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class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Struttura</span> </div> </a> <button aria-controls="toc-Struttura-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Attiva/disattiva la sottosezione Struttura</span> </button> <ul id="toc-Struttura-sublist" class="vector-toc-list"> <li id="toc-Amminoacidi_standard" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Amminoacidi_standard"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Amminoacidi standard</span> </div> </a> <ul id="toc-Amminoacidi_standard-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Amminoacidi_speciali" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Amminoacidi_speciali"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Amminoacidi speciali</span> 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class="firstHeading mw-first-heading"><span class="mw-page-title-main">Amminoacidi proteinogenici</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="Vai a una voce in un'altra lingua. 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class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Proteinogena_aminokiselina" title="Proteinogena aminokiselina - bosniaco" lang="bs" hreflang="bs" data-title="Proteinogena aminokiselina" data-language-autonym="Bosanski" data-language-local-name="bosniaco" 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/Amino%C3%A0cid_prote%C3%AFnogen" title="Aminoàcid proteïnogen - catalano" lang="ca" hreflang="ca" data-title="Aminoàcid proteïnogen" data-language-autonym="Català" data-language-local-name="catalano" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Standardaminosyre" title="Standardaminosyre - danese" lang="da" hreflang="da" data-title="Standardaminosyre" data-language-autonym="Dansk" data-language-local-name="danese" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A0%CF%81%CF%89%CF%84%CE%B5%CF%8A%CE%BD%CE%BF%CE%B3%CF%8C%CE%BD%CE%B1_%CE%B1%CE%BC%CE%B9%CE%BD%CE%BF%CE%BE%CE%AD%CE%B1" title="Πρωτεϊνογόνα αμινοξέα - greco" lang="el" hreflang="el" data-title="Πρωτεϊνογόνα αμινοξέα" data-language-autonym="Ελληνικά" data-language-local-name="greco" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Proteinogenic_amino_acid" title="Proteinogenic amino acid - inglese" lang="en" hreflang="en" data-title="Proteinogenic amino acid" data-language-autonym="English" data-language-local-name="inglese" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%D8%B3%DB%8C%D8%AF_%D8%A2%D9%85%DB%8C%D9%86%D9%87_%D9%BE%D8%B1%D9%88%D8%AA%D8%A6%DB%8C%D9%86%E2%80%8C%D8%B2%D8%A7" title="اسید آمینه پروتئین‌زا - persiano" lang="fa" hreflang="fa" data-title="اسید آمینه پروتئین‌زا" data-language-autonym="فارسی" data-language-local-name="persiano" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Proteiinisynteesiin_osallistuvat_aminohapot" title="Proteiinisynteesiin osallistuvat aminohapot - finlandese" lang="fi" hreflang="fi" data-title="Proteiinisynteesiin osallistuvat aminohapot" data-language-autonym="Suomi" data-language-local-name="finlandese" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Acide_amin%C3%A9_prot%C3%A9inog%C3%A8ne" title="Acide aminé protéinogène - francese" lang="fr" hreflang="fr" data-title="Acide aminé protéinogène" data-language-autonym="Français" data-language-local-name="francese" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Aim%C3%ADonaig%C3%A9ad_pr%C3%B3it%C3%A9inigineach" title="Aimíonaigéad próitéinigineach - irlandese" lang="ga" hreflang="ga" data-title="Aimíonaigéad próitéinigineach" data-language-autonym="Gaeilge" data-language-local-name="irlandese" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Amino%C3%A1cido_proteinox%C3%A9nico" title="Aminoácido proteinoxénico - galiziano" lang="gl" hreflang="gl" data-title="Aminoácido proteinoxénico" data-language-autonym="Galego" data-language-local-name="galiziano" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%BF%E3%83%B3%E3%83%91%E3%82%AF%E8%B3%AA%E3%82%92%E6%A7%8B%E6%88%90%E3%81%99%E3%82%8B%E3%82%A2%E3%83%9F%E3%83%8E%E9%85%B8" title="タンパク質を構成するアミノ酸 - giapponese" lang="ja" hreflang="ja" data-title="タンパク質を構成するアミノ酸" data-language-autonym="日本語" data-language-local-name="giapponese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%8B%A8%EB%B0%B1%EC%A7%88%EC%83%9D%EC%84%B1%EC%84%B1_%EC%95%84%EB%AF%B8%EB%85%B8%EC%82%B0" title="단백질생성성 아미노산 - coreano" lang="ko" hreflang="ko" data-title="단백질생성성 아미노산" data-language-autonym="한국어" data-language-local-name="coreano" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Asid_amino_proteinogenik" title="Asid amino proteinogenik - malese" lang="ms" hreflang="ms" data-title="Asid amino proteinogenik" data-language-autonym="Bahasa Melayu" data-language-local-name="malese" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Prote%C3%AFnogeen_aminozuur" title="Proteïnogeen aminozuur - olandese" lang="nl" hreflang="nl" data-title="Proteïnogeen aminozuur" data-language-autonym="Nederlands" data-language-local-name="olandese" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Aminokwasy_bia%C5%82kowe" title="Aminokwasy białkowe - polacco" lang="pl" hreflang="pl" data-title="Aminokwasy białkowe" data-language-autonym="Polski" data-language-local-name="polacco" 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/Amino%C3%A1cido_proteinog%C3%A9nico" title="Aminoácido proteinogénico - portoghese" lang="pt" hreflang="pt" data-title="Aminoácido proteinogénico" data-language-autonym="Português" data-language-local-name="portoghese" 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/Aminoacid_proteinogen" title="Aminoacid proteinogen - rumeno" lang="ro" hreflang="ro" data-title="Aminoacid proteinogen" data-language-autonym="Română" data-language-local-name="rumeno" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Proteinogena_aminokiselina" title="Proteinogena aminokiselina - serbo-croato" lang="sh" hreflang="sh" data-title="Proteinogena aminokiselina" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="serbo-croato" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Prote%C3%ADnog%C3%A9nna_aminokyselina" title="Proteínogénna aminokyselina - slovacco" lang="sk" hreflang="sk" data-title="Proteínogénna aminokyselina" data-language-autonym="Slovenčina" data-language-local-name="slovacco" 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/Proteinogena_aminokiselina" title="Proteinogena aminokiselina - serbo" lang="sr" hreflang="sr" data-title="Proteinogena aminokiselina" data-language-autonym="Српски / srpski" data-language-local-name="serbo" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Asam_amino_prot%C3%A9inogenik" title="Asam amino protéinogenik - sundanese" lang="su" hreflang="su" data-title="Asam amino protéinogenik" data-language-autonym="Sunda" data-language-local-name="sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%85%E0%AE%AE%E0%AE%BF%E0%AE%A9%E0%AF%8B_%E0%AE%85%E0%AE%AE%E0%AE%BF%E0%AE%B2%E0%AE%AE%E0%AF%8D_(%E0%AE%AA%E0%AF%81%E0%AE%B0%E0%AE%A4%E0%AE%AE%E0%AE%BE%E0%AE%95%E0%AF%8D%E0%AE%95%E0%AF%81%E0%AE%AA%E0%AE%B5%E0%AF%88)" title="அமினோ அமிலம் (புரதமாக்குபவை) - tamil" lang="ta" hreflang="ta" data-title="அமினோ அமிலம் (புரதமாக்குபவை)" data-language-autonym="தமிழ்" data-language-local-name="tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%9B%8B%E7%99%BD%E8%83%BA%E5%9F%BA%E9%85%B8" title="蛋白胺基酸 - cinese" lang="zh" hreflang="zh" data-title="蛋白胺基酸" data-language-autonym="中文" data-language-local-name="cinese" 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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="it" dir="ltr"><p>Gli <b>amminoacidi proteinogenici</b> sono gli <a href="/wiki/Amminoacidi" class="mw-redirect" title="Amminoacidi">amminoacidi</a> che vengono usati per la costruzione delle <a href="/wiki/Proteine" title="Proteine">proteine</a>.<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> Essi costituiscono solo una piccola frazione di tutti amminoacidi noti: 20, detti "standard", sono codificati dal <a href="/wiki/Codice_genetico" title="Codice genetico">codice genetico</a> umano, a questi si aggiungono 2 considerati "speciali" (la <a href="/wiki/Selenocisteina" title="Selenocisteina">selenocisteina</a> e la <a href="/wiki/Pirrolisina" title="Pirrolisina">pirrolisina</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> mentre un ulteriore amminoacido, la <a href="/wiki/FMET" title="FMET">N-formilmetionina</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> è considerato tale solo da alcuni autori, essendo un derivato della <a href="/wiki/Metionina" title="Metionina">metionina</a>, portando il totale a 22 o 23.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Dei 22 amminoacidi sopra citati, 21 sono codificati dagli <a href="/wiki/Eucarioti" class="mw-redirect" title="Eucarioti">eucarioti</a>, mentre 1 (la pirrolisina) è codificato solo nei <a href="/wiki/Procarioti" class="mw-redirect" title="Procarioti">procarioti</a>. Siccome l'uomo può sintetizzarne solo 11 partendo da altri composti, mentre gli altri 9 devono essere introdotti attraverso l'alimentazione, si identificano gli <i><a href="/wiki/Amminoacidi_essenziali" title="Amminoacidi essenziali">amminoacidi essenziali</a></i> (9) e gli <i>amminoacidi non essenziali</i> (11). </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Struttura">Struttura</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amminoacidi_proteinogenici&veaction=edit&section=1" title="Modifica la sezione Struttura" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Amminoacidi_proteinogenici&action=edit&section=1" title="Edit section's source code: Struttura"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tra tutti gli amminoacidi conosciuti, solo 23 sono quelli proteinogenici. Queste 23 molecole sono molto simili tra loro e si differenziano solo per la loro porzione laterale (<span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {-R}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>R</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {-R}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/605c2359a472e43cdaeece289f0d9cfd3ad5f187" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:3.519ex; height:2.343ex;" alt="{\displaystyle {\ce {-R}}}"></span>). Esse condividono: </p> <ul><li>Un <a href="/wiki/Ammine" title="Ammine">gruppo amminico</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 {\ce {-NH2}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>NH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {-NH2}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/45f55f89d98655b98d04e2afe2ca14c7a4bdb493" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:6.349ex; height:2.843ex;" alt="{\displaystyle {\ce {-NH2}}}"></span>) e <a href="/wiki/Acidi_carbossilici" title="Acidi carbossilici">uno carbossilico</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 {\ce {-COOH}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>COOH</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {-COOH}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/6a189021951b72ae494c3a64ce3ead4c58c5e94a" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:8.846ex; height:2.343ex;" alt="{\displaystyle {\ce {-COOH}}}"></span>), i quali danno i nomi alla categoria di molecole;</li> <li>Un atomo di <a href="/wiki/Carbonio" title="Carbonio">carbonio</a> chiamato α (C<sub>α</sub>) a cui sono legati: il gruppo amminico, quello carbossilico, la porzione laterale (<span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {-R}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>R</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {-R}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/605c2359a472e43cdaeece289f0d9cfd3ad5f187" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:3.519ex; height:2.343ex;" alt="{\displaystyle {\ce {-R}}}"></span>) e un atomo di <a href="/wiki/Idrogeno" title="Idrogeno">idrogeno</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 {\ce {-H}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>H</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {-H}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/51fae9b82d7452dc1dbace378bf553606055c9a5" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:3.551ex; height:2.343ex;" alt="{\displaystyle {\ce {-H}}}"></span>). Siccome a questo carbonio sono legate 4 specie chimiche diverse, questo atomo si comporta da <a href="/wiki/Elemento_stereogenico" title="Elemento stereogenico">stereocentro</a> (la glicina fa eccezione, in quanto porta legati al C<sub>α</sub> 2 atomi di idrogeno);</li> <li>La stereoisomeria del C<sub>α</sub> è <a href="/wiki/Chiralit%C3%A0_(chimica)" title="Chiralità (chimica)">levogira</a>;</li> <li>I gruppi amminici sono <a href="/wiki/Ammina_primaria" class="mw-redirect" title="Ammina primaria">ammine primarie</a>, cioè nella forma <span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {-NH2}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>NH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {-NH2}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/45f55f89d98655b98d04e2afe2ca14c7a4bdb493" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:6.349ex; height:2.843ex;" alt="{\displaystyle {\ce {-NH2}}}"></span> e non <span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {-NH-R}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>NH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>R</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {-NH-R}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/883358e6651ce1876e343bf25e06c9cc9285ffe9" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:8.813ex; height:2.343ex;" alt="{\displaystyle {\ce {-NH-R}}}"></span> (che identificano le ammine secondarie) o <span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {-N-R2}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>N</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <msubsup> <mtext>R</mtext> <mrow class="MJX-TeXAtom-ORD"> <mn>2</mn> </mrow> <mrow class="MJX-TeXAtom-ORD"> <mspace width="0pt" height="0pt" depth=".2em" /> </mrow> </msubsup> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {-N-R2}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/4af28b42c2c7682832f5a74e6d41b60744d8d6f5" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:8.124ex; height:2.843ex;" alt="{\displaystyle {\ce {-N-R2}}}"></span> (che identificano quelle terziarie) (la prolina fa eccezione, in quanto il suo gruppo amminico è <span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {-NH-R}}}"> <semantics> <mrow class="MJX-TeXAtom-ORD"> <mstyle displaystyle="true" scriptlevel="0"> <mrow class="MJX-TeXAtom-ORD"> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>NH</mtext> <mrow class="MJX-TeXAtom-ORD"> <mo>−</mo> </mrow> <mtext>R</mtext> </mrow> </mstyle> </mrow> <annotation encoding="application/x-tex">{\displaystyle {\ce {-NH-R}}}</annotation> </semantics> </math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/883358e6651ce1876e343bf25e06c9cc9285ffe9" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -0.505ex; width:8.813ex; height:2.343ex;" alt="{\displaystyle {\ce {-NH-R}}}"></span> e rientra dunque nelle ammine secondarie).</li></ul> <p>Visto che tutti gli amminoacidi proteinogenici hanno questa struttura, vengono definiti <i>L-α-amminoacidi</i> (anche glicina e prolina che di fatto non sono L o α). Tutti gli altri amminoacidi sono classificabili come <a href="/wiki/Amminoacidi_non_proteinogenici" title="Amminoacidi non proteinogenici">amminoacidi non proteinogenici</a>. </p><p>Di seguito sono illustrate le strutture chimiche non dissociate dei 23 amminoacidi proteinogenici. Le strutture dissociate sono in realtà quelle in <a href="/wiki/Soluzione_acquosa" title="Soluzione acquosa">soluzione acquosa</a> e possono presentare sia cariche positive, sia negative, sia bilanciate in numero e posizione, sia sbilanciate, a seconda del pH e della struttura tridimensionale dell'amminoacido. </p> <div class="mw-heading mw-heading3"><h3 id="Amminoacidi_standard">Amminoacidi standard</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amminoacidi_proteinogenici&veaction=edit&section=2" title="Modifica la sezione Amminoacidi standard" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Amminoacidi_proteinogenici&action=edit&section=2" title="Edit section's source code: Amminoacidi standard"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-alanine-skeletal.png" class="mw-file-description" title="Alanina (Ala / A)"><img alt="Alanina (Ala / A)" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/L-alanine-skeletal.png/120px-L-alanine-skeletal.png" decoding="async" width="120" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/L-alanine-skeletal.png/180px-L-alanine-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/05/L-alanine-skeletal.png/240px-L-alanine-skeletal.png 2x" data-file-width="1396" data-file-height="1004" /></a></span></div> <div class="gallerytext">Alanina<br />(Ala / A)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-arginine-skeletal-(tall).png" class="mw-file-description" title="Arginina (Arg / R)"><img alt="Arginina (Arg / R)" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/L-arginine-skeletal-%28tall%29.png/71px-L-arginine-skeletal-%28tall%29.png" decoding="async" width="71" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/L-arginine-skeletal-%28tall%29.png/107px-L-arginine-skeletal-%28tall%29.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/L-arginine-skeletal-%28tall%29.png/142px-L-arginine-skeletal-%28tall%29.png 2x" data-file-width="1267" data-file-height="2135" /></a></span></div> <div class="gallerytext">Arginina<br />(Arg / R)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-asparagine-skeletal.png" class="mw-file-description" title="Asparagina (Asn / N)"><img alt="Asparagina (Asn / N)" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/L-asparagine-skeletal.png/102px-L-asparagine-skeletal.png" decoding="async" width="102" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/L-asparagine-skeletal.png/152px-L-asparagine-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/L-asparagine-skeletal.png/203px-L-asparagine-skeletal.png 2x" data-file-width="1267" data-file-height="1496" /></a></span></div> <div class="gallerytext">Asparagina<br />(Asn / N)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-aspartic-acid-skeletal.png" class="mw-file-description" title="Acido aspartico (Asp / D)"><img alt="Acido aspartico (Asp / D)" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/L-aspartic-acid-skeletal.png/102px-L-aspartic-acid-skeletal.png" decoding="async" width="102" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/L-aspartic-acid-skeletal.png/153px-L-aspartic-acid-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6e/L-aspartic-acid-skeletal.png/204px-L-aspartic-acid-skeletal.png 2x" data-file-width="1267" data-file-height="1487" /></a></span></div> <div class="gallerytext">Acido aspartico<br />(Asp / D)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-cysteine-skeletal.png" class="mw-file-description" title="Cisteina (Cys / C)"><img alt="Cisteina (Cys / C)" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/L-cysteine-skeletal.png/118px-L-cysteine-skeletal.png" decoding="async" width="118" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a5/L-cysteine-skeletal.png/177px-L-cysteine-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a5/L-cysteine-skeletal.png/236px-L-cysteine-skeletal.png 2x" data-file-width="1267" data-file-height="1288" /></a></span></div> <div class="gallerytext">Cisteina<br />(Cys / C)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-glutamic-acid-skeletal.png" class="mw-file-description" title="Acido glutammico (Glu / E)"><img alt="Acido glutammico (Glu / E)" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a8/L-glutamic-acid-skeletal.png/120px-L-glutamic-acid-skeletal.png" decoding="async" width="120" height="105" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a8/L-glutamic-acid-skeletal.png/180px-L-glutamic-acid-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a8/L-glutamic-acid-skeletal.png/240px-L-glutamic-acid-skeletal.png 2x" data-file-width="1587" data-file-height="1394" /></a></span></div> <div class="gallerytext">Acido glutammico<br />(Glu / E)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-glutamine-skeletal.png" class="mw-file-description" title="Glutammina (Gln / Q)"><img alt="Glutammina (Gln / Q)" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/91/L-glutamine-skeletal.png/120px-L-glutamine-skeletal.png" decoding="async" width="120" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/91/L-glutamine-skeletal.png/180px-L-glutamine-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/91/L-glutamine-skeletal.png/240px-L-glutamine-skeletal.png 2x" data-file-width="1748" data-file-height="1422" /></a></span></div> <div class="gallerytext">Glutammina<br />(Gln / Q)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Glycine-skeletal.png" class="mw-file-description" title="Glicina (Gly / G)"><img alt="Glicina (Gly / G)" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Glycine-skeletal.png/120px-Glycine-skeletal.png" decoding="async" width="120" height="64" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Glycine-skeletal.png/180px-Glycine-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Glycine-skeletal.png/240px-Glycine-skeletal.png 2x" data-file-width="1396" data-file-height="743" /></a></span></div> <div class="gallerytext">Glicina<br />(Gly / G)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-histidine-skeletal.png" class="mw-file-description" title="Istidina (His / H)"><img alt="Istidina (His / H)" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/L-histidine-skeletal.png/101px-L-histidine-skeletal.png" decoding="async" width="101" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/L-histidine-skeletal.png/152px-L-histidine-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/L-histidine-skeletal.png/203px-L-histidine-skeletal.png 2x" data-file-width="1446" data-file-height="1711" /></a></span></div> <div class="gallerytext">Istidina<br />(His / H)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-isoleucine-skeletal.svg" class="mw-file-description" title="Isoleucina (Ile / I)"><img alt="Isoleucina (Ile / I)" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/L-isoleucine-skeletal.svg/120px-L-isoleucine-skeletal.svg.png" decoding="async" width="120" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e8/L-isoleucine-skeletal.svg/180px-L-isoleucine-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e8/L-isoleucine-skeletal.svg/240px-L-isoleucine-skeletal.svg.png 2x" data-file-width="512" data-file-height="495" /></a></span></div> <div class="gallerytext">Isoleucina<br />(Ile / I)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-leucine-skeletal.png" class="mw-file-description" title="Leucina (Leu / L)"><img alt="Leucina (Leu / L)" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/L-leucine-skeletal.png/113px-L-leucine-skeletal.png" decoding="async" width="113" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/L-leucine-skeletal.png/170px-L-leucine-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/29/L-leucine-skeletal.png/227px-L-leucine-skeletal.png 2x" data-file-width="1396" data-file-height="1476" /></a></span></div> <div class="gallerytext">Leucina<br />(Leu / L)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-lysine-skeletal.png" class="mw-file-description" title="Lisina (Lys / K)"><img alt="Lisina (Lys / K)" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/04/L-lysine-skeletal.png/120px-L-lysine-skeletal.png" decoding="async" width="120" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/04/L-lysine-skeletal.png/180px-L-lysine-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/04/L-lysine-skeletal.png/240px-L-lysine-skeletal.png 2x" data-file-width="1977" data-file-height="1462" /></a></span></div> <div class="gallerytext">Lisina<br />(Lys / K)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-methionine-skeletal.png" class="mw-file-description" title="Metionina (Met / M)"><img alt="Metionina (Met / M)" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/L-methionine-skeletal.png/120px-L-methionine-skeletal.png" decoding="async" width="120" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/L-methionine-skeletal.png/180px-L-methionine-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/db/L-methionine-skeletal.png/240px-L-methionine-skeletal.png 2x" data-file-width="1467" data-file-height="1235" /></a></span></div> <div class="gallerytext">Metionina<br />(Met / M)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-phenylalanine-skeletal.png" class="mw-file-description" title="Fenilalanina (Phe / F)"><img alt="Fenilalanina (Phe / F)" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/L-phenylalanine-skeletal.png/118px-L-phenylalanine-skeletal.png" decoding="async" width="118" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/42/L-phenylalanine-skeletal.png/177px-L-phenylalanine-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/42/L-phenylalanine-skeletal.png/235px-L-phenylalanine-skeletal.png 2x" data-file-width="1551" data-file-height="1581" /></a></span></div> <div class="gallerytext">Fenilalanina<br />(Phe / F)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-proline-skeletal.png" class="mw-file-description" title="Prolina (Pro / P)"><img alt="Prolina (Pro / P)" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/L-proline-skeletal.png/120px-L-proline-skeletal.png" decoding="async" width="120" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/L-proline-skeletal.png/180px-L-proline-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d7/L-proline-skeletal.png/240px-L-proline-skeletal.png 2x" data-file-width="1355" data-file-height="1046" /></a></span></div> <div class="gallerytext">Prolina<br />(Pro / P)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-serine-skeletal.png" class="mw-file-description" title="Serina (Ser / S)"><img alt="Serina (Ser / S)" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/L-serine-skeletal.png/120px-L-serine-skeletal.png" decoding="async" width="120" height="106" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/L-serine-skeletal.png/180px-L-serine-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e2/L-serine-skeletal.png/240px-L-serine-skeletal.png 2x" data-file-width="1267" data-file-height="1115" /></a></span></div> <div class="gallerytext">Serina<br />(Ser / S)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-threonine-skeletal.png" class="mw-file-description" title="Treonina (Thr / T)"><img alt="Treonina (Thr / T)" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/L-threonine-skeletal.png/120px-L-threonine-skeletal.png" decoding="async" width="120" height="107" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/L-threonine-skeletal.png/180px-L-threonine-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3e/L-threonine-skeletal.png/240px-L-threonine-skeletal.png 2x" data-file-width="2520" data-file-height="2240" /></a></span></div> <div class="gallerytext">Treonina<br />(Thr / T)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-tryptophan-skeletal.png" class="mw-file-description" title="Triptofano (Trp / W)"><img alt="Triptofano (Trp / W)" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b8/L-tryptophan-skeletal.png/111px-L-tryptophan-skeletal.png" decoding="async" width="111" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b8/L-tryptophan-skeletal.png/167px-L-tryptophan-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b8/L-tryptophan-skeletal.png/223px-L-tryptophan-skeletal.png 2x" data-file-width="1780" data-file-height="1916" /></a></span></div> <div class="gallerytext">Triptofano<br />(Trp / W)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-tyrosine-skeletal.png" class="mw-file-description" title="Tirosina (Tyr / Y)"><img alt="Tirosina (Tyr / Y)" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/L-tyrosine-skeletal.png/120px-L-tyrosine-skeletal.png" decoding="async" width="120" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/L-tyrosine-skeletal.png/180px-L-tyrosine-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5c/L-tyrosine-skeletal.png/240px-L-tyrosine-skeletal.png 2x" data-file-width="2000" data-file-height="1643" /></a></span></div> <div class="gallerytext">Tirosina<br />(Tyr / Y)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-valine-skeletal.png" class="mw-file-description" title="Valina (Val / V)"><img alt="Valina (Val / V)" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/52/L-valine-skeletal.png/120px-L-valine-skeletal.png" decoding="async" width="120" height="102" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/52/L-valine-skeletal.png/180px-L-valine-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/52/L-valine-skeletal.png/240px-L-valine-skeletal.png 2x" data-file-width="1396" data-file-height="1186" /></a></span></div> <div class="gallerytext">Valina<br />(Val / V)</div> </li> </ul> <div class="mw-heading mw-heading3"><h3 id="Amminoacidi_speciali">Amminoacidi speciali</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amminoacidi_proteinogenici&veaction=edit&section=3" title="Modifica la sezione Amminoacidi speciali" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Amminoacidi_proteinogenici&action=edit&section=3" title="Edit section's source code: Amminoacidi speciali"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:L-selenocysteine-2D-skeletal.png" class="mw-file-description" title="Selenocysteine (Sec / U)"><img alt="Selenocysteine (Sec / U)" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/L-selenocysteine-2D-skeletal.png/120px-L-selenocysteine-2D-skeletal.png" decoding="async" width="120" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/L-selenocysteine-2D-skeletal.png/180px-L-selenocysteine-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3a/L-selenocysteine-2D-skeletal.png/240px-L-selenocysteine-2D-skeletal.png 2x" data-file-width="1100" data-file-height="928" /></a></span></div> <div class="gallerytext">Selenocysteine<br />(Sec / U)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Pyrrolysine.svg" class="mw-file-description" title="Pyrrolysine (Pyl / O)"><img alt="Pyrrolysine (Pyl / O)" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Pyrrolysine.svg/120px-Pyrrolysine.svg.png" decoding="async" width="120" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Pyrrolysine.svg/180px-Pyrrolysine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/71/Pyrrolysine.svg/240px-Pyrrolysine.svg.png 2x" data-file-width="560" data-file-height="180" /></a></span></div> <div class="gallerytext">Pyrrolysine<br />(Pyl / O)</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:(S)-N-Formylmethionine_V.1.svg" class="mw-file-description" title="N-Formilmetionina (fMet)"><img alt="N-Formilmetionina (fMet)" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/%28S%29-N-Formylmethionine_V.1.svg/120px-%28S%29-N-Formylmethionine_V.1.svg.png" decoding="async" width="120" height="81" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/%28S%29-N-Formylmethionine_V.1.svg/180px-%28S%29-N-Formylmethionine_V.1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2f/%28S%29-N-Formylmethionine_V.1.svg/240px-%28S%29-N-Formylmethionine_V.1.svg.png 2x" data-file-width="430" data-file-height="289" /></a></span></div> <div class="gallerytext">N-Formilmetionina<br />(fMet)</div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="Proprietà_Chimiche"><span id="Propriet.C3.A0_Chimiche"></span>Proprietà Chimiche</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amminoacidi_proteinogenici&veaction=edit&section=4" title="Modifica la sezione Proprietà Chimiche" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Amminoacidi_proteinogenici&action=edit&section=4" title="Edit section's source code: Proprietà Chimiche"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>La tabella mostra le proprietà chimiche degli amminoacidi proteinogenici. La stima delle masse si basa sulle medie pesate degli isotopi e delle abbondanze naturali. </p> <table class="wikitable sortable" style="text-align:center;"> <tbody><tr> <th>Amminoacido </th> <th>Abbreviazione <p>(lettera) </p> </th> <th>Abbreviazione <p>(sigla) </p> </th> <th><a href="/wiki/Massa_molecolare" title="Massa molecolare">Massa molecolare</a> (<a href="/wiki/Unit%C3%A0_di_massa_atomica" title="Unità di massa atomica">U.m.a.</a>) </th> <th><a href="/wiki/Punto_isoelettrico" title="Punto isoelettrico">Punto isoelettrico</a> </th> <th><a href="/wiki/Costante_di_dissociazione_acida" title="Costante di dissociazione acida">pK<sub>1</sub></a><br />(α-COOH) </th> <th><a href="/wiki/Costante_di_dissociazione_acida" title="Costante di dissociazione acida">pK<sub>2</sub></a><br />(α-<sup>+</sup>NH<sub>3</sub>) </th></tr> <tr> <th><a href="/wiki/Alanina" title="Alanina">Alanina</a> </th> <td>A </td> <td>Ala </td> <td>89.09404 </td> <td>6.01 </td> <td>2.35 </td> <td>9.87 </td></tr> <tr> <th><a href="/wiki/Cisteina" title="Cisteina">Cisteina</a> </th> <td>C </td> <td>Cys </td> <td>121.15404 </td> <td>5.05 </td> <td>1.92 </td> <td>10.70 </td></tr> <tr> <th><a href="/wiki/Acido_aspartico" title="Acido aspartico">Acido aspartico</a> </th> <td>D </td> <td>Asp </td> <td>133.10384 </td> <td>2.85 </td> <td>1.99 </td> <td>9.90 </td></tr> <tr> <th><a href="/wiki/Acido_glutammico" title="Acido glutammico">Acido glutammico</a> </th> <td>E </td> <td>Glu </td> <td>147.13074 </td> <td>3.15 </td> <td>2.10 </td> <td>9.47 </td></tr> <tr> <th><a href="/wiki/Fenilalanina" title="Fenilalanina">Fenilalanina</a> </th> <td>F </td> <td>Phe </td> <td>165.19184 </td> <td>5.49 </td> <td>2.20 </td> <td>9.31 </td></tr> <tr> <th><a href="/wiki/Glicina" title="Glicina">Glicina</a> </th> <td>G </td> <td>Gly </td> <td>75.06714 </td> <td>6.06 </td> <td>2.35 </td> <td>9.78 </td></tr> <tr> <th><a href="/wiki/Istidina" title="Istidina">Istidina</a> </th> <td>H </td> <td>His </td> <td>155.15634 </td> <td>7.60 </td> <td>1.80 </td> <td>9.33 </td></tr> <tr> <th><a href="/wiki/Isoleucina" title="Isoleucina">Isoleucina</a> </th> <td>I </td> <td>Ile </td> <td>131.17464 </td> <td>6.05 </td> <td>2.32 </td> <td>9.76 </td></tr> <tr> <th><a href="/wiki/Lisina" title="Lisina">Lisina</a> </th> <td>K </td> <td>Lys </td> <td>146.18934 </td> <td>9.60 </td> <td>2.16 </td> <td>9.06 </td></tr> <tr> <th><a href="/wiki/Leucina" title="Leucina">Leucina</a> </th> <td>L </td> <td>Leu </td> <td>131.17464 </td> <td>6.01 </td> <td>2.33 </td> <td>9.74 </td></tr> <tr> <th><a href="/wiki/Metionina" title="Metionina">Metionina</a> </th> <td>M </td> <td>Met </td> <td>149.20784 </td> <td>5.74 </td> <td>2.13 </td> <td>9.28 </td></tr> <tr> <th><a href="/wiki/Asparagina" title="Asparagina">Asparagina</a> </th> <td>N </td> <td>Asn </td> <td>132.11904 </td> <td>5.41 </td> <td>2.14 </td> <td>8.72 </td></tr> <tr> <th><a href="/wiki/Pirrolisina" title="Pirrolisina">Pirrolisina</a> </th> <td>O </td> <td>Pyl </td> <td>255.31 </td> <td> </td> <td> </td> <td> </td></tr> <tr> <th><a href="/wiki/Prolina" title="Prolina">Prolina</a> </th> <td>P </td> <td>Pro </td> <td>115.13194 </td> <td>6.30 </td> <td>1.95 </td> <td>10.64 </td></tr> <tr> <th><a href="/wiki/Glutammina" title="Glutammina">Glutammina</a> </th> <td>Q </td> <td>Gln </td> <td>146.14594 </td> <td>5.65 </td> <td>2.17 </td> <td>9.13 </td></tr> <tr> <th><a href="/wiki/Arginina" title="Arginina">Arginina</a> </th> <td>R </td> <td>Arg </td> <td>174.20274 </td> <td>10.76 </td> <td>1.82 </td> <td>8.99 </td></tr> <tr> <th><a href="/wiki/Serina_(chimica)" title="Serina (chimica)">Serina</a> </th> <td>S </td> <td>Ser </td> <td>105.09344 </td> <td>5.68 </td> <td>2.19 </td> <td>9.21 </td></tr> <tr> <th><a href="/wiki/Treonina" title="Treonina">Treonina</a> </th> <td>T </td> <td>Thr </td> <td>119.12034 </td> <td>5.60 </td> <td>2.09 </td> <td>9.10 </td></tr> <tr> <th><a href="/wiki/Selenocisteina" title="Selenocisteina">Selenocisteina</a> </th> <td>U </td> <td>Sec </td> <td>168.053 </td> <td>5.47 </td> <td> </td> <td> </td></tr> <tr> <th><a href="/wiki/Valina" title="Valina">Valina</a> </th> <td>V </td> <td>Val </td> <td>117.14784 </td> <td>6.00 </td> <td>2.39 </td> <td>9.74 </td></tr> <tr> <th><a href="/wiki/Triptofano" title="Triptofano">Triptofano</a> </th> <td>W </td> <td>Trp </td> <td>204.22844 </td> <td>5.89 </td> <td>2.46 </td> <td>9.41 </td></tr> <tr> <th><a href="/wiki/Tirosina" title="Tirosina">Tirosina</a> </th> <td>Y </td> <td>Tyr </td> <td>181.19124 </td> <td>5.64 </td> <td>2.20 </td> <td>9.21 </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Codice_genetico">Codice genetico</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amminoacidi_proteinogenici&veaction=edit&section=5" title="Modifica la sezione Codice genetico" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Amminoacidi_proteinogenici&action=edit&section=5" title="Edit section's source code: Codice genetico"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>I 22 amminoacidi proteinogenici sono codificati nell'<a href="/wiki/RNA" title="RNA">RNA</a>, e quindi anche nel <a href="/wiki/DNA" title="DNA">DNA</a>, in <a href="/wiki/Codone" title="Codone">codoni</a>, ossia in sequenze di 3 <a href="/wiki/Base_azotata" title="Base azotata">basi azotate</a>. Questa codifica è condivisa da tutti gli esseri viventi conosciuti, il ché suggerisce che il <a href="/wiki/Codice_genetico" title="Codice genetico">codice genetico</a> si sia evoluto prima di qualsiasi forma di vita e che si sia mantenuto invariato durante tutta l'evoluzione. </p><p>Il numero di possibili sequenze ternarie è 4<sup>3</sup> cioè 64, ma siccome gli amminoacidi sono 22 è naturale a molti di questi corrispondano più sequenze codificanti. Questa caratteristica del codice genetico è definita <i>ridondanza</i> ed è un meccanismo di prevenzione dalle mutazioni genetiche, che modificando i codoni possono modificare, a valle, la struttura di una proteina, rendendola potenzialmente inefficiente. </p> <table class="wikitable sortable" style="text-align:center;"> <tbody><tr> <th>Amminoacido </th> <th>Abbreviazione (lettera) </th> <th>Abbreviazione (sigla) </th> <th><a href="/wiki/Codone" title="Codone">Codoni</a> che lo codificano </th> <th>Frequenza nelle proteine <a href="/wiki/Archaea" title="Archaea">Archeane</a> (%)<sup id="cite_ref-:1_5-0" class="reference"><a href="#cite_note-:1-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:0_6-0" class="reference"><a href="#cite_note-:0-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </th> <th>Frequenza nelle proteine <a href="/wiki/Bacteria" title="Bacteria">batteriche</a> (%)<sup id="cite_ref-:1_5-1" class="reference"><a href="#cite_note-:1-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:0_6-1" class="reference"><a href="#cite_note-:0-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </th> <th>Frequenza nelle proteine <a href="/wiki/Eukaryota" title="Eukaryota">eucariotiche</a> (%)<sup id="cite_ref-:1_5-2" class="reference"><a href="#cite_note-:1-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:0_6-2" class="reference"><a href="#cite_note-:0-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </th> <th>Frequenza nelle proteine <a href="/wiki/Homo_sapiens" title="Homo sapiens">umane</a> (%)<sup id="cite_ref-:1_5-3" class="reference"><a href="#cite_note-:1-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:0_6-3" class="reference"><a href="#cite_note-:0-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </th> <th><a href="/wiki/Amminoacidi_essenziali" title="Amminoacidi essenziali">Amminoacido essenziale</a><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> </th> <th>Abbondanza per cellula di <i><a href="/wiki/Escherichia_coli" title="Escherichia coli">E. coli</a></i><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><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> </th></tr> <tr> <th><a href="/wiki/Alanina" title="Alanina">Alanina</a> </th> <td>A </td> <td>Ala </td> <td>GCU, GCC, GCA, GCG </td> <td>8.2 </td> <td>10.06 </td> <td>7.63 </td> <td>7.01 </td> <td>- </td> <td>2,9 </td></tr> <tr> <th><a href="/wiki/Cisteina" title="Cisteina">Cisteina</a> </th> <td>C </td> <td>Cys </td> <td>UGU, UGC </td> <td>0.98 </td> <td>0.94 </td> <td>1.76 </td> <td>2.3 </td> <td>+- </td> <td>0,52 </td></tr> <tr> <th><a href="/wiki/Acido_aspartico" title="Acido aspartico">Acido aspartico</a> </th> <td>D </td> <td>Asp </td> <td>GAU, GAC </td> <td>6.21 </td> <td>5.59 </td> <td>5.4 </td> <td>4.73 </td> <td>- </td> <td>1,4 </td></tr> <tr> <th><a href="/wiki/Acido_glutammico" title="Acido glutammico">Acido glutammico</a> </th> <td>E </td> <td>Glu </td> <td>GAA, GAG </td> <td>7.69 </td> <td>6.15 </td> <td>6.42 </td> <td>7.09 </td> <td>+- </td> <td>1,5 </td></tr> <tr> <th><a href="/wiki/Fenilalanina" title="Fenilalanina">Fenilalanina</a> </th> <td>F </td> <td>Phe </td> <td>UUU, UUC </td> <td>3.86 </td> <td>3.89 </td> <td>3.87 </td> <td>3.65 </td> <td>- </td> <td>1,1 </td></tr> <tr> <th><a href="/wiki/Glicina" title="Glicina">Glicina</a> </th> <td>G </td> <td>Gly </td> <td>GGU, GGC, GGA, GGG </td> <td>7.58 </td> <td>7.76 </td> <td>6.33 </td> <td>6.58 </td> <td>+- </td> <td>3,5 </td></tr> <tr> <th><a href="/wiki/Istidina" title="Istidina">Istidina</a> </th> <td>H </td> <td>His </td> <td>CAU, CAC </td> <td>1.77 </td> <td>2.06 </td> <td>2.44 </td> <td>2.63 </td> <td>+ </td> <td>0,54 </td></tr> <tr> <th><a href="/wiki/Isoleucina" title="Isoleucina">Isoleucina</a> </th> <td>I </td> <td>Ile </td> <td>AUU, AUC, AUA </td> <td>7.03 </td> <td>5.89 </td> <td>5.1 </td> <td>4.33 </td> <td>+ </td> <td>1,7 </td></tr> <tr> <th><a href="/wiki/Lisina" title="Lisina">Lisina</a> </th> <td>K </td> <td>Lys </td> <td>AAA, AAG </td> <td>5.27 </td> <td>4.68 </td> <td>5.64 </td> <td>5.72 </td> <td>+ </td> <td>2,0 </td></tr> <tr> <th><a href="/wiki/Leucina" title="Leucina">Leucina</a> </th> <td>L </td> <td>Leu </td> <td>UUA, UUG, CUU, CUC, CUA, CUG </td> <td>9.31 </td> <td>10.09 </td> <td>9.29 </td> <td>9.97 </td> <td>+ </td> <td>2,6 </td></tr> <tr> <th><a href="/wiki/Metionina" title="Metionina">Metionina</a> </th> <td>M </td> <td>Met </td> <td>AUG </td> <td>2.35 </td> <td>2.38 </td> <td>2.25 </td> <td>2.13 </td> <td>+ </td> <td>0,88 </td></tr> <tr> <th><a href="/wiki/Asparagina" title="Asparagina">Asparagina</a> </th> <td>N </td> <td>Asn </td> <td>AAU, AAC </td> <td>3.68 </td> <td>3.58 </td> <td>4.28 </td> <td>3.58 </td> <td>- </td> <td>1,4 </td></tr> <tr> <th><a href="/wiki/Pirrolisina" title="Pirrolisina">Pirrolisina</a> </th> <td>O </td> <td>Pyl </td> <td>UAG<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </td> <td>0 </td> <td>0 </td> <td>0 </td> <td>0 </td> <td>- </td> <td> </td></tr> <tr> <th><a href="/wiki/Prolina" title="Prolina">Prolina</a> </th> <td>P </td> <td>Pro </td> <td>CCU, CCC, CCA, CCG </td> <td>4.26 </td> <td>4.61 </td> <td>5.41 </td> <td>6.31 </td> <td>- </td> <td>1,3 </td></tr> <tr> <th><a href="/wiki/Glutammina" title="Glutammina">Glutammina</a> </th> <td>Q </td> <td>Gln </td> <td>CAA, CAG </td> <td>2.38 </td> <td>3.58 </td> <td>4.21 </td> <td>4.77 </td> <td>- </td> <td>1,5 </td></tr> <tr> <th><a href="/wiki/Arginina" title="Arginina">Arginina</a> </th> <td>R </td> <td>Arg </td> <td>CGU, CGC, CGA, CGG, AGA, AGG </td> <td>5.51 </td> <td>5.88 </td> <td>5.71 </td> <td>5.64 </td> <td>+- </td> <td>1,7 </td></tr> <tr> <th><a href="/wiki/Serina_(chimica)" title="Serina (chimica)">Serina</a> </th> <td>S </td> <td>Ser </td> <td>UCU, UCC, UCA, UCG, AGU, AGC </td> <td>6.17 </td> <td>5.85 </td> <td>8.34 </td> <td>8.33 </td> <td>- </td> <td>1,2 </td></tr> <tr> <th><a href="/wiki/Treonina" title="Treonina">Treonina</a> </th> <td>T </td> <td>Thr </td> <td>ACU, ACC, ACA, ACG </td> <td>5.44 </td> <td>5.52 </td> <td>5.56 </td> <td>5.36 </td> <td>+ </td> <td>1,5 </td></tr> <tr> <th><a href="/wiki/Selenocisteina" title="Selenocisteina">Selenocisteina</a> </th> <td>U </td> <td>Sec </td> <td>UGA<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </td> <td>0 </td> <td>0 </td> <td>0 </td> <td>>0 </td> <td>- </td> <td> </td></tr> <tr> <th><a href="/wiki/Valina" title="Valina">Valina</a> </th> <td>V </td> <td>Val </td> <td>GUU, GUC, GUA, GUG </td> <td>7.8 </td> <td>7.27 </td> <td>6.2 </td> <td>5.96 </td> <td>+ </td> <td>2,4 </td></tr> <tr> <th><a href="/wiki/Triptofano" title="Triptofano">Triptofano</a> </th> <td>W </td> <td>Trp </td> <td>UGG </td> <td>1.03 </td> <td>1.27 </td> <td>1.24 </td> <td>1.22 </td> <td>+ </td> <td>0,33 </td></tr> <tr> <th><a href="/wiki/Tirosina" title="Tirosina">Tirosina</a> </th> <td>Y </td> <td>Tyr </td> <td>UAU, UAC </td> <td>3.35 </td> <td>2.94 </td> <td>2.87 </td> <td>2.66 </td> <td>+- </td> <td>0,76 </td></tr> <tr> <th><a href="/wiki/Codone_di_stop" title="Codone di stop">Stop</a> </th> <td>Stop </td> <td>Stop </td> <td>UAA, UAG, UGA<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </td> <td>- </td> <td>- </td> <td>- </td> <td>- </td> <td> </td> <td>- </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Spettrometria_di_massa">Spettrometria di massa</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amminoacidi_proteinogenici&veaction=edit&section=6" title="Modifica la sezione Spettrometria di massa" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Amminoacidi_proteinogenici&action=edit&section=6" title="Edit section's source code: Spettrometria di massa"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Nella <a href="/wiki/Spettrometria_di_massa" title="Spettrometria di massa">spettrometria di massa</a> dei peptidi e delle proteine è utile conoscere le masse dei residui, in quanto la massa del peptide o della proteina è la somma della massa dei residui più la massa della molecola di acqua (che viene persa durante la formazione del <a href="/wiki/Legame_peptidico" title="Legame peptidico">legame peptidico</a>).<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable sortable" style="text-align: center"> <tbody><tr> <th>Amminoacido </th> <th>Abbr. breve </th> <th>Abbreviazione </th> <th>Formula </th> <th>Massa monoisotopica (<a href="/wiki/Peso_atomico" class="mw-redirect" title="Peso atomico">Masse atomiche</a>) </th> <th>Massa media (Masse atomiche) </th></tr> <tr> <th><a href="/wiki/Alanina" title="Alanina">Alanina</a> </th> <td>A </td> <td>Ala </td> <td>C<sub>3</sub>H<sub>5</sub>NO </td> <td>71.03711 </td> <td>71.0788 </td></tr> <tr> <th><a href="/wiki/Cisteina" title="Cisteina">Cisteina</a> </th> <td>C </td> <td>Cys </td> <td>C<sub>3</sub>H<sub>5</sub>NOS </td> <td>103.00919 </td> <td>103.1388 </td></tr> <tr> <th><a href="/wiki/Acido_aspartico" title="Acido aspartico">Acido aspartico</a> </th> <td>D </td> <td>Asp </td> <td>C<sub>4</sub>H<sub>5</sub>NO<sub>3</sub> </td> <td>115.02694 </td> <td>115.0886 </td></tr> <tr> <th><a href="/wiki/Acido_glutammico" title="Acido glutammico">Acido glutammico</a> </th> <td>E </td> <td>Glu </td> <td>C<sub>5</sub>H<sub>7</sub>NO<sub>3</sub> </td> <td>129.04259 </td> <td>129.1155 </td></tr> <tr> <th><a href="/wiki/Fenilalanina" title="Fenilalanina">Fenilalanina</a> </th> <td>F </td> <td>Phe </td> <td>C<sub>9</sub>H<sub>9</sub>NO </td> <td>147.06841 </td> <td>147.1766 </td></tr> <tr> <th><a href="/wiki/Glicina" title="Glicina">Glicina</a> </th> <td>G </td> <td>Gly </td> <td>C<sub>2</sub>H<sub>3</sub>NO </td> <td>57.02146 </td> <td>57.0519 </td></tr> <tr> <th><a href="/wiki/Istidina" title="Istidina">Istidina</a> </th> <td>H </td> <td>His </td> <td>C<sub>6</sub>H<sub>7</sub>N<sub>3</sub>O </td> <td>137.05891 </td> <td>137.1411 </td></tr> <tr> <th><a href="/wiki/Isoleucina" title="Isoleucina">Isoleucina</a> </th> <td>I </td> <td>Ile </td> <td>C<sub>6</sub>H<sub>11</sub>NO </td> <td>113.08406 </td> <td>113.1594 </td></tr> <tr> <th><a href="/wiki/Lisina" title="Lisina">Lisina</a> </th> <td>K </td> <td>Lys </td> <td>C<sub>6</sub>H<sub>12</sub>N<sub>2</sub>O </td> <td>128.09496 </td> <td>128.1741 </td></tr> <tr> <th><a href="/wiki/Leucina" title="Leucina">Leucina</a> </th> <td>L </td> <td>Leu </td> <td>C<sub>6</sub>H<sub>11</sub>NO </td> <td>113.08406 </td> <td>113.1594 </td></tr> <tr> <th><a href="/wiki/Metionina" title="Metionina">Metionina</a> </th> <td>M </td> <td>Met </td> <td>C<sub>5</sub>H<sub>9</sub>NOS </td> <td>131.04049 </td> <td>131.1986 </td></tr> <tr> <th><a href="/wiki/Asparagina" title="Asparagina">Asparagina</a> </th> <td>N </td> <td>Asn </td> <td>C<sub>4</sub>H<sub>6</sub>N<sub>2</sub>O<sub>2</sub> </td> <td>114.04293 </td> <td>114.1039 </td></tr> <tr> <th><a href="/wiki/Pirrolisina" title="Pirrolisina">Pirrolisina</a> </th> <td>O </td> <td>Pyl </td> <td>C<sub>12</sub>H<sub>21</sub>N<sub>3</sub>O<sub>3</sub> </td> <td>255.15829 </td> <td>255.3172 </td></tr> <tr> <th><a href="/wiki/Prolina" title="Prolina">Prolina</a> </th> <td>P </td> <td>Pro </td> <td>C<sub>5</sub>H<sub>7</sub>NO </td> <td>97.05276 </td> <td>97.1167 </td></tr> <tr> <th><a href="/wiki/Glutammina" title="Glutammina">Glutammina</a> </th> <td>Q </td> <td>Gln </td> <td>C<sub>5</sub>H<sub>8</sub>N<sub>2</sub>O<sub>2</sub> </td> <td>128.05858 </td> <td>128.1307 </td></tr> <tr> <th><a href="/wiki/Arginina" title="Arginina">Arginina</a> </th> <td>R </td> <td>Arg </td> <td>C<sub>6</sub>H<sub>12</sub>N<sub>4</sub>O </td> <td>156.10111 </td> <td>156.1875 </td></tr> <tr> <th><a href="/wiki/Serina_(chimica)" title="Serina (chimica)">Serina</a> </th> <td>S </td> <td>Ser </td> <td>C<sub>3</sub>H<sub>5</sub>NO<sub>2</sub> </td> <td>87.03203 </td> <td>87.0782 </td></tr> <tr> <th><a href="/wiki/Treonina" title="Treonina">Treonina</a> </th> <td>T </td> <td>Thr </td> <td>C<sub>4</sub>H<sub>7</sub>NO<sub>2</sub> </td> <td>101.04768 </td> <td>101.1051 </td></tr> <tr> <th><a href="/wiki/Selenocisteina" title="Selenocisteina">Selenocisteina</a> </th> <td>U </td> <td>Sec </td> <td>C<sub>3</sub>H<sub>5</sub>NOSe </td> <td>150.95364 </td> <td>150.0388 </td></tr> <tr> <th><a href="/wiki/Valina" title="Valina">Valina</a> </th> <td>V </td> <td>Val </td> <td>C<sub>5</sub>H<sub>9</sub>NO </td> <td>99.06841 </td> <td>99.1326 </td></tr> <tr> <th><a href="/wiki/Triptofano" title="Triptofano">Triptofano</a> </th> <td>W </td> <td>Trp </td> <td>C<sub>11</sub>H<sub>10</sub>N<sub>2</sub>O </td> <td>186.07931 </td> <td>186.2132 </td></tr> <tr> <th><a href="/wiki/Tirosina" title="Tirosina">Tirosina</a> </th> <td>Y </td> <td>Tyr </td> <td>C<sub>9</sub>H<sub>9</sub>NO<sub>2</sub> </td> <td>163.06333 </td> <td>163.1760 </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Note">Note</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amminoacidi_proteinogenici&veaction=edit&section=7" title="Modifica la sezione Note" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Amminoacidi_proteinogenici&action=edit&section=7" title="Edit section's source code: Note"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><a href="#cite_ref-1"><b>^</b></a> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal"> Ambrogelly A, Palioura S, Söll D, <a rel="nofollow" class="external text" href="https://www.nature.com/nchembio/journal/v3/n1/abs/nchembio847.html"><span style="font-style:italic;">Natural expansion of the genetic code</span></a>, in <span style="font-style:italic;">Nat Chem Biol</span>, vol. 3, n. 1, Jan 2007, pp. 29–35, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1038%2Fnchembio847">10.1038/nchembio847</a>, <a href="/wiki/PMID" title="PMID">PMID</a> <a rel="nofollow" class="external text" href="//www.ncbi.nlm.nih.gov/pubmed/17173027">17173027</a>.</cite></span> </li> <li id="cite_note-2"><a href="#cite_ref-2"><b>^</b></a> <span class="reference-text">Michael Rother, Joseph A. Krzycki. Selenocysteine, Pyrrolysine, and the Unique Energy Metabolism of Methanogenic Archaea. Archaea. 2010; 2010: 453642.Published online 2010 August 17. doi: 10.1155/2010/453642 PMCID: PMC2933860. <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2933860/">Selenocysteine, Pyrrolysine, and the Unique Energy Metabolism of Methanogenic Archaea - PMC</a></span> </li> <li id="cite_note-3"><a href="#cite_ref-3"><b>^</b></a> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal"> Sherman F., Stewart J.W., and Tsunasawa S., <a rel="nofollow" class="external text" href="http://onlinelibrary.wiley.com/doi/10.1002/bies.950030108/abstract"><span style="font-style:italic;">Methionine or not methionine at the beginning of a protein</span></a>, in <span style="font-style:italic;">BioEssays</span>, vol. 3, n. 1, 1985, pp. 27–31, <a href="/wiki/PMID" title="PMID">PMID</a> <a rel="nofollow" class="external text" href="//www.ncbi.nlm.nih.gov/pubmed/3024631">3024631</a>.</cite></span> </li> <li id="cite_note-4"><a href="#cite_ref-4"><b>^</b></a> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal"> Qian Wang, Angela R. Parrish e Lei Wang, <a rel="nofollow" class="external text" href="https://dx.doi.org/10.1016/j.chembiol.2009.03.001"><span style="font-style:italic;">Expanding the Genetic Code for Biological Studies</span></a>, in <span style="font-style:italic;">Chemistry & Biology</span>, vol. 16, n. 3, pp. 323–336, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1016%2Fj.chembiol.2009.03.001">10.1016/j.chembiol.2009.03.001</a>. <small>URL consultato il 16 aprile 2018</small>.</cite></span> </li> <li id="cite_note-:1-5"><span class="mw-cite-backlink"><b>^</b> <sup><i><a href="#cite_ref-:1_5-0">a</a></i></sup> <sup><i><a href="#cite_ref-:1_5-1">b</a></i></sup> <sup><i><a href="#cite_ref-:1_5-2">c</a></i></sup> <sup><i><a href="#cite_ref-:1_5-3">d</a></i></sup></span> <span class="reference-text">La frequenza di aminoacidi si basa sul <a href="/wiki/Genoma" title="Genoma">genoma</a> di: 135 specie di <a href="/wiki/Archaea" title="Archaea">Archaea</a>, 3775 di <a href="/wiki/Bacteria" title="Bacteria">Bacteria</a>, 614 di <a href="/wiki/Eukaryota" title="Eukaryota">Eukariota</a> e sul <a href="/wiki/Proteoma" title="Proteoma">proteoma</a> di <i><a href="/wiki/Homo_sapiens" title="Homo sapiens">Homo Sapiens</a></i> (21000 proteine circa) rispettivamente.</span> </li> <li id="cite_note-:0-6"><span class="mw-cite-backlink"><b>^</b> <sup><i><a href="#cite_ref-:0_6-0">a</a></i></sup> <sup><i><a href="#cite_ref-:0_6-1">b</a></i></sup> <sup><i><a href="#cite_ref-:0_6-2">c</a></i></sup> <sup><i><a href="#cite_ref-:0_6-3">d</a></i></sup></span> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal"> Lukasz P. Kozlowski, <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pubmed/27789699"><span style="font-style:italic;">Proteome-pI: proteome isoelectric point database</span></a>, in <span style="font-style:italic;">Nucleic Acids Research</span>, vol. 45, D1, 4 gennaio 2017, pp. D1112–D1116, <a href="/wiki/Digital_object_identifier" title="Digital object identifier">DOI</a>:<a rel="nofollow" class="external text" href="https://dx.doi.org/10.1093%2Fnar%2Fgkw978">10.1093/nar/gkw978</a>. <small>URL consultato il 16 aprile 2018</small>.</cite></span> </li> <li id="cite_note-7"><a href="#cite_ref-7"><b>^</b></a> <span class="reference-text">Un aminoacido essenziale non può essere sintetizzato nell'uomo e pertanto deve essere fornito nella dieta. Gli amminoacidi condizionalmente essenziali non sono normalmente richiesti nella dieta, ma devono essere forniti esogeni a popolazioni specifiche che non lo sintetizzano in quantità adeguate.</span> </li> <li id="cite_note-8"><a href="#cite_ref-8"><b>^</b></a> <span class="reference-text"><cite class="citation pubblicazione" style="font-style:normal"> V. R. Young, <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pubmed/8064412"><span style="font-style:italic;">Adult amino acid requirements: the case for a major revision in current recommendations</span></a>, in <span style="font-style:italic;">The Journal of Nutrition</span>, vol. 124, 8 Suppl, August 1994, pp. 1517S–1523S. <small>URL consultato il 16 aprile 2018</small>.</cite></span> </li> <li id="cite_note-9"><a href="#cite_ref-9"><b>^</b></a> <span class="reference-text">I numeri di questa colonna rappresentano il numero di molecole in media in E.Coli. Tale numero va moltiplicato per 10<sup>8</sup></span> </li> <li id="cite_note-10"><a href="#cite_ref-10"><b>^</b></a> <span class="reference-text"><i>Physical Biology of the Cell</i> (Garland Science) p. 178</span> </li> <li id="cite_note-11"><a href="#cite_ref-11"><b>^</b></a> <span class="reference-text">UAG è normalmente il <a href="/wiki/Codone_di_stop" title="Codone di stop">codone di stop <i>Ambra</i></a>, ma codifica pirrolisina se è presente un elemento PYLIS.</span> </li> <li id="cite_note-12"><a href="#cite_ref-12"><b>^</b></a> <span class="reference-text">UGA è normalmente il codone di stop opale (o ombra), ma codifica la selenocisteina se è presente un elemento SECIS.</span> </li> <li id="cite_note-13"><a href="#cite_ref-13"><b>^</b></a> <span class="reference-text">UAG e UGA non agiscono sempre come codoni di stop.</span> </li> <li id="cite_note-14"><a href="#cite_ref-14"><b>^</b></a> <span class="reference-text"><cite class="citation web" style="font-style:normal"> <a rel="nofollow" class="external text" href="http://education.expasy.org/student_projects/isotopident/htdocs/aa-list.html"><span style="font-style:italic;">The amino acid masses</span></a>, su <span style="font-style:italic;">education.expasy.org</span>, ExPASy. <small>URL consultato il 17 giugno 2015</small>.</cite></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Altri_progetti">Altri progetti</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amminoacidi_proteinogenici&veaction=edit&section=8" title="Modifica la sezione Altri progetti" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Amminoacidi_proteinogenici&action=edit&section=8" title="Edit section's source code: Altri progetti"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <div id="interProject" class="toccolours" style="display: none; clear: both; margin-top: 2em"><p id="sisterProjects" style="background-color: #efefef; color: black; font-weight: bold; margin: 0"><span>Altri progetti</span></p><ul title="Collegamenti verso gli altri progetti Wikimedia"> <li class="" title=""><span class="plainlinks" title="commons:Category:Proteinogenic amino acids"><a class="external text" href="https://commons.wikimedia.org/wiki/Category:Proteinogenic_amino_acids?uselang=it">Wikimedia Commons</a></span></li></ul></div> <ul><li><span typeof="mw:File"><a href="https://commons.wikimedia.org/wiki/?uselang=it" title="Collabora a Wikimedia Commons"><img alt="Collabora a Wikimedia Commons" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png" decoding="async" width="18" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Commons-logo.svg/27px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Commons-logo.svg/36px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></a></span> <span class="plainlinks"><a class="external text" href="https://commons.wikimedia.org/wiki/?uselang=it">Wikimedia Commons</a></span> contiene immagini o altri file su <b><span class="plainlinks"><a class="external text" href="https://commons.wikimedia.org/wiki/Category:Proteinogenic_amino_acids?uselang=it">amminoacidi proteinogenici</a></span></b></li></ul> <div class="noprint" style="width:100%; 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