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class="vector-toc-list"> <li id="toc-Methanogenesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Methanogenesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Methanogenesis</span> </div> </a> <ul id="toc-Methanogenesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-O-methyltransferases" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#O-methyltransferases"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>O-methyltransferases</span> </div> </a> <ul id="toc-O-methyltransferases-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Proteins" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Proteins"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Proteins</span> </div> </a> <ul id="toc-Proteins-sublist" class="vector-toc-list"> <li id="toc-Methionine_synthase" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Methionine_synthase"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3.1</span> <span>Methionine synthase</span> </div> </a> <ul id="toc-Methionine_synthase-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Heavy_metals:_arsenic,_mercury,_cadmium" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Heavy_metals:_arsenic,_mercury,_cadmium"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>Heavy metals: arsenic, mercury, cadmium</span> </div> </a> <ul id="toc-Heavy_metals:_arsenic,_mercury,_cadmium-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Epigenetic_methylation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Epigenetic_methylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.5</span> <span>Epigenetic methylation</span> </div> </a> <ul id="toc-Epigenetic_methylation-sublist" class="vector-toc-list"> <li id="toc-DNA_methylation" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#DNA_methylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.5.1</span> <span>DNA methylation</span> </div> </a> <ul id="toc-DNA_methylation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-RNA_methylation" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#RNA_methylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.5.2</span> <span>RNA methylation</span> </div> </a> <ul id="toc-RNA_methylation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Protein_methylation" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Protein_methylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.5.3</span> <span>Protein methylation</span> </div> </a> <ul id="toc-Protein_methylation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Evolution" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Evolution"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.6</span> <span>Evolution</span> </div> </a> <ul id="toc-Evolution-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-In_chemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#In_chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>In chemistry</span> </div> </a> <button aria-controls="toc-In_chemistry-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 In chemistry subsection</span> </button> <ul id="toc-In_chemistry-sublist" class="vector-toc-list"> <li id="toc-Electrophilic_methylation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Electrophilic_methylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Electrophilic methylation</span> </div> </a> <ul id="toc-Electrophilic_methylation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Eschweiler–Clarke_methylation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Eschweiler–Clarke_methylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Eschweiler–Clarke methylation</span> </div> </a> <ul id="toc-Eschweiler–Clarke_methylation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Diazomethane_and_trimethylsilyldiazomethane" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Diazomethane_and_trimethylsilyldiazomethane"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Diazomethane and trimethylsilyldiazomethane</span> </div> </a> <ul id="toc-Diazomethane_and_trimethylsilyldiazomethane-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nucleophilic_methylation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nucleophilic_methylation"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Nucleophilic methylation</span> </div> </a> <ul id="toc-Nucleophilic_methylation-sublist" class="vector-toc-list"> </ul> </li> </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">3</span> <span>See also</span> </div> </a> <button aria-controls="toc-See_also-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 See also subsection</span> </button> <ul id="toc-See_also-sublist" class="vector-toc-list"> <li id="toc-Biology_topics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biology_topics"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Biology topics</span> </div> </a> <ul id="toc-Biology_topics-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Organic_chemistry_topics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Organic_chemistry_topics"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Organic chemistry topics</span> </div> </a> <ul id="toc-Organic_chemistry_topics-sublist" class="vector-toc-list"> </ul> </li> </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">4</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</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">Methylation</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 35 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-35" 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">35 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%85%D8%AB%D9%8A%D9%84%D8%A9" title="مثيلة – Arabic" lang="ar" hreflang="ar" data-title="مثيلة" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Metilacija" title="Metilacija – Bosnian" lang="bs" hreflang="bs" data-title="Metilacija" 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/Metilaci%C3%B3" title="Metilació – Catalan" lang="ca" hreflang="ca" data-title="Metilació" 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/Methylace" title="Methylace – Czech" lang="cs" hreflang="cs" data-title="Methylace" 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/Methylering" title="Methylering – Danish" lang="da" hreflang="da" data-title="Methylering" 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/Methylierung" title="Methylierung – German" lang="de" hreflang="de" data-title="Methylierung" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Metilaci%C3%B3n" title="Metilación – Spanish" lang="es" hreflang="es" data-title="Metilación" 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/Metilacio" title="Metilacio – Esperanto" lang="eo" hreflang="eo" data-title="Metilacio" 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/Metilazio" title="Metilazio – Basque" lang="eu" hreflang="eu" data-title="Metilazio" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%85%D8%AA%DB%8C%D9%84%E2%80%8C%D8%AF%D8%A7%D8%B1_%DA%A9%D8%B1%D8%AF%D9%86" title="متیل‌دار کردن – Persian" lang="fa" hreflang="fa" data-title="متیل‌دار کردن" 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/M%C3%A9thylation" title="Méthylation – French" lang="fr" hreflang="fr" data-title="Méthylation" 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/Metilaci%C3%B3n" title="Metilación – Galician" lang="gl" hreflang="gl" data-title="Metilación" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%A9%94%ED%8B%B8%ED%99%94" title="메틸화 – Korean" lang="ko" hreflang="ko" data-title="메틸화" 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%84%D5%A5%D5%A9%D5%AB%D5%AC%D5%A1%D6%81%D5%B8%D6%82%D5%B4" title="Մեթիլացում – Armenian" lang="hy" hreflang="hy" data-title="Մեթիլացում" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Metilasi" title="Metilasi – Indonesian" lang="id" hreflang="id" data-title="Metilasi" 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/Metilazione" title="Metilazione – Italian" lang="it" hreflang="it" data-title="Metilazione" 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%9E%D7%AA%D7%99%D7%9C%D7%A6%D7%99%D7%94" title="מתילציה – Hebrew" lang="he" hreflang="he" data-title="מתילציה" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%9B%E1%83%94%E1%83%97%E1%83%98%E1%83%9A%E1%83%98%E1%83%A0%E1%83%94%E1%83%91%E1%83%90" title="მეთილირება – Georgian" lang="ka" hreflang="ka" data-title="მეთილირება" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9C%D0%B5%D1%82%D0%B8%D0%BB%D0%B4%D0%B5%D1%83" title="Метилдеу – Kazakh" lang="kk" hreflang="kk" data-title="Метилдеу" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Pemetilan" title="Pemetilan – Malay" lang="ms" hreflang="ms" data-title="Pemetilan" 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/Methylering" title="Methylering – Dutch" lang="nl" hreflang="nl" data-title="Methylering" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%A1%E3%83%81%E3%83%AB%E5%8C%96" title="メチル化 – Japanese" lang="ja" hreflang="ja" data-title="メチル化" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Metylowanie" title="Metylowanie – Polish" lang="pl" hreflang="pl" data-title="Metylowanie" 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/Metila%C3%A7%C3%A3o" title="Metilação – Portuguese" lang="pt" hreflang="pt" data-title="Metilação" 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/Metilare" title="Metilare – Romanian" lang="ro" hreflang="ro" data-title="Metilare" 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%9C%D0%B5%D1%82%D0%B8%D0%BB%D0%B8%D1%80%D0%BE%D0%B2%D0%B0%D0%BD%D0%B8%D0%B5" title="Метилирование – Russian" lang="ru" hreflang="ru" data-title="Метилирование" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Metilacija" title="Metilacija – Slovenian" lang="sl" hreflang="sl" data-title="Metilacija" 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/Metilacija" title="Metilacija – Serbian" lang="sr" hreflang="sr" data-title="Metilacija" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Metilacija" title="Metilacija – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Metilacija" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Metylaatio" title="Metylaatio – Finnish" lang="fi" hreflang="fi" data-title="Metylaatio" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Metylering" title="Metylering – Swedish" lang="sv" hreflang="sv" data-title="Metylering" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Metilasyon" title="Metilasyon – Turkish" lang="tr" hreflang="tr" data-title="Metilasyon" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9C%D0%B5%D1%82%D0%B8%D0%BB%D1%8E%D0%B2%D0%B0%D0%BD%D0%BD%D1%8F" title="Метилювання – Ukrainian" lang="uk" hreflang="uk" data-title="Метилювання" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D9%85%DB%8C%D8%AB%D8%A7%D8%A6%D9%84%DB%8C%D8%AA" title="میثائلیت – Urdu" lang="ur" hreflang="ur" data-title="میثائلیت" 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data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical process in which a methyl (CH3) group is covalently attached to a molecule</div> <p> <b>Methylation</b>, in the <a href="/wiki/Chemistry" title="Chemistry">chemical sciences</a>, is the addition of a <a href="/wiki/Methyl_group" title="Methyl group">methyl group</a> on a <a href="/wiki/Substrate_(chemistry)" title="Substrate (chemistry)">substrate</a>, or the substitution of an atom (or group) by a methyl group. Methylation is a form of <a href="/wiki/Alkylation" title="Alkylation">alkylation</a>, with a methyl group replacing a <a href="/wiki/Hydrogen#Compounds" title="Hydrogen">hydrogen</a> atom. These terms are commonly used in <a href="/wiki/Chemistry" title="Chemistry">chemistry</a>, <a href="/wiki/Biochemistry" title="Biochemistry">biochemistry</a>, <a href="/wiki/Soil_science" title="Soil science">soil science</a>, and <a href="/wiki/Biology" title="Biology">biology</a>. </p><p>In <a href="/wiki/Biological_systems" class="mw-redirect" title="Biological systems">biological systems</a>, methylation is <a href="/wiki/Catalysis" title="Catalysis">catalyzed</a> by <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>; such methylation can be involved in modification of <a href="/wiki/Heavy_metals" class="mw-redirect" title="Heavy metals">heavy metals</a>, regulation of <a href="/wiki/Gene_expression" title="Gene expression">gene expression</a>, regulation of <a href="/wiki/Protein#Functions" title="Protein">protein function</a>, and <a href="/wiki/RNA_processing" class="mw-redirect" title="RNA processing">RNA processing</a>. <i>In vitro</i> methylation of tissue samples is also a way to reduce some <a href="/wiki/Histology#Histological_Artifacts" title="Histology">histological staining artifacts</a>. The reverse of methylation is <a href="/wiki/Demethylation" title="Demethylation">demethylation</a>. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="In_biology">In biology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylation&action=edit&section=1" title="Edit section: In biology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In biological systems, methylation is accomplished by enzymes. Methylation can modify heavy metals and can regulate gene expression, RNA processing, and protein function. It is a key process underlying <a href="/wiki/Epigenetics" title="Epigenetics">epigenetics</a>. Sources of methyl groups include S-methylmethionine, methyl folate, methyl B12.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Methanogenesis">Methanogenesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylation&action=edit&section=2" title="Edit section: Methanogenesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Methanogenesis" title="Methanogenesis">Methanogenesis</a>, the process that generates methane from CO<sub>2</sub>, involves a series of methylation reactions. These reactions are caused by a set of enzymes harbored by a family of anaerobic microbes.<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> </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Methanogenesis_cycle.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/Methanogenesis_cycle.png/320px-Methanogenesis_cycle.png" decoding="async" width="320" height="254" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/Methanogenesis_cycle.png/480px-Methanogenesis_cycle.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/29/Methanogenesis_cycle.png/640px-Methanogenesis_cycle.png 2x" data-file-width="3413" data-file-height="2714" /></a><figcaption>Cycle for methanogenesis, showing intermediates</figcaption></figure> <p>In reverse methanogenesis, methane is the methylating agent.<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> </p> <div class="mw-heading mw-heading3"><h3 id="O-methyltransferases">O-methyltransferases</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylation&action=edit&section=3" title="Edit section: O-methyltransferases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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">Main article: <a href="/wiki/O-methyltransferase" title="O-methyltransferase">O-methyltransferase</a></div> <p>A wide variety of <a href="/wiki/Phenols" title="Phenols">phenols</a> undergo O-methylation to give <a href="/wiki/Anisole" title="Anisole">anisole</a> derivatives. This process, catalyzed by such enzymes as <a href="/wiki/Caffeoyl-CoA_O-methyltransferase" title="Caffeoyl-CoA O-methyltransferase">caffeoyl-CoA O-methyltransferase</a>, is a key reaction in the biosynthesis of <a href="/wiki/Monolignol" title="Monolignol">lignols</a>, <a href="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">percursors</a> to <a href="/wiki/Lignin" title="Lignin">lignin</a>, a major structural component of plants. </p><p>Plants produce flavonoids and isoflavones with methylations on hydroxyl groups, i.e. <a href="/wiki/Methoxy_group" title="Methoxy group">methoxy bonds</a>. This 5-O-methylation affects the flavonoid's water solubility. Examples are <a href="/wiki/5-O-Methylgenistein" title="5-O-Methylgenistein">5-O-methylgenistein</a>, <a href="/wiki/5-O-Methylmyricetin" title="5-O-Methylmyricetin">5-O-methylmyricetin</a>, and <a href="/wiki/5-O-Methylquercetin" class="mw-redirect" title="5-O-Methylquercetin">5-O-methylquercetin</a> (azaleatin). </p> <div class="mw-heading mw-heading3"><h3 id="Proteins">Proteins</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylation&action=edit&section=4" title="Edit section: Proteins"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Along with <a href="/wiki/Ubiquitin" title="Ubiquitin">ubiquitination</a> and <a href="/wiki/Phosphorylation" title="Phosphorylation">phosphorylation</a>, methylation is a major biochemical process for modifying protein function. The most prevalent protein methylations affect arginine and lysine residue of specific histones. Otherwise histidine, glutamate, asparagine, cysteine are susceptible to methylation. Some of these products include <a href="/wiki/S-Methylcysteine" title="S-Methylcysteine"><i>S</i>-methylcysteine</a>, two isomers of <i>N</i>-methylhistidine, and two isomers of <i>N</i>-methylarginine.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Methionine_synthase">Methionine synthase</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylation&action=edit&section=5" title="Edit section: Methionine synthase"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:VitaminB12_2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/VitaminB12_2.png/220px-VitaminB12_2.png" decoding="async" width="220" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/VitaminB12_2.png/330px-VitaminB12_2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/VitaminB12_2.png/440px-VitaminB12_2.png 2x" data-file-width="446" data-file-height="297" /></a><figcaption>The methylation reaction catalyzed by <a href="/wiki/Methionine_synthase" title="Methionine synthase">methionine synthase</a></figcaption></figure> <p><a href="/wiki/Methionine_synthase" title="Methionine synthase">Methionine synthase</a> regenerates <a href="/wiki/Methionine" title="Methionine">methionine</a> (Met) from <a href="/wiki/Homocysteine" title="Homocysteine">homocysteine</a> (Hcy). The overall reaction transforms <a href="/wiki/5-methyltetrahydrofolate" class="mw-redirect" title="5-methyltetrahydrofolate">5-methyltetrahydrofolate</a> (N<sup>5</sup>-MeTHF) into <a href="/wiki/Tetrahydrofolate" class="mw-redirect" title="Tetrahydrofolate">tetrahydrofolate</a> (THF) while transferring a methyl group to Hcy to form Met. Methionine Syntheses can be cobalamin-dependent and cobalamin-independent: Plants have both, animals depend on the methylcobalamin-dependent form. </p><p>In methylcobalamin-dependent forms of the enzyme, the reaction proceeds by two steps in a ping-pong reaction. The enzyme is initially primed into a reactive state by the transfer of a methyl group from N<sup>5</sup>-MeTHF to Co(I) in enzyme-bound <a href="/wiki/Cobalamin" class="mw-redirect" title="Cobalamin">cobalamin</a> ((Cob), also known as vitamine B12)) , , forming methyl-cobalamin(Me-Cob) that now contains Me-Co(III) and activating the enzyme. Then, a Hcy that has coordinated to an enzyme-bound <a href="/wiki/Zinc" title="Zinc">zinc</a> to form a reactive thiolate reacts with the Me-Cob. The activated methyl group is transferred from Me-Cob to the Hcy thiolate, which regenerates Co(I) in Cob, and Met is released from the enzyme.<sup id="cite_ref-Zinc_5-0" class="reference"><a href="#cite_note-Zinc-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Heavy_metals:_arsenic,_mercury,_cadmium"><span id="Heavy_metals:_arsenic.2C_mercury.2C_cadmium"></span>Heavy metals: arsenic, mercury, cadmium</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylation&action=edit&section=6" title="Edit section: Heavy metals: arsenic, mercury, cadmium"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Biomethylation is the pathway for converting some heavy elements into more mobile or more lethal derivatives that can enter the <a href="/wiki/Food_chain" title="Food chain">food chain</a>. The <a href="/wiki/Biomethylation" class="mw-redirect" title="Biomethylation">biomethylation</a> of <a href="/wiki/Arsenic" title="Arsenic">arsenic</a> compounds starts with the formation of <a href="/wiki/Methanearsonate" class="mw-redirect" title="Methanearsonate">methanearsonates</a>. Thus, trivalent inorganic arsenic compounds are methylated to give methanearsonate. <a href="/wiki/S-adenosylmethionine" class="mw-redirect" title="S-adenosylmethionine">S-adenosylmethionine</a> is the methyl donor. The methanearsonates are the precursors to dimethylarsonates, again by the cycle of <a href="/wiki/Redox" title="Redox">reduction</a> (to methylarsonous acid) followed by a second methylation.<sup id="cite_ref-Cullen_6-0" class="reference"><a href="#cite_note-Cullen-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Related pathways are found in the <a href="/wiki/Mercury_methylation#Microbial" title="Mercury methylation">microbial methylation</a> of mercury to <a href="/wiki/Methylmercury" title="Methylmercury">methylmercury</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Epigenetic_methylation">Epigenetic methylation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylation&action=edit&section=7" title="Edit section: Epigenetic methylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="DNA_methylation">DNA methylation</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylation&action=edit&section=8" title="Edit section: DNA methylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/DNA_methylation" title="DNA methylation">DNA methylation</a> is the conversion of the cytosine to <a href="/wiki/5-methylcytosine" class="mw-redirect" title="5-methylcytosine">5-methylcytosine</a>. The formation of Me-CpG is <a href="/wiki/Catalysis" title="Catalysis">catalyzed</a> by the enzyme <a href="/wiki/DNA_methyltransferase" title="DNA methyltransferase">DNA methyltransferase</a>. In vertebrates, DNA methylation typically occurs at <a href="/wiki/CpG_site" title="CpG site">CpG sites</a> (cytosine-phosphate-guanine sites—that is, sites where a <a href="/wiki/Cytosine" title="Cytosine">cytosine</a> is directly followed by a <a href="/wiki/Guanine" title="Guanine">guanine</a> in the DNA sequence). In mammals, DNA methylation is common in body cells,<sup id="cite_ref-pmid19842073_7-0" class="reference"><a href="#cite_note-pmid19842073-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> and methylation of CpG sites seems to be the default.<sup id="cite_ref-ReferenceC_8-0" class="reference"><a href="#cite_note-ReferenceC-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><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> Human DNA has about 80–90% of CpG sites methylated, but there are certain areas, known as <a href="/wiki/CpG_site#CpG_islands" title="CpG site">CpG islands</a>, that are CG-rich (high cytosine and guanine content, made up of about 65% CG <a href="/wiki/Residue_(chemistry)" title="Residue (chemistry)">residues</a>), wherein none is methylated. These are associated with the <a href="/wiki/Promoter_(genetics)" title="Promoter (genetics)">promoters</a> of 56% of mammalian genes, including all <a href="/wiki/Housekeeping_gene" title="Housekeeping gene">ubiquitously expressed genes</a>. One to two percent of the human genome are CpG clusters, and there is an inverse relationship between CpG methylation and transcriptional activity. Methylation contributing to epigenetic inheritance can occur through either DNA methylation or protein methylation. Improper methylations of human genes can lead to disease development,<sup id="cite_ref-Rotondo_2013_10-0" class="reference"><a href="#cite_note-Rotondo_2013-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Rotondo_2012_11-0" class="reference"><a href="#cite_note-Rotondo_2012-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> including cancer.<sup id="cite_ref-pmid27223861_12-0" class="reference"><a href="#cite_note-pmid27223861-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Rotondo_2018_13-0" class="reference"><a href="#cite_note-Rotondo_2018-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>In <a href="/wiki/Honey_bee" title="Honey bee">honey bees</a>, DNA methylation is associated with alternative splicing and gene regulation based on functional genomic research published in 2013.<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 addition, DNA methylation is associated with expression changes in immune genes when honey bees were under lethal viral infection.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Several review papers have been published on the topics of DNA methylation in social insects.<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><sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="RNA_methylation">RNA methylation</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylation&action=edit&section=9" title="Edit section: RNA methylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><b>RNA methylation</b> occurs in different RNA species viz. <a href="/wiki/TRNA" class="mw-redirect" title="TRNA">tRNA</a>, <a href="/wiki/RRNA" class="mw-redirect" title="RRNA">rRNA</a>, <a href="/wiki/MRNA" class="mw-redirect" title="MRNA">mRNA</a>, <a href="/wiki/TmRNA" class="mw-redirect" title="TmRNA">tmRNA</a>, <a href="/wiki/SnRNA" class="mw-redirect" title="SnRNA">snRNA</a>, <a href="/wiki/SnoRNA" class="mw-redirect" title="SnoRNA">snoRNA</a>, <a href="/wiki/MiRNA" class="mw-redirect" title="MiRNA">miRNA</a>, and viral RNA. Different catalytic strategies are employed for RNA methylation by a variety of RNA-methyltransferases. RNA methylation is thought to have existed before DNA methylation in the early forms of life evolving on earth.<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><a href="/wiki/N6-Methyladenosine" title="N6-Methyladenosine">N6-methyladenosine (m6A)</a> is the most common and abundant methylation modification in RNA molecules (mRNA) present in eukaryotes. 5-methylcytosine (5-mC) also commonly occurs in various RNA molecules. Recent data strongly suggest that m6A and 5-mC RNA methylation affects the regulation of various biological processes such as RNA stability and mRNA translation,<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> and that abnormal RNA methylation contributes to etiology of human diseases.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>In social insects such as honey bees, RNA methylation is studied as a possible epigenetic mechanism underlying aggression via reciprocal crosses.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Protein_methylation">Protein methylation</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylation&action=edit&section=10" title="Edit section: Protein methylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Protein_methylation" title="Protein methylation">Protein methylation</a> typically takes place on <a href="/wiki/Arginine" title="Arginine">arginine</a> or <a href="/wiki/Lysine" title="Lysine">lysine</a> <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> residues in the protein sequence.<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> <span class="anchor" id="Arginine_methylation"></span>Arginine can be methylated once (monomethylated arginine) or twice, with either both methyl groups on one terminal nitrogen (<a href="/wiki/Asymmetric_dimethylarginine" title="Asymmetric dimethylarginine">asymmetric dimethylarginine</a>) or one on both nitrogens (symmetric dimethylarginine), by <a href="/w/index.php?title=Protein_arginine_methyltransferases&action=edit&redlink=1" class="new" title="Protein arginine methyltransferases (page does not exist)">protein arginine methyltransferases</a> (PRMTs). Lysine can be methylated once, twice, or three times by <a href="/w/index.php?title=Lysine_methyltransferases&action=edit&redlink=1" class="new" title="Lysine methyltransferases (page does not exist)">lysine methyltransferases</a>. Protein methylation has been most studied in the <a href="/wiki/Histone" title="Histone">histones</a>. The transfer of <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> groups from <a href="/wiki/S-adenosyl_methionine" class="mw-redirect" title="S-adenosyl methionine">S-adenosyl methionine</a> to histones is catalyzed by enzymes known as <a href="/wiki/Histone_methyltransferase" title="Histone methyltransferase">histone methyltransferases</a>. Histones that are methylated on certain residues can act <a href="/wiki/Epigenetics" title="Epigenetics">epigenetically</a> to repress or activate gene expression.<sup id="cite_ref-Grewal2004_23-0" class="reference"><a href="#cite_note-Grewal2004-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nakayama2001_24-0" class="reference"><a href="#cite_note-Nakayama2001-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Protein methylation is one type of <a href="/wiki/Post-translational_modification" title="Post-translational modification">post-translational modification</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Evolution">Evolution</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylation&action=edit&section=11" title="Edit section: Evolution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Methyl metabolism is very ancient and can be found in all organisms on earth, from bacteria to humans, indicating the importance of methyl metabolism for physiology.<sup id="cite_ref-Kozbial_25-0" class="reference"><a href="#cite_note-Kozbial-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Indeed, pharmacological inhibition of global methylation in species ranging from human, mouse, fish, fly, roundworm, plant, algae, and cyanobacteria causes the same effects on their biological rhythms, demonstrating conserved physiological roles of methylation during evolution.<sup id="cite_ref-Fustin_26-0" class="reference"><a href="#cite_note-Fustin-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="In_chemistry">In chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylation&action=edit&section=12" title="Edit section: In chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The term methylation in <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a> refers to the <a href="/wiki/Alkylation" title="Alkylation">alkylation</a> process used to describe the delivery of 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">CH<sub class="template-chem2-sub">3</sub></span> group.<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="Electrophilic_methylation">Electrophilic methylation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylation&action=edit&section=13" title="Edit section: Electrophilic methylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Methylations are commonly performed using <a href="/wiki/Electrophile" title="Electrophile"><i>electrophilic</i></a> methyl sources such as <a href="/wiki/Iodomethane" title="Iodomethane">iodomethane</a>,<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Dimethyl_sulfate" title="Dimethyl sulfate">dimethyl sulfate</a>,<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Dimethyl_carbonate" title="Dimethyl carbonate">dimethyl carbonate</a>,<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> or <a href="/wiki/Tetramethylammonium_chloride" title="Tetramethylammonium chloride">tetramethylammonium chloride</a>.<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> Less common but more powerful (and more dangerous) methylating reagents include <a href="/wiki/Methyl_triflate" class="mw-redirect" title="Methyl triflate">methyl triflate</a>,<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> <a href="/wiki/Diazomethane" title="Diazomethane">diazomethane</a>,<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> and methyl fluorosulfonate (<a href="/wiki/Magic_methyl" class="mw-redirect" title="Magic methyl">magic methyl</a>). These reagents all react via S<sub>N</sub>2 <a href="/wiki/Nucleophilic_substitution" title="Nucleophilic substitution">nucleophilic substitutions</a>. For example, a <a href="/wiki/Carboxylate" title="Carboxylate">carboxylate</a> may be methylated on oxygen to give a methyl <a href="/wiki/Ester" title="Ester">ester</a>; an <a href="/wiki/Alkoxide" title="Alkoxide">alkoxide</a> salt <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RO<sup class="template-chem2-sup">−</sup></span> may be likewise methylated to give an <a href="/wiki/Ether" title="Ether">ether</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">ROCH<sub class="template-chem2-sub">3</sub></span>; or a ketone <a href="/wiki/Enolate" title="Enolate">enolate</a> may be methylated on carbon to produce a new <a href="/wiki/Ketone" title="Ketone">ketone</a>. </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Iodomethane_rxn1.png" class="mw-file-description" title="Methylation of a carboxylic acid salt and a phenol using iodomethane"><img alt="Methylation of a carboxylic acid salt and a phenol using iodomethane" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Iodomethane_rxn1.png/350px-Iodomethane_rxn1.png" decoding="async" width="350" height="76" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Iodomethane_rxn1.png/525px-Iodomethane_rxn1.png 1.5x, //upload.wikimedia.org/wikipedia/commons/d/db/Iodomethane_rxn1.png 2x" data-file-width="556" data-file-height="121" /></a></span></dd></dl> <p>The <a href="/wiki/Purdie_methylation" class="mw-redirect" title="Purdie methylation">Purdie methylation</a> is a specific for the methylation at oxygen of <a href="/wiki/Carbohydrate" title="Carbohydrate">carbohydrates</a> using <a href="/wiki/Iodomethane" title="Iodomethane">iodomethane</a> and <a href="/wiki/Silver_oxide" title="Silver oxide">silver oxide</a>.<sup id="cite_ref-Purdie1903_35-0" class="reference"><a href="#cite_note-Purdie1903-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Purdie_methylation.png" class="mw-file-description" title="Purdie methylation"><img alt="Purdie methylation" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/Purdie_methylation.png/500px-Purdie_methylation.png" decoding="async" width="500" height="106" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/Purdie_methylation.png/750px-Purdie_methylation.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/29/Purdie_methylation.png/1000px-Purdie_methylation.png 2x" data-file-width="3761" data-file-height="799" /></a></span></dd></dl> <div class="mw-heading mw-heading3"><h3 id="Eschweiler–Clarke_methylation"><span id="Eschweiler.E2.80.93Clarke_methylation"></span>Eschweiler–Clarke methylation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylation&action=edit&section=14" title="Edit section: Eschweiler–Clarke methylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Eschweiler%E2%80%93Clarke_reaction" title="Eschweiler–Clarke reaction">Eschweiler–Clarke reaction</a> is a method for methylation of <a href="/wiki/Amine" title="Amine">amines</a>.<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> This method avoids the risk of <a href="/wiki/Quaternization" class="mw-redirect" title="Quaternization">quaternization</a>, which occurs when amines are methylated with methyl halides. </p> <figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Eschweiler-Clarke_Reaction.svg" class="mw-file-description" title="The Eschweiler–Clarke reaction is used to methylate amines."><img alt="The Eschweiler–Clarke reaction is used to methylate amines." src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Eschweiler-Clarke_Reaction.svg/300px-Eschweiler-Clarke_Reaction.svg.png" decoding="async" width="300" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Eschweiler-Clarke_Reaction.svg/450px-Eschweiler-Clarke_Reaction.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Eschweiler-Clarke_Reaction.svg/600px-Eschweiler-Clarke_Reaction.svg.png 2x" data-file-width="512" data-file-height="169" /></a><figcaption>The <a href="/wiki/Eschweiler%E2%80%93Clarke_reaction" title="Eschweiler–Clarke reaction">Eschweiler–Clarke reaction</a> is used to methylate amines.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Diazomethane_and_trimethylsilyldiazomethane">Diazomethane and trimethylsilyldiazomethane</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylation&action=edit&section=15" title="Edit section: Diazomethane and trimethylsilyldiazomethane"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Diazomethane" title="Diazomethane">Diazomethane</a> and the safer analogue <a href="/wiki/Trimethylsilyldiazomethane" title="Trimethylsilyldiazomethane">trimethylsilyldiazomethane</a> methylate carboxylic acids, phenols, and even alcohols: </p> <dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {RCO2H + tmsCHN2 + CH3OH -> RCO2CH3 + CH3Otms + N2}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <msubsup> <mtext>RCO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>H</mtext> <mo>+</mo> <msubsup> <mtext>tmsCHN</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>OH</mtext> <mo stretchy="false">⟶</mo> <msubsup> <mtext>RCO</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mo>+</mo> <msubsup> <mtext>CH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>3</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> <mtext>Otms</mtext> <mo>+</mo> <msubsup> <mtext>N</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {RCO2H + tmsCHN2 + CH3OH -> RCO2CH3 + CH3Otms + N2}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/99e6a069dc908747dac07cd0714c61760f4b816a" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:66.018ex; height:2.843ex;" alt="{\displaystyle {\ce {RCO2H + tmsCHN2 + CH3OH -> RCO2CH3 + CH3Otms + N2}}}"></span></dd></dl> <p>The method offers the advantage that the side products are easily removed from the product mixture.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Nucleophilic_methylation">Nucleophilic methylation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylation&action=edit&section=16" title="Edit section: Nucleophilic methylation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Methylation sometimes involve use of <a href="/wiki/Nucleophile" title="Nucleophile"><i>nucleophilic</i></a> methyl reagents. Strongly nucleophilic methylating agents include <a href="/wiki/Methyllithium" title="Methyllithium">methyllithium</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>Li</span>)<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> or <a href="/wiki/Grignard_reagent" title="Grignard reagent">Grignard reagents</a> such as <a href="/wiki/Methylmagnesium_bromide" class="mw-redirect" title="Methylmagnesium bromide">methylmagnesium bromide</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>MgX</span>).<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> For example, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>Li</span> will add methyl groups to the <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> (C=O) of ketones and aldehyde.: </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:MeLi_on_acetone.png" class="mw-file-description" title="Methylation of acetone by methyl lithium"><img alt="Methylation of acetone by methyl lithium" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/MeLi_on_acetone.png/250px-MeLi_on_acetone.png" decoding="async" width="250" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/MeLi_on_acetone.png/375px-MeLi_on_acetone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/MeLi_on_acetone.png/500px-MeLi_on_acetone.png 2x" data-file-width="1249" data-file-height="668" /></a></span></dd></dl> <p>Milder methylating agents include <a href="/wiki/Tetramethyltin" title="Tetramethyltin">tetramethyltin</a>, <a href="/wiki/Dimethylzinc" title="Dimethylzinc">dimethylzinc</a>, and <a href="/wiki/Trimethylaluminium" title="Trimethylaluminium">trimethylaluminium</a>.<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> </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=Methylation&action=edit&section=17" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239009302">.mw-parser-output .portalbox{padding:0;margin:0.5em 0;display:table;box-sizing:border-box;max-width:175px;list-style:none}.mw-parser-output .portalborder{border:1px solid 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height="28" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/42px-Papapishu-Lab-icon-6.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Papapishu-Lab-icon-6.svg/56px-Papapishu-Lab-icon-6.svg.png 2x" data-file-width="512" data-file-height="512" /></span></span></span><span class="portalbox-link"><a href="/wiki/Portal:Chemistry" title="Portal:Chemistry">Chemistry portal</a></span></li><li class="portalbox-entry"><span class="portalbox-image"><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Issoria_lathonia.jpg" class="mw-file-description"><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Issoria_lathonia.jpg/32px-Issoria_lathonia.jpg" decoding="async" width="32" height="23" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Issoria_lathonia.jpg/48px-Issoria_lathonia.jpg 1.5x, 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thermophoresis</a> – a biophysical method to determine the methylisation state of DNA<sup id="cite_ref-Wienken2_41-0" class="reference"><a href="#cite_note-Wienken2-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Remethylation" title="Remethylation">Remethylation</a>, the reversible removal of methyl group in <a href="/wiki/Methionine" title="Methionine">methionine</a> and <a href="/wiki/5-Methylcytosine" title="5-Methylcytosine">5-methylcytosine</a></li></ul> <div class="mw-heading mw-heading3"><h3 id="Organic_chemistry_topics">Organic chemistry topics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Methylation&action=edit&section=19" title="Edit section: Organic chemistry topics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Alkylation" title="Alkylation">Alkylation</a></li> <li><a href="/wiki/Methoxy" class="mw-redirect" title="Methoxy">Methoxy</a></li> <li><a href="/wiki/Organozinc_compound#Titanium–zinc_methylenation" class="mw-redirect" title="Organozinc compound">Titanium–zinc methylenation</a></li> <li><a href="/wiki/Petasis_reagent" title="Petasis reagent">Petasis reagent</a></li> <li><a href="/wiki/Nysted_reagent" title="Nysted reagent">Nysted reagent</a></li> <li><a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a></li> <li><a href="/wiki/Tebbe%27s_reagent" title="Tebbe's reagent">Tebbe's reagent</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=Methylation&action=edit&section=20" 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"> <div class="mw-references-wrap mw-references-columns"><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 id="CITEREFRagsdale2008" class="citation book cs1">Ragsdale, Stephen W. (2008). "Catalysis of Methyl Group Transfers Involving Tetrahydrofolate and B12". <i>Folic Acid and Folates</i>. Vitamins & Hormones. Vol. 79. pp. 293–324. <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%2FS0083-6729%2808%2900410-X">10.1016/S0083-6729(08)00410-X</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-374232-2" title="Special:BookSources/978-0-12-374232-2"><bdi>978-0-12-374232-2</bdi></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/PMC3037834">3037834</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/18804699">18804699</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Catalysis+of+Methyl+Group+Transfers+Involving+Tetrahydrofolate+and+B12&rft.btitle=Folic+Acid+and+Folates&rft.series=Vitamins+%26+Hormones&rft.pages=293-324&rft.date=2008&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3037834%23id-name%3DPMC&rft_id=info%3Apmid%2F18804699&rft_id=info%3Adoi%2F10.1016%2FS0083-6729%2808%2900410-X&rft.isbn=978-0-12-374232-2&rft.aulast=Ragsdale&rft.aufirst=Stephen+W.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" 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">Thauer, R. K., "Biochemistry of Methanogenesis: a Tribute to Marjory Stephenson", Microbiology, 1998, volume 144, pages 2377-2406.</span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTimmersWelteKoehorstPlugge2017" class="citation journal cs1">Timmers, Peer H. A.; Welte, Cornelia U.; Koehorst, Jasper J.; Plugge, Caroline M.; Jetten, Mike S. M.; Stams, Alfons J. M. (2017). <a rel="nofollow" class="external text" href="https://doi.org/10.1155%2F2017%2F1654237">"Reverse Methanogenesis and Respiration in Methanotrophic Archaea"</a>. <i>Archaea</i>. <b>2017</b>: 1–22. <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/10.1155%2F2017%2F1654237">10.1155/2017/1654237</a></span>. <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/1822%2F47121">1822/47121</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Archaea&rft.atitle=Reverse+Methanogenesis+and+Respiration+in+Methanotrophic+Archaea&rft.volume=2017&rft.pages=1-22&rft.date=2017&rft_id=info%3Ahdl%2F1822%2F47121&rft_id=info%3Adoi%2F10.1155%2F2017%2F1654237&rft.aulast=Timmers&rft.aufirst=Peer+H.+A.&rft.au=Welte%2C+Cornelia+U.&rft.au=Koehorst%2C+Jasper+J.&rft.au=Plugge%2C+Caroline+M.&rft.au=Jetten%2C+Mike+S.+M.&rft.au=Stams%2C+Alfons+J.+M.&rft_id=https%3A%2F%2Fdoi.org%2F10.1155%252F2017%252F1654237&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFClarke2018" class="citation journal cs1">Clarke, Steven G. (2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6036201">"The ribosome: A hot spot for the identification of new types of protein methyltransferases"</a>. <i>Journal of Biological Chemistry</i>. <b>293</b> (27): 10438–10446. <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/10.1074%2Fjbc.AW118.003235">10.1074/jbc.AW118.003235</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/PMC6036201">6036201</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/29743234">29743234</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Biological+Chemistry&rft.atitle=The+ribosome%3A+A+hot+spot+for+the+identification+of+new+types+of+protein+methyltransferases&rft.volume=293&rft.issue=27&rft.pages=10438-10446&rft.date=2018&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6036201%23id-name%3DPMC&rft_id=info%3Apmid%2F29743234&rft_id=info%3Adoi%2F10.1074%2Fjbc.AW118.003235&rft.aulast=Clarke&rft.aufirst=Steven+G.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6036201&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-Zinc-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-Zinc_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMatthewsSmithZhouTaurog2003" class="citation journal cs1">Matthews, R. G.; Smith, A. E.; Zhou, Z. S.; Taurog, R. E.; Bandarian, V.; Evans, J. C.; Ludwig, M. (2003). "Cobalamin-Dependent and Cobalamin-Independent Methionine Synthases: Are There Two Solutions to the Same Chemical Problem?". <i>Helvetica Chimica Acta</i>. <b>86</b> (12): 3939–3954. <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%2Fhlca.200390329">10.1002/hlca.200390329</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Helvetica+Chimica+Acta&rft.atitle=Cobalamin-Dependent+and+Cobalamin-Independent+Methionine+Synthases%3A+Are+There+Two+Solutions+to+the+Same+Chemical+Problem%3F&rft.volume=86&rft.issue=12&rft.pages=3939-3954&rft.date=2003&rft_id=info%3Adoi%2F10.1002%2Fhlca.200390329&rft.aulast=Matthews&rft.aufirst=R.+G.&rft.au=Smith%2C+A.+E.&rft.au=Zhou%2C+Z.+S.&rft.au=Taurog%2C+R.+E.&rft.au=Bandarian%2C+V.&rft.au=Evans%2C+J.+C.&rft.au=Ludwig%2C+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-Cullen-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-Cullen_6-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStyblo,_M.Del_Razo,_L._M.Vega,_L.Germolec,_D._R.2000" class="citation journal cs1">Styblo, M.; Del Razo, L. M.; Vega, L.; Germolec, D. R.; LeCluyse, E. L.; Hamilton, G. A.; Reed, W.; Wang, C.; Cullen, W. R.; Thomas, D. J. (2000). "Comparative toxicity of trivalent and pentavalent inorganic and methylated arsenicals in rat and human cells". <i>Archives of Toxicology</i>. <b>74</b> (6): 289–299. <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%2Fs002040000134">10.1007/s002040000134</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/11005674">11005674</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:1025140">1025140</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Archives+of+Toxicology&rft.atitle=Comparative+toxicity+of+trivalent+and+pentavalent+inorganic+and+methylated+arsenicals+in+rat+and+human+cells&rft.volume=74&rft.issue=6&rft.pages=289-299&rft.date=2000&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A1025140%23id-name%3DS2CID&rft_id=info%3Apmid%2F11005674&rft_id=info%3Adoi%2F10.1007%2Fs002040000134&rft.au=Styblo%2C+M.&rft.au=Del+Razo%2C+L.+M.&rft.au=Vega%2C+L.&rft.au=Germolec%2C+D.+R.&rft.au=LeCluyse%2C+E.+L.&rft.au=Hamilton%2C+G.+A.&rft.au=Reed%2C+W.&rft.au=Wang%2C+C.&rft.au=Cullen%2C+W.+R.&rft.au=Thomas%2C+D.+J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-pmid19842073-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid19842073_7-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTost_J2010" class="citation journal cs1">Tost J (2010). "DNA methylation: an introduction to the biology and the disease-associated changes of a promising biomarker". <i>Mol Biotechnol</i>. <b>44</b> (1): 71–81. <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%2Fs12033-009-9216-2">10.1007/s12033-009-9216-2</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/19842073">19842073</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:20307488">20307488</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Mol+Biotechnol&rft.atitle=DNA+methylation%3A+an+introduction+to+the+biology+and+the+disease-associated+changes+of+a+promising+biomarker.&rft.volume=44&rft.issue=1&rft.pages=71-81&rft.date=2010&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A20307488%23id-name%3DS2CID&rft_id=info%3Apmid%2F19842073&rft_id=info%3Adoi%2F10.1007%2Fs12033-009-9216-2&rft.au=Tost+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-ReferenceC-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-ReferenceC_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFListerPelizzolaDowenHawkins2009" class="citation journal cs1">Lister R, Pelizzola M, Dowen RH, Hawkins RD, Hon G, Tonti-Filippini J, Nery JR, Lee L, Ye Z, Ngo QM, Edsall L, Antosiewicz-Bourget J, Stewart R, Ruotti V, Millar AH, Thomson JA, Ren B, Ecker JR (November 2009). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2857523">"Human DNA methylomes at base resolution show widespread epigenomic differences"</a>. <i>Nature</i>. <b>462</b> (7271): 315–22. <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/2009Natur.462..315L">2009Natur.462..315L</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fnature08514">10.1038/nature08514</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/PMC2857523">2857523</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/19829295">19829295</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature&rft.atitle=Human+DNA+methylomes+at+base+resolution+show+widespread+epigenomic+differences&rft.volume=462&rft.issue=7271&rft.pages=315-22&rft.date=2009-11&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2857523%23id-name%3DPMC&rft_id=info%3Apmid%2F19829295&rft_id=info%3Adoi%2F10.1038%2Fnature08514&rft_id=info%3Abibcode%2F2009Natur.462..315L&rft.aulast=Lister&rft.aufirst=R&rft.au=Pelizzola%2C+M&rft.au=Dowen%2C+RH&rft.au=Hawkins%2C+RD&rft.au=Hon%2C+G&rft.au=Tonti-Filippini%2C+J&rft.au=Nery%2C+JR&rft.au=Lee%2C+L&rft.au=Ye%2C+Z&rft.au=Ngo%2C+QM&rft.au=Edsall%2C+L&rft.au=Antosiewicz-Bourget%2C+J&rft.au=Stewart%2C+R&rft.au=Ruotti%2C+V&rft.au=Millar%2C+AH&rft.au=Thomson%2C+JA&rft.au=Ren%2C+B&rft.au=Ecker%2C+JR&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2857523&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" 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="CITEREFStadlerMurrBurgerIvanek2011" class="citation journal cs1">Stadler MB, Murr R, Burger L, Ivanek R, Lienert F, Schöler A, van Nimwegen E, Wirbelauer C, Oakeley EJ, Gaidatzis D, Tiwari VK, Schübeler D (December 2011). <a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fnature11086">"DNA-binding factors shape the mouse methylome at distal regulatory regions"</a>. <i>Nature</i>. <b>480</b> (7378): 490–5. <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%2Fnature11086">10.1038/nature11086</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/22170606">22170606</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature&rft.atitle=DNA-binding+factors+shape+the+mouse+methylome+at+distal+regulatory+regions&rft.volume=480&rft.issue=7378&rft.pages=490-5&rft.date=2011-12&rft_id=info%3Adoi%2F10.1038%2Fnature11086&rft_id=info%3Apmid%2F22170606&rft.aulast=Stadler&rft.aufirst=MB&rft.au=Murr%2C+R&rft.au=Burger%2C+L&rft.au=Ivanek%2C+R&rft.au=Lienert%2C+F&rft.au=Sch%C3%B6ler%2C+A&rft.au=van+Nimwegen%2C+E&rft.au=Wirbelauer%2C+C&rft.au=Oakeley%2C+EJ&rft.au=Gaidatzis%2C+D&rft.au=Tiwari%2C+VK&rft.au=Sch%C3%BCbeler%2C+D&rft_id=https%3A%2F%2Fdoi.org%2F10.1038%252Fnature11086&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-Rotondo_2013-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-Rotondo_2013_10-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRotondoSelvaticiDi_DomenicoMarci2013" class="citation journal cs1">Rotondo JC, Selvatici R, Di Domenico M, Marci R, Vesce F, Tognon M, Martini F (September 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3883776">"Methylation loss at H19 imprinted gene correlates with methylenetetrahydrofolate reductase gene promoter hypermethylation in semen samples from infertile males"</a>. <i>Epigenetics</i>. <b>8</b> (9): 990–7. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.4161%2Fepi.25798">10.4161/epi.25798</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/PMC3883776">3883776</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/23975186">23975186</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Epigenetics&rft.atitle=Methylation+loss+at+H19+imprinted+gene+correlates+with+methylenetetrahydrofolate+reductase+gene+promoter+hypermethylation+in+semen+samples+from+infertile+males&rft.volume=8&rft.issue=9&rft.pages=990-7&rft.date=2013-09&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3883776%23id-name%3DPMC&rft_id=info%3Apmid%2F23975186&rft_id=info%3Adoi%2F10.4161%2Fepi.25798&rft.aulast=Rotondo&rft.aufirst=JC&rft.au=Selvatici%2C+R&rft.au=Di+Domenico%2C+M&rft.au=Marci%2C+R&rft.au=Vesce%2C+F&rft.au=Tognon%2C+M&rft.au=Martini%2C+F&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3883776&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-Rotondo_2012-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-Rotondo_2012_11-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRotondoBosiBazzanDi_Domenico2012" class="citation journal cs1">Rotondo JC, Bosi S, Bazzan E, Di Domenico M, De Mattei M, Selvatici R, Patella A, Marci R, Tognon M, Martini F (December 2012). <a rel="nofollow" class="external text" href="https://academic.oup.com/humrep/article/27/12/3632/651064">"Methylenetetrahydrofolate reductase gene promoter hypermethylation in semen samples of infertile couples correlates with recurrent spontaneous abortion"</a>. <i>Human Reproduction</i>. <b>27</b> (12): 3632–8. <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%2Fhumrep%2Fdes319">10.1093/humrep/des319</a></span>. <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/11392%2F1689715">11392/1689715</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/23010533">23010533</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Human+Reproduction&rft.atitle=Methylenetetrahydrofolate+reductase+gene+promoter+hypermethylation+in+semen+samples+of+infertile+couples+correlates+with+recurrent+spontaneous+abortion&rft.volume=27&rft.issue=12&rft.pages=3632-8&rft.date=2012-12&rft_id=info%3Ahdl%2F11392%2F1689715&rft_id=info%3Apmid%2F23010533&rft_id=info%3Adoi%2F10.1093%2Fhumrep%2Fdes319&rft.aulast=Rotondo&rft.aufirst=JC&rft.au=Bosi%2C+S&rft.au=Bazzan%2C+E&rft.au=Di+Domenico%2C+M&rft.au=De+Mattei%2C+M&rft.au=Selvatici%2C+R&rft.au=Patella%2C+A&rft.au=Marci%2C+R&rft.au=Tognon%2C+M&rft.au=Martini%2C+F&rft_id=https%3A%2F%2Facademic.oup.com%2Fhumrep%2Farticle%2F27%2F12%2F3632%2F651064&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-pmid27223861-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid27223861_12-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRotondoBorghiSelvaticiMagri2016" class="citation journal cs1">Rotondo JC, Borghi A, Selvatici R, Magri E, Bianchini E, Montinari E, Corazza M, Virgili A, Tognon M, Martini F (2016). "Hypermethylation-Induced Inactivation of the IRF6 Gene as a Possible Early Event in Progression of Vulvar Squamous Cell Carcinoma Associated With Lichen Sclerosus". <i>JAMA Dermatology</i>. <b>152</b> (8): 928–33. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1001%2Fjamadermatol.2016.1336">10.1001/jamadermatol.2016.1336</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/27223861">27223861</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=JAMA+Dermatology&rft.atitle=Hypermethylation-Induced+Inactivation+of+the+IRF6+Gene+as+a+Possible+Early+Event+in+Progression+of+Vulvar+Squamous+Cell+Carcinoma+Associated+With+Lichen+Sclerosus&rft.volume=152&rft.issue=8&rft.pages=928-33&rft.date=2016&rft_id=info%3Adoi%2F10.1001%2Fjamadermatol.2016.1336&rft_id=info%3Apmid%2F27223861&rft.aulast=Rotondo&rft.aufirst=JC&rft.au=Borghi%2C+A&rft.au=Selvatici%2C+R&rft.au=Magri%2C+E&rft.au=Bianchini%2C+E&rft.au=Montinari%2C+E&rft.au=Corazza%2C+M&rft.au=Virgili%2C+A&rft.au=Tognon%2C+M&rft.au=Martini%2C+F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-Rotondo_2018-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-Rotondo_2018_13-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRotondoBorghiSelvaticiMazzoni2018" class="citation journal cs1">Rotondo JC, Borghi A, Selvatici R, Mazzoni E, Bononi I, Corazza M, Kussini J, Montinari E, Gafà R, Tognon M, Martini F (2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6128494">"Association of Retinoic Acid Receptor β Gene With Onset and Progression of Lichen Sclerosus-Associated Vulvar Squamous Cell Carcinoma"</a>. <i>JAMA Dermatology</i>. <b>154</b> (7): 819–823. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1001%2Fjamadermatol.2018.1373">10.1001/jamadermatol.2018.1373</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/PMC6128494">6128494</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/29898214">29898214</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=JAMA+Dermatology&rft.atitle=Association+of+Retinoic+Acid+Receptor+%CE%B2+Gene+With+Onset+and+Progression+of+Lichen+Sclerosus-Associated+Vulvar+Squamous+Cell+Carcinoma&rft.volume=154&rft.issue=7&rft.pages=819-823&rft.date=2018&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6128494%23id-name%3DPMC&rft_id=info%3Apmid%2F29898214&rft_id=info%3Adoi%2F10.1001%2Fjamadermatol.2018.1373&rft.aulast=Rotondo&rft.aufirst=JC&rft.au=Borghi%2C+A&rft.au=Selvatici%2C+R&rft.au=Mazzoni%2C+E&rft.au=Bononi%2C+I&rft.au=Corazza%2C+M&rft.au=Kussini%2C+J&rft.au=Montinari%2C+E&rft.au=Gaf%C3%A0%2C+R&rft.au=Tognon%2C+M&rft.au=Martini%2C+F&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6128494&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" 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 id="CITEREFLi-ByarlayLiStroudFeng2013" class="citation journal cs1">Li-Byarlay, Hongmei; Li, Yang; Stroud, Hume; Feng, Suhua; Newman, Thomas C.; Kaneda, Megan; Hou, Kirk K.; Worley, Kim C.; Elsik, Christine G.; Wickline, Samuel A.; Jacobsen, Steven E.; Ma, Jian; Robinson, Gene E. (30 July 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3732956">"RNA interference knockdown of DNA methyl-transferase 3 affects gene alternative splicing in the honey bee"</a>. <i>Proceedings of the National Academy of Sciences</i>. <b>110</b> (31): 12750–12755. <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/2013PNAS..11012750L">2013PNAS..11012750L</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.1310735110">10.1073/pnas.1310735110</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/PMC3732956">3732956</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/23852726">23852726</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+National+Academy+of+Sciences&rft.atitle=RNA+interference+knockdown+of+DNA+methyl-transferase+3+affects+gene+alternative+splicing+in+the+honey+bee&rft.volume=110&rft.issue=31&rft.pages=12750-12755&rft.date=2013-07-30&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3732956%23id-name%3DPMC&rft_id=info%3Apmid%2F23852726&rft_id=info%3Adoi%2F10.1073%2Fpnas.1310735110&rft_id=info%3Abibcode%2F2013PNAS..11012750L&rft.aulast=Li-Byarlay&rft.aufirst=Hongmei&rft.au=Li%2C+Yang&rft.au=Stroud%2C+Hume&rft.au=Feng%2C+Suhua&rft.au=Newman%2C+Thomas+C.&rft.au=Kaneda%2C+Megan&rft.au=Hou%2C+Kirk+K.&rft.au=Worley%2C+Kim+C.&rft.au=Elsik%2C+Christine+G.&rft.au=Wickline%2C+Samuel+A.&rft.au=Jacobsen%2C+Steven+E.&rft.au=Ma%2C+Jian&rft.au=Robinson%2C+Gene+E.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3732956&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLi-ByarlayBoncristianiHowellHerman2020" class="citation journal cs1">Li-Byarlay, Hongmei; Boncristiani, Humberto; Howell, Gary; Herman, Jake; Clark, Lindsay; Strand, Micheline K.; Tarpy, David; Rueppell, Olav (24 September 2020). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7546774">"Transcriptomic and Epigenomic Dynamics of Honey Bees in Response to Lethal Viral Infection"</a>. <i>Frontiers in Genetics</i>. <b>11</b>. <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/10.3389%2Ffgene.2020.566320">10.3389/fgene.2020.566320</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/PMC7546774">7546774</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/33101388">33101388</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Frontiers+in+Genetics&rft.atitle=Transcriptomic+and+Epigenomic+Dynamics+of+Honey+Bees+in+Response+to+Lethal+Viral+Infection&rft.volume=11&rft.date=2020-09-24&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7546774%23id-name%3DPMC&rft_id=info%3Apmid%2F33101388&rft_id=info%3Adoi%2F10.3389%2Ffgene.2020.566320&rft.aulast=Li-Byarlay&rft.aufirst=Hongmei&rft.au=Boncristiani%2C+Humberto&rft.au=Howell%2C+Gary&rft.au=Herman%2C+Jake&rft.au=Clark%2C+Lindsay&rft.au=Strand%2C+Micheline+K.&rft.au=Tarpy%2C+David&rft.au=Rueppell%2C+Olav&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7546774&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></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 id="CITEREFLi-Byarlay2016" class="citation journal cs1">Li-Byarlay, Hongmei (19 May 2016). <a rel="nofollow" class="external text" href="https://doi.org/10.3389%2Ffevo.2016.00057">"The Function of DNA Methylation Marks in Social Insects"</a>. <i>Frontiers in Ecology and Evolution</i>. <b>4</b>. <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/10.3389%2Ffevo.2016.00057">10.3389/fevo.2016.00057</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Frontiers+in+Ecology+and+Evolution&rft.atitle=The+Function+of+DNA+Methylation+Marks+in+Social+Insects&rft.volume=4&rft.date=2016-05-19&rft_id=info%3Adoi%2F10.3389%2Ffevo.2016.00057&rft.aulast=Li-Byarlay&rft.aufirst=Hongmei&rft_id=https%3A%2F%2Fdoi.org%2F10.3389%252Ffevo.2016.00057&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" 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 id="CITEREFWangLi-Byarlay2015" class="citation book cs1">Wang, Ying; Li-Byarlay, Hongmei (2015). <i>Physiological and Molecular Mechanisms of Nutrition in Honey Bees</i>. Advances in Insect Physiology. Vol. 49. pp. 25–58. <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%2Fbs.aiip.2015.06.002">10.1016/bs.aiip.2015.06.002</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-802586-4" title="Special:BookSources/978-0-12-802586-4"><bdi>978-0-12-802586-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Physiological+and+Molecular+Mechanisms+of+Nutrition+in+Honey+Bees&rft.series=Advances+in+Insect+Physiology&rft.pages=25-58&rft.date=2015&rft_id=info%3Adoi%2F10.1016%2Fbs.aiip.2015.06.002&rft.isbn=978-0-12-802586-4&rft.aulast=Wang&rft.aufirst=Ying&rft.au=Li-Byarlay%2C+Hongmei&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" 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 id="CITEREFRanaAnkri2016" class="citation journal cs1">Rana, Ajay K.; Ankri, Serge (6 June 2016). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4893491">"Reviving the RNA World: An Insight into the Appearance of RNA Methyltransferases"</a>. <i>Frontiers in Genetics</i>. <b>7</b>: 99. <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/10.3389%2Ffgene.2016.00099">10.3389/fgene.2016.00099</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/PMC4893491">4893491</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/27375676">27375676</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Frontiers+in+Genetics&rft.atitle=Reviving+the+RNA+World%3A+An+Insight+into+the+Appearance+of+RNA+Methyltransferases&rft.volume=7&rft.pages=99&rft.date=2016-06-06&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4893491%23id-name%3DPMC&rft_id=info%3Apmid%2F27375676&rft_id=info%3Adoi%2F10.3389%2Ffgene.2016.00099&rft.aulast=Rana&rft.aufirst=Ajay+K.&rft.au=Ankri%2C+Serge&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4893491&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" 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 id="CITEREFChoiIeongDemirciChen2016" class="citation journal cs1">Choi, Junhong; Ieong, Ka-Weng; Demirci, Hasan; Chen, Jin; Petrov, Alexey; Prabhakar, Arjun; O'Leary, Seán E; Dominissini, Dan; Rechavi, Gideon; Soltis, S Michael; Ehrenberg, Måns; Puglisi, Joseph D (February 2016). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4826618">"N6-methyladenosine in mRNA disrupts tRNA selection and translation-elongation dynamics"</a>. <i>Nature Structural & Molecular Biology</i>. <b>23</b> (2): 110–115. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fnsmb.3148">10.1038/nsmb.3148</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/PMC4826618">4826618</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/26751643">26751643</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature+Structural+%26+Molecular+Biology&rft.atitle=N6-methyladenosine+in+mRNA+disrupts+tRNA+selection+and+translation-elongation+dynamics&rft.volume=23&rft.issue=2&rft.pages=110-115&rft.date=2016-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4826618%23id-name%3DPMC&rft_id=info%3Apmid%2F26751643&rft_id=info%3Adoi%2F10.1038%2Fnsmb.3148&rft.aulast=Choi&rft.aufirst=Junhong&rft.au=Ieong%2C+Ka-Weng&rft.au=Demirci%2C+Hasan&rft.au=Chen%2C+Jin&rft.au=Petrov%2C+Alexey&rft.au=Prabhakar%2C+Arjun&rft.au=O%27Leary%2C+Se%C3%A1n+E&rft.au=Dominissini%2C+Dan&rft.au=Rechavi%2C+Gideon&rft.au=Soltis%2C+S+Michael&rft.au=Ehrenberg%2C+M%C3%A5ns&rft.au=Puglisi%2C+Joseph+D&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4826618&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStewart2017" class="citation web cs1">Stewart, Kendal (15 September 2017). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20171012202147/https://www.genomixnutrition.com/methylation-testing-s/2.htm">"Methylation (MTHFR) Testing & Folate Deficiency"</a>. Archived from <a rel="nofollow" class="external text" href="https://www.genomixnutrition.com/methylation-testing-s/2.htm">the original</a> on 12 October 2017<span class="reference-accessdate">. Retrieved <span class="nowrap">11 October</span> 2017</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Methylation+%28MTHFR%29+Testing+%26+Folate+Deficiency&rft.date=2017-09-15&rft.aulast=Stewart&rft.aufirst=Kendal&rft_id=https%3A%2F%2Fwww.genomixnutrition.com%2Fmethylation-testing-s%2F2.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBresnahanLeeClarkMa2023" class="citation journal cs1">Bresnahan, Sean T.; Lee, Ellen; Clark, Lindsay; Ma, Rong; Rangel, Juliana; Grozinger, Christina M.; Li-Byarlay, Hongmei (12 June 2023). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10258952">"Examining parent-of-origin effects on transcription and RNA methylation in mediating aggressive behavior in honey bees (Apis mellifera)"</a>. <i>BMC Genomics</i>. <b>24</b> (1): 315. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1186%2Fs12864-023-09411-4">10.1186/s12864-023-09411-4</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/PMC10258952">10258952</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/37308882">37308882</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=BMC+Genomics&rft.atitle=Examining+parent-of-origin+effects+on+transcription+and+RNA+methylation+in+mediating+aggressive+behavior+in+honey+bees+%28Apis+mellifera%29&rft.volume=24&rft.issue=1&rft.pages=315&rft.date=2023-06-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10258952%23id-name%3DPMC&rft_id=info%3Apmid%2F37308882&rft_id=info%3Adoi%2F10.1186%2Fs12864-023-09411-4&rft.aulast=Bresnahan&rft.aufirst=Sean+T.&rft.au=Lee%2C+Ellen&rft.au=Clark%2C+Lindsay&rft.au=Ma%2C+Rong&rft.au=Rangel%2C+Juliana&rft.au=Grozinger%2C+Christina+M.&rft.au=Li-Byarlay%2C+Hongmei&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10258952&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" 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="CITEREFWalsh2006" class="citation book cs1">Walsh, Christopher (2006). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JGBfQXIzdwgC&pg=PA121">"Protein Methylation"</a>. <i>Posttranslational Modification of Proteins: Expanding Nature's Inventory</i>. Roberts and Company Publishers. pp. 121–149. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-9747077-3-0" title="Special:BookSources/978-0-9747077-3-0"><bdi>978-0-9747077-3-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Protein+Methylation&rft.btitle=Posttranslational+Modification+of+Proteins%3A+Expanding+Nature%27s+Inventory&rft.pages=121-149&rft.pub=Roberts+and+Company+Publishers&rft.date=2006&rft.isbn=978-0-9747077-3-0&rft.aulast=Walsh&rft.aufirst=Christopher&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJGBfQXIzdwgC%26pg%3DPA121&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-Grewal2004-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-Grewal2004_23-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGrewalRice2004" class="citation journal cs1">Grewal, Shiv IS; Rice, Judd C (June 2004). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1258832">"Regulation of heterochromatin by histone methylation and small RNAs"</a>. <i>Current Opinion in Cell Biology</i>. <b>16</b> (3): 230–238. <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.ceb.2004.04.002">10.1016/j.ceb.2004.04.002</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/15145346">15145346</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Opinion+in+Cell+Biology&rft.atitle=Regulation+of+heterochromatin+by+histone+methylation+and+small+RNAs&rft.volume=16&rft.issue=3&rft.pages=230-238&rft.date=2004-06&rft_id=info%3Adoi%2F10.1016%2Fj.ceb.2004.04.002&rft_id=info%3Apmid%2F15145346&rft.aulast=Grewal&rft.aufirst=Shiv+IS&rft.au=Rice%2C+Judd+C&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1258832&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-Nakayama2001-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-Nakayama2001_24-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNakayamaRiceStrahlAllis2001" class="citation journal cs1">Nakayama, Jun-ichi; Rice, Judd C.; Strahl, Brian D.; Allis, C. David; Grewal, Shiv I. S. (6 April 2001). "Role of Histone H3 Lysine 9 Methylation in Epigenetic Control of Heterochromatin Assembly". <i>Science</i>. <b>292</b> (5514): 110–113. <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/2001Sci...292..110N">2001Sci...292..110N</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.1060118">10.1126/science.1060118</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/11283354">11283354</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science&rft.atitle=Role+of+Histone+H3+Lysine+9+Methylation+in+Epigenetic+Control+of+Heterochromatin+Assembly&rft.volume=292&rft.issue=5514&rft.pages=110-113&rft.date=2001-04-06&rft_id=info%3Apmid%2F11283354&rft_id=info%3Adoi%2F10.1126%2Fscience.1060118&rft_id=info%3Abibcode%2F2001Sci...292..110N&rft.aulast=Nakayama&rft.aufirst=Jun-ichi&rft.au=Rice%2C+Judd+C.&rft.au=Strahl%2C+Brian+D.&rft.au=Allis%2C+C.+David&rft.au=Grewal%2C+Shiv+I.+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-Kozbial-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-Kozbial_25-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKozbialMushegian2005" class="citation journal cs1">Kozbial, Piotr Z; Mushegian, Arcady R (December 2005). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1282579">"Natural history of S-adenosylmethionine-binding proteins"</a>. <i>BMC Structural Biology</i>. <b>5</b> (1): 19. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1186%2F1472-6807-5-19">10.1186/1472-6807-5-19</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/PMC1282579">1282579</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/16225687">16225687</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=BMC+Structural+Biology&rft.atitle=Natural+history+of+S-adenosylmethionine-binding+proteins&rft.volume=5&rft.issue=1&rft.pages=19&rft.date=2005-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1282579%23id-name%3DPMC&rft_id=info%3Apmid%2F16225687&rft_id=info%3Adoi%2F10.1186%2F1472-6807-5-19&rft.aulast=Kozbial&rft.aufirst=Piotr+Z&rft.au=Mushegian%2C+Arcady+R&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1282579&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-Fustin-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-Fustin_26-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFustinYeRakersKaneko2020" class="citation journal cs1">Fustin, Jean-Michel; Ye, Shiqi; Rakers, Christin; Kaneko, Kensuke; Fukumoto, Kazuki; Yamano, Mayu; Versteven, Marijke; Grünewald, Ellen; Cargill, Samantha J.; Tamai, T. Katherine; Xu, Yao; Jabbur, Maria Luísa; Kojima, Rika; Lamberti, Melisa L.; Yoshioka-Kobayashi, Kumiko; Whitmore, David; Tammam, Stephanie; Howell, P. Lynne; Kageyama, Ryoichiro; Matsuo, Takuya; Stanewsky, Ralf; Golombek, Diego A.; Johnson, Carl Hirschie; Kakeya, Hideaki; van Ooijen, Gerben; Okamura, Hitoshi (6 May 2020). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7203018">"Methylation deficiency disrupts biological rhythms from bacteria to humans"</a>. <i>Communications Biology</i>. <b>3</b> (1): 211. <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%2Fs42003-020-0942-0">10.1038/s42003-020-0942-0</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/PMC7203018">7203018</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/32376902">32376902</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Communications+Biology&rft.atitle=Methylation+deficiency+disrupts+biological+rhythms+from+bacteria+to+humans&rft.volume=3&rft.issue=1&rft.pages=211&rft.date=2020-05-06&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7203018%23id-name%3DPMC&rft_id=info%3Apmid%2F32376902&rft_id=info%3Adoi%2F10.1038%2Fs42003-020-0942-0&rft.aulast=Fustin&rft.aufirst=Jean-Michel&rft.au=Ye%2C+Shiqi&rft.au=Rakers%2C+Christin&rft.au=Kaneko%2C+Kensuke&rft.au=Fukumoto%2C+Kazuki&rft.au=Yamano%2C+Mayu&rft.au=Versteven%2C+Marijke&rft.au=Gr%C3%BCnewald%2C+Ellen&rft.au=Cargill%2C+Samantha+J.&rft.au=Tamai%2C+T.+Katherine&rft.au=Xu%2C+Yao&rft.au=Jabbur%2C+Maria+Lu%C3%ADsa&rft.au=Kojima%2C+Rika&rft.au=Lamberti%2C+Melisa+L.&rft.au=Yoshioka-Kobayashi%2C+Kumiko&rft.au=Whitmore%2C+David&rft.au=Tammam%2C+Stephanie&rft.au=Howell%2C+P.+Lynne&rft.au=Kageyama%2C+Ryoichiro&rft.au=Matsuo%2C+Takuya&rft.au=Stanewsky%2C+Ralf&rft.au=Golombek%2C+Diego+A.&rft.au=Johnson%2C+Carl+Hirschie&rft.au=Kakeya%2C+Hideaki&rft.au=van+Ooijen%2C+Gerben&rft.au=Okamura%2C+Hitoshi&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7203018&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></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 class="citation book cs1">"Aromatic Substitution, Nucleophilic and Organometallic". <i>March's Advanced Organic Chemistry</i>. 2006. pp. 853–933. <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%2F9780470084960.ch13">10.1002/9780470084960.ch13</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-72091-1" title="Special:BookSources/978-0-471-72091-1"><bdi>978-0-471-72091-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Aromatic+Substitution%2C+Nucleophilic+and+Organometallic&rft.btitle=March%27s+Advanced+Organic+Chemistry&rft.pages=853-933&rft.date=2006&rft_id=info%3Adoi%2F10.1002%2F9780470084960.ch13&rft.isbn=978-0-471-72091-1&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" 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="CITEREFVyasShah1951" class="citation journal cs1">Vyas, G. N.; Shah, N. M. (1951). "Quninacetophenone monomethyl ether". <i><a href="/wiki/Organic_Syntheses" title="Organic Syntheses">Organic Syntheses</a></i>. <b>31</b>: 90. <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.031.0090">10.15227/orgsyn.031.0090</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=Quninacetophenone+monomethyl+ether&rft.volume=31&rft.pages=90&rft.date=1951&rft_id=info%3Adoi%2F10.15227%2Forgsyn.031.0090&rft.aulast=Vyas&rft.aufirst=G.+N.&rft.au=Shah%2C+N.+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" 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 id="CITEREFHiers1929" class="citation journal cs1">Hiers, G. S. (1929). "Anisole". <i>Organic Syntheses</i>. <b>9</b>: 12. <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.009.0012">10.15227/orgsyn.009.0012</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=Anisole&rft.volume=9&rft.pages=12&rft.date=1929&rft_id=info%3Adoi%2F10.15227%2Forgsyn.009.0012&rft.aulast=Hiers&rft.aufirst=G.+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" 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="CITEREFIckeRedemannWisegarverAlles1949" class="citation journal cs1">Icke, Roland N.; Redemann, Ernst; Wisegarver, Burnett B.; Alles, Gordon A. (1949). "m-Methoxybenzaldehyde". <i>Organic Syntheses</i>. <b>29</b>: 63. <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.029.0063">10.15227/orgsyn.029.0063</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=m-Methoxybenzaldehyde&rft.volume=29&rft.pages=63&rft.date=1949&rft_id=info%3Adoi%2F10.15227%2Forgsyn.029.0063&rft.aulast=Icke&rft.aufirst=Roland+N.&rft.au=Redemann%2C+Ernst&rft.au=Wisegarver%2C+Burnett+B.&rft.au=Alles%2C+Gordon+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" 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="CITEREFTundoSelvaBomben1999" class="citation journal cs1">Tundo, Pietro; Selva, Maurizio; Bomben, Andrea (1999). "Mono-C-methylathion of arylacetonitriles and methyl arylacetates by dimethyl carbonate: a general method for the synthesis of pure 2-arylpropionic acids. 2-Phenylpropionic acid". <i>Organic Syntheses</i>. <b>76</b>: 169. <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.076.0169">10.15227/orgsyn.076.0169</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=Mono-C-methylathion+of+arylacetonitriles+and+methyl+arylacetates+by+dimethyl+carbonate%3A+a+general+method+for+the+synthesis+of+pure+2-arylpropionic+acids.+2-Phenylpropionic+acid&rft.volume=76&rft.pages=169&rft.date=1999&rft_id=info%3Adoi%2F10.15227%2Forgsyn.076.0169&rft.aulast=Tundo&rft.aufirst=Pietro&rft.au=Selva%2C+Maurizio&rft.au=Bomben%2C+Andrea&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" 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="CITEREFNenadPolancKočevar2008" class="citation journal cs1">Nenad, Maraš; Polanc, Slovenko; Kočevar, Marijan (2008). "Microwave-assisted methylation of phenols with tetramethylammonium chloride in the presence of K<sub>2</sub>CO<sub>3</sub> or Cs<sub>2</sub>CO<sub>3</sub>". <i>Tetrahedron</i>. <b>64</b> (51): 11618–11624. <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.tet.2008.10.024">10.1016/j.tet.2008.10.024</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron&rft.atitle=Microwave-assisted+methylation+of+phenols+with+tetramethylammonium+chloride+in+the+presence+of+K%3Csub%3E2%3C%2Fsub%3ECO%3Csub%3E3%3C%2Fsub%3E+or+Cs%3Csub%3E2%3C%2Fsub%3ECO%3Csub%3E3%3C%2Fsub%3E&rft.volume=64&rft.issue=51&rft.pages=11618-11624&rft.date=2008&rft_id=info%3Adoi%2F10.1016%2Fj.tet.2008.10.024&rft.aulast=Nenad&rft.aufirst=Mara%C5%A1&rft.au=Polanc%2C+Slovenko&rft.au=Ko%C4%8Devar%2C+Marijan&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" 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 id="CITEREFPoonAlbiniakDudley2007" class="citation journal cs1">Poon, Kevin W. C.; Albiniak, Philip A.; Dudley, Gregory B. (2007). "Protection of alcohols using 2-benzyloxy-1-methylpyridinium trifluoromethanesulfanonate: Methyl (R)-(-)-3-benzyloxy-2-methyl propanoate". <i>Organic Syntheses</i>. <b>84</b>: 295. <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.084.0295">10.15227/orgsyn.084.0295</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=Protection+of+alcohols+using+2-benzyloxy-1-methylpyridinium+trifluoromethanesulfanonate%3A+Methyl+%28R%29-%28-%29-3-benzyloxy-2-methyl+propanoate&rft.volume=84&rft.pages=295&rft.date=2007&rft_id=info%3Adoi%2F10.15227%2Forgsyn.084.0295&rft.aulast=Poon&rft.aufirst=Kevin+W.+C.&rft.au=Albiniak%2C+Philip+A.&rft.au=Dudley%2C+Gregory+B.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-34">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNeemanJohnson1961" class="citation journal cs1">Neeman, M.; Johnson, William S. (1961). "Cholestanyl methyl ether". <i>Organic Syntheses</i>. <b>41</b>: 9. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.041.0009">10.15227/orgsyn.041.0009</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=Cholestanyl+methyl+ether&rft.volume=41&rft.pages=9&rft.date=1961&rft_id=info%3Adoi%2F10.15227%2Forgsyn.041.0009&rft.aulast=Neeman&rft.aufirst=M.&rft.au=Johnson%2C+William+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-Purdie1903-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-Purdie1903_35-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPurdieIrvine1903" class="citation journal cs1">Purdie, T.; Irvine, J. C. (1903). <a rel="nofollow" class="external text" href="https://zenodo.org/record/2039403">"C.?The alkylation of sugars"</a>. <i>Journal of the Chemical Society, Transactions</i>. <b>83</b>: 1021–1037. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FCT9038301021">10.1039/CT9038301021</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+Chemical+Society%2C+Transactions&rft.atitle=C.%3FThe+alkylation+of+sugars&rft.volume=83&rft.pages=1021-1037&rft.date=1903&rft_id=info%3Adoi%2F10.1039%2FCT9038301021&rft.aulast=Purdie&rft.aufirst=T.&rft.au=Irvine%2C+J.+C.&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F2039403&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" 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="CITEREFIckeWisegarverAlles1945" class="citation journal cs1">Icke, Roland N.; Wisegarver, Burnett B.; Alles, Gordon A. (1945). "β-Phenylethyldimethylamine". <i>Organic Syntheses</i>. <b>25</b>: 89. <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.025.0089">10.15227/orgsyn.025.0089</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=%CE%B2-Phenylethyldimethylamine&rft.volume=25&rft.pages=89&rft.date=1945&rft_id=info%3Adoi%2F10.15227%2Forgsyn.025.0089&rft.aulast=Icke&rft.aufirst=Roland+N.&rft.au=Wisegarver%2C+Burnett+B.&rft.au=Alles%2C+Gordon+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" 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="CITEREFShioiriAoyamaSnowden2001" class="citation encyclopaedia cs1">Shioiri T, Aoyama T, Snowden T (2001). "Trimethylsilyldiazomethane". <i>Encyclopedia of Reagents for Organic Synthesis</i>. <i>e-EROS Encyclopedia of Reagents for Organic Synthesis</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%2F047084289X.rt298.pub2">10.1002/047084289X.rt298.pub2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-471-93623-7" title="Special:BookSources/978-0-471-93623-7"><bdi>978-0-471-93623-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Encyclopedia+of+Reagents+for+Organic+Synthesis&rft.btitle=e-EROS+Encyclopedia+of+Reagents+for+Organic+Synthesis&rft.date=2001&rft_id=info%3Adoi%2F10.1002%2F047084289X.rt298.pub2&rft.isbn=978-0-471-93623-7&rft.aulast=Shioiri&rft.aufirst=T&rft.au=Aoyama%2C+T&rft.au=Snowden%2C+T&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" 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="CITEREFLipskyHall1976" class="citation journal cs1">Lipsky, Sharon D.; Hall, Stan S. (1976). "Aromatic Hydrocarbons from aromatic ketones and aldehydes: 1,1-Diphenylethane". <i>Organic Syntheses</i>. <b>55</b>: 7. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.15227%2Forgsyn.055.0007">10.15227/orgsyn.055.0007</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=Aromatic+Hydrocarbons+from+aromatic+ketones+and+aldehydes%3A+1%2C1-Diphenylethane&rft.volume=55&rft.pages=7&rft.date=1976&rft_id=info%3Adoi%2F10.15227%2Forgsyn.055.0007&rft.aulast=Lipsky&rft.aufirst=Sharon+D.&rft.au=Hall%2C+Stan+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" 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="CITEREFGrummittBecker1950" class="citation journal cs1">Grummitt, Oliver; Becker, Ernest I. (1950). "trans-1-Phenyl-1,3-butadiene". <i>Organic Syntheses</i>. <b>30</b>: 75. <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.030.0075">10.15227/orgsyn.030.0075</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=trans-1-Phenyl-1%2C3-butadiene&rft.volume=30&rft.pages=75&rft.date=1950&rft_id=info%3Adoi%2F10.15227%2Forgsyn.030.0075&rft.aulast=Grummitt&rft.aufirst=Oliver&rft.au=Becker%2C+Ernest+I.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" 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="CITEREFNegishiMatsushita1984" class="citation journal cs1">Negishi, Ei-ichi; Matsushita, Hajime (1984). "Palladium-Catalyzed Synthesis of 1,4-Dienes by Allylation of Alkenyalane: α-Farnesene". <i>Organic Syntheses</i>. <b>62</b>: 31. <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.062.0031">10.15227/orgsyn.062.0031</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=Palladium-Catalyzed+Synthesis+of+1%2C4-Dienes+by+Allylation+of+Alkenyalane%3A+%CE%B1-Farnesene&rft.volume=62&rft.pages=31&rft.date=1984&rft_id=info%3Adoi%2F10.15227%2Forgsyn.062.0031&rft.aulast=Negishi&rft.aufirst=Ei-ichi&rft.au=Matsushita%2C+Hajime&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> <li id="cite_note-Wienken2-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-Wienken2_41-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWienkenBaaskeDuhrBraun2011" class="citation journal cs1">Wienken CJ, Baaske P, Duhr S, Braun D (2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3082908">"Thermophoretic melting curves quantify the conformation and stability of RNA and DNA"</a>. <i>Nucleic Acids Research</i>. <b>39</b> (8): e52. <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%2Fnar%2Fgkr035">10.1093/nar/gkr035</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/PMC3082908">3082908</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/21297115">21297115</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nucleic+Acids+Research&rft.atitle=Thermophoretic+melting+curves+quantify+the+conformation+and+stability+of+RNA+and+DNA&rft.volume=39&rft.issue=8&rft.pages=e52&rft.date=2011&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3082908%23id-name%3DPMC&rft_id=info%3Apmid%2F21297115&rft_id=info%3Adoi%2F10.1093%2Fnar%2Fgkr035&rft.aulast=Wienken&rft.aufirst=CJ&rft.au=Baaske%2C+P&rft.au=Duhr%2C+S&rft.au=Braun%2C+D&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3082908&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMethylation" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a 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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:Methylation" class="extiw" title="commons:Category:Methylation">Methylation</a></span>.</div></div> </div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1235681985"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1237033735"><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/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/40px-Wiktionary-logo-en-v2.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/60px-Wiktionary-logo-en-v2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/80px-Wiktionary-logo-en-v2.svg.png 2x" data-file-width="512" data-file-height="512" /></span></span></div> <div class="side-box-text plainlist">Look up <i><b><a href="https://en.wiktionary.org/wiki/Special:Search/methylation" class="extiw" title="wiktionary:Special:Search/methylation">methylation</a></b></i> in Wiktionary, the free dictionary.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20160418034750/http://www.detectorvision.com/deltaMasses/">deltaMasses</a> Detection of Methylations after Mass Spectrometry</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 dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": 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.navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Protein_primary_structure_and_posttranslational_modifications" 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 .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Protein_primary_structure" title="Template:Protein primary structure"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Protein_primary_structure" title="Template talk:Protein primary structure"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Protein_primary_structure" title="Special:EditPage/Template:Protein primary structure"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Protein_primary_structure_and_posttranslational_modifications" style="font-size:114%;margin:0 4em"><a href="/wiki/Protein_primary_structure" title="Protein primary structure">Protein primary structure</a> and <a href="/wiki/Posttranslational_modification" class="mw-redirect" title="Posttranslational modification">posttranslational modifications</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">General</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/Peptide_bond" title="Peptide bond">Peptide bond</a></li> <li><a href="/wiki/Protein_biosynthesis" title="Protein biosynthesis">Protein biosynthesis</a></li> <li><a href="/wiki/Proteolysis" title="Proteolysis">Proteolysis</a></li> <li><a href="/wiki/Racemization" title="Racemization">Racemization</a></li> <li><a href="/w/index.php?title=N%E2%80%93O_acyl_shift&action=edit&redlink=1" class="new" title="N–O acyl shift (page does not exist)">N–O acyl shift</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/N_terminus" class="mw-redirect" title="N terminus">N terminus</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/Acetylation" title="Acetylation">Acetylation</a></li> <li><a href="/wiki/Carbamylation" class="mw-redirect" title="Carbamylation">Carbamylation</a></li> <li><a href="/wiki/Formylation" title="Formylation">Formylation</a></li> <li><a href="/wiki/Glycation" title="Glycation">Glycation</a></li> <li><a class="mw-selflink selflink">Methylation</a></li> <li><a href="/wiki/Myristoylation" title="Myristoylation">Myristoylation</a> (Gly)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/C_terminus" class="mw-redirect" title="C terminus">C terminus</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/Amide" title="Amide">Amidation</a></li> <li><a href="/wiki/Glycophosphatidylinositol" class="mw-redirect" title="Glycophosphatidylinositol">Glycosyl phosphatidylinositol (GPI)</a></li> <li><a href="/w/index.php?title=O-methylation&action=edit&redlink=1" class="new" title="O-methylation (page does not exist)">O-methylation</a></li> <li><a href="/wiki/Detyrosination" title="Detyrosination">Detyrosination</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Single specific <a href="/wiki/Amino_acid" title="Amino acid">AAs</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/Serine" title="Serine">Serine</a>/<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/Phosphorylation" title="Phosphorylation">Phosphorylation</a></li> <li><a href="/wiki/Dephosphorylation" title="Dephosphorylation">Dephosphorylation</a></li> <li><a href="/wiki/Glycosylation" title="Glycosylation">Glycosylation</a></li> <li><a href="/wiki/O-GlcNAc" title="O-GlcNAc"><i>O</i>-GlcNAc</a></li> <li><a href="/wiki/ADP-ribosylation" title="ADP-ribosylation">ADP-ribosylation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</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/Phosphorylation" title="Phosphorylation">Phosphorylation</a></li> <li><a href="/wiki/Dephosphorylation" title="Dephosphorylation">Dephosphorylation</a></li> <li><a href="/wiki/ADP-ribosylation" title="ADP-ribosylation">ADP-ribosylation</a></li> <li><a href="/wiki/Tyrosine_sulfation" title="Tyrosine sulfation">Sulfation</a></li> <li><a href="/wiki/Porphyrin" title="Porphyrin">Porphyrin ring linkage</a></li> <li><a href="/wiki/Adenylylation" title="Adenylylation">Adenylylation</a></li> <li><a href="/wiki/Flavin_group" title="Flavin group">Flavin linkage</a></li> <li><a href="/wiki/Topaquinone" title="Topaquinone">Topaquinone (TPQ) formation</a></li> <li><a href="/wiki/Detyrosination" title="Detyrosination">Detyrosination</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cysteine" title="Cysteine">Cysteine</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/Palmitoylation" title="Palmitoylation">Palmitoylation</a></li> <li><a href="/wiki/Prenylation" title="Prenylation">Prenylation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aspartate" class="mw-redirect" title="Aspartate">Aspartate</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/Deamidation" title="Deamidation">Succinimide formation</a></li> <li><a href="/wiki/ADP-ribosylation" title="ADP-ribosylation">ADP-ribosylation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">Glutamate</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/Carboxylation" title="Carboxylation">Carboxylation</a></li> <li><a href="/wiki/ADP-ribosylation" title="ADP-ribosylation">ADP-ribosylation</a></li> <li><a class="mw-selflink selflink">Methylation</a></li> <li><a href="/wiki/Polyglutamylation" title="Polyglutamylation">Polyglutamylation</a></li> <li><a href="/wiki/Polyglycylation" title="Polyglycylation">Polyglycylation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Asparagine" title="Asparagine">Asparagine</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/Deamidation" title="Deamidation">Deamidation</a></li> <li><a href="/wiki/Glycosylation" title="Glycosylation">Glycosylation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glutamine" title="Glutamine">Glutamine</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/Transglutamination" class="mw-redirect" title="Transglutamination">Transglutamination</a></li></ul> </div></td></tr><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 class="mw-selflink selflink">Methylation</a></li> <li><a href="/wiki/Acetylation" title="Acetylation">Acetylation</a></li> <li><a href="/wiki/Acylation" title="Acylation">Acylation</a></li> <li><a href="/wiki/Adenylylation" title="Adenylylation">Adenylylation</a></li> <li><a href="/wiki/Hydroxylation" title="Hydroxylation">Hydroxylation</a></li> <li><a href="/wiki/Ubiquitination" class="mw-redirect" title="Ubiquitination">Ubiquitination</a></li> <li><a href="/wiki/SUMO_protein" title="SUMO protein">Sumoylation</a></li> <li><a href="/wiki/ADP-ribosylation" title="ADP-ribosylation">ADP-ribosylation</a></li> <li><a href="/wiki/Deamination" title="Deamination">Deamination</a></li> <li><a href="/wiki/Allysine" title="Allysine">Oxidative deamination to aldehyde</a></li> <li><a href="/wiki/O-glycosylation" class="mw-redirect" title="O-glycosylation"><i>O</i>-glycosylation</a></li> <li><a href="/wiki/Imine" title="Imine">Imine formation</a></li> <li><a href="/wiki/Glycation" title="Glycation">Glycation</a></li> <li><a href="/wiki/Carbamylation" class="mw-redirect" title="Carbamylation">Carbamylation</a></li> <li><a href="/wiki/Succinylation" title="Succinylation">Succinylation</a></li> <li><a href="/w/index.php?title=Lactylation&action=edit&redlink=1" class="new" title="Lactylation (page does not exist)">Lactylation</a></li> <li><a href="/wiki/Propionylation" title="Propionylation">Propionylation</a></li> <li><a href="/w/index.php?title=Butyrylation&action=edit&redlink=1" class="new" title="Butyrylation (page does not exist)">Butyrylation</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-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Citrullination" title="Citrullination">Citrullination</a></li> <li><a class="mw-selflink selflink">Methylation</a></li> <li><a href="/wiki/ADP-ribosylation" title="ADP-ribosylation">ADP-ribosylation</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-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hydroxylation" title="Hydroxylation">Hydroxylation</a></li></ul> </div></td></tr><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-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diphthamide" title="Diphthamide">Diphthamide</a> formation</li> <li><a href="/wiki/Adenylylation" title="Adenylylation">Adenylylation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</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/Glycosylation#C-mannosylation" title="Glycosylation">C-mannosylation</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Crosslinks between two <a href="/wiki/Amino_acid" title="Amino acid">AAs</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/Cysteine" title="Cysteine">Cysteine</a>–<a href="/wiki/Cysteine" title="Cysteine">Cysteine</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/Disulfide_bond" class="mw-redirect" title="Disulfide bond">Disulfide bond</a></li> <li><a href="/wiki/ADP-ribosylation" title="ADP-ribosylation">ADP-ribosylation</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Methionine" title="Methionine">Methionine</a>–<a href="/wiki/Hydroxylysine" title="Hydroxylysine">Hydroxylysine</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/Sulfilimine_bond" class="mw-redirect" title="Sulfilimine bond">Sulfilimine bond</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lysine" title="Lysine">Lysine</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="/w/index.php?title=Lysine_tyrosylquinone&action=edit&redlink=1" class="new" title="Lysine tyrosylquinone (page does not exist)">Lysine tyrosylquinone (LTQ) formation</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/Tryptophan" title="Tryptophan">Tryptophan</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/Tryptophan_tryptophylquinone" title="Tryptophan tryptophylquinone">Tryptophan tryptophylquinone (TTQ) formation</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Crosslinks between three <a href="/wiki/Amino_acid" title="Amino acid">AAs</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/Serine" title="Serine">Serine</a>–<a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a>–<a href="/wiki/Glycine" title="Glycine">Glycine</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/Green_Fluorescent_Protein#Autocatalytic_formation_of_the_chromophore_in_wtGFP" class="mw-redirect" title="Green Fluorescent Protein">p-Hydroxybenzylidene-imidazolinone (HBI) formation</a> (chromophore)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Histidine" title="Histidine">Histidine</a>–<a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a>–<a href="/wiki/Glycine" title="Glycine">Glycine</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/Kaede_(protein)" title="Kaede (protein)">4-(p-hydroxybenzylidene)-5-imidazolinone (HBI) formation</a> (chromophore)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alanine" title="Alanine">Alanine</a>–<a href="/wiki/Serine" title="Serine">Serine</a>–<a href="/wiki/Glycine" title="Glycine">Glycine</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/Histidine_ammonia-lyase" title="Histidine ammonia-lyase">Methylidene-imidazolone (MIO) formation</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Crosslinks between four <a href="/wiki/Amino_acid" title="Amino acid">AAs</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 id="Allysine–Allysine–Allysine–Lysine" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Allysine" title="Allysine">Allysine</a>–<a href="/wiki/Allysine" title="Allysine">Allysine</a>–<a href="/wiki/Allysine" title="Allysine">Allysine</a>–<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/Desmosine" title="Desmosine">Desmosine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div 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