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<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">Phosphodiester 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 32 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-32" 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">32 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_%D9%81%D9%88%D8%B3%D9%81%D8%A7%D8%AA_%D8%AB%D9%86%D8%A7%D8%A6%D9%8A_%D8%A7%D9%84%D8%A3%D8%B3%D8%AA%D8%B1" title="رابطة فوسفات ثنائي الأستر – Arabic" lang="ar" hreflang="ar" data-title="رابطة فوسفات ثنائي الأستر" 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%AB%E0%A6%B8%E0%A6%AB%E0%A7%8B%E0%A6%A1%E0%A6%BE%E0%A6%87%E0%A6%8F%E0%A6%B8%E0%A7%8D%E0%A6%9F%E0%A6%BE%E0%A6%B0_%E0%A6%AC%E0%A6%A8%E0%A7%8D%E0%A6%A7%E0%A6%A8" title="ফসফোডাইএস্টার বন্ধন – Bangla" lang="bn" hreflang="bn" data-title="ফসফোডাইএস্টার বন্ধন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Fosfodiesterska_veza" title="Fosfodiesterska veza – Bosnian" lang="bs" hreflang="bs" data-title="Fosfodiesterska 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/Fosfodi%C3%A8ster" title="Fosfodièster – Catalan" lang="ca" hreflang="ca" data-title="Fosfodièster" 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/Fosfodiesterov%C3%A1_vazba" title="Fosfodiesterová vazba – Czech" lang="cs" hreflang="cs" data-title="Fosfodiesterová 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/Fosfodiester" title="Fosfodiester – Danish" lang="da" hreflang="da" data-title="Fosfodiester" 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/Phosphodiesterbindung" title="Phosphodiesterbindung – German" lang="de" hreflang="de" data-title="Phosphodiesterbindung" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A6%CF%89%CF%83%CF%86%CE%BF%CE%B4%CE%B9%CE%B5%CF%83%CF%84%CE%B5%CF%81%CE%B9%CE%BA%CF%8C%CF%82_%CE%B4%CE%B5%CF%83%CE%BC%CF%8C%CF%82" title="Φωσφοδιεστερικός δεσμός – Greek" lang="el" hreflang="el" data-title="Φωσφοδιεστερικός 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_fosfodi%C3%A9ster" title="Enlace fosfodiéster – Spanish" lang="es" hreflang="es" data-title="Enlace fosfodiéster" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</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%81%D8%B3%D9%81%D9%88%D8%AF%DB%8C%E2%80%8C%D8%A7%D8%B3%D8%AA%D8%B1" title="پیوند فسفودی‌استر – Persian" lang="fa" hreflang="fa" data-title="پیوند فسفودی‌استر" 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_phosphodiester" title="Liaison phosphodiester – French" lang="fr" hreflang="fr" data-title="Liaison phosphodiester" 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_fosfodi%C3%A9ster" title="Enlace fosfodiéster – Galician" lang="gl" hreflang="gl" data-title="Enlace fosfodiéster" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%9D%B8%EC%82%B0%EB%8B%A4%EC%9D%B4%EC%97%90%EC%8A%A4%ED%84%B0_%EA%B2%B0%ED%95%A9" title="인산다이에스터 결합 – Korean" lang="ko" hreflang="ko" data-title="인산다이에스터 결합" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Fosfodiesterska_veza" title="Fosfodiesterska veza – Croatian" lang="hr" hreflang="hr" data-title="Fosfodiesterska veza" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Ikatan_fosfodiester" title="Ikatan fosfodiester – Indonesian" lang="id" hreflang="id" data-title="Ikatan fosfodiester" 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_fosfodiesterico" title="Legame fosfodiesterico – Italian" lang="it" hreflang="it" data-title="Legame fosfodiesterico" 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%95%D7%A1%D7%A4%D7%95%D7%93%D7%99%D7%90%D7%A1%D7%98%D7%A8%D7%99" title="קשר פוספודיאסטרי – Hebrew" lang="he" hreflang="he" data-title="קשר פוספודיאסטרי" 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%A4%E1%83%9D%E1%83%A1%E1%83%A4%E1%83%9D%E1%83%93%E1%83%98%E1%83%94%E1%83%97%E1%83%94%E1%83%A0%E1%83%A3%E1%83%9A%E1%83%98_%E1%83%91%E1%83%9B%E1%83%90" title="ფოსფოდიეთერული ბმა – Georgian" lang="ka" hreflang="ka" data-title="ფოსფოდიეთერული ბმა" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A4%D0%BE%D1%81%D1%84%D0%BE%D0%B4%D0%B8%D0%B5%D1%81%D1%82%D0%B5%D1%80%D1%81%D0%BA%D0%B0_%D0%B2%D1%80%D1%81%D0%BA%D0%B0" title="Фосфодиестерска врска – Macedonian" lang="mk" hreflang="mk" data-title="Фосфодиестерска врска" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Fosfodi-esterbinding" title="Fosfodi-esterbinding – Dutch" lang="nl" hreflang="nl" data-title="Fosfodi-esterbinding" 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%9B%E3%82%B9%E3%83%9B%E3%82%B8%E3%82%A8%E3%82%B9%E3%83%86%E3%83%AB%E7%B5%90%E5%90%88" title="ホスホジエステル結合 – Japanese" lang="ja" hreflang="ja" data-title="ホスホジエステル結合" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Wi%C4%85zanie_fosfodiestrowe" title="Wiązanie fosfodiestrowe – Polish" lang="pl" hreflang="pl" data-title="Wiązanie fosfodiestrowe" 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_fosfodi%C3%A9ster" title="Ligação fosfodiéster – Portuguese" lang="pt" hreflang="pt" data-title="Ligação fosfodiéster" 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_fosfodiesteric%C4%83" title="Legătură fosfodiesterică – Romanian" lang="ro" hreflang="ro" data-title="Legătură fosfodiesterică" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Fosfodiesterov%C3%A1_v%C3%A4zba" title="Fosfodiesterová väzba – Slovak" lang="sk" hreflang="sk" data-title="Fosfodiesterová väzba" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A4%D0%BE%D1%81%D1%84%D0%BE%D0%B4%D0%B8%D0%B5%D1%81%D1%82%D0%B0%D1%80%D1%81%D0%BA%D0%B0_%D0%B2%D0%B5%D0%B7%D0%B0" title="Фосфодиестарска веза – Serbian" lang="sr" hreflang="sr" data-title="Фосфодиестарска веза" 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/Fosfodiestarska_veza" title="Fosfodiestarska veza – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Fosfodiestarska 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/Fosfodiesterisidos" title="Fosfodiesterisidos – Finnish" lang="fi" hreflang="fi" data-title="Fosfodiesterisidos" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Fosfodiester_ba%C4%9F%C4%B1" title="Fosfodiester bağı – Turkish" lang="tr" hreflang="tr" data-title="Fosfodiester 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%A4%D0%BE%D1%81%D1%84%D0%BE%D0%B4%D1%96%D0%B5%D1%81%D1%82%D0%B5%D1%80%D0%BD%D0%B8%D0%B9_%D0%B7%D0%B2%27%D1%8F%D0%B7%D0%BE%D0%BA" title="Фосфодіестерний зв'язок – Ukrainian" lang="uk" hreflang="uk" data-title="Фосфодіестерний 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-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D9%81%D8%A7%D8%B3%D9%81%D9%88%DA%88%D8%A7%D8%A6%DB%8C_%D8%A7%DB%8C%D8%B3%D9%B9%D8%B1_%D8%A8%D8%A7%D9%86%DA%88" title="فاسفوڈائی ایسٹر بانڈ – Urdu" lang="ur" hreflang="ur" data-title="فاسفوڈائی ایسٹر بانڈ" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%A3%B7%E9%85%B8%E4%BA%8C%E9%85%AF%E9%8D%B5" title="磷酸二酯鍵 – Chinese" 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<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">–O– linkage between phosphoric acid and two other compounds</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Phosphodiester_Bond_Diagram.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Phosphodiester_Bond_Diagram.svg/200px-Phosphodiester_Bond_Diagram.svg.png" decoding="async" width="200" height="339" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Phosphodiester_Bond_Diagram.svg/300px-Phosphodiester_Bond_Diagram.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a5/Phosphodiester_Bond_Diagram.svg/400px-Phosphodiester_Bond_Diagram.svg.png 2x" data-file-width="413" data-file-height="700" /></a><figcaption>Diagram of phosphodiester bonds (<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">PO<span class="template-chem2-su"><span>3−</span><span>4</span></span></span>) between three <a href="/wiki/Nucleotide" title="Nucleotide">nucleotides</a>. The 5' end has a 5' carbon attached to a phosphate, and the other end, the 3' end, has a 3' carbon attached to a hydroxyl group.</figcaption></figure> <p>In <a href="/wiki/Chemistry" title="Chemistry">chemistry</a>, a <b>phosphodiester bond</b> occurs when exactly two of the <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl groups</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−OH</span>) in <a href="/wiki/Phosphoric_acid" title="Phosphoric acid">phosphoric acid</a> react with hydroxyl groups on other molecules to form two <a href="/wiki/Ester" title="Ester">ester</a> bonds. The "bond" involves this linkage <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">C−O−PO<span class="template-chem2-su"><span>−</span><span>2</span></span>O−C</span>.<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> Discussion of phosphodiesters is dominated by their prevalence in <a href="/wiki/DNA" title="DNA">DNA</a> and <a href="/wiki/RNA" title="RNA">RNA</a>, but phosphodiesters occur in other biomolecules, e.g. <a href="/wiki/Acyl_carrier_protein" title="Acyl carrier protein">acyl carrier proteins</a>, <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a> and the cyclic forms of GMP and AMP (cGMP and cAMP).<sup id="cite_ref-:03_2-0" class="reference"><a href="#cite_note-:03-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Phosphodiester_Backbone_of_DNA_and_RNA">Phosphodiester Backbone of DNA and RNA</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phosphodiester_bond&action=edit&section=1" title="Edit section: Phosphodiester Backbone of DNA and RNA"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phosphodiester bonds make up the <a href="/wiki/Polymer_backbone" title="Polymer backbone">backbones</a> of <a href="/wiki/DNA" title="DNA">DNA</a> and <a href="/wiki/RNA" title="RNA">RNA</a>. In the phosphodiester bonds of nucleic acids, a phosphate is attached to the 5' carbon of one nucleoside and to the 3' carbon of the adjacent nucleoside. Specifically, it is the phosphodiester bonds that link the <a href="/wiki/Directionality_(molecular_biology)" title="Directionality (molecular biology)">3' carbon atom</a> of one sugar molecule and the 5' carbon atom of another (hence the name 3', 5' phosphodiester linkage used with reference to this kind of bond in DNA and RNA chains).<sup id="cite_ref-:1_3-0" class="reference"><a href="#cite_note-:1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The involved saccharide groups are <a href="/wiki/Deoxyribose" title="Deoxyribose">deoxyribose</a> in DNA and <a href="/wiki/Ribose" title="Ribose">ribose</a> in RNA. In order for the phosphodiester bond to form<b>,</b> joining the <a href="/wiki/Nucleoside" title="Nucleoside">nucleosides</a>, the tri-phosphate or di-phosphate forms of the nucleotide building blocks are broken apart to give off energy required to drive the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a>-catalyzed reaction.<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> In DNA replication, for example, formation of the phosphodiester bonds is catalyzed by a <a href="/wiki/DNA_polymerase" title="DNA polymerase">DNA polymerase</a> <a href="/wiki/Enzyme" title="Enzyme">enzyme</a>, using a pair of <a href="/wiki/Magnesium" title="Magnesium">magnesium</a> <a href="/wiki/Ion" title="Ion">cations</a> and other supporting structures.<sup id="cite_ref-:1_3-1" class="reference"><a href="#cite_note-:1-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Formation of the bond occurs not only in DNA and RNA replication, but also in the repair and recombination of nucleic acids, and may require the involvement of various polymerases, primers, and/or ligases. During the replication of DNA, for example, the <a href="/wiki/DNA_polymerase_I" title="DNA polymerase I">DNA polymerase I</a> leaves behind a hole between the phosphates in the newly formed backbone. <a href="/wiki/DNA_ligase" title="DNA ligase">DNA ligase</a> is able to form a phosphodiester bond between the nucleotides on each side of the gap.<sup id="cite_ref-:03_2-1" class="reference"><a href="#cite_note-:03-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Phosphodiesters are negatively charged at <a href="/wiki/PH" title="PH">pH</a> 7.<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> The negative charge attracts <a href="/wiki/Histones" class="mw-redirect" title="Histones">histones</a>, metal cations such as <a href="/wiki/Magnesium_in_biology#Nucleic_acids" title="Magnesium in biology">magnesium</a>, and <a href="/wiki/Polyamine" title="Polyamine">polyamines</a> [needs citation]. Repulsion between these negative charges influences the conformation of the polynucleic acids. </p> <div class="mw-heading mw-heading2"><h2 id="Breaking_the_Phosphodiester_Bond">Breaking the Phosphodiester Bond</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phosphodiester_bond&action=edit&section=2" title="Edit section: Breaking the Phosphodiester Bond"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Hydrolysis" title="Hydrolysis">Hydrolysis</a> (breaking) of phosphodiester bonds can be promoted in several ways. <a href="/wiki/Phosphodiesterase" title="Phosphodiesterase">Phosphodiesterases</a> are enzymes that catalyze the hydrolysis of the phosphodiester bond. These enzymes are involved in repairing DNA and RNA sequences, nucleotide salvage, and in the conversion of cGMP and cAMP to GMP and AMP, respectively.<sup id="cite_ref-:03_2-2" class="reference"><a href="#cite_note-:03-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Hydrolysis of the phosphodiester bond also occurs chemically and spontaneously, without the aid of enzymes. For example, simple <a href="/wiki/Ribose" title="Ribose">ribose</a> (in RNA) has one more <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl group</a> than <a href="/wiki/Deoxyribose" title="Deoxyribose">deoxyribose</a> (in DNA), making the former less stable and more susceptible to <a href="/wiki/Alkaline_hydrolysis" class="mw-redirect" title="Alkaline hydrolysis">alkaline hydrolysis</a>, wherein relatively high pH conditions induce the breaking of the phosphodiester linkage between two <a href="/wiki/Ribonucleotide" title="Ribonucleotide">ribonucleotides</a>. The relative instability of RNA under hydroxyl attack of its phosphodiester bonds makes it inadequate for the storage of genomic information, but contributes to its usefulness in <a href="/wiki/Transcription_(biology)" title="Transcription (biology)">transcription</a> and <a href="/wiki/Translation_(biology)" title="Translation (biology)">translation</a>. <sup id="cite_ref-:03_2-3" class="reference"><a href="#cite_note-:03-2"><span class="cite-bracket">[</span>2<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=Phosphodiester_bond&action=edit&section=3" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Phosphodiesterase" title="Phosphodiesterase">Phosphodiesterase</a></li> <li><a href="/wiki/Phosphodiesterase_inhibitor" title="Phosphodiesterase inhibitor">Phosphodiesterase inhibitor</a></li> <li><a href="/wiki/DNA_replication" title="DNA replication">DNA replication</a>, <a href="/wiki/DNA" title="DNA">DNA</a>, <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/Teichoic_acid" title="Teichoic acid">Teichoic acid</a>, <a href="/wiki/DNase_I" class="mw-redirect" title="DNase I">DNase I</a></li> <li><a href="/wiki/PDE5" class="mw-redirect" title="PDE5">PDE5</a></li> <li><a href="/wiki/Nick_(DNA)" title="Nick (DNA)">Nick (DNA)</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=Phosphodiester_bond&action=edit&section=4" 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 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.citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20170630085140/https://teaching.ncl.ac.uk/bms/wiki/index.php/Phosphodiester_bond">"Phosphodiester bond"</a>. <i>School of BioMedical Sciences Wiki</i>. Archived from <a rel="nofollow" class="external text" href="https://teaching.ncl.ac.uk/bms/wiki/index.php/Phosphodiester_bond">the original</a> on 2017-06-30<span class="reference-accessdate">. Retrieved <span class="nowrap">2014-10-29</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=School+of+BioMedical+Sciences+Wiki&rft.atitle=Phosphodiester+bond&rft_id=https%3A%2F%2Fteaching.ncl.ac.uk%2Fbms%2Fwiki%2Findex.php%2FPhosphodiester_bond&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhosphodiester+bond" class="Z3988"></span></span> </li> <li id="cite_note-:03-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-:03_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:03_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:03_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-:03_2-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMiesfeldMcEvoy2021" class="citation book cs1">Miesfeld, Roger L.; McEvoy, Megan M. (2021). <i>Biochemistry</i> (2nd ed.). New York: W.W. Norton & Company. pp. 110, 397, 941, 1034–1058. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780393690453" title="Special:BookSources/9780393690453"><bdi>9780393690453</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Biochemistry&rft.place=New+York&rft.pages=110%2C+397%2C+941%2C+1034-1058&rft.edition=2nd&rft.pub=W.W.+Norton+%26+Company&rft.date=2021&rft.isbn=9780393690453&rft.aulast=Miesfeld&rft.aufirst=Roger+L.&rft.au=McEvoy%2C+Megan+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhosphodiester+bond" class="Z3988"></span></span> </li> <li id="cite_note-:1-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-:1_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:1_3-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNelsonCox2013" class="citation book cs1">Nelson, David L.; Cox, Michael M. (2013). <i>Lehninger Principles of Biochemistry</i> (6th ed.). New York: W.H. Freeman and Company. pp. 284–286, 1014–1018. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4292-3414-6" title="Special:BookSources/978-1-4292-3414-6"><bdi>978-1-4292-3414-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Lehninger+Principles+of+Biochemistry&rft.place=New+York&rft.pages=284-286%2C+1014-1018&rft.edition=6th&rft.pub=W.H.+Freeman+and+Company&rft.date=2013&rft.isbn=978-1-4292-3414-6&rft.aulast=Nelson&rft.aufirst=David+L.&rft.au=Cox%2C+Michael+M.&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhosphodiester+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="CITEREFKulkarni2008" class="citation book cs1">Kulkarni; et al. (2008). <i>Biochemistry</i>. Pragati Books. pp. 57–60.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Biochemistry&rft.pages=57-60&rft.pub=Pragati+Books&rft.date=2008&rft.au=Kulkarni&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhosphodiester+bond" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPlaisance,_Laplace2007" class="citation book cs1">Plaisance, Laplace (2007). <i>Fundamental Biochemistry</i> (3 ed.). McGraf Educational. pp. 331–334.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Fundamental+Biochemistry&rft.pages=331-334&rft.edition=3&rft.pub=McGraf+Educational&rft.date=2007&rft.au=Plaisance%2C+Laplace&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhosphodiester+bond" class="Z3988"></span></span> </li> </ol></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Phosphodiester_bond&oldid=1240193736">https://en.wikipedia.org/w/index.php?title=Phosphodiester_bond&oldid=1240193736</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Organophosphates" title="Category:Organophosphates">Organophosphates</a></li><li><a href="/wiki/Category:Molecular_biology" title="Category:Molecular biology">Molecular biology</a></li><li><a href="/wiki/Category:Biology_and_pharmacology_of_chemical_elements" title="Category:Biology and pharmacology of chemical elements">Biology and pharmacology of chemical elements</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 14 August 2024, at 01:37<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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