining chiral amino acids, having lighter atoms in that position, have <i>S</i> chirality. Replacing sulfur with <a href="/wiki/Selenium" title="Selenium">selenium</a> gives <a href="/wiki/Selenocysteine" title="Selenocysteine">selenocysteine</a>. </p> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Betain-Cystein.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Betain-Cystein.png/250px-Betain-Cystein.png" decoding="async" width="250" height="78" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Betain-Cystein.png/375px-Betain-Cystein.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4e/Betain-Cystein.png/500px-Betain-Cystein.png 2x" data-file-width="3384" data-file-height="1057" /></a><figcaption>(<i>R</i>)-Cysteine (left) and (<i>S</i>)-Cysteine (right) in zwitterionic form at neutral pH</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Dietary_sources">Dietary sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=2" title="Edit section: Dietary sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cysteinyl is a residue in high-<a href="/wiki/Protein" title="Protein">protein</a> foods. Some foods considered rich in cysteine include poultry, eggs, beef, and whole grains. In high-protein diets, cysteine may be partially responsible for reduced blood pressure and stroke risk.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Although classified as a non<a href="/wiki/Essential_amino_acid" title="Essential amino acid">essential amino acid</a>,<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> in rare cases, cysteine may be essential for infants, the elderly, and individuals with certain metabolic diseases or who suffer from <a href="/wiki/Malabsorption" title="Malabsorption">malabsorption</a> <a href="/wiki/Syndrome" title="Syndrome">syndromes</a>. Cysteine can usually be synthesized by the human body under normal physiological conditions if a sufficient quantity of <a href="/wiki/Methionine" title="Methionine">methionine</a> is available. </p> <div class="mw-heading mw-heading2"><h2 id="Industrial_sources">Industrial sources<span class="anchor" id="Dietary_restrictions"></span></h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=3" title="Edit section: Industrial sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The majority of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-cysteine is obtained industrially by <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> of animal materials, such as poultry feathers or hog hair. Despite widespread rumor,<sup id="cite_ref-Kashrut_15-0" class="reference"><a href="#cite_note-Kashrut-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> human hair is rarely a source material.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Indeed, food additive or cosmetic product manufactures may not legally source from human hair in the European Union.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>Some animal-originating sources of <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-cysteine as a food additive contravene kosher, halal, vegan, or vegetarian diets.<sup id="cite_ref-Kashrut_15-1" class="reference"><a href="#cite_note-Kashrut-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> To avoid this problem, synthetic <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-cysteine, compliant with Jewish <a href="/wiki/Kosher" class="mw-redirect" title="Kosher">kosher</a> and Muslim <a href="/wiki/Halal" title="Halal">halal</a> laws, is also available, albeit at a higher price.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> The typical synthetic route involves fermentation with an artificial <i><a href="/wiki/Escherichia_coli" title="Escherichia coli">E. coli</a></i> strain.<sup id="cite_ref-Ullmann_20-0" class="reference"><a href="#cite_note-Ullmann-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>Alternatively, <a href="/wiki/Evonik" class="mw-redirect" title="Evonik">Evonik</a> (formerly Degussa) introduced a route from substituted <a href="/wiki/Thiazoline" title="Thiazoline">thiazolines</a>.<sup id="cite_ref-Martens_21-0" class="reference"><a href="#cite_note-Martens-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> <i>Pseudomonas thiazolinophilum</i> hydrolyzes racemic 2‑amino-Δ<sup>2</sup>‑thiazoline-4‑carboxylic acid to <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>‑cysteine.<sup id="cite_ref-Ullmann_20-1" class="reference"><a href="#cite_note-Ullmann-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=4" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Cysteine_biosynthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Cysteine_biosynthesis.svg/150px-Cysteine_biosynthesis.svg.png" decoding="async" width="150" height="264" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Cysteine_biosynthesis.svg/225px-Cysteine_biosynthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a0/Cysteine_biosynthesis.svg/300px-Cysteine_biosynthesis.svg.png 2x" data-file-width="403" data-file-height="710" /></a><figcaption>Cysteine synthesis: <a href="/wiki/Cystathionine_beta_synthase" title="Cystathionine beta synthase">Cystathionine beta synthase</a> catalyzes the upper reaction and <a href="/wiki/Cystathionine_gamma-lyase" title="Cystathionine gamma-lyase">cystathionine gamma-lyase</a> catalyzes the lower reaction.</figcaption></figure> <p>In animals, biosynthesis begins with the amino acid <a href="/wiki/Serine" title="Serine">serine</a>. The sulfur is derived from <a href="/wiki/Methionine" title="Methionine">methionine</a>, which is converted to <a href="/wiki/Homocysteine" title="Homocysteine">homocysteine</a> through the intermediate <a href="/wiki/S-adenosylmethionine" class="mw-redirect" title="S-adenosylmethionine"><i>S</i>-adenosylmethionine</a>. <a href="/wiki/Cystathionine_beta-synthase" class="mw-redirect" title="Cystathionine beta-synthase">Cystathionine beta-synthase</a> then combines homocysteine and serine to form the asymmetrical thioether <a href="/wiki/Cystathionine" title="Cystathionine">cystathionine</a>. The enzyme <a href="/wiki/Cystathionine_gamma-lyase" title="Cystathionine gamma-lyase">cystathionine gamma-lyase</a> converts the cystathionine into cysteine and <a href="/wiki/Alpha-ketobutyrate" class="mw-redirect" title="Alpha-ketobutyrate">alpha-ketobutyrate</a>. In <a href="/wiki/Plant" title="Plant">plants</a> and <a href="/wiki/Bacteria" title="Bacteria">bacteria</a>, cysteine biosynthesis also starts from serine, which is converted to <a href="/wiki/O-acetylserine" class="mw-redirect" title="O-acetylserine"><i>O</i>-acetylserine</a> by the enzyme <a href="/wiki/Serine_transacetylase" class="mw-redirect" title="Serine transacetylase">serine transacetylase</a>. The enzyme <a href="/wiki/Cysteine_synthase" title="Cysteine synthase">cysteine synthase</a>, using sulfide sources, converts this ester into cysteine, releasing acetate.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biological_functions">Biological functions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=5" title="Edit section: Biological functions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The cysteine sulfhydryl group is <a href="/wiki/Nucleophile" title="Nucleophile">nucleophilic</a> and easily oxidized. The reactivity is enhanced when the thiol is ionized, and cysteine <a href="/wiki/Amino_acid_residue" class="mw-redirect" title="Amino acid residue">residues</a> in proteins have <a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">pK<sub>a</sub></a> values close to neutrality, so are often in their reactive <a href="/wiki/Thiolate" class="mw-redirect" title="Thiolate">thiolate</a> form in the cell.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Because of its high reactivity, the sulfhydryl group of cysteine has numerous biological functions. </p> <div class="mw-heading mw-heading3"><h3 id="Precursor_to_the_antioxidant_glutathione">Precursor to the antioxidant glutathione</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=6" title="Edit section: Precursor to the antioxidant glutathione"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Due to the ability of thiols to undergo redox reactions, cysteine and cysteinyl residues have <a href="/wiki/Antioxidant" title="Antioxidant">antioxidant</a> properties. Its antioxidant properties are typically expressed in the tripeptide <a href="/wiki/Glutathione" title="Glutathione">glutathione</a>, which occurs in humans and other organisms. The systemic availability of oral glutathione (GSH) is negligible; so it must be biosynthesized from its constituent amino acids, cysteine, <a href="/wiki/Glycine" title="Glycine">glycine</a>, and <a href="/wiki/Glutamic_acid" title="Glutamic acid">glutamic acid</a>. While glutamic acid is usually sufficient because amino acid nitrogen is recycled through glutamate as an intermediary, dietary cysteine and glycine supplementation can improve synthesis of glutathione.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Precursor_to_iron-sulfur_clusters">Precursor to iron-sulfur clusters</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=7" title="Edit section: Precursor to iron-sulfur clusters"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cysteine is an important source of <a href="/wiki/Sulfide" title="Sulfide">sulfide</a> in human <a href="/wiki/Metabolism" title="Metabolism">metabolism</a>. The sulfide in <a href="/wiki/Iron-sulfur_cluster" class="mw-redirect" title="Iron-sulfur cluster">iron-sulfur clusters</a> and in <a href="/wiki/Nitrogenase" title="Nitrogenase">nitrogenase</a> is extracted from cysteine, which is converted to <a href="/wiki/Alanine" title="Alanine">alanine</a> in the process.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Metal_ion_binding">Metal ion binding</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=8" title="Edit section: Metal ion binding"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Beyond the iron-sulfur proteins, many other metal cofactors in enzymes are bound to the thiolate substituent of cysteinyl residues. Examples include zinc in <a href="/wiki/Zinc_finger" title="Zinc finger">zinc fingers</a> and <a href="/wiki/Alcohol_dehydrogenase" title="Alcohol dehydrogenase">alcohol dehydrogenase</a>, copper in the <a href="/wiki/Plastocyanin" title="Plastocyanin">blue copper proteins</a>, iron in <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a>, and nickel in the [NiFe]-<a href="/wiki/Hydrogenase" title="Hydrogenase">hydrogenases</a>.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> The sulfhydryl group also has a high <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> for <a href="/wiki/Heavy_metal_(chemistry)" class="mw-redirect" title="Heavy metal (chemistry)">heavy metals</a>, so that proteins containing cysteine, such as <a href="/wiki/Metallothionein" title="Metallothionein">metallothionein</a>, will <a href="/wiki/Ligand" title="Ligand">bind</a> metals such as mercury, lead, and cadmium tightly.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Roles_in_protein_structure">Roles in protein structure</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=9" title="Edit section: Roles in protein structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the translation of messenger RNA molecules to produce polypeptides, cysteine is coded for by the UGU and UGC <a href="/wiki/Codon" class="mw-redirect" title="Codon">codons</a>. </p><p>Cysteine has traditionally been considered to be a <a href="/wiki/Hydrophilic" class="mw-redirect" title="Hydrophilic">hydrophilic</a> amino acid, based largely on the chemical parallel between its <a href="/wiki/Thiol_group" class="mw-redirect" title="Thiol group">sulfhydryl group</a> and the <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> groups in the side chains of other polar amino acids. However, the cysteine side chain has been shown to stabilize hydrophobic interactions in micelles to a greater degree than the side chain in the nonpolar amino acid glycine and the polar amino acid serine.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> In a statistical analysis of the frequency with which amino acids appear in various proteins, cysteine residues were found to associate with hydrophobic regions of proteins. Their hydrophobic tendency was equivalent to that of known nonpolar amino acids such as <a href="/wiki/Methionine" title="Methionine">methionine</a> and <a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a> (tyrosine is polar aromatic but also hydrophobic<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup>), those of which were much greater than that of known polar amino acids such as serine and <a href="/wiki/Threonine" title="Threonine">threonine</a>.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Hydrophobicity_scales" title="Hydrophobicity scales">Hydrophobicity scales</a>, which rank amino acids from most hydrophobic to most hydrophilic, consistently place cysteine towards the hydrophobic end of the spectrum, even when they are based on methods that are not influenced by the tendency of cysteines to form disulfide bonds in proteins. Therefore, cysteine is now often grouped among the hydrophobic amino acids,<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> though it is sometimes also classified as slightly polar,<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> or polar.<sup id="cite_ref-microbial_7-1" class="reference"><a href="#cite_note-microbial-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>Most cysteine residues are covalently bonded to other cysteine residues to form <a href="/wiki/Disulfide_bond" class="mw-redirect" title="Disulfide bond">disulfide bonds</a>, which play an important role in the folding and stability of some proteins, usually proteins secreted to the extracellular medium.<sup id="cite_ref-Sevier_34-0" class="reference"><a href="#cite_note-Sevier-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> Since most cellular compartments are <a href="/wiki/Reducing_environment" class="mw-redirect" title="Reducing environment">reducing environments</a>, disulfide bonds are generally unstable in the <a href="/wiki/Cytosol" title="Cytosol">cytosol</a> with some exceptions as noted below. </p> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Cystine-skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/Cystine-skeletal.png/150px-Cystine-skeletal.png" decoding="async" width="150" height="191" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/Cystine-skeletal.png/225px-Cystine-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/22/Cystine-skeletal.png/300px-Cystine-skeletal.png 2x" data-file-width="1897" data-file-height="2415" /></a><figcaption>Figure 2: <a href="/wiki/Cystine" title="Cystine">Cystine</a> (shown here in its neutral form), two cysteines bound together by a disulfide bond</figcaption></figure> <p>Disulfide bonds in proteins are formed by oxidation of the sulfhydryl group of cysteine residues. The other sulfur-containing amino acid, methionine, cannot form disulfide bonds. More aggressive oxidants convert cysteine to the corresponding <a href="/wiki/Sulfinic_acid" title="Sulfinic acid">sulfinic acid</a> and <a href="/wiki/Sulfonic_acid" title="Sulfonic acid">sulfonic acid</a>. Cysteine residues play a valuable role by crosslinking proteins, which increases the rigidity of proteins and also functions to confer proteolytic resistance (since protein export is a costly process, minimizing its necessity is advantageous). Inside the cell, disulfide bridges between cysteine residues within a polypeptide support the protein's tertiary structure. <a href="/wiki/Insulin" title="Insulin">Insulin</a> is an example of a protein with cystine crosslinking, wherein two separate peptide chains are connected by a pair of disulfide bonds. </p><p><a href="/wiki/Protein_disulfide_isomerase" class="mw-redirect" title="Protein disulfide isomerase">Protein disulfide isomerases</a> catalyze the proper formation of <a href="/wiki/Disulfide_bond" class="mw-redirect" title="Disulfide bond">disulfide bonds</a>; the cell transfers <a href="/wiki/Dehydroascorbic_acid" title="Dehydroascorbic acid">dehydroascorbic acid</a> to the <a href="/wiki/Endoplasmic_reticulum" title="Endoplasmic reticulum">endoplasmic reticulum</a>, which oxidizes the environment. In this environment, cysteines are, in general, oxidized to cystine and are no longer functional as a nucleophiles. </p><p>Aside from its oxidation to cystine, cysteine participates in numerous <a href="/wiki/Post-translational_modification" title="Post-translational modification">post-translational modifications</a>. The <a href="/wiki/Nucleophilic" class="mw-redirect" title="Nucleophilic">nucleophilic</a> sulfhydryl group allows cysteine to conjugate to other groups, e.g., in <a href="/wiki/Prenylation" title="Prenylation">prenylation</a>. <a href="/wiki/Ubiquitin" title="Ubiquitin">Ubiquitin</a> <a href="/wiki/Ligase" title="Ligase">ligases</a> transfer ubiquitin to its pendant, proteins, and <a href="/wiki/Caspase" title="Caspase">caspases</a>, which engage in proteolysis in the apoptotic cycle. <a href="/wiki/Intein" class="mw-redirect" title="Intein">Inteins</a> often function with the help of a catalytic cysteine. These roles are typically limited to the intracellular milieu, where the environment is reducing, and cysteine is not oxidized to cystine. </p> <div class="mw-heading mw-heading2"><h2 id="Evolutionary_role_of_cysteine">Evolutionary role of cysteine</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=10" title="Edit section: Evolutionary role of cysteine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cysteine is considered a "newcomer" amino acid, being the 17th amino acid incorporated into the <a href="/wiki/Genetic_code" title="Genetic code">genetic code</a>.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> Similar to other later-added amino acids such as <a href="/wiki/Methionine" title="Methionine">methionine</a>, <a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a>, and <a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a>, cysteine exhibits strong nucleophilic and redox-active properties.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> These properties contribute to the depletion of cysteine from <a href="/wiki/Electron_transport_chain" title="Electron transport chain">respiratory chain</a> complexes, such as <a href="/wiki/Respiratory_complex_I" title="Respiratory complex I">Complexes I</a> and <a href="/wiki/Complex_IV" class="mw-redirect" title="Complex IV">IV</a>,<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> since reactive oxygen species (<a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">ROS</a>) produced by the respiratory chain can react with the cysteine residues in these complexes, leading to dysfunctional proteins and potentially contributing to aging. The primary response of a protein to ROS is the oxidation of cysteine and the loss of free thiol groups,<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> resulting in increased <a href="/wiki/Thiyl_radical" title="Thiyl radical">thiyl radicals</a> and associated protein cross-linking.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> In contrast, another sulfur-containing, redox-active amino acid, methionine, does not exhibit these biochemical properties and its content is relatively upregulated in <a href="/wiki/Mitochondrion" title="Mitochondrion">mitochondrially</a> encoded proteins.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=11" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cysteine, mainly the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-<a href="/wiki/Enantiomer" title="Enantiomer">enantiomer</a>, is a <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">precursor</a> in the food, pharmaceutical, and personal-care industries. One of the largest applications is the production of flavors. For example, the reaction of cysteine with sugars in a <a href="/wiki/Maillard_reaction" title="Maillard reaction">Maillard reaction</a> yields meat flavors.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-Cysteine is also used as a <a href="/wiki/Improving_agent" class="mw-redirect" title="Improving agent">processing aid</a> for baking.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p><p>In the field of personal care, cysteine is used for <a href="/wiki/Permanent_wave" class="mw-redirect" title="Permanent wave">permanent-wave</a> applications, predominantly in Asia. Again, the cysteine is used for breaking up the disulfide bonds in the <a href="/wiki/Hair" title="Hair">hair</a>'s <a href="/wiki/Keratin" title="Keratin">keratin</a>. </p><p>Cysteine is a very popular target for site-directed labeling experiments to investigate biomolecular structure and dynamics. <a href="/wiki/Maleimide" title="Maleimide">Maleimides</a> selectively attach to cysteine using a covalent <a href="/wiki/Michael_addition" class="mw-redirect" title="Michael addition">Michael addition</a>. <a href="/wiki/Site-directed_spin_labeling" title="Site-directed spin labeling">Site-directed spin labeling</a> for EPR or paramagnetic relaxation-enhanced NMR also uses cysteine extensively. </p> <div class="mw-heading mw-heading3"><h3 id="Reducing_toxic_effects_of_alcohol">Reducing toxic effects of alcohol</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=12" title="Edit section: Reducing toxic effects of alcohol"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cysteine has been proposed as a preventive or antidote for some of the negative effects of alcohol, including liver damage and <a href="/wiki/Hangover" title="Hangover">hangover</a>. It counteracts the poisonous effects of <a href="/wiki/Acetaldehyde" title="Acetaldehyde">acetaldehyde</a>.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> It binds to acetaldehyde to form the low-toxicity heterocycle methyl<a href="/wiki/Thioproline" title="Thioproline">thioproline</a>.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p><p>In a <a href="/wiki/Rat" title="Rat">rat</a> study, test animals received an <a href="/wiki/Lethal_dose" title="Lethal dose">LD<sub>90</sub></a> dose of acetaldehyde. Those that received cysteine had an 80% survival rate; when both cysteine and <a href="/wiki/Thiamine" title="Thiamine">thiamine</a> were administered, all animals survived. The <a href="/wiki/Control_group" class="mw-redirect" title="Control group">control group</a> had a 10% survival rate.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p><p>In 2020 an article was published that suggests L-cysteine might also work in humans.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="N-Acetylcysteine"><i>N</i>-Acetylcysteine</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=13" title="Edit section: N-Acetylcysteine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/N-Acetylcysteine" class="mw-redirect" title="N-Acetylcysteine"><i>N</i>-Acetyl-<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r920966791"><span class="smallcaps">l</span>-cysteine</a> is a derivative of cysteine wherein an <a href="/wiki/Acetyl_group" title="Acetyl group">acetyl group</a> is attached to the nitrogen atom. This compound is sold as a dietary supplement, and used as an <a href="/wiki/Antidote" title="Antidote">antidote</a> in cases of <a href="/wiki/Acetaminophen" class="mw-redirect" title="Acetaminophen">acetaminophen</a> overdose.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Sheep">Sheep</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=14" title="Edit section: Sheep"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cysteine is required by <a href="/wiki/Sheep" title="Sheep">sheep</a> to produce wool. It is an essential amino acid that is taken in from their feed. As a consequence, during drought conditions, sheep produce less wool; however, <a href="/wiki/Transgenic" class="mw-redirect" title="Transgenic">transgenic</a> sheep that can make their own cysteine have been developed.<sup id="cite_ref-Transgenic_sheep_51-0" class="reference"><a href="#cite_note-Transgenic_sheep-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_reactions">Chemical reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=15" title="Edit section: Chemical reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Being multifunctional, cysteine undergoes a variety of reactions. Much attention has focused on protecting the sulfhydryl group.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Methylation" title="Methylation">Methylation</a> of cysteine gives <a href="/wiki/S-Methylcysteine" title="S-Methylcysteine">S-methylcysteine</a>. Treatment with formaldehyde gives the <a href="/wiki/Thiazolidine" title="Thiazolidine">thiazolidine</a> <a href="/wiki/Thioproline" title="Thioproline">thioproline</a>. Cysteine forms a variety of <a href="/wiki/Coordination_complex" title="Coordination complex">coordination complexes</a> upon treatment with metal ions.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=16" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Relative to most other amino acids, cysteine is much more toxic.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=17" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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/Cystine" title="Cystine">Cystine</a></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Expand_section plainlinks metadata ambox mbox-small-left ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><span typeof="mw:File"><a href="/wiki/File:Wiki_letter_w_cropped.svg" class="mw-file-description"><img alt="[icon]" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/20px-Wiki_letter_w_cropped.svg.png" decoding="async" width="20" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/30px-Wiki_letter_w_cropped.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Wiki_letter_w_cropped.svg/40px-Wiki_letter_w_cropped.svg.png 2x" data-file-width="44" data-file-height="31" /></a></span></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs expansion</b>. You can help by <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Cysteine&action=edit&section=">adding to it</a>. <span class="date-container"><i>(<span class="date">January 2023</span>)</i></span></div></td></tr></tbody></table> <p>In 1884 German chemist <a href="/wiki/Eugen_Baumann" title="Eugen Baumann">Eugen Baumann</a> found that when cystine was treated with a reducing agent, cystine revealed itself to be a <a href="/wiki/Dimer_(chemistry)" class="mw-redirect" title="Dimer (chemistry)">dimer</a> of a <a href="/wiki/Monomer" title="Monomer">monomer</a> which he named "cysteïne".<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=18" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .sistersitebox img[src*="Wiktionary-logo-en-v2.svg"]{background-color:white}}</style><div class="side-box side-box-right plainlinks sistersitebox"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"> <div class="side-box-flex"> <div class="side-box-image"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/30px-Commons-logo.svg.png" decoding="async" width="30" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/45px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/59px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span></div> <div class="side-box-text plainlist">Wikimedia Commons has media related to <span style="font-weight: bold; font-style: italic;"><a href="https://commons.wikimedia.org/wiki/Category:Cysteine" class="extiw" title="commons:Category:Cysteine">Cysteine</a></span>.</div></div> </div> <ul><li><a href="/wiki/Amino_acid" title="Amino acid">Amino acids</a></li> <li><a href="/wiki/Cysteine_metabolism" title="Cysteine metabolism">Cysteine metabolism</a></li> <li><a href="/wiki/Cystinuria" title="Cystinuria">Cystinuria</a></li> <li><a href="/wiki/Saville_reaction" title="Saville reaction">Saville reaction</a></li> <li><a href="/wiki/Sullivan_reaction" title="Sullivan reaction">Sullivan reaction</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=19" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/Cysteine#section=Solubility">"PubChem data"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=PubChem+data&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2FCysteine%23section%3DSolubility&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBelitzGroschSchieberle2009" class="citation book cs1">Belitz, H.-D; Grosch, Werner; Schieberle, Peter (2009-02-27). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=xteiARU46SQC&pg=PA15"><i>Food Chemistry</i></a>. Springer. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783540699330" title="Special:BookSources/9783540699330"><bdi>9783540699330</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Food+Chemistry&rft.pub=Springer&rft.date=2009-02-27&rft.isbn=9783540699330&rft.aulast=Belitz&rft.aufirst=H.-D&rft.au=Grosch%2C+Werner&rft.au=Schieberle%2C+Peter&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DxteiARU46SQC%26pg%3DPA15&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text">Kirste, Burkhard (23 Jan 1998). "<a rel="nofollow" class="external text" href="http://www.chemie.fu-berlin.de/chemistry/bio/aminoacid/cystein_en.html">Cysteine</a>". <i><a rel="nofollow" class="external text" href="https://web.archive.org/web/20161107053630/http://www.chemie.fu-berlin.de/chemistry/bio/amino-acids_en.html">Overview of Amino Acids</a></i>. <a href="/wiki/Free_University_of_Berlin" title="Free University of Berlin">Free University of Berlin</a> Dep't. of Biology, Chemistry, and Pharmacy. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161110090138/http://www.chemie.fu-berlin.de/chemistry/bio/aminoacid/cystein_en.html">Archived</a> 2016-11-10 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWeast1981" class="citation book cs1">Weast, Robert C., ed. (1981). <i>CRC Handbook of Chemistry and Physics</i> (62nd ed.). Boca Raton, FL: CRC Press. p. C-259. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-8493-0462-8" title="Special:BookSources/0-8493-0462-8"><bdi>0-8493-0462-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=CRC+Handbook+of+Chemistry+and+Physics&rft.place=Boca+Raton%2C+FL&rft.pages=C-259&rft.edition=62nd&rft.pub=CRC+Press&rft.date=1981&rft.isbn=0-8493-0462-8&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span>.</span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation cs2">"Nomenclature and symbolism for amino acids and peptides (IUPAC-IUB Recommendations 1983)", <i>Pure Appl. Chem.</i>, <b>56</b> (5): 595–624, 1984, <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1351%2Fpac198456050595">10.1351/pac198456050595</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pure+Appl.+Chem.&rft.atitle=Nomenclature+and+symbolism+for+amino+acids+and+peptides+%28IUPAC-IUB+Recommendations+1983%29&rft.volume=56&rft.issue=5&rft.pages=595-624&rft.date=1984&rft_id=info%3Adoi%2F10.1351%2Fpac198456050595&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20160925134245/https://en.oxforddictionaries.com/definition/cysteine">"cysteine - Definition of cysteine in English by Oxford Dictionaries"</a>. <i>Oxford Dictionaries - English</i>. Archived from <a rel="nofollow" class="external text" href="https://en.oxforddictionaries.com/definition/cysteine">the original</a> on September 25, 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">15 April</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Oxford+Dictionaries+-+English&rft.atitle=cysteine+-+Definition+of+cysteine+in+English+by+Oxford+Dictionaries&rft_id=https%3A%2F%2Fen.oxforddictionaries.com%2Fdefinition%2Fcysteine&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-microbial-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-microbial_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-microbial_7-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20130525095344/http://www.microbiologytext.com/index.php?module=Book&func=displayarticle&art_id=661">"The primary structure of proteins is the amino acid sequence"</a>. <i>The Microbial World</i>. University of Wisconsin-Madison Bacteriology Department. Archived from <a rel="nofollow" class="external text" href="http://www.microbiologytext.com/index.php?module=Book&func=displayarticle&art_id=661">the original</a> on 25 May 2013<span class="reference-accessdate">. Retrieved <span class="nowrap">16 September</span> 2012</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=The+Microbial+World&rft.atitle=The+primary+structure+of+proteins+is+the+amino+acid+sequence&rft_id=http%3A%2F%2Fwww.microbiologytext.com%2Findex.php%3Fmodule%3DBook%26func%3Ddisplayarticle%26art_id%3D661&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSemenzaHarrazAbramsonMalla2021" class="citation journal cs1">Semenza, Evan R.; Harraz, Maged M.; Abramson, Efrat; Malla, Adarsha P.; Vasavda, Chirag; Gadalla, Moataz M.; Kornberg, Michael D.; Snyder, Solomon H.; Roychaudhuri, Robin (23 Sep 2021) [18 Aug 2021]. <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8488618">"D-cysteine is an endogenous regulator of neural progenitor cell dynamics in the mammalian brain"</a>. <i><a href="/wiki/PNAS" class="mw-redirect" title="PNAS">PNAS</a></i>. <b>118</b> (39): e2110610118. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2021PNAS..11810610S">2021PNAS..11810610S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.2110610118">10.1073/pnas.2110610118</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8488618">8488618</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/34556581">34556581</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=PNAS&rft.atitle=D-cysteine+is+an+endogenous+regulator+of+neural+progenitor+cell+dynamics+in+the+mammalian+brain&rft.volume=118&rft.issue=39&rft.pages=e2110610118&rft.date=2021-09-23&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8488618%23id-name%3DPMC&rft_id=info%3Apmid%2F34556581&rft_id=info%3Adoi%2F10.1073%2Fpnas.2110610118&rft_id=info%3Abibcode%2F2021PNAS..11810610S&rft.aulast=Semenza&rft.aufirst=Evan+R.&rft.au=Harraz%2C+Maged+M.&rft.au=Abramson%2C+Efrat&rft.au=Malla%2C+Adarsha+P.&rft.au=Vasavda%2C+Chirag&rft.au=Gadalla%2C+Moataz+M.&rft.au=Kornberg%2C+Michael+D.&rft.au=Snyder%2C+Solomon+H.&rft.au=Roychaudhuri%2C+Robin&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8488618&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSaffran1998" class="citation journal cs1">Saffran, M. (April 1998). <a rel="nofollow" class="external text" href="https://dx.doi.org/10.1016/s0307-4412(97)00167-2">"Amino acid names and parlor games: from trivial names to a one-letter code, amino acid names have strained students' memories. Is a more rational nomenclature possible?"</a>. <i>Biochemical Education</i>. <b>26</b> (2): 116–118. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0307-4412%2897%2900167-2">10.1016/s0307-4412(97)00167-2</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/0307-4412">0307-4412</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochemical+Education&rft.atitle=Amino+acid+names+and+parlor+games%3A+from+trivial+names+to+a+one-letter+code%2C+amino+acid+names+have+strained+students%27+memories.+Is+a+more+rational+nomenclature+possible%3F&rft.volume=26&rft.issue=2&rft.pages=116-118&rft.date=1998-04&rft_id=info%3Adoi%2F10.1016%2Fs0307-4412%2897%2900167-2&rft.issn=0307-4412&rft.aulast=Saffran&rft.aufirst=M.&rft_id=http%3A%2F%2Fdx.doi.org%2F10.1016%2Fs0307-4412%2897%2900167-2&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-:0-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-:0_10-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20220522002234/https://ambermd.org/tutorials/advanced/tutorial1_orig/section1.htm">"Amber Workshop - Tutorial A1 - Section 1: Do some editing of the PDB file"</a>. <i>ambermd.org</i>. Archived from <a rel="nofollow" class="external text" href="https://ambermd.org/tutorials/advanced/tutorial1_orig/section1.htm">the original</a> on 2022-05-22<span class="reference-accessdate">. Retrieved <span class="nowrap">2022-06-02</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ambermd.org&rft.atitle=Amber+Workshop+-+Tutorial+A1+-+Section+1%3A+Do+some+editing+of+the+PDB+file&rft_id=https%3A%2F%2Fambermd.org%2Ftutorials%2Fadvanced%2Ftutorial1_orig%2Fsection1.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-:1-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-:1_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:1_11-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLeeHitzenbergerRiegerKern2020" class="citation journal cs1">Lee, Jumin; Hitzenberger, Manuel; Rieger, Manuel; Kern, Nathan R.; Zacharias, Martin; Im, Wonpil (21 July 2020). <a rel="nofollow" class="external text" href="https://doi.org/10.1063%2F5.0012280">"CHARMM-GUI supports the Amber force fields"</a>. <i>The Journal of Chemical Physics</i>. <b>153</b> (3): 035103. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1063%2F5.0012280">10.1063/5.0012280</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/32716185">32716185</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:220796795">220796795</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Chemical+Physics&rft.atitle=CHARMM-GUI+supports+the+Amber+force+fields&rft.volume=153&rft.issue=3&rft.pages=035103&rft.date=2020-07-21&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A220796795%23id-name%3DS2CID&rft_id=info%3Apmid%2F32716185&rft_id=info%3Adoi%2F10.1063%2F5.0012280&rft.aulast=Lee&rft.aufirst=Jumin&rft.au=Hitzenberger%2C+Manuel&rft.au=Rieger%2C+Manuel&rft.au=Kern%2C+Nathan+R.&rft.au=Zacharias%2C+Martin&rft.au=Im%2C+Wonpil&rft_id=https%3A%2F%2Fdoi.org%2F10.1063%252F5.0012280&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-:02-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-:02_12-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20220522002234/https://ambermd.org/tutorials/advanced/tutorial1_orig/section1.htm">"Amber Workshop - Tutorial A1 - Section 1: Do some editing of the PDB file"</a>. <i>ambermd.org</i>. Archived from <a rel="nofollow" class="external text" href="https://ambermd.org/tutorials/advanced/tutorial1_orig/section1.htm">the original</a> on 2022-05-22<span class="reference-accessdate">. Retrieved <span class="nowrap">2022-06-02</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=ambermd.org&rft.atitle=Amber+Workshop+-+Tutorial+A1+-+Section+1%3A+Do+some+editing+of+the+PDB+file&rft_id=https%3A%2F%2Fambermd.org%2Ftutorials%2Fadvanced%2Ftutorial1_orig%2Fsection1.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLarssonHåkanssonWolk2015" class="citation journal cs1">Larsson, Susanna C.; Håkansson, Niclas; Wolk, Alicja (April 2015). <a rel="nofollow" class="external text" href="http://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-397364">"Dietary Cysteine and Other Amino Acids and Stroke Incidence in Women"</a>. <i>Stroke</i>. <b>46</b> (4): 922–926. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1161%2FSTROKEAHA.114.008022">10.1161/STROKEAHA.114.008022</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/25669310">25669310</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:14895681">14895681</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Stroke&rft.atitle=Dietary+Cysteine+and+Other+Amino+Acids+and+Stroke+Incidence+in+Women&rft.volume=46&rft.issue=4&rft.pages=922-926&rft.date=2015-04&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A14895681%23id-name%3DS2CID&rft_id=info%3Apmid%2F25669310&rft_id=info%3Adoi%2F10.1161%2FSTROKEAHA.114.008022&rft.aulast=Larsson&rft.aufirst=Susanna+C.&rft.au=H%C3%A5kansson%2C+Niclas&rft.au=Wolk%2C+Alicja&rft_id=http%3A%2F%2Furn.kb.se%2Fresolve%3Furn%3Durn%3Anbn%3Ase%3Auu%3Adiva-397364&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.urmc.rochester.edu/encyclopedia/content.aspx?contenttypeid=19&contentid=Cysteine#:~:text=Cysteine%20is%20a%20non-essential,is%20important%20for%20making%20collagen.">"Cysteine - Health Encyclopedia - University of Rochester Medical Center"</a>. <i>www.urmc.rochester.edu</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2024-05-13</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.urmc.rochester.edu&rft.atitle=Cysteine+-+Health+Encyclopedia+-+University+of+Rochester+Medical+Center&rft_id=https%3A%2F%2Fwww.urmc.rochester.edu%2Fencyclopedia%2Fcontent.aspx%3Fcontenttypeid%3D19%26contentid%3DCysteine%23%3A~%3Atext%3DCysteine%2520is%2520a%2520non-essential%2Cis%2520important%2520for%2520making%2520collagen.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-Kashrut-15"><span class="mw-cite-backlink">^ <a href="#cite_ref-Kashrut_15-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Kashrut_15-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">See, e.g., <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBlech2003" class="citation news cs1">Blech, Zushe Yosef (May 2003). <a rel="nofollow" class="external text" href="http://www.kashrut.com/articles/L_cysteine/">"Like mountains hanging by a hair: Kosher issues in L-cysteine (Commentary on Chagiga I:8)"</a>. <i>MK News and Views</i>. Vol. IV, no. 6. <a href="/wiki/Montreal_Kosher" title="Montreal Kosher">Montreal Kosher</a> – via kashrut.com.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=MK+News+and+Views&rft.atitle=Like+mountains+hanging+by+a+hair%3A+Kosher+issues+in+L-cysteine+%28Commentary+on+Chagiga+I%3A8%29&rft.volume=IV&rft.issue=6&rft.date=2003-05&rft.aulast=Blech&rft.aufirst=Zushe+Yosef&rft_id=http%3A%2F%2Fwww.kashrut.com%2Farticles%2FL_cysteine%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span> Rabbi Blech does not address hog hair-derived cysteine, which is almost certainly <i><a href="/wiki/Treyf" class="mw-redirect" title="Treyf">treyf</a></i>.</span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.vrg.org/vrgnews/2007jul.htm#s2">"VRG-News July 2007 -- the Vegetarian Resource Group"</a>. <i>vrg.org</i><span class="reference-accessdate">. Retrieved <span class="nowrap">26 August</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=vrg.org&rft.atitle=VRG-News+July+2007+--+the+Vegetarian+Resource+Group&rft_id=https%3A%2F%2Fwww.vrg.org%2Fvrgnews%2F2007jul.htm%23s2&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2012:083:0001:0295:EN:PDF">"EU Chemical Requirements"</a><span class="reference-accessdate">. Retrieved <span class="nowrap">May 24,</span> 2020</span>. <q>...L-cysteine hydrochloride or hydrochloride monohydrate. Human hair may not be used as a source for this substance</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=EU+Chemical+Requirements&rft_id=http%3A%2F%2Feur-lex.europa.eu%2FLexUriServ%2FLexUriServ.do%3Furi%3DOJ%3AL%3A2012%3A083%3A0001%3A0295%3AEN%3APDF&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://eur-lex.europa.eu/legal-content/en/TXT/?uri=CELEX%3A32009R1223">"Regulation (EC) No 1223/2009 of the European Parliament and of the Council of 30 November 2009 on cosmetic products"</a><span class="reference-accessdate">. Retrieved <span class="nowrap">July 28,</span> 2021</span>. <q>...ANNEX II LIST OF SUBSTANCES PROHIBITED IN COSMETIC PRODUCTS...416 Cells, tissues or products of human origin</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Regulation+%28EC%29+No+1223%2F2009+of+the+European+Parliament+and+of+the+Council+of+30+November+2009+on+cosmetic+products&rft_id=https%3A%2F%2Feur-lex.europa.eu%2Flegal-content%2Fen%2FTXT%2F%3Furi%3DCELEX%253A32009R1223&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.vrg.org/nutshell/faqingredients.htm#cystine">"Questions About Food Ingredients: What is L-cysteine/cysteine/cystine?"</a>. Vegetarian Resource Group.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Questions+About+Food+Ingredients%3A+What+is+L-cysteine%2Fcysteine%2Fcystine%3F&rft.pub=Vegetarian+Resource+Group&rft_id=http%3A%2F%2Fwww.vrg.org%2Fnutshell%2Ffaqingredients.htm%23cystine&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-Ullmann-20"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_20-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_20-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDrauzGraysonKleemannKrimmer2007" class="citation book cs1">Drauz, Karlheinz; Grayson, Ian; Kleemann, Axel; Krimmer, Hans-Peter; Leuchtenberger, Wolfgang; Weckbecker, Christoph (2007). "Amino Acids". <i>Ullmann's Encyclopedia of Industrial Chemistry</i>. <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%2F14356007.a02_057.pub2">10.1002/14356007.a02_057.pub2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-30673-2" title="Special:BookSources/978-3-527-30673-2"><bdi>978-3-527-30673-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Amino+Acids&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.date=2007&rft_id=info%3Adoi%2F10.1002%2F14356007.a02_057.pub2&rft.isbn=978-3-527-30673-2&rft.aulast=Drauz&rft.aufirst=Karlheinz&rft.au=Grayson%2C+Ian&rft.au=Kleemann%2C+Axel&rft.au=Krimmer%2C+Hans-Peter&rft.au=Leuchtenberger%2C+Wolfgang&rft.au=Weckbecker%2C+Christoph&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-Martens-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-Martens_21-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMartensOffermannsScherberich1981" class="citation journal cs1">Martens, Jürgen; <a href="/wiki/Heribert_Offermanns" title="Heribert Offermanns">Offermanns, Heribert</a>; Scherberich, Paul (1981). "Facile Synthesis of Racemic Cysteine". <i>Angewandte Chemie International Edition in English</i>. <b>20</b> (8): 668. <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.198106681">10.1002/anie.198106681</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie+International+Edition+in+English&rft.atitle=Facile+Synthesis+of+Racemic+Cysteine&rft.volume=20&rft.issue=8&rft.pages=668&rft.date=1981&rft_id=info%3Adoi%2F10.1002%2Fanie.198106681&rft.aulast=Martens&rft.aufirst=J%C3%BCrgen&rft.au=Offermanns%2C+Heribert&rft.au=Scherberich%2C+Paul&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHell_R1997" class="citation journal cs1">Hell R (1997). "Molecular physiology of plant sulfur metabolism". <i>Planta</i>. <b>202</b> (2): 138–48. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1997Plant.202..138H">1997Plant.202..138H</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs004250050112">10.1007/s004250050112</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/9202491">9202491</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:2539629">2539629</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Planta&rft.atitle=Molecular+physiology+of+plant+sulfur+metabolism&rft.volume=202&rft.issue=2&rft.pages=138-48&rft.date=1997&rft_id=info%3Adoi%2F10.1007%2Fs004250050112&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A2539629%23id-name%3DS2CID&rft_id=info%3Apmid%2F9202491&rft_id=info%3Abibcode%2F1997Plant.202..138H&rft.au=Hell+R&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBulajKortemmeGoldenberg1998" class="citation journal cs1">Bulaj G, Kortemme T, Goldenberg DP (June 1998). "Ionization-reactivity relationships for cysteine thiols in polypeptides". <i>Biochemistry</i>. <b>37</b> (25): 8965–72. <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%2Fbi973101r">10.1021/bi973101r</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/9636038">9636038</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochemistry&rft.atitle=Ionization-reactivity+relationships+for+cysteine+thiols+in+polypeptides&rft.volume=37&rft.issue=25&rft.pages=8965-72&rft.date=1998-06&rft_id=info%3Adoi%2F10.1021%2Fbi973101r&rft_id=info%3Apmid%2F9636038&rft.aulast=Bulaj&rft.aufirst=G&rft.au=Kortemme%2C+T&rft.au=Goldenberg%2C+DP&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSekharPatel2011" class="citation journal cs1">Sekhar, Rajagopal V; Patel, Sanjeet G (2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3155927">"Deficient synthesis of glutathione underlies oxidative stress in aging and can be corrected by dietary cysteine and glycine supplementation"</a>. <i>The American Journal of Clinical Nutrition</i>. <b>94</b> (3): 847–853. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3945%2Fajcn.110.003483">10.3945/ajcn.110.003483</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3155927">3155927</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21795440">21795440</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+American+Journal+of+Clinical+Nutrition&rft.atitle=Deficient+synthesis+of+glutathione+underlies+oxidative+stress+in+aging+and+can+be+corrected+by+dietary+cysteine+and+glycine+supplementation&rft.volume=94&rft.issue=3&rft.pages=847-853&rft.date=2011&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3155927%23id-name%3DPMC&rft_id=info%3Apmid%2F21795440&rft_id=info%3Adoi%2F10.3945%2Fajcn.110.003483&rft.aulast=Sekhar&rft.aufirst=Rajagopal+V&rft.au=Patel%2C+Sanjeet+G&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3155927&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span> <span style="position:relative; top: -2px;"><span typeof="mw:File"><a href="/wiki/Open_access" title="open access publication – free to read"><img alt="Open access icon" 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></span></span></span> </li> <li id="cite_note-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-25">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLillMühlenhoff2006" class="citation journal cs1">Lill R, Mühlenhoff U (2006). <a rel="nofollow" class="external text" href="http://nbn-resolving.de/urn:nbn:de:bvb:12-bsb00055966-1">"Iron-sulfur protein biogenesis in eukaryotes: components and mechanisms"</a>. <i>Annu. Rev. Cell Dev. Biol</i>. <b>22</b>: 457–86. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1146%2Fannurev.cellbio.22.010305.104538">10.1146/annurev.cellbio.22.010305.104538</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/16824008">16824008</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annu.+Rev.+Cell+Dev.+Biol.&rft.atitle=Iron-sulfur+protein+biogenesis+in+eukaryotes%3A+components+and+mechanisms&rft.volume=22&rft.pages=457-86&rft.date=2006&rft_id=info%3Adoi%2F10.1146%2Fannurev.cellbio.22.010305.104538&rft_id=info%3Apmid%2F16824008&rft.aulast=Lill&rft.aufirst=R&rft.au=M%C3%BChlenhoff%2C+U&rft_id=http%3A%2F%2Fnbn-resolving.de%2Furn%3Anbn%3Ade%3Abvb%3A12-bsb00055966-1&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-26">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLippardBerg1994" class="citation book cs1">Lippard, Stephen J.; Berg, Jeremy M. (1994). <i>Principles of Bioinorganic Chemistry</i>. Mill Valley, CA: University Science Books. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-935702-73-6" title="Special:BookSources/978-0-935702-73-6"><bdi>978-0-935702-73-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Principles+of+Bioinorganic+Chemistry&rft.place=Mill+Valley%2C+CA&rft.pub=University+Science+Books&rft.date=1994&rft.isbn=978-0-935702-73-6&rft.aulast=Lippard&rft.aufirst=Stephen+J.&rft.au=Berg%2C+Jeremy+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (July 2013)">page needed</span></a></i>]</sup></span> </li> <li id="cite_note-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-27">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBakerCzarnecki-Maulden1987" class="citation journal cs1">Baker DH, Czarnecki-Maulden GL (June 1987). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fjn%2F117.6.1003">"Pharmacologic role of cysteine in ameliorating or exacerbating mineral toxicities"</a>. <i>J. Nutr</i>. <b>117</b> (6): 1003–10. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fjn%2F117.6.1003">10.1093/jn/117.6.1003</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/3298579">3298579</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Nutr.&rft.atitle=Pharmacologic+role+of+cysteine+in+ameliorating+or+exacerbating+mineral+toxicities&rft.volume=117&rft.issue=6&rft.pages=1003-10&rft.date=1987-06&rft_id=info%3Adoi%2F10.1093%2Fjn%2F117.6.1003&rft_id=info%3Apmid%2F3298579&rft.aulast=Baker&rft.aufirst=DH&rft.au=Czarnecki-Maulden%2C+GL&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Fjn%252F117.6.1003&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-28">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHeitmann_P1968" class="citation journal cs1">Heitmann P (January 1968). <a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1432-1033.1968.tb19535.x">"A model for sulfhydryl groups in proteins. Hydrophobic interactions of the cystein side chain in micelles"</a>. <i>Eur. J. Biochem</i>. <b>3</b> (3): 346–50. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1432-1033.1968.tb19535.x">10.1111/j.1432-1033.1968.tb19535.x</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/5650851">5650851</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Eur.+J.+Biochem.&rft.atitle=A+model+for+sulfhydryl+groups+in+proteins.+Hydrophobic+interactions+of+the+cystein+side+chain+in+micelles&rft.volume=3&rft.issue=3&rft.pages=346-50&rft.date=1968-01&rft_id=info%3Adoi%2F10.1111%2Fj.1432-1033.1968.tb19535.x&rft_id=info%3Apmid%2F5650851&rft.au=Heitmann+P&rft_id=https%3A%2F%2Fdoi.org%2F10.1111%252Fj.1432-1033.1968.tb19535.x&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-29">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20150907052410/http://wbiomed.curtin.edu.au/biochem/tutorials/AAs/AA.html">"A Review of Amino Acids (tutorial)"</a>. Curtin University. Archived from <a rel="nofollow" class="external text" href="http://wbiomed.curtin.edu.au/biochem/tutorials/AAs/AA.html">the original</a> on 2015-09-07<span class="reference-accessdate">. Retrieved <span class="nowrap">2015-09-09</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=A+Review+of+Amino+Acids+%28tutorial%29&rft.pub=Curtin+University&rft_id=http%3A%2F%2Fwbiomed.curtin.edu.au%2Fbiochem%2Ftutorials%2FAAs%2FAA.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-30">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNaganoOtaNishikawa1999" class="citation journal cs1">Nagano N, Ota M, Nishikawa K (September 1999). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0014-5793%2899%2901122-9">"Strong hydrophobic nature of cysteine residues in proteins"</a>. <i>FEBS Lett</i>. <b>458</b> (1): 69–71. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1999FEBSL.458...69N">1999FEBSL.458...69N</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0014-5793%2899%2901122-9">10.1016/S0014-5793(99)01122-9</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/10518936">10518936</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:34980474">34980474</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=FEBS+Lett.&rft.atitle=Strong+hydrophobic+nature+of+cysteine+residues+in+proteins&rft.volume=458&rft.issue=1&rft.pages=69-71&rft.date=1999-09&rft_id=info%3Adoi%2F10.1016%2FS0014-5793%2899%2901122-9&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A34980474%23id-name%3DS2CID&rft_id=info%3Apmid%2F10518936&rft_id=info%3Abibcode%2F1999FEBSL.458...69N&rft.aulast=Nagano&rft.aufirst=N&rft.au=Ota%2C+M&rft.au=Nishikawa%2C+K&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252FS0014-5793%252899%252901122-9&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-31">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBettsR.B._Russell2003" class="citation web cs1">Betts, M.J.; R.B. Russell (2003). <a rel="nofollow" class="external text" href="http://www.russelllab.org/aas/hydrophobic.html">"Hydrophobic amino acids"</a>. <i>Amino Acid Properties and Consequences of Substitutions, In: Bioinformatics for Geneticists</i>. Wiley<span class="reference-accessdate">. Retrieved <span class="nowrap">2012-09-16</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Amino+Acid+Properties+and+Consequences+of+Substitutions%2C+In%3A+Bioinformatics+for+Geneticists&rft.atitle=Hydrophobic+amino+acids&rft.date=2003&rft.aulast=Betts&rft.aufirst=M.J.&rft.au=R.B.+Russell&rft_id=http%3A%2F%2Fwww.russelllab.org%2Faas%2Fhydrophobic.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-32">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGorga1998–2001" class="citation web cs1">Gorga, Frank R. (1998–2001). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20120905162400/http://webhost.bridgew.edu/fgorga/proteins/nonpolar.htm">"Introduction to Protein Structure--Non-Polar Amino Acids"</a>. Archived from <a rel="nofollow" class="external text" href="http://webhost.bridgew.edu/fgorga/proteins/nonpolar.htm">the original</a> on 2012-09-05<span class="reference-accessdate">. Retrieved <span class="nowrap">2012-09-16</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Introduction+to+Protein+Structure--Non-Polar+Amino+Acids&rft.date=1998%2F2001&rft.aulast=Gorga&rft.aufirst=Frank+R.&rft_id=http%3A%2F%2Fwebhost.bridgew.edu%2Ffgorga%2Fproteins%2Fnonpolar.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-33">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20121002050150/http://www.elmhurst.edu/~chm/vchembook/561aminostructure.html">"Virtual Chembook--Amino Acid Structure"</a>. Elmhurst College. Archived from <a rel="nofollow" class="external text" href="http://www.elmhurst.edu/~chm/vchembook/561aminostructure.html">the original</a> on 2012-10-02<span class="reference-accessdate">. Retrieved <span class="nowrap">2012-09-16</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Virtual+Chembook--Amino+Acid+Structure&rft.pub=Elmhurst+College&rft_id=http%3A%2F%2Fwww.elmhurst.edu%2F~chm%2Fvchembook%2F561aminostructure.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-Sevier-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-Sevier_34-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSevierKaiser2002" class="citation journal cs1">Sevier CS, Kaiser CA (November 2002). <a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fnrm954">"Formation and transfer of disulphide bonds in living cells"</a>. <i>Nat. Rev. Mol. Cell Biol</i>. <b>3</b> (11): 836–47. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fnrm954">10.1038/nrm954</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12415301">12415301</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:2885059">2885059</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nat.+Rev.+Mol.+Cell+Biol.&rft.atitle=Formation+and+transfer+of+disulphide+bonds+in+living+cells&rft.volume=3&rft.issue=11&rft.pages=836-47&rft.date=2002-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A2885059%23id-name%3DS2CID&rft_id=info%3Apmid%2F12415301&rft_id=info%3Adoi%2F10.1038%2Fnrm954&rft.aulast=Sevier&rft.aufirst=CS&rft.au=Kaiser%2C+CA&rft_id=https%3A%2F%2Fdoi.org%2F10.1038%252Fnrm954&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-35">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOsawaJukesWatanabeMuto1992" class="citation journal cs1">Osawa, S; Jukes, T H; Watanabe, K; Muto, A (March 1992). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC372862">"Recent evidence for evolution of the genetic code"</a>. <i>Microbiological Reviews</i>. <b>56</b> (1): 229–264. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1128%2Fmr.56.1.229-264.1992">10.1128/mr.56.1.229-264.1992</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/0146-0749">0146-0749</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC372862">372862</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/1579111">1579111</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Microbiological+Reviews&rft.atitle=Recent+evidence+for+evolution+of+the+genetic+code&rft.volume=56&rft.issue=1&rft.pages=229-264&rft.date=1992-03&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC372862%23id-name%3DPMC&rft.issn=0146-0749&rft_id=info%3Apmid%2F1579111&rft_id=info%3Adoi%2F10.1128%2Fmr.56.1.229-264.1992&rft.aulast=Osawa&rft.aufirst=S&rft.au=Jukes%2C+T+H&rft.au=Watanabe%2C+K&rft.au=Muto%2C+A&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC372862&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-36"><span class="mw-cite-backlink"><b><a href="#cite_ref-36">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTrifonov2009" class="citation journal cs1">Trifonov, Edward N. (September 2009). <a rel="nofollow" class="external text" href="https://linkinghub.elsevier.com/retrieve/pii/S0923250809000576">"The origin of the genetic code and of the earliest oligopeptides"</a>. <i>Research in Microbiology</i>. <b>160</b> (7): 481–486. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.resmic.2009.05.004">10.1016/j.resmic.2009.05.004</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/19524038">19524038</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Research+in+Microbiology&rft.atitle=The+origin+of+the+genetic+code+and+of+the+earliest+oligopeptides&rft.volume=160&rft.issue=7&rft.pages=481-486&rft.date=2009-09&rft_id=info%3Adoi%2F10.1016%2Fj.resmic.2009.05.004&rft_id=info%3Apmid%2F19524038&rft.aulast=Trifonov&rft.aufirst=Edward+N.&rft_id=https%3A%2F%2Flinkinghub.elsevier.com%2Fretrieve%2Fpii%2FS0923250809000576&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-37"><span class="mw-cite-backlink"><b><a href="#cite_ref-37">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPaulsenCarroll2013" class="citation journal cs1">Paulsen, Candice E.; Carroll, Kate S. (2013-07-10). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4303468">"Cysteine-Mediated Redox Signaling: Chemistry, Biology, and Tools for Discovery"</a>. <i>Chemical Reviews</i>. <b>113</b> (7): 4633–4679. <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%2Fcr300163e">10.1021/cr300163e</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>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4303468">4303468</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23514336">23514336</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=Cysteine-Mediated+Redox+Signaling%3A+Chemistry%2C+Biology%2C+and+Tools+for+Discovery&rft.volume=113&rft.issue=7&rft.pages=4633-4679&rft.date=2013-07-10&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4303468%23id-name%3DPMC&rft.issn=0009-2665&rft_id=info%3Apmid%2F23514336&rft_id=info%3Adoi%2F10.1021%2Fcr300163e&rft.aulast=Paulsen&rft.aufirst=Candice+E.&rft.au=Carroll%2C+Kate+S.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4303468&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-38"><span class="mw-cite-backlink"><b><a href="#cite_ref-38">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGilesWattsGilesFry2003" class="citation journal cs1">Giles, Niroshini M; Watts, Aaron B; Giles, Gregory I; Fry, Fiona H; Littlechild, Jennifer A; Jacob, Claus (August 2003). <a rel="nofollow" class="external text" href="https://doi.org/10.1016/S1074-5521(03)00174-1">"Metal and Redox Modulation of Cysteine Protein Function"</a>. <i>Chemistry & Biology</i>. <b>10</b> (8): 677–693. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs1074-5521%2803%2900174-1">10.1016/s1074-5521(03)00174-1</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/1074-5521">1074-5521</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/12954327">12954327</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemistry+%26+Biology&rft.atitle=Metal+and+Redox+Modulation+of+Cysteine+Protein+Function&rft.volume=10&rft.issue=8&rft.pages=677-693&rft.date=2003-08&rft.issn=1074-5521&rft_id=info%3Apmid%2F12954327&rft_id=info%3Adoi%2F10.1016%2Fs1074-5521%2803%2900174-1&rft.aulast=Giles&rft.aufirst=Niroshini+M&rft.au=Watts%2C+Aaron+B&rft.au=Giles%2C+Gregory+I&rft.au=Fry%2C+Fiona+H&rft.au=Littlechild%2C+Jennifer+A&rft.au=Jacob%2C+Claus&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%2FS1074-5521%2803%2900174-1&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-39"><span class="mw-cite-backlink"><b><a href="#cite_ref-39">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMoosmannBehl2008" class="citation journal cs1">Moosmann, Bernd; Behl, Christian (February 2008). <a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1474-9726.2007.00349.x">"Mitochondrially encoded cysteine predicts animal lifespan"</a>. <i>Aging Cell</i>. <b>7</b> (1): 32–46. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1474-9726.2007.00349.x">10.1111/j.1474-9726.2007.00349.x</a></span>. <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/1474-9718">1474-9718</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/18028257">18028257</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Aging+Cell&rft.atitle=Mitochondrially+encoded+cysteine+predicts+animal+lifespan&rft.volume=7&rft.issue=1&rft.pages=32-46&rft.date=2008-02&rft.issn=1474-9718&rft_id=info%3Apmid%2F18028257&rft_id=info%3Adoi%2F10.1111%2Fj.1474-9726.2007.00349.x&rft.aulast=Moosmann&rft.aufirst=Bernd&rft.au=Behl%2C+Christian&rft_id=https%3A%2F%2Fdoi.org%2F10.1111%252Fj.1474-9726.2007.00349.x&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-40"><span class="mw-cite-backlink"><b><a href="#cite_ref-40">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSohal2002" class="citation journal cs1">Sohal, Rajindar S (2002-07-01). <a rel="nofollow" class="external text" href="https://www.sciencedirect.com/science/article/pii/S0891584902008560">"Role of oxidative stress and protein oxidation in the aging process1, 2"</a>. <i>Free Radical Biology and Medicine</i>. <b>33</b> (1): 37–44. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0891-5849%2802%2900856-0">10.1016/S0891-5849(02)00856-0</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/0891-5849">0891-5849</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/12086680">12086680</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Free+Radical+Biology+and+Medicine&rft.atitle=Role+of+oxidative+stress+and+protein+oxidation+in+the+aging+process1%2C+2&rft.volume=33&rft.issue=1&rft.pages=37-44&rft.date=2002-07-01&rft.issn=0891-5849&rft_id=info%3Apmid%2F12086680&rft_id=info%3Adoi%2F10.1016%2FS0891-5849%2802%2900856-0&rft.aulast=Sohal&rft.aufirst=Rajindar+S&rft_id=https%3A%2F%2Fwww.sciencedirect.com%2Fscience%2Farticle%2Fpii%2FS0891584902008560&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-41">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJacobGilesGilesSies2003" class="citation journal cs1">Jacob, Claus; Giles, Gregory I.; Giles, Niroshini M.; Sies, Helmut (2003-10-13). <a rel="nofollow" class="external text" href="https://onlinelibrary.wiley.com/doi/10.1002/anie.200300573">"Sulfur and Selenium: The Role of Oxidation State in Protein Structure and Function"</a>. <i>Angewandte Chemie International Edition</i>. <b>42</b> (39): 4742–4758. <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.200300573">10.1002/anie.200300573</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/1433-7851">1433-7851</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/14562341">14562341</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie+International+Edition&rft.atitle=Sulfur+and+Selenium%3A+The+Role+of+Oxidation+State+in+Protein+Structure+and+Function&rft.volume=42&rft.issue=39&rft.pages=4742-4758&rft.date=2003-10-13&rft.issn=1433-7851&rft_id=info%3Apmid%2F14562341&rft_id=info%3Adoi%2F10.1002%2Fanie.200300573&rft.aulast=Jacob&rft.aufirst=Claus&rft.au=Giles%2C+Gregory+I.&rft.au=Giles%2C+Niroshini+M.&rft.au=Sies%2C+Helmut&rft_id=https%3A%2F%2Fonlinelibrary.wiley.com%2Fdoi%2F10.1002%2Fanie.200300573&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-42">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNauserPellingSchöneich2004" class="citation journal cs1">Nauser, Thomas; Pelling, Jill; Schöneich, Christian (2004-10-01). <a rel="nofollow" class="external text" href="https://pubs.acs.org/doi/10.1021/tx049856y">"Thiyl Radical Reaction with Amino Acid Side Chains: Rate Constants for Hydrogen Transfer and Relevance for Posttranslational Protein Modification"</a>. <i>Chemical Research in Toxicology</i>. <b>17</b> (10): 1323–1328. <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%2Ftx049856y">10.1021/tx049856y</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/0893-228X">0893-228X</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/15487892">15487892</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Research+in+Toxicology&rft.atitle=Thiyl+Radical+Reaction+with+Amino+Acid+Side+Chains%3A+Rate+Constants+for+Hydrogen+Transfer+and+Relevance+for+Posttranslational+Protein+Modification&rft.volume=17&rft.issue=10&rft.pages=1323-1328&rft.date=2004-10-01&rft.issn=0893-228X&rft_id=info%3Apmid%2F15487892&rft_id=info%3Adoi%2F10.1021%2Ftx049856y&rft.aulast=Nauser&rft.aufirst=Thomas&rft.au=Pelling%2C+Jill&rft.au=Sch%C3%B6neich%2C+Christian&rft_id=https%3A%2F%2Fpubs.acs.org%2Fdoi%2F10.1021%2Ftx049856y&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-43">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMoosmannHajievaBehl2006" class="citation cs2">Moosmann, Bernd; Hajieva, Parvana; Behl, Christian (2006), "The antioxidant function of protein methionine explains about the evolution of a non-standard genetic code in mitochondria", <i>Free Radical Biology and Medicine</i>, <b>41</b> 402: S149–S150, <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.freeradbiomed.2006.10.015">10.1016/j.freeradbiomed.2006.10.015</a></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Free+Radical+Biology+and+Medicine&rft.atitle=The+antioxidant+function+of+protein+methionine+explains+about+the+evolution+of+a+non-standard+genetic+code+in+mitochondria&rft.volume=41&rft.artnum=402&rft.pages=S149-S150&rft.date=2006&rft_id=info%3Adoi%2F10.1016%2Fj.freeradbiomed.2006.10.015&rft.aulast=Moosmann&rft.aufirst=Bernd&rft.au=Hajieva%2C+Parvana&rft.au=Behl%2C+Christian&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-44">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHuangHo2001" class="citation book cs1">Huang, Tzou-Chi; Ho, Chi-Tang (2001-07-27). Hui, Y. H.; Nip, Wai-Kit; Rogers, Robert (eds.). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=651Zv5hUzyIC&pg=PA71"><i>Meat Science and Applications, ch. Flavors of Meat Products</i></a>. CRC. pp. 71–102. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-203-90808-2" title="Special:BookSources/978-0-203-90808-2"><bdi>978-0-203-90808-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Meat+Science+and+Applications%2C+ch.+Flavors+of+Meat+Products&rft.pages=71-102&rft.pub=CRC&rft.date=2001-07-27&rft.isbn=978-0-203-90808-2&rft.aulast=Huang&rft.aufirst=Tzou-Chi&rft.au=Ho%2C+Chi-Tang&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D651Zv5hUzyIC%26pg%3DPA71&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-45"><span class="mw-cite-backlink"><b><a href="#cite_ref-45">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20090512090657/https://www.cfsan.fda.gov/~dms/foodic.html">"Food Ingredients and Colors"</a>. U.S. Food and Drug Administration. November 2004. Archived from <a rel="nofollow" class="external text" href="http://www.cfsan.fda.gov/~dms/foodic.html">the original</a> on 2009-05-12<span class="reference-accessdate">. Retrieved <span class="nowrap">2009-09-06</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Food+Ingredients+and+Colors&rft.pub=U.S.+Food+and+Drug+Administration&rft.date=2004-11&rft_id=http%3A%2F%2Fwww.cfsan.fda.gov%2F~dms%2Ffoodic.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-46"><span class="mw-cite-backlink"><b><a href="#cite_ref-46">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOtoyamaHamadaKimuraNamba2019" class="citation journal cs1">Otoyama, Ippo; Hamada, Hironobu; Kimura, Tatsushi; Namba, Haruchi; Sekikawa, Kiyokazu; Kamikawa, Norimichi; Kajiwara, Teruki; Aizawa, Fumiya; Sato, Yoshinobu M. (2019). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6440629">"L-cysteine improves blood fluidity impaired by acetaldehyde: In vitro evaluation"</a>. <i>PLOS ONE</i>. <b>14</b> (3): e0214585. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2019PLoSO..1414585O">2019PLoSO..1414585O</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1371%2Fjournal.pone.0214585">10.1371/journal.pone.0214585</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6440629">6440629</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/30925182">30925182</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=PLOS+ONE&rft.atitle=L-cysteine+improves+blood+fluidity+impaired+by+acetaldehyde%3A+In+vitro+evaluation&rft.volume=14&rft.issue=3&rft.pages=e0214585&rft.date=2019&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6440629%23id-name%3DPMC&rft_id=info%3Apmid%2F30925182&rft_id=info%3Adoi%2F10.1371%2Fjournal.pone.0214585&rft_id=info%3Abibcode%2F2019PLoSO..1414585O&rft.aulast=Otoyama&rft.aufirst=Ippo&rft.au=Hamada%2C+Hironobu&rft.au=Kimura%2C+Tatsushi&rft.au=Namba%2C+Haruchi&rft.au=Sekikawa%2C+Kiyokazu&rft.au=Kamikawa%2C+Norimichi&rft.au=Kajiwara%2C+Teruki&rft.au=Aizawa%2C+Fumiya&rft.au=Sato%2C+Yoshinobu+M.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6440629&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-47"><span class="mw-cite-backlink"><b><a href="#cite_ref-47">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSalaspuro2006" class="citation thesis cs1">Salaspuro, Ville (2006). <a rel="nofollow" class="external text" href="https://helda.helsinki.fi/items/8d28d7d1-e6f4-4a2c-89e9-9a25bdffdf93"><i>Interaction of alcohol and smoking in the pathogenesis of upper digestive tract cancers: possible chemoprevention with cysteine</i></a> (Academic dissertation). <a href="/wiki/University_of_Helsinki" title="University of Helsinki">University of Helsinki</a>. pp. 41–44. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<a rel="nofollow" class="external text" href="https://hdl.handle.net/10138%2F22689">10138/22689</a>. <a rel="nofollow" class="external free" href="URN:ISBN:952-10-3056-9">URN:ISBN:952-10-3056-9</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adissertation&rft.title=Interaction+of+alcohol+and+smoking+in+the+pathogenesis+of+upper+digestive+tract+cancers%3A+possible+chemoprevention+with+cysteine&rft.inst=University+of+Helsinki&rft.date=2006&rft_id=info%3Ahdl%2F10138%2F22689&rft.aulast=Salaspuro&rft.aufirst=Ville&rft_id=https%3A%2F%2Fhelda.helsinki.fi%2Fitems%2F8d28d7d1-e6f4-4a2c-89e9-9a25bdffdf93&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-48"><span class="mw-cite-backlink"><b><a href="#cite_ref-48">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSprinceParkerSmithGonzales1974" class="citation journal cs1">Sprince H, Parker CM, Smith GG, Gonzales LJ (April 1974). "Protection against acetaldehyde toxicity in the rat by L-cysteine, thiamin and L-2-methylthiazolidine-4-carboxylic acid". <i>Agents Actions</i>. <b>4</b> (2): 125–30. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2FBF01966822">10.1007/BF01966822</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/4842541">4842541</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:5924137">5924137</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Agents+Actions&rft.atitle=Protection+against+acetaldehyde+toxicity+in+the+rat+by+L-cysteine%2C+thiamin+and+L-2-methylthiazolidine-4-carboxylic+acid&rft.volume=4&rft.issue=2&rft.pages=125-30&rft.date=1974-04&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A5924137%23id-name%3DS2CID&rft_id=info%3Apmid%2F4842541&rft_id=info%3Adoi%2F10.1007%2FBF01966822&rft.aulast=Sprince&rft.aufirst=H&rft.au=Parker%2C+CM&rft.au=Smith%2C+GG&rft.au=Gonzales%2C+LJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-49"><span class="mw-cite-backlink"><b><a href="#cite_ref-49">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFErikssonMetsäläMöykkynenMäkisalo2020" class="citation journal cs1">Eriksson, C J Peter; Metsälä, Markus; Möykkynen, Tommi; Mäkisalo, Heikki; Kärkkäinen, Olli; Palmén, Maria; Salminen, Joonas E; Kauhanen, Jussi (20 October 2020). "L-Cysteine Containing Vitamin Supplement Which Prevents or Alleviates Alcohol-related Hangover Symptoms: Nausea, Headache, Stress and Anxiety". <i>Alcohol and Alcoholism</i>. <b>55</b> (6): 660–666. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Falcalc%2Fagaa082">10.1093/alcalc/agaa082</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/10138%2F339340">10138/339340</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/32808029">32808029</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Alcohol+and+Alcoholism&rft.atitle=L-Cysteine+Containing+Vitamin+Supplement+Which+Prevents+or+Alleviates+Alcohol-related+Hangover+Symptoms%3A+Nausea%2C+Headache%2C+Stress+and+Anxiety&rft.volume=55&rft.issue=6&rft.pages=660-666&rft.date=2020-10-20&rft_id=info%3Ahdl%2F10138%2F339340&rft_id=info%3Apmid%2F32808029&rft_id=info%3Adoi%2F10.1093%2Falcalc%2Fagaa082&rft.aulast=Eriksson&rft.aufirst=C+J+Peter&rft.au=Mets%C3%A4l%C3%A4%2C+Markus&rft.au=M%C3%B6ykkynen%2C+Tommi&rft.au=M%C3%A4kisalo%2C+Heikki&rft.au=K%C3%A4rkk%C3%A4inen%2C+Olli&rft.au=Palm%C3%A9n%2C+Maria&rft.au=Salminen%2C+Joonas+E&rft.au=Kauhanen%2C+Jussi&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-50"><span class="mw-cite-backlink"><b><a href="#cite_ref-50">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKanter_MZ2006" class="citation journal cs1">Kanter MZ (October 2006). "Comparison of oral and i.v. acetylcysteine in the treatment of acetaminophen poisoning". <i>Am J Health Syst Pharm</i>. <b>63</b> (19): 1821–7. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2146%2Fajhp060050">10.2146/ajhp060050</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/16990628">16990628</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:9209528">9209528</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Am+J+Health+Syst+Pharm&rft.atitle=Comparison+of+oral+and+i.v.+acetylcysteine+in+the+treatment+of+acetaminophen+poisoning&rft.volume=63&rft.issue=19&rft.pages=1821-7&rft.date=2006-10&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A9209528%23id-name%3DS2CID&rft_id=info%3Apmid%2F16990628&rft_id=info%3Adoi%2F10.2146%2Fajhp060050&rft.au=Kanter+MZ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-Transgenic_sheep-51"><span class="mw-cite-backlink"><b><a href="#cite_ref-Transgenic_sheep_51-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPowellWalkerBawdenSivaprasad1994" class="citation journal cs1">Powell BC, Walker SK, Bawden CS, Sivaprasad AV, Rogers GE (1994). "Transgenic sheep and wool growth: possibilities and current status". <i>Reprod. Fertil. Dev</i>. <b>6</b> (5): 615–23. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1071%2FRD9940615">10.1071/RD9940615</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/7569041">7569041</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Reprod.+Fertil.+Dev.&rft.atitle=Transgenic+sheep+and+wool+growth%3A+possibilities+and+current+status&rft.volume=6&rft.issue=5&rft.pages=615-23&rft.date=1994&rft_id=info%3Adoi%2F10.1071%2FRD9940615&rft_id=info%3Apmid%2F7569041&rft.aulast=Powell&rft.aufirst=BC&rft.au=Walker%2C+SK&rft.au=Bawden%2C+CS&rft.au=Sivaprasad%2C+AV&rft.au=Rogers%2C+GE&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-52"><span class="mw-cite-backlink"><b><a href="#cite_ref-52">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMilkowskiVeberHirschmann1979" class="citation journal cs1">Milkowski, John D.; Veber, Daniel F.; Hirschmann, Ralph (1979). "Thiol Protection with the Acetamidomethyl Group: S-Acetamidomethyl-L-Cysteine Hydrochloride". <i>Organic Syntheses</i>. <b>59</b>: 190. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.059.0190">10.15227/orgsyn.059.0190</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Syntheses&rft.atitle=Thiol+Protection+with+the+Acetamidomethyl+Group%3A+S-Acetamidomethyl-L-Cysteine+Hydrochloride&rft.volume=59&rft.pages=190&rft.date=1979&rft_id=info%3Adoi%2F10.15227%2Forgsyn.059.0190&rft.aulast=Milkowski&rft.aufirst=John+D.&rft.au=Veber%2C+Daniel+F.&rft.au=Hirschmann%2C+Ralph&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-53"><span class="mw-cite-backlink"><b><a href="#cite_ref-53">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFArnoldJackson1990" class="citation journal cs1">Arnold, Alan P.; Jackson, W. Gregory (1990). "Stereospecificity in the Synthesis of the Tris((<i>R</i>)-Cysteinato-<i>N,S</i>)- and Tris((<i>R</i>)-Cysteinesulfinato-N,S)cobaltate(III) Ions". <i>Inorganic Chemistry</i>. <b>29</b> (18): 3618–3620. <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%2Fic00343a061">10.1021/ic00343a061</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Inorganic+Chemistry&rft.atitle=Stereospecificity+in+the+Synthesis+of+the+Tris%28%28R%29-Cysteinato-N%2CS%29-+and+Tris%28%28R%29-Cysteinesulfinato-N%2CS%29cobaltate%28III%29+Ions&rft.volume=29&rft.issue=18&rft.pages=3618-3620&rft.date=1990&rft_id=info%3Adoi%2F10.1021%2Fic00343a061&rft.aulast=Arnold&rft.aufirst=Alan+P.&rft.au=Jackson%2C+W.+Gregory&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-54"><span class="mw-cite-backlink"><b><a href="#cite_ref-54">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAndersonMeister1987" class="citation book cs1">Anderson, Mary E.; Meister, Alton (1987). "Intracellular delivery of cysteine". <i>Sulfur and Sulfur Amino Acids</i>. Methods in Enzymology. Vol. 143. pp. 313–325. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0076-6879%2887%2943059-0">10.1016/0076-6879(87)43059-0</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780121820435" title="Special:BookSources/9780121820435"><bdi>9780121820435</bdi></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/3309557">3309557</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Intracellular+delivery+of+cysteine&rft.btitle=Sulfur+and+Sulfur+Amino+Acids&rft.series=Methods+in+Enzymology&rft.pages=313-325&rft.date=1987&rft_id=info%3Apmid%2F3309557&rft_id=info%3Adoi%2F10.1016%2F0076-6879%2887%2943059-0&rft.isbn=9780121820435&rft.aulast=Anderson&rft.aufirst=Mary+E.&rft.au=Meister%2C+Alton&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></span> </li> <li id="cite_note-55"><span class="mw-cite-backlink"><b><a href="#cite_ref-55">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBaumann1884" class="citation journal cs1 cs1-prop-foreign-lang-source">Baumann, E. (1884). <a rel="nofollow" class="external text" href="https://babel.hathitrust.org/cgi/pt?id=coo.31924078260563&view=1up&seq=309">"Ueber Cystin und Cysteïn"</a> [On cystine and cysteine]. <i>Zeitschrift für physiologische Chemie</i> (in German). <b>8</b>: 299–305.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Zeitschrift+f%C3%BCr+physiologische+Chemie&rft.atitle=Ueber+Cystin+und+Cyste%C3%AFn&rft.volume=8&rft.pages=299-305&rft.date=1884&rft.aulast=Baumann&rft.aufirst=E.&rft_id=https%3A%2F%2Fbabel.hathitrust.org%2Fcgi%2Fpt%3Fid%3Dcoo.31924078260563%26view%3D1up%26seq%3D309&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span> From pp. 301-302: <i>"Die Analyse der Substanz ergibt Werthe, welche den vom Cystin (C<sub>6</sub>H<sub>12</sub>N<sub>2</sub>S<sub>2</sub>O<sub>4</sub>) verlangten sich nähern, […] nenne ich dieses Reduktionsprodukt des Cystins: Cysteïn."</i> (Analysis of the substance [cysteine] reveals values which approximate those [that are] required by cystine (C<sub>6</sub>H<sub>12</sub>N<sub>2</sub>S<sub>2</sub>O<sub>4</sub>), however the new base [cysteine] can clearly be recognized as a reduction product of cystine, to which the [empirical] formula C<sub>3</sub>H<sub>7</sub>NSO<sub>2</sub>, [which had] previously [been] ascribed to cystine, is [now] ascribed. In order to indicate the relationships of this substance to cystine, I name this reduction product of cystine: "cysteïne".) Note: Baumann's proposed structures for cysteine and cystine (see p.302) are incorrect: for cysteine, he proposed CH<sub>3</sub>CNH<sub>2</sub>(SH)COOH .</span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=20" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNaganoOtaNishikawa1999" class="citation journal cs1">Nagano N, Ota M, Nishikawa K (September 1999). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0014-5793%2899%2901122-9">"Strong hydrophobic nature of cysteine residues in proteins"</a>. <i>FEBS Lett</i>. <b>458</b> (1): 69–71. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1999FEBSL.458...69N">1999FEBSL.458...69N</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0014-5793%2899%2901122-9">10.1016/S0014-5793(99)01122-9</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/10518936">10518936</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:34980474">34980474</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=FEBS+Lett.&rft.atitle=Strong+hydrophobic+nature+of+cysteine+residues+in+proteins&rft.volume=458&rft.issue=1&rft.pages=69-71&rft.date=1999-09&rft_id=info%3Adoi%2F10.1016%2FS0014-5793%2899%2901122-9&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A34980474%23id-name%3DS2CID&rft_id=info%3Apmid%2F10518936&rft_id=info%3Abibcode%2F1999FEBSL.458...69N&rft.aulast=Nagano&rft.aufirst=N&rft.au=Ota%2C+M&rft.au=Nishikawa%2C+K&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252FS0014-5793%252899%252901122-9&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACysteine" class="Z3988"></span></li></ul> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cysteine&action=edit&section=21" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Holly (2005). <i><a rel="nofollow" class="external text" href="https://web.archive.org/web/20130521211422/http://cystinuriaclearinghouse.com/index.html">Cystinuria Clearinghouse</a></i></li> <li><a rel="nofollow" class="external text" href="http://gmd.mpimp-golm.mpg.de/Spectrums/90eac3d9-ee59-4f02-a245-631bde944b66.aspx">Cysteine MS Spectrum</a></li> <li><a rel="nofollow" class="external text" href="http://www.iksi.org">International Kidney Stone Institute</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20190513095547/http://www.iksi.org/">Archived</a> 2019-05-13 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></li></ul> <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 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td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Cough_and_cold_preparations_(R05)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse 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"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output 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.navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Cough_and_cold_preparations" title="Template:Cough and cold preparations"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cough_and_cold_preparations" title="Template talk:Cough and cold preparations"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cough_and_cold_preparations" title="Special:EditPage/Template:Cough and cold preparations"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Cough_and_cold_preparations_(R05)" style="font-size:114%;margin:0 4em"><a href="/wiki/Cough_medicine" class="mw-redirect" title="Cough medicine">Cough and cold preparations</a> (<a href="/wiki/ATC_code_R05" title="ATC code R05">R05</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mucolytic_agent" class="mw-redirect" title="Mucolytic agent">Expectorants</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Althaea_(plant)" title="Althaea (plant)">Althea root</a></li> <li><a href="/wiki/Ammonium_chloride" title="Ammonium chloride">Ammonium chloride</a></li> <li><a href="/wiki/Antimony_pentasulfide" title="Antimony pentasulfide">Antimony pentasulfide</a></li> <li><a href="/wiki/Cineole" class="mw-redirect" title="Cineole">Cineole</a></li> <li><a href="/wiki/Creosote" title="Creosote">Creosote</a></li> <li><a href="/wiki/Guaiacolsulfonate" class="mw-redirect" title="Guaiacolsulfonate">Guaiacolsulfonate</a></li> <li><a href="/wiki/Guaifenesin" title="Guaifenesin">Guaifenesin</a> (<a href="/wiki/Guaifenesin/codeine" title="Guaifenesin/codeine">+codeine</a>, <a href="/wiki/Hydrocodone/guaifenesin" title="Hydrocodone/guaifenesin">+hydrocodone</a>, <a href="/wiki/Oxomemazine/guaifenesin" title="Oxomemazine/guaifenesin">+oxomemazine</a>)</li> <li><a href="/wiki/Hedera_helix" title="Hedera helix">Hederae helicis folium</a></li> <li><a href="/wiki/Carapichea_ipecacuanha" title="Carapichea ipecacuanha">Ipecacuanha</a> (<a href="/wiki/Syrup_of_ipecac" title="Syrup of ipecac">Syrup of ipecac</a>)</li> <li><a href="/wiki/Levoverbenone" title="Levoverbenone">Levoverbenone</a></li> <li><a href="/wiki/Potassium_iodide" title="Potassium iodide">Potassium iodide</a></li> <li><a href="/wiki/Polygala_senega" class="mw-redirect" title="Polygala senega">Senega</a></li> <li><a href="/wiki/Tyloxapol" title="Tyloxapol">Tyloxapol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mucolytic_agent" class="mw-redirect" title="Mucolytic agent">Mucolytics</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetylcysteine" title="Acetylcysteine">Acetylcysteine</a><sup>#</sup></li> <li><a href="/wiki/Ambroxol" title="Ambroxol">Ambroxol</a></li> <li><a href="/wiki/Bromhexine" title="Bromhexine">Bromhexine</a></li> <li><a href="/wiki/Carbocisteine" title="Carbocisteine">Carbocisteine</a></li> <li><a href="/w/index.php?title=Dembrexine_hydrochloride&action=edit&redlink=1" class="new" title="Dembrexine hydrochloride (page does not exist)">Dembrexine hydrochloride</a></li> <li><a href="/wiki/Domiodol" title="Domiodol">Domiodol</a></li> <li><a href="/wiki/Dornase_alfa" title="Dornase alfa">Dornase alfa</a></li> <li><a href="/wiki/Eprazinone" title="Eprazinone">Eprazinone</a></li> <li><a href="/wiki/Erdosteine" title="Erdosteine">Erdosteine</a></li> <li><a href="/wiki/Letosteine" title="Letosteine">Letosteine</a></li> <li><a href="/wiki/Mannitol" title="Mannitol">Mannitol</a></li> <li><a href="/wiki/Mesna" title="Mesna">Mesna</a></li> <li><a href="/wiki/Neltenexine" title="Neltenexine">Neltenexine</a></li> <li><a href="/wiki/Sobrerol" title="Sobrerol">Sobrerol</a></li> <li><a href="/wiki/Stepronin" title="Stepronin">Stepronin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cough_suppressant" class="mw-redirect" title="Cough suppressant">Cough suppressants</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Opium" title="Opium">Opium</a> alkaloids,<br /><a href="/wiki/Opioid" title="Opioid">opioids</a>,<br />and derivatives</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/Acetyldihydrocodeine" title="Acetyldihydrocodeine">Acetyldihydrocodeine</a></li> <li><a href="/wiki/Benzylmorphine" title="Benzylmorphine">Benzylmorphine</a></li> <li><a href="/wiki/Butorphanol" title="Butorphanol">Butorphanol</a></li> <li><a href="/wiki/Codeine" title="Codeine">Codeine</a><sup>#</sup> (<a href="/wiki/Guaifenesin/codeine" title="Guaifenesin/codeine">+guaifenesin</a>)</li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan</a></li> <li><a href="/wiki/Dihydrocodeine" title="Dihydrocodeine">Dihydrocodeine</a></li> <li><a href="/wiki/Dimemorfan" title="Dimemorfan">Dimemorfan</a></li> <li><a href="/wiki/Ethylmorphine" title="Ethylmorphine">Ethylmorphine</a></li> <li><a href="/wiki/Heroin" title="Heroin">Heroin</a></li> <li><a href="/wiki/Hydrocodone" title="Hydrocodone">Hydrocodone</a> (<a href="/wiki/Hydrocodone/guaifenesin" title="Hydrocodone/guaifenesin">+guaifenesin</a>, <a href="/wiki/Hydrocodone/homatropine" title="Hydrocodone/homatropine">+homatropine</a>)</li> <li><a href="/wiki/Hydromorphone" title="Hydromorphone">Hydromorphone</a></li> <li><a href="/wiki/Laudanum" title="Laudanum">Laudanum</a></li> <li><a href="/wiki/Levomethadone" title="Levomethadone">Levomethadone</a></li> <li><a href="/wiki/Levopropoxyphene" title="Levopropoxyphene">Levopropoxyphene</a></li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a></li> <li><a href="/wiki/Nicocodeine" title="Nicocodeine">Nicocodeine</a></li> <li><a href="/wiki/Nicodicodeine" class="mw-redirect" title="Nicodicodeine">Nicodicodeine</a></li> <li><a href="/wiki/Normethadone" title="Normethadone">Normethadone</a></li> <li><a href="/wiki/Noscapine" title="Noscapine">Noscapine</a></li> <li><a href="/wiki/Pholcodine" title="Pholcodine">Pholcodine</a></li> <li><a href="/wiki/Dihydrocodeinone_enol_acetate" class="mw-redirect" title="Dihydrocodeinone enol acetate">Thebacon</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/Alloclamide" title="Alloclamide">Alloclamide</a></li> <li><a href="/wiki/Benproperine" title="Benproperine">Benproperine</a></li> <li><a href="/wiki/Benzonatate" title="Benzonatate">Benzonatate</a></li> <li><a href="/wiki/Bibenzonium_bromide" title="Bibenzonium bromide">Bibenzonium bromide</a></li> <li><a href="/wiki/Butamirate" title="Butamirate">Butamirate</a></li> <li><a href="/wiki/Clobutinol" title="Clobutinol">Clobutinol</a></li> <li><a href="/wiki/Clofedanol" title="Clofedanol">Clofedanol</a></li> <li><a href="/wiki/Cloperastine" title="Cloperastine">Cloperastine</a></li> <li><a href="/wiki/Dibunate" title="Dibunate">Dibunate</a></li> <li><a href="/wiki/Dimethoxanate" title="Dimethoxanate">Dimethoxanate</a></li> <li><a href="/wiki/Diphenhydramine" title="Diphenhydramine">Diphenhydramine</a></li> <li><a href="/wiki/Dropropizine" title="Dropropizine">Dropropizine</a></li> <li><a href="/wiki/Droxypropine" title="Droxypropine">Droxypropine</a></li> <li><a href="/wiki/Fedrilate" title="Fedrilate">Fedrilate</a></li> <li><a href="/wiki/Fominoben" title="Fominoben">Fominoben</a></li> <li><a href="/wiki/Gefapixant" title="Gefapixant">Gefapixant</a></li> <li><a href="/wiki/Glaucine" title="Glaucine">Glaucine</a></li> <li><a href="/wiki/Isoaminile" title="Isoaminile">Isoaminile</a></li> <li><a href="/wiki/Levodropropizine" title="Levodropropizine">Levodropropizine</a></li> <li><a href="/wiki/Meprotixol" title="Meprotixol">Meprotixol</a></li> <li><a href="/wiki/Moguisteine" title="Moguisteine">Moguisteine</a></li> <li><a href="/wiki/Morclofone" title="Morclofone">Morclofone</a></li> <li><a href="/wiki/Nepinalone" title="Nepinalone">Nepinalone</a></li> <li><a href="/wiki/Oxeladin" title="Oxeladin">Oxeladin</a></li> <li><a href="/wiki/Oxolamine" title="Oxolamine">Oxolamine</a></li> <li><a href="/wiki/Pentoxyverine" title="Pentoxyverine">Pentoxyverine</a></li> <li><a href="/wiki/Pipazetate" title="Pipazetate">Pipazetate</a></li> <li><a href="/wiki/Piperidione" title="Piperidione">Piperidione</a></li> <li><a href="/wiki/Prenoxdiazine" title="Prenoxdiazine">Prenoxdiazine</a></li> <li><a href="/wiki/Tipepidine" title="Tipepidine">Tipepidine</a></li> <li><a href="/wiki/Zipeprol" title="Zipeprol">Zipeprol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Antidotes_(V03AB)" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="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:Antidotes" title="Template:Antidotes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Antidotes" title="Template talk:Antidotes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Antidotes" title="Special:EditPage/Template:Antidotes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antidotes_(V03AB)" style="font-size:114%;margin:0 4em"><a href="/wiki/Antidote" title="Antidote">Antidotes</a> (<a href="/wiki/ATC_code_V03#V03AB" title="ATC code V03">V03AB</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nervous_system" title="Nervous system">Nervous<br /> system</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/Alcohol_intoxication" title="Alcohol intoxication">Alcohol intoxication</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/Metadoxine" title="Metadoxine">Metadoxine</a></li> <li><a href="/wiki/Thiamine" title="Thiamine">Thiamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Barbiturate_overdose" title="Barbiturate overdose">Barbiturate<br /> overdose</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/Bemegride" title="Bemegride">Bemegride</a></li> <li><a href="/wiki/Etamivan" title="Etamivan">Ethamivan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Benzodiazepine_overdose" title="Benzodiazepine overdose">Benzodiazepine<br /> overdose</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/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Flumazenil" title="Flumazenil">Flumazenil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/GHB_overdose" class="mw-redirect" title="GHB overdose">GHB overdose</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/Physostigmine" title="Physostigmine">Physostigmine</a></li> <li><a href="/wiki/SCH-50911" title="SCH-50911">SCH-50911</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nerve_agent" title="Nerve agent">Nerve agent</a> /<br /> <a href="/wiki/Organophosphate_poisoning" title="Organophosphate poisoning">Organophosphate<br /> poisoning</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/Atropine" title="Atropine">Atropine</a><sup>#</sup></li> <li><a href="/wiki/Biperiden" title="Biperiden">Biperiden</a></li> <li><a href="/wiki/Diazepam" title="Diazepam">Diazepam</a><sup>#</sup></li> <li><a href="/wiki/Oxime" title="Oxime">Oximes</a> <ul><li><a href="/wiki/Obidoxime" title="Obidoxime">Obidoxime</a></li> <li><a href="/wiki/Pralidoxime" title="Pralidoxime">Pralidoxime</a></li></ul></li> <li><i>see also:</i> <a href="/wiki/Cholinesterase" title="Cholinesterase">Cholinesterase</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Opioid_overdose" title="Opioid overdose">Opioid overdose</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/Diprenorphine" title="Diprenorphine">Diprenorphine</a></li> <li><a href="/wiki/Doxapram" title="Doxapram">Doxapram</a></li> <li><a href="/wiki/Nalmefene" title="Nalmefene">Nalmefene</a></li> <li><a href="/wiki/Nalorphine" title="Nalorphine">Nalorphine</a></li> <li><a href="/wiki/Naloxone" title="Naloxone">Naloxone</a><sup>#</sup></li> <li><a href="/wiki/Naltrexone" title="Naltrexone">Naltrexone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Reversal of<br /> <a href="/wiki/Neuromuscular-blocking_drug" title="Neuromuscular-blocking drug">neuromuscular blockade</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/Sugammadex" title="Sugammadex">Sugammadex</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/Circulatory_system" title="Circulatory system">Circulatory<br /> system</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/Beta_blocker#Adverse_effects" title="Beta blocker">Beta blocker</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/Glucagon" title="Glucagon">Glucagon</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Digoxin_toxicity" title="Digoxin toxicity">Digoxin toxicity</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/Digoxin_immune_fab" title="Digoxin immune fab">Digoxin immune fab</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anticoagulant" title="Anticoagulant">Anticoagulants</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>against <a href="/wiki/Direct_Xa_inhibitor" class="mw-redirect" title="Direct Xa inhibitor">direct Xa inhibitors</a> (<a href="/wiki/Andexanet_alfa" title="Andexanet alfa">Andexanet alfa</a>)</li> <li>against <a href="/wiki/Heparin" title="Heparin">heparin</a> (<a href="/wiki/Protamine_sulfate" title="Protamine sulfate">Protamine</a><sup>#</sup>)</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" 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/Arsenic_poisoning" title="Arsenic poisoning">Arsenic poisoning</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/Dimercaprol" title="Dimercaprol">Dimercaprol</a><sup>#</sup></li> <li><a href="/wiki/Dimercaptosuccinic_acid" class="mw-redirect" title="Dimercaptosuccinic acid">Succimer</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cyanide_poisoning" title="Cyanide poisoning">Cyanide poisoning</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-Dimethylaminophenol" title="4-Dimethylaminophenol">4-Dimethylaminophenol</a></li> <li><a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">Hydroxocobalamin</a></li> <li><i><a href="/wiki/Nitrite" title="Nitrite">nitrite</a></i> <ul><li><a href="/wiki/Amyl_nitrite" title="Amyl nitrite">Amyl nitrite</a></li> <li><a href="/wiki/Sodium_nitrite" title="Sodium nitrite">Sodium nitrite</a><sup>#</sup></li></ul></li> <li><a href="/wiki/Sodium_thiosulfate_(medical_use)" title="Sodium thiosulfate (medical use)">Sodium thiosulfate</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrofluoric_acid" title="Hydrofluoric acid">Hydrofluoric acid</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/Calcium_gluconate" title="Calcium gluconate">Calcium gluconate</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Methanol" title="Methanol">Methanol</a> /<br /> <a href="/wiki/Ethylene_glycol_poisoning" title="Ethylene glycol poisoning">Ethylene glycol<br /> poisoning</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>Primary alcohols: <a href="/wiki/Alcohol_(medicine)" class="mw-redirect" title="Alcohol (medicine)">Ethanol</a></li> <li><a href="/wiki/Fomepizole" title="Fomepizole">Fomepizole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Paracetamol_poisoning" title="Paracetamol poisoning">Paracetamol toxicity</a><br /> (Acetaminophen)</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/Acetylcysteine" title="Acetylcysteine">Acetylcysteine</a><sup>#</sup></li> <li><a href="/wiki/Glutathione" title="Glutathione">Glutathione</a></li> <li><a href="/wiki/Methionine" title="Methionine">Methionine</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Toxic_metal" class="mw-redirect" title="Toxic metal">Toxic metals</a> (<a href="/wiki/Cadmium_poisoning" title="Cadmium poisoning">cadmium</a> <ul><li><a href="/wiki/Lead_poisoning" title="Lead poisoning">lead</a></li> <li><a href="/wiki/Mercury_poisoning" title="Mercury poisoning">mercury</a></li> <li><a href="/wiki/Thallium_poisoning" title="Thallium poisoning">thallium</a>)</li></ul></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <li><a href="/wiki/Dimercaprol" title="Dimercaprol">Dimercaprol</a><sup>#</sup></li> <li><a href="/wiki/Ethylenediaminetetraacetic_acid" title="Ethylenediaminetetraacetic acid">Edetates</a></li> <li><a href="/wiki/Prussian_blue" title="Prussian blue">Prussian blue</a><sup>#</sup></li> </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" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Iodine-131" title="Iodine-131">iodine-131</a></i> <ul><li><a href="/wiki/Potassium_iodide" title="Potassium iodide">Potassium iodide</a></li></ul></li> <li><a href="/wiki/Methylene_blue" title="Methylene blue">Methylthioninium chloride</a><sup>#</sup></li> <li><i><a href="/wiki/Oxidizing_agent" title="Oxidizing agent">oxidizing agent</a></i> <ul><li><a href="/wiki/Potassium_permanganate" title="Potassium permanganate">Potassium permanganate</a></li></ul></li> <li><a href="/wiki/Prednisolone/promethazine" title="Prednisolone/promethazine">Prednisolone/promethazine</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/Emetic" class="mw-redirect" title="Emetic">Emetic</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/Copper(II)_sulfate" title="Copper(II) sulfate">Copper sulfate</a></li> <li><a href="/wiki/Psychotria_ipecacuanha" class="mw-redirect" title="Psychotria ipecacuanha">Ipecacuanha</a> <ul><li><a href="/wiki/Syrup_of_ipecac" title="Syrup of ipecac">Syrup of ipecac</a></li></ul></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Encoded_(proteinogenic)_amino_acids" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="3"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><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: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><span typeof="mw:File"><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></span></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 (p<i>K</i><sub>a</sub>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Lysine" title="Lysine">Lysine</a> (≈10.8)</li> <li><a href="/wiki/Arginine" title="Arginine">Arginine</a> (≈12.5)</li> <li><a href="/wiki/Histidine" title="Histidine">Histidine</a> (≈6.1)</li> <li><a href="/wiki/Pyrrolysine" title="Pyrrolysine">Pyrrolysine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Negative charge (p<i>K</i><sub>a</sub>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aspartic_acid" title="Aspartic acid">Aspartic acid</a> (≈3.9)</li> <li><a href="/wiki/Glutamic_acid" title="Glutamic acid">Glutamic acid</a> (≈4.1)</li> <li><a href="/wiki/Selenocysteine" title="Selenocysteine">Selenocysteine</a> (≈5.4)</li> <li><a class="mw-selflink selflink">Cysteine</a> (≈8.3)</li> <li><a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a> (≈10.1)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="3"><div><div class="hlist" style="font-size:88%;"> <ul><li><b><a href="/wiki/Amino_acids" class="mw-redirect" title="Amino acids">Amino acids</a> types</b>: <a href="/wiki/Template:Encoded_amino_acids" class="mw-redirect" title="Template:Encoded amino acids">Encoded (proteins)</a></li> <li><a href="/wiki/Essential_amino_acids" class="mw-redirect" title="Essential amino acids">Essential</a></li> <li><a href="/wiki/Template:Non-proteinogenic_amino_acids" title="Template:Non-proteinogenic amino acids">Non-proteinogenic</a></li> <li><a href="/wiki/Ketogenic_amino_acids" class="mw-redirect" title="Ketogenic amino acids">Ketogenic</a></li> <li><a href="/wiki/Glucogenic_amino_acids" class="mw-redirect" title="Glucogenic amino acids">Glucogenic</a></li> <li><a href="/wiki/Secondary_amino_acid" title="Secondary amino acid">Secondary amino</a></li> <li><a href="/wiki/Imino_acid" title="Imino acid">Imino acids</a></li> <li><a href="/wiki/D-amino_acids" class="mw-redirect" title="D-amino acids">D-amino acids</a></li> <li><a href="/wiki/Dehydroamino_acid" title="Dehydroamino acid">Dehydroamino acids</a></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="E_numbers" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse 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:E_number_infobox_920-929" title="Template:E number infobox 920-929"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:E_number_infobox_920-929" title="Template talk:E number infobox 920-929"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:E_number_infobox_920-929" title="Special:EditPage/Template:E number infobox 920-929"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="E_numbers" style="font-size:114%;margin:0 4em"><a href="/wiki/E_number" title="E number">E numbers</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Food_coloring" title="Food coloring">Colours</a> (E100–199)</li> <li><a href="/wiki/Preservative" title="Preservative">Preservatives</a> (E200–299)</li> <li><a href="/wiki/Antioxidant" title="Antioxidant">Antioxidants</a> & <a href="/wiki/Acidity_regulator" title="Acidity regulator">acidity regulators</a> (E300–399)</li> <li><a href="/wiki/Thickening_agent" title="Thickening agent">Thickeners</a>, <a href="/wiki/Food_additive#Categories" title="Food additive">stabilisers</a> & <a href="/wiki/Emulsifier" class="mw-redirect" title="Emulsifier">emulsifiers</a> (E400–499)</li> <li><a href="/wiki/PH" title="PH">pH</a> <a href="/wiki/Acidity_regulator" title="Acidity regulator">regulators</a> & <a href="/wiki/Anticaking_agent" title="Anticaking agent">anticaking agents</a> (E500–599)</li> <li><a href="/wiki/Flavoring" title="Flavoring">Flavour enhancers</a> (E600–699)</li> <li><b>Miscellaneous (E900–999)</b></li> <li>Additional chemicals (E1100–1599)</li></ul> <hr /> <ul><li><a href="/wiki/Wax" title="Wax">Waxes</a> (E900–909)</li> <li><a href="/wiki/Glazing_agent" title="Glazing agent">Synthetic glazes</a> (E910–919)</li> <li><b><a href="/wiki/Flour_treatment_agent" class="mw-redirect" title="Flour treatment agent">Improving agents</a> (E920–929)</b></li> <li><a href="/wiki/Packaging_gas" title="Packaging gas">Packaging gases</a> (E930–949)</li> <li><a href="/wiki/Sugar_substitute" title="Sugar substitute">Sweeteners</a> (E950–969)</li> <li><a href="/wiki/Foaming_agent" title="Foaming agent">Foaming agents</a> (E990–999)</li></ul> <hr /> <ul><li><a class="mw-selflink selflink"><small>L</small>-cysteine</a> (E920)</li> <li><a href="/wiki/Cystine" title="Cystine"><small>L</small>-cystine</a> (E921)</li> <li><a href="/wiki/Potassium_persulfate" title="Potassium persulfate">Potassium persulfate</a> (E922)</li> <li><a href="/wiki/Ammonium_persulfate" title="Ammonium persulfate">Ammonium persulfate</a> (E923)</li> <li><a href="/wiki/Potassium_bromate" title="Potassium bromate">Potassium bromate</a> (E924)</li> <li><a href="/wiki/Chlorine" title="Chlorine">Chlorine</a> (E925)</li> <li><a href="/wiki/Chlorine_dioxide" title="Chlorine dioxide">Chlorine dioxide</a> (E926)</li> <li><a href="/wiki/Azodicarbonamide" title="Azodicarbonamide">Azodicarbonamide</a> (E927)</li> <li><a href="/wiki/Urea" title="Urea">Carbamide</a> (E927b)</li> <li><a href="/wiki/Benzoyl_peroxide" title="Benzoyl peroxide">Benzoyl peroxide</a> (E928)</li></ul> </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 href="/wiki/Lysine" title="Lysine">lysine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Saccharopine" title="Saccharopine">Saccharopine</a></li> <li><a href="/wiki/Allysine" title="Allysine">Allysine</a></li> <li><a href="/wiki/Alpha-Aminoadipic_acid" class="mw-redirect" title="Alpha-Aminoadipic acid">α-Aminoadipic acid</a></li> <li><a href="/wiki/2-Oxoadipic_acid" title="2-Oxoadipic acid">2-Oxoadipic acid</a></li> <li><a href="/wiki/Glutaryl-CoA" title="Glutaryl-CoA">Glutaryl-CoA</a></li> <li><a href="/wiki/Glutaconyl-CoA" title="Glutaconyl-CoA">Glutaconyl-CoA</a></li> <li><a href="/wiki/Crotonyl-CoA" title="Crotonyl-CoA">Crotonyl-CoA</a></li> <li><a href="/wiki/Beta-Hydroxybutyryl-CoA" class="mw-redirect" title="Beta-Hydroxybutyryl-CoA">β-Hydroxybutyryl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a 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"><i>N</i>′-Formylkynurenine</a></li> <li><a href="/wiki/Kynurenine" title="Kynurenine">Kynurenine</a></li> <li><a href="/wiki/Anthranilic_acid" title="Anthranilic acid">Anthranilic acid</a></li> <li><a href="/wiki/3-Hydroxykynurenine" title="3-Hydroxykynurenine">3-Hydroxykynurenine</a></li> <li><a href="/wiki/3-Hydroxyanthranilic_acid" title="3-Hydroxyanthranilic acid">3-Hydroxyanthranilic acid</a></li> <li><a href="/wiki/2-Amino-3-carboxymuconic_semialdehyde" title="2-Amino-3-carboxymuconic semialdehyde">2-Amino-3-carboxymuconic semialdehyde</a></li> <li><a href="/wiki/2-Aminomuconic_semialdehyde" title="2-Aminomuconic semialdehyde">2-Aminomuconic semialdehyde</a></li> <li><a href="/wiki/2-Aminomuconic_acid" title="2-Aminomuconic acid">2-Aminomuconic acid</a></li> <li><a href="/wiki/Glutaryl-CoA" title="Glutaryl-CoA">Glutaryl-CoA</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glucogenic_amino_acid" title="Glucogenic amino acid">G</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Pyruvate" class="mw-redirect" title="Pyruvate">pyruvate</a>→ <br /><a href="/wiki/Citrate" class="mw-redirect" title="Citrate">citrate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="glycine→serine→" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glycine" title="Glycine">glycine</a>→<br /><a href="/wiki/Serine" title="Serine">serine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Phosphoglyceric_acid" title="3-Phosphoglyceric acid">3-Phosphoglyceric acid</a></li></ul> <ul><li><a href="/wiki/Glycine" title="Glycine">glycine</a>→<a href="/wiki/Creatine" title="Creatine">creatine</a>: <a href="/wiki/Glycocyamine" title="Glycocyamine">Glycocyamine</a></li> <li><a href="/wiki/Phosphocreatine" title="Phosphocreatine">Phosphocreatine</a></li> <li><a href="/wiki/Creatinine" title="Creatinine">Creatinine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a>→<br /><a href="/wiki/Alpha-Ketoglutaric_acid" class="mw-redirect" title="Alpha-Ketoglutaric acid">α-ketoglutarate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Histidine" title="Histidine">histidine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Urocanic_acid" title="Urocanic acid">Urocanic acid</a></li> <li><a href="/wiki/Imidazol-4-one-5-propionic_acid" title="Imidazol-4-one-5-propionic acid">Imidazol-4-one-5-propionic acid</a></li> <li><a href="/wiki/Formiminoglutamic_acid" title="Formiminoglutamic acid">Formiminoglutamic acid</a></li> <li><a href="/wiki/Glutamate-1-semialdehyde" title="Glutamate-1-semialdehyde">Glutamate-1-semialdehyde</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Proline" title="Proline">proline</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1-Pyrroline-5-carboxylic_acid" title="1-Pyrroline-5-carboxylic acid">1-Pyrroline-5-carboxylic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arginine" title="Arginine">arginine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Agmatine" title="Agmatine">Agmatine</a></li> <li><a href="/wiki/Ornithine" title="Ornithine">Ornithine</a></li> <li><a href="/wiki/Citrulline" title="Citrulline">Citrulline</a></li> <li><a href="/wiki/Cadaverine" title="Cadaverine">Cadaverine</a></li> <li><a href="/wiki/Putrescine" title="Putrescine">Putrescine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">cysteine</a>+<a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a>→<a href="/wiki/Glutathione" title="Glutathione">glutathione</a>: <a href="/wiki/Gamma-Glutamylcysteine" class="mw-redirect" title="Gamma-Glutamylcysteine">γ-Glutamylcysteine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">propionyl-CoA</a>→<br /><a href="/wiki/Succinyl-CoA" title="Succinyl-CoA">succinyl-CoA</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Valine" title="Valine">valine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alpha-Ketoisovaleric_acid" class="mw-redirect" title="Alpha-Ketoisovaleric acid">α-Ketoisovaleric acid</a></li> <li><a href="/wiki/Isobutyryl-CoA" title="Isobutyryl-CoA">Isobutyryl-CoA</a></li> <li><a href="/wiki/Methacrylyl-CoA" title="Methacrylyl-CoA">Methacrylyl-CoA</a></li> <li><a href="/wiki/3-Hydroxyisobutyryl-CoA" title="3-Hydroxyisobutyryl-CoA">3-Hydroxyisobutyryl-CoA</a></li> <li><a href="/wiki/3-Hydroxyisobutyric_acid" title="3-Hydroxyisobutyric acid">3-Hydroxyisobutyric acid</a></li> <li><a href="/wiki/2-Methyl-3-oxopropanoic_acid" class="mw-redirect" title="2-Methyl-3-oxopropanoic acid">2-Methyl-3-oxopropanoic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isoleucine" title="Isoleucine">isoleucine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2,3-Dihydroxy-3-methylpentanoic_acid" title="2,3-Dihydroxy-3-methylpentanoic acid">2,3-Dihydroxy-3-methylpentanoic acid</a></li> <li><a href="/wiki/2-Methylbutyryl-CoA" title="2-Methylbutyryl-CoA">2-Methylbutyryl-CoA</a></li> <li><a href="/wiki/Tiglyl-CoA" title="Tiglyl-CoA">Tiglyl-CoA</a></li> <li><a href="/wiki/2-Methylacetoacetyl-CoA" title="2-Methylacetoacetyl-CoA">2-Methylacetoacetyl-CoA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Methionine" title="Methionine">methionine</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Methionine#Generation_of_homocysteine" title="Methionine">generation of homocysteine</a>:</i> <a href="/wiki/S-Adenosyl_methionine" title="S-Adenosyl methionine"><i>S</i>-Adenosyl methionine</a></li> <li><a href="/wiki/S-Adenosyl-L-homocysteine" title="S-Adenosyl-L-homocysteine"><i>S</i>-Adenosyl-<span class="smallcaps"><span style="font-variant: small-caps; text-transform: lowercase;">L</span></span>-homocysteine</a></li> <li><a href="/wiki/Homocysteine" title="Homocysteine">Homocysteine</a></li></ul> <ul><li><i><a href="/wiki/Methionine#Conversion_to_cysteine" title="Methionine">conversion to cysteine</a>:</i> <a href="/wiki/Cystathionine" title="Cystathionine">Cystathionine</a></li> <li><a href="/wiki/Alpha-Ketobutyric_acid" class="mw-redirect" title="Alpha-Ketobutyric acid">α-Ketobutyric acid</a> + <a class="mw-selflink selflink">Cysteine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Threonine" title="Threonine">threonine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alpha-Ketobutyric_acid" class="mw-redirect" title="Alpha-Ketobutyric acid">α-Ketobutyric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">propionyl-CoA</a>→</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Methylmalonyl-CoA" title="Methylmalonyl-CoA">Methylmalonyl-CoA</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Fumarate" class="mw-redirect" title="Fumarate">fumarate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a>→<a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a>→</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Hydroxyphenylpyruvic_acid" title="4-Hydroxyphenylpyruvic acid">4-Hydroxyphenylpyruvic acid</a></li> <li><a href="/wiki/Homogentisic_acid" title="Homogentisic acid">Homogentisic acid</a></li> <li><a href="/wiki/4-Maleylacetoacetic_acid" title="4-Maleylacetoacetic acid">4-Maleylacetoacetic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">G→<a href="/wiki/Oxaloacetate" class="mw-redirect" title="Oxaloacetate">oxaloacetate</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>see <a href="/wiki/Urea_cycle" title="Urea cycle">urea cycle</a></i></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a 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 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"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style></div><div role="navigation" class="navbox 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