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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Peptide bond</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 50 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-50" 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">50 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%B1%D8%A7%D8%A8%D8%B7%D8%A9_%D8%A8%D8%A8%D8%AA%D9%8A%D8%AF%D9%8A%D8%A9" title="رابطة ببتيدية – Arabic" lang="ar" hreflang="ar" data-title="رابطة ببتيدية" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AA%E0%A7%87%E0%A6%AA%E0%A6%9F%E0%A6%BE%E0%A6%87%E0%A6%A1_%E0%A6%AC%E0%A6%A8%E0%A7%8D%E0%A6%A7%E0%A6%A8" title="পেপটাইড বন্ধন – Bangla" lang="bn" hreflang="bn" data-title="পেপটাইড বন্ধন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%9F%D0%B5%D0%BF%D1%82%D1%8B%D0%B4%D0%BD%D0%B0%D1%8F_%D1%81%D1%83%D0%B2%D1%8F%D0%B7%D1%8C" title="Пептыдная сувязь – Belarusian" lang="be" hreflang="be" data-title="Пептыдная сувязь" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9F%D0%B5%D0%BF%D1%82%D0%B8%D0%B4%D0%BD%D0%B0_%D0%B2%D1%80%D1%8A%D0%B7%D0%BA%D0%B0" title="Пептидна връзка – Bulgarian" lang="bg" hreflang="bg" data-title="Пептидна връзка" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Peptidna_veza" title="Peptidna veza – Bosnian" lang="bs" hreflang="bs" data-title="Peptidna veza" 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/Enlla%C3%A7_pept%C3%ADdic" title="Enllaç peptídic – Catalan" lang="ca" hreflang="ca" data-title="Enllaç peptídic" 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/Peptidov%C3%A1_vazba" title="Peptidová vazba – Czech" lang="cs" hreflang="cs" data-title="Peptidová vazba" 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/Peptidbinding" title="Peptidbinding – Danish" lang="da" hreflang="da" data-title="Peptidbinding" 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/Peptidbindung" title="Peptidbindung – German" lang="de" hreflang="de" data-title="Peptidbindung" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Peptiidside" title="Peptiidside – Estonian" lang="et" hreflang="et" data-title="Peptiidside" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A0%CE%B5%CF%80%CF%84%CE%B9%CE%B4%CE%B9%CE%BA%CF%8C%CF%82_%CE%B4%CE%B5%CF%83%CE%BC%CF%8C%CF%82" title="Πεπτιδικός δεσμός – Greek" lang="el" hreflang="el" data-title="Πεπτιδικός δεσμός" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Enlace_pept%C3%ADdico" title="Enlace peptídico – Spanish" lang="es" hreflang="es" data-title="Enlace peptídico" 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/Peptida_ligilo" title="Peptida ligilo – Esperanto" lang="eo" hreflang="eo" data-title="Peptida ligilo" 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/Lotura_peptidiko" title="Lotura peptidiko – Basque" lang="eu" hreflang="eu" data-title="Lotura peptidiko" 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%BE%DB%8C%D9%88%D9%86%D8%AF_%D9%BE%D9%BE%D8%AA%DB%8C%D8%AF%DB%8C" title="پیوند پپتیدی – Persian" lang="fa" hreflang="fa" data-title="پیوند پپتیدی" 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/Liaison_peptidique" title="Liaison peptidique – French" lang="fr" hreflang="fr" data-title="Liaison peptidique" 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/Enlace_pept%C3%ADdico" title="Enlace peptídico – Galician" lang="gl" hreflang="gl" data-title="Enlace peptídico" 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/%ED%8E%A9%ED%83%80%EC%9D%B4%EB%93%9C_%EA%B2%B0%ED%95%A9" title="펩타이드 결합 – Korean" lang="ko" hreflang="ko" data-title="펩타이드 결합" 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%8A%D5%A5%D5%BA%D5%BF%D5%AB%D5%A4%D5%A1%D5%B5%D5%AB%D5%B6_%D5%AF%D5%A1%D5%BA" title="Պեպտիդային կապ – Armenian" lang="hy" hreflang="hy" data-title="Պեպտիդային կապ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AA%E0%A5%87%E0%A4%AA%E0%A5%8D%E0%A4%9F%E0%A4%BE%E0%A4%87%E0%A4%A1_%E0%A4%AC%E0%A4%82%E0%A4%A7" title="पेप्टाइड बंध – Hindi" lang="hi" hreflang="hi" data-title="पेप्टाइड बंध" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Peptida_ligilo" title="Peptida ligilo – Ido" lang="io" hreflang="io" data-title="Peptida ligilo" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Ikatan_peptida" title="Ikatan peptida – Indonesian" lang="id" hreflang="id" data-title="Ikatan peptida" 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/Legame_peptidico" title="Legame peptidico – Italian" lang="it" hreflang="it" data-title="Legame peptidico" 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%A7%D7%A9%D7%A8_%D7%A4%D7%A4%D7%98%D7%99%D7%93%D7%99" title="קשר פפטידי – Hebrew" lang="he" hreflang="he" data-title="קשר פפטידי" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Peptidk%C3%B6t%C3%A9s" title="Peptidkötés – Hungarian" lang="hu" hreflang="hu" data-title="Peptidkötés" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Ikatan_peptida" title="Ikatan peptida – Malay" lang="ms" hreflang="ms" data-title="Ikatan peptida" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%9F%D0%B5%D0%BF%D1%82%D0%B8%D0%B4%D0%B8%D0%B9%D0%BD_%D1%85%D0%BE%D0%BB%D0%B1%D0%BE%D0%BE" title="Пептидийн холбоо – Mongolian" lang="mn" hreflang="mn" data-title="Пептидийн холбоо" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Peptidebinding" title="Peptidebinding – Dutch" lang="nl" hreflang="nl" data-title="Peptidebinding" 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%9A%E3%83%97%E3%83%81%E3%83%89%E7%B5%90%E5%90%88" title="ペプチド結合 – Japanese" lang="ja" hreflang="ja" data-title="ペプチド結合" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Peptidbinding" title="Peptidbinding – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Peptidbinding" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Ligam_peptidic" title="Ligam peptidic – Occitan" lang="oc" hreflang="oc" data-title="Ligam peptidic" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Wi%C4%85zanie_peptydowe" title="Wiązanie peptydowe – Polish" lang="pl" hreflang="pl" data-title="Wiązanie peptydowe" 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/Liga%C3%A7%C3%A3o_pept%C3%ADdica" title="Ligação peptídica – Portuguese" lang="pt" hreflang="pt" data-title="Ligação peptídica" 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/Leg%C4%83tur%C4%83_peptidic%C4%83" title="Legătură peptidică – Romanian" lang="ro" hreflang="ro" data-title="Legătură peptidică" 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%9F%D0%B5%D0%BF%D1%82%D0%B8%D0%B4%D0%BD%D0%B0%D1%8F_%D1%81%D0%B2%D1%8F%D0%B7%D1%8C" title="Пептидная связь – Russian" lang="ru" hreflang="ru" data-title="Пептидная связь" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Peptide_bond" title="Peptide bond – Simple English" lang="en-simple" hreflang="en-simple" data-title="Peptide bond" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Peptidov%C3%A1_v%C3%A4zba" title="Peptidová väzba – Slovak" lang="sk" hreflang="sk" data-title="Peptidová väzba" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Peptidna_vez" title="Peptidna vez – Slovenian" lang="sl" hreflang="sl" data-title="Peptidna vez" 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/Peptidna_veza" title="Peptidna veza – Serbian" lang="sr" hreflang="sr" data-title="Peptidna veza" 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/Peptidna_veza" title="Peptidna veza – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Peptidna veza" 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/Peptidisidos" title="Peptidisidos – Finnish" lang="fi" hreflang="fi" data-title="Peptidisidos" 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/Peptidbindning" title="Peptidbindning – Swedish" lang="sv" hreflang="sv" data-title="Peptidbindning" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AA%E0%AF%86%E0%AE%AA%E0%AF%8D%E0%AE%9F%E0%AF%88%E0%AE%9F%E0%AF%81_%E0%AE%AA%E0%AE%BF%E0%AE%A3%E0%AF%88%E0%AE%AA%E0%AF%8D%E0%AE%AA%E0%AF%81" title="பெப்டைடு பிணைப்பு – Tamil" lang="ta" hreflang="ta" data-title="பெப்டைடு பிணைப்பு" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%9E%E0%B8%B1%E0%B8%99%E0%B8%98%E0%B8%B0%E0%B9%80%E0%B8%9E%E0%B8%9B%E0%B9%84%E0%B8%97%E0%B8%94%E0%B9%8C" title="พันธะเพปไทด์ – Thai" lang="th" hreflang="th" data-title="พันธะเพปไทด์" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Peptit_ba%C4%9F%C4%B1" title="Peptit bağı – Turkish" lang="tr" hreflang="tr" data-title="Peptit bağı" 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%9F%D0%B5%D0%BF%D1%82%D0%B8%D0%B4%D0%BD%D0%B8%D0%B9_%D0%B7%D0%B2%27%D1%8F%D0%B7%D0%BE%D0%BA" title="Пептидний зв'язок – Ukrainian" lang="uk" hreflang="uk" data-title="Пептидний зв'язок" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Li%C3%AAn_k%E1%BA%BFt_peptide" title="Liên kết peptide – Vietnamese" lang="vi" hreflang="vi" data-title="Liên kết peptide" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%82%BD%E9%94%AE" title="肽键 – Wu" lang="wuu" hreflang="wuu" data-title="肽键" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E8%82%BD%E9%8D%B5" title="肽鍵 – Cantonese" lang="yue" hreflang="yue" data-title="肽鍵" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%82%BD%E9%94%AE" title="肽键 – Chinese" lang="zh" hreflang="zh" data-title="肽键" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q33293#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div 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class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Peptide_bond.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Peptide_bond.png/220px-Peptide_bond.png" decoding="async" width="220" height="150" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Peptide_bond.png/330px-Peptide_bond.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Peptide_bond.png/440px-Peptide_bond.png 2x" data-file-width="709" data-file-height="482" /></a><figcaption>Peptide bond</figcaption></figure> <p>In <a href="/wiki/Organic_chemistry" title="Organic chemistry">organic chemistry</a>, a <b>peptide bond</b> is an <a href="/wiki/Amide" title="Amide">amide</a> type of <a href="/wiki/Covalent_bond" title="Covalent bond">covalent</a> <a href="/wiki/Chemical_bond" title="Chemical bond">chemical bond</a> linking two consecutive <a href="/wiki/Alpha-amino_acid" class="mw-redirect" title="Alpha-amino acid">alpha-amino acids</a> from C1 (<a href="/wiki/Carbon" title="Carbon">carbon</a> number one) of one alpha-amino acid and N2 (<a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> number two) of another, along a <a href="/wiki/Peptide" title="Peptide">peptide</a> or <a href="/wiki/Protein" title="Protein">protein</a> chain.<sup id="cite_ref-:0_1-0" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>It can also be called a <b>eupeptide bond</b><sup id="cite_ref-:0_1-1" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> to distinguish it from an <a href="/wiki/Isopeptide_bond" title="Isopeptide bond">isopeptide bond</a>, which is another type of amide bond between two amino acids. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Peptide_bond&action=edit&section=1" title="Edit section: Synthesis"><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:Peptidformationball.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Peptidformationball.svg/220px-Peptidformationball.svg.png" decoding="async" width="220" height="182" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Peptidformationball.svg/330px-Peptidformationball.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Peptidformationball.svg/440px-Peptidformationball.svg.png 2x" data-file-width="990" data-file-height="820" /></a><figcaption>Peptide bond formation via <a href="/wiki/Dehydration_reaction" title="Dehydration reaction">dehydration reaction</a></figcaption></figure> <p>When two amino acids form a <i><a href="/wiki/Dipeptide" title="Dipeptide">dipeptide</a></i> through a <i>peptide bond</i>,<sup id="cite_ref-:0_1-2" class="reference"><a href="#cite_note-:0-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> it is a type of <a href="/wiki/Condensation_reaction" title="Condensation reaction">condensation reaction</a>.<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> In this kind of condensation, two amino acids approach each other, with the non-<a href="/wiki/Side_chain" title="Side chain">side chain</a> (C1) <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> <a href="/wiki/Functional_group" title="Functional group">moiety</a> of one coming near the non-side chain (N2) <a href="/wiki/Amino" class="mw-redirect" title="Amino">amino</a> moiety of the other. One loses a <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a> and oxygen from its carboxyl group (COOH) and the other loses a hydrogen from its amino group (NH<sub>2</sub>). This reaction produces a molecule of water (H<sub>2</sub>O) and two amino acids joined by a peptide bond (−CO−NH−). The two joined amino acids are called a dipeptide. </p><p>The amide bond is synthesized when the <a href="/wiki/Carboxyl_group" class="mw-redirect" title="Carboxyl group">carboxyl group</a> of one amino acid molecule reacts with the <a href="/wiki/Amino_group" class="mw-redirect" title="Amino group">amino group</a> of the other amino acid molecule, causing the release of a molecule of <a href="/wiki/Water" title="Water">water</a> (H<sub>2</sub>O), hence the process is a <a href="/wiki/Dehydration_synthesis" class="mw-redirect" title="Dehydration synthesis">dehydration synthesis</a> reaction. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:AminoacidCondensation.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6b/AminoacidCondensation.svg/590px-AminoacidCondensation.svg.png" decoding="async" width="590" height="137" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6b/AminoacidCondensation.svg/885px-AminoacidCondensation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6b/AminoacidCondensation.svg/1180px-AminoacidCondensation.svg.png 2x" data-file-width="576" data-file-height="134" /></a><figcaption>The dehydration condensation of two <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a> to form a peptide bond (red) with expulsion of water (blue)</figcaption></figure> <p>The formation of the peptide bond consumes energy, which, in organisms, is derived from <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a>.<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> Peptides and <a href="/wiki/Protein" title="Protein">proteins</a> are chains of <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a> held together by peptide bonds (and sometimes by a few <a href="/wiki/Isopeptide_bond" title="Isopeptide bond">isopeptide bonds</a>). Organisms use <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> to produce <a href="/wiki/Nonribosomal_peptide" title="Nonribosomal peptide">nonribosomal peptides</a>,<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Ribosome" title="Ribosome">ribosomes</a> to produce proteins via reactions that differ in details from dehydration synthesis.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Some peptides, like <a href="/wiki/Alpha-amanitin" class="mw-redirect" title="Alpha-amanitin">alpha-amanitin</a>, are called ribosomal peptides as they are made by ribosomes,<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> but many are <a href="/wiki/Nonribosomal_peptide" title="Nonribosomal peptide">nonribosomal peptides</a> as they are synthesized by specialized enzymes rather than ribosomes. For example, the tripeptide <a href="/wiki/Glutathione" title="Glutathione">glutathione</a> is synthesized in two steps from free <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a>, by two <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>: <a href="/wiki/Glutamate%E2%80%93cysteine_ligase" title="Glutamate–cysteine ligase">glutamate–cysteine ligase</a> (forms an <a href="/wiki/Isopeptide_bond" title="Isopeptide bond">isopeptide bond</a>, which is not a peptide bond) and <a href="/wiki/Glutathione_synthetase" title="Glutathione synthetase">glutathione synthetase</a> (forms a peptide bond).<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Degradation">Degradation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Peptide_bond&action=edit&section=2" title="Edit section: Degradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A peptide bond can be broken by <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> (the addition of water). The hydrolysis of peptide bonds in water releases 8–16 <a href="/wiki/Joule" title="Joule">kJ</a>/<a href="/wiki/Mole_(unit)" title="Mole (unit)">mol</a> (2–4 <a href="/wiki/Calorie" title="Calorie">kcal</a>/<a href="/wiki/Mole_(unit)" title="Mole (unit)">mol</a>) of <a href="/wiki/Gibbs_energy" class="mw-redirect" title="Gibbs energy">Gibbs energy</a>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> This process is extremely slow, with the <a href="/wiki/Half_life" class="mw-redirect" title="Half life">half life</a> at 25 °C of between 350 and 600 years per bond.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>In living organisms, the process is normally <a href="/wiki/Catalysis" title="Catalysis">catalyzed</a> by <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> known as peptidases or <a href="/wiki/Protease" title="Protease">proteases</a>, although there are reports of peptide bond hydrolysis caused by conformational strain as the peptide/protein folds into the native structure.<sup id="cite_ref-pmid18308334_11-0" class="reference"><a href="#cite_note-pmid18308334-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> This non-enzymatic process is thus not accelerated by transition state stabilization, but rather by ground-state destabilization. </p> <div class="mw-heading mw-heading2"><h2 id="Spectra">Spectra</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Peptide_bond&action=edit&section=3" title="Edit section: Spectra"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Wavelength" title="Wavelength">wavelength</a> of absorption for a peptide bond is 190–230 nm,<sup id="cite_ref-pmid14907727_12-0" class="reference"><a href="#cite_note-pmid14907727-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> which makes it particularly susceptible to <a href="/wiki/UV" class="mw-redirect" title="UV">UV</a> radiation. </p> <div class="mw-heading mw-heading2"><h2 id="Cis/trans_isomers_of_the_peptide_group"><span id="Cis.2Ftrans_isomers_of_the_peptide_group"></span>Cis/trans isomers of the peptide group</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Peptide_bond&action=edit&section=4" title="Edit section: Cis/trans isomers of the peptide group"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Significant delocalisation of the <a href="/wiki/Lone_pair" title="Lone pair">lone pair</a> of electrons on the nitrogen atom gives the group a <a href="/wiki/Amide#Structure_and_bonding" title="Amide">partial double-bond</a> character. The partial double bond renders the amide group <a href="/wiki/Plane_(geometry)" class="mw-redirect" title="Plane (geometry)">planar</a>, occurring in either the <a href="/wiki/Cis-trans_isomerism" class="mw-redirect" title="Cis-trans isomerism">cis</a> or <a href="/wiki/Trans_isomer" class="mw-redirect" title="Trans isomer">trans isomers</a>. In the unfolded state of proteins, the peptide groups are free to isomerize and adopt both isomers; however, in the folded state, only a single isomer is adopted at each position (with rare exceptions). The trans form is preferred overwhelmingly in most peptide bonds (roughly 1000:1 ratio in trans:cis populations). However, X-Pro peptide groups tend to have a roughly 30:1 ratio, presumably because the symmetry between the C<sup>α</sup> and C<sup>δ</sup> atoms of <a href="/wiki/Proline" title="Proline">proline</a> makes the cis and trans isomers nearly equal in energy, as shown in the figure below. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Cis_trans_isomerization_kinetics_X_Pro_peptide_bonds.png" class="mw-file-description"><img alt="Diagram of the isomerization of an X-Pro peptide bond. The diagram shows the cis isomer on the left, the transition states in the center, and the trans isomer on the right, with bidirectional arrows between each pair of states." src="//upload.wikimedia.org/wikipedia/commons/thumb/8/80/Cis_trans_isomerization_kinetics_X_Pro_peptide_bonds.png/500px-Cis_trans_isomerization_kinetics_X_Pro_peptide_bonds.png" decoding="async" width="500" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/8/80/Cis_trans_isomerization_kinetics_X_Pro_peptide_bonds.png 1.5x" data-file-width="704" data-file-height="310" /></a><figcaption>Isomerization of an X-Pro peptide bond. Cis and trans isomers are at far left and far right, respectively, separated by the transition states.</figcaption></figure> <p>The <a href="/wiki/Dihedral_angle" title="Dihedral angle">dihedral angle</a> associated with the peptide group (defined by the four atoms C<sup>α</sup>–C'–N–C<sup>α</sup>) is denoted <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 \omega }"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mi>ω</mi> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle \omega }</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/48eff443f9de7a985bb94ca3bde20813ea737be8" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.338ex; width:1.446ex; height:1.676ex;" alt="{\displaystyle \omega }"></span>; <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 \omega =0^{\circ }}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mi>ω</mi> <mo>=</mo> <msup> <mn>0</mn> <mrow class="MJX-TeXAtom-ORD"> <mo>∘</mo> </mrow> </msup> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle \omega =0^{\circ }}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/e9b710be60b69c480e4c079e2001af5a6b590b1d" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.338ex; width:6.761ex; height:2.343ex;" alt="{\displaystyle \omega =0^{\circ }}"></span> for the cis isomer (<a href="/wiki/Synperiplanar" class="mw-redirect" title="Synperiplanar">synperiplanar</a> conformation), and <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 \omega =180^{\circ }}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mi>ω</mi> <mo>=</mo> <msup> <mn>180</mn> <mrow class="MJX-TeXAtom-ORD"> <mo>∘</mo> </mrow> </msup> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle \omega =180^{\circ }}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/2da9a8d9f24ecd1f9f4454704d205fc14f45a7b2" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.338ex; width:9.086ex; height:2.343ex;" alt="{\displaystyle \omega =180^{\circ }}"></span> for the trans isomer (<a href="/wiki/Antiperiplanar" class="mw-redirect" title="Antiperiplanar">antiperiplanar</a> conformation). Amide groups can isomerize about the C'–N bond between the cis and trans forms, albeit slowly (<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 \tau \sim 20}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mi>τ</mi> <mo>∼</mo> <mn>20</mn> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle \tau \sim 20}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/626b7a367037ee55737a8e7f0987964da61751f5" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.338ex; width:6.625ex; height:2.176ex;" alt="{\displaystyle \tau \sim 20}"></span> seconds at room temperature). The <a href="/wiki/Transition_state" title="Transition state">transition states</a> <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 \omega =\pm 90^{\circ }}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mi>ω</mi> <mo>=</mo> <mo>±</mo> <msup> <mn>90</mn> <mrow class="MJX-TeXAtom-ORD"> <mo>∘</mo> </mrow> </msup> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle \omega =\pm 90^{\circ }}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/6e89ff7465313c9f9f34fc03fc8b366907091dd7" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.338ex; width:9.732ex; height:2.343ex;" alt="{\displaystyle \omega =\pm 90^{\circ }}"></span> requires that the partial double bond be broken, so that the activation energy is roughly 80 kJ/mol (20 kcal/mol). However, the <a href="/wiki/Activation_energy" title="Activation energy">activation energy</a> can be lowered (and the isomerization <a href="/wiki/Catalysis" title="Catalysis">catalyzed</a>) by changes that favor the single-bonded form, such as placing the peptide group in a hydrophobic environment or donating a hydrogen bond to the nitrogen atom of an X-Pro peptide group. Both of these mechanisms for lowering the activation energy have been observed in <i>peptidyl prolyl isomerases</i> (PPIases), which are naturally occurring enzymes that catalyze the cis-trans isomerization of X-Pro peptide bonds. </p><p>Conformational <a href="/wiki/Protein_folding" title="Protein folding">protein folding</a> is usually much faster (typically 10–100 ms) than cis-trans isomerization (10–100 s). A nonnative isomer of some peptide groups can disrupt the conformational folding significantly, either slowing it or preventing it from even occurring until the native isomer is reached. However, not all peptide groups have the same effect on folding; nonnative isomers of other peptide groups may not affect folding at all. </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_reactions">Chemical reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Peptide_bond&action=edit&section=5" title="Edit section: Chemical reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Due to its resonance stabilization, the peptide bond is relatively unreactive under physiological conditions, even less than similar compounds such as <a href="/wiki/Ester" title="Ester">esters</a>. Nevertheless, peptide bonds can undergo chemical reactions, usually through an attack of an <a href="/wiki/Electronegativity" title="Electronegativity">electronegative</a> atom on the <a href="/wiki/Carbonyl" class="mw-redirect" title="Carbonyl">carbonyl</a> <a href="/wiki/Carbon" title="Carbon">carbon</a>, breaking the carbonyl double bond and forming a tetrahedral intermediate. This is the pathway followed in <a href="/wiki/Proteolysis" title="Proteolysis">proteolysis</a> and, more generally, in N–O acyl exchange reactions such as those of <a href="/wiki/Intein" class="mw-redirect" title="Intein">inteins</a>. When the functional group attacking the peptide bond is a <a href="/wiki/Thiol" title="Thiol">thiol</a>, <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> or <a href="/wiki/Amine" title="Amine">amine</a>, the resulting molecule may be called a <a href="/wiki/Cyclol" title="Cyclol">cyclol</a> or, more specifically, a thiacyclol, an oxacyclol or an azacyclol, respectively. </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=Peptide_bond&action=edit&section=6" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/The_Proteolysis_Map" title="The Proteolysis Map">The Proteolysis Map</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=Peptide_bond&action=edit&section=7" 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-:0-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-:0_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:0_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:0_1-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation journal cs1"><a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1432-1033.1984.tb07877.x">"Nomenclature and Symbolism for Amino Acids and Peptides. 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Menlo Park, CA: The Benjamin/Cummings Publishing Company, Inc. p. <a rel="nofollow" class="external text" href="https://archive.org/details/molecularbiology0004unse/page/168">168</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8053-9614-0" title="Special:BookSources/978-0-8053-9614-0"><bdi>978-0-8053-9614-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Molecualar+Biology+of+the+Gene&rft.place=Menlo+Park%2C+CA&rft.pages=168&rft.edition=Fourth&rft.pub=The+Benjamin%2FCummings+Publishing+Company%2C+Inc.&rft.date=1987&rft.isbn=978-0-8053-9614-0&rft.aulast=Watson&rft.aufirst=James&rft.au=Hopkins%2C+Nancy&rft.au=Roberts%2C+Jeffrey&rft.au=Agetsinger+Steitz%2C+Joan&rft.au=Weiner%2C+Alan&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fmolecularbiology0004unse%2Fpage%2F168&rfr_id=info%3Asid%2Fen.wikipedia.org%3APeptide+bond" 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="CITEREFMiller_B._R.Gulick_A._M.2016" class="citation book cs1">Miller B. 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href="/wiki/Template_talk:Chemical_bonds" title="Template talk:Chemical bonds"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chemical_bonds" title="Special:EditPage/Template:Chemical bonds"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Chemical_bonds" style="font-size:114%;margin:0 4em"><a href="/wiki/Chemical_bond" title="Chemical bond">Chemical bonds</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Intramolecular_force" title="Intramolecular force">Intramolecular</a><br />(strong)</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/Covalent_bond" title="Covalent bond">Covalent</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/Electron_deficiency" title="Electron deficiency">Electron deficiency</a> <ul><li><a href="/wiki/Three-center_two-electron_bond" title="Three-center two-electron bond">3c–2e</a></li> <li><a href="/wiki/Four-center_two-electron_bond" title="Four-center two-electron bond">4c–2e</a></li> <li><a href="/wiki/Eight-center_two-electron_bond" class="mw-redirect" title="Eight-center two-electron bond">8c–2e</a></li></ul></li> <li><a href="/wiki/Hypervalent_molecule" title="Hypervalent molecule">Hypervalence</a> <ul><li><a href="/wiki/Three-center_four-electron_bond" title="Three-center four-electron bond">3c–4e</a></li></ul></li> <li><a href="/wiki/Agostic_interaction" title="Agostic interaction">Agostic</a></li> <li><a href="/wiki/Bent_bond" title="Bent bond">Bent</a></li> <li><a href="/wiki/Coordinate_covalent_bond" title="Coordinate covalent bond">Coordinate (dipolar)</a></li> <li><a href="/wiki/Pi_backbonding" title="Pi backbonding">Pi backbond</a></li> <li><a href="/wiki/Metal%E2%80%93ligand_multiple_bond" title="Metal–ligand multiple bond">Metal–ligand multiple bond</a></li> <li><a href="/wiki/Charge-shift_bond" title="Charge-shift bond">Charge-shift</a></li> <li><a href="/wiki/Hapticity" title="Hapticity">Hapticity</a></li> <li><a href="/wiki/Conjugated_system" title="Conjugated system">Conjugation</a></li> <li><a href="/wiki/Hyperconjugation" title="Hyperconjugation">Hyperconjugation</a></li> <li><a href="/wiki/Aromaticity" title="Aromaticity">Aromaticity</a> <ul><li><a href="/wiki/Homoaromaticity" title="Homoaromaticity">homo</a></li> <li><a href="/wiki/Bicycloaromaticity" title="Bicycloaromaticity">bicyclo</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Metallic_bonding" title="Metallic bonding">Metallic</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/Metal_aromaticity" title="Metal aromaticity">Metal aromaticity</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ionic_bonding" title="Ionic bonding">Ionic</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 class="mw-empty-elt"></li></ul> </div></td></tr></tbody></table><div></div></td><td class="noviewer navbox-image" rowspan="4" style="width:1px;padding:0 0 0 2px"><div><span typeof="mw:File"><a href="/wiki/File:Ligatio-covalens.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/200px-Ligatio-covalens.svg.png" decoding="async" width="200" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/300px-Ligatio-covalens.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/Ligatio-covalens.svg/400px-Ligatio-covalens.svg.png 2x" data-file-width="597" data-file-height="265" /></a></span><br /><span typeof="mw:File"><a href="/wiki/File:Chemfm_carbon_monoxide_3_1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/200px-Chemfm_carbon_monoxide_3_1.svg.png" decoding="async" width="200" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/300px-Chemfm_carbon_monoxide_3_1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/Chemfm_carbon_monoxide_3_1.svg/400px-Chemfm_carbon_monoxide_3_1.svg.png 2x" data-file-width="99" data-file-height="56" /></a></span><br /><span typeof="mw:File"><a href="/wiki/File:Pi-Bond.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/200px-Pi-Bond.svg.png" decoding="async" width="200" height="113" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/300px-Pi-Bond.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/70/Pi-Bond.svg/400px-Pi-Bond.svg.png 2x" data-file-width="1920" data-file-height="1080" /></a></span></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Intermolecular_force" title="Intermolecular force">Intermolecular</a><br />(weak)</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/Van_der_Waals_force" title="Van der Waals force">Van der Waals<br />forces</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/London_dispersion_force" title="London dispersion force">London dispersion</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hydrogen_bond" title="Hydrogen bond">Hydrogen</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/Low-barrier_hydrogen_bond" title="Low-barrier hydrogen bond">Low-barrier</a></li> <li><a href="/wiki/Resonance-assisted_hydrogen_bond" class="mw-redirect" title="Resonance-assisted hydrogen bond">Resonance-assisted</a></li> <li><a href="/wiki/Symmetric_hydrogen_bond" title="Symmetric hydrogen bond">Symmetric</a></li> <li><a href="/wiki/Dihydrogen_bond" title="Dihydrogen bond">Dihydrogen bonds</a></li> <li><a href="/wiki/C%E2%80%93H%C2%B7%C2%B7%C2%B7O_interaction" title="C–H···O interaction">C–H···O interaction</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Non-covalent_interactions" class="mw-redirect" title="Non-covalent interactions">Noncovalent</a><br />other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mechanically_interlocked_molecular_architectures" title="Mechanically interlocked molecular architectures">Mechanical</a></li> <li><a href="/wiki/Halogen_bond" title="Halogen bond">Halogen</a></li> <li><a href="/wiki/Chalcogen_bond" title="Chalcogen bond">Chalcogen</a></li> <li><a href="/wiki/Metallophilic_interaction" title="Metallophilic interaction">Metallophilic</a> (<a href="/wiki/Aurophilicity" title="Aurophilicity">aurophilic</a>)</li> <li><a href="/wiki/Intercalation_(chemistry)" title="Intercalation (chemistry)">Intercalation</a></li> <li><a href="/wiki/Stacking_(chemistry)" title="Stacking (chemistry)">Stacking</a></li> <li><a href="/wiki/Cation%E2%80%93pi_interaction" class="mw-redirect" title="Cation–pi interaction">Cation–pi</a></li> <li><a href="/wiki/Cation%E2%80%93pi_interaction#Anion–π_interaction" class="mw-redirect" title="Cation–pi interaction">Anion–pi</a></li> <li><a href="/wiki/Salt_bridge_(protein_and_supramolecular)" title="Salt bridge (protein and supramolecular)">Salt bridge</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bond_cleavage" title="Bond cleavage">Bond cleavage</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/Heterolysis_(chemistry)" title="Heterolysis (chemistry)">Heterolysis</a></li> <li><a href="/wiki/Homolysis_(chemistry)" title="Homolysis (chemistry)">Homolysis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Electron_counting" title="Electron counting">Electron counting</a> rules</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/Aromaticity" title="Aromaticity">Aromaticity</a> <ul><li><a href="/wiki/H%C3%BCckel%27s_rule" title="Hückel's rule">Hückel's rule</a></li> <li><a href="/wiki/Baird%27s_rule" title="Baird's rule">Baird's rule</a></li> <li><a href="/wiki/M%C3%B6bius_aromaticity" title="Möbius aromaticity">Möbius</a></li> <li><a href="/wiki/Spherical_aromaticity" title="Spherical aromaticity">spherical</a></li></ul></li> <li><a href="/wiki/Polyhedral_skeletal_electron_pair_theory" title="Polyhedral skeletal electron pair theory">Polyhedral skeletal electron pair theory</a></li> <li><a href="/wiki/Jemmis_mno_rules" title="Jemmis mno rules">Jemmis mno rules</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template: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 class="mw-selflink selflink">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 href="/wiki/Methylation" title="Methylation">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 href="/wiki/Methylation" title="Methylation">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 href="/wiki/Methylation" title="Methylation">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 href="/wiki/Methylation" title="Methylation">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 class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q33293#identifiers" title="Edit this at Wikidata"><img 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