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Piridossalfosfato - Wikipedia
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vector-toc-level-2"> <a class="vector-toc-link" href="#Biologica"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Biologica</span> </div> </a> <ul id="toc-Biologica-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Industriale" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Industriale"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Industriale</span> </div> </a> <ul id="toc-Industriale-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Bibliografia" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Bibliografia"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Bibliografia</span> </div> </a> <ul id="toc-Bibliografia-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Altri_progetti" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Altri_progetti"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Altri progetti</span> </div> </a> <ul id="toc-Altri_progetti-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Indice" 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="Mostra/Nascondi l'indice" > <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">Mostra/Nascondi l'indice</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">Piridossalfosfato</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. Disponibile in 23 lingue" > <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-23" 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">23 lingue</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%81%D9%88%D8%B3%D9%81%D8%A7%D8%AA_%D8%A7%D9%84%D8%A8%D9%8A%D8%B1%D9%8A%D8%AF%D9%88%D9%83%D8%B3%D8%A7%D9%84" title="فوسفات البيريدوكسال - arabo" lang="ar" hreflang="ar" data-title="فوسفات البيريدوكسال" data-language-autonym="العربية" data-language-local-name="arabo" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%BE%DB%8C%D8%B1%DB%8C%D8%AF%D9%88%DA%A9%D8%B3%D8%A7%D9%84_%D9%81%D9%88%D8%B3%D9%81%D8%A7%D8%AA" title="پیریدوکسال فوسفات - South Azerbaijani" lang="azb" hreflang="azb" data-title="پیریدوکسال فوسفات" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Fosfat_de_piridoxal" title="Fosfat de piridoxal - catalano" lang="ca" hreflang="ca" data-title="Fosfat de piridoxal" data-language-autonym="Català" data-language-local-name="catalano" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Pyridoxalphosphat" title="Pyridoxalphosphat - tedesco" lang="de" hreflang="de" data-title="Pyridoxalphosphat" data-language-autonym="Deutsch" data-language-local-name="tedesco" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate - inglese" lang="en" hreflang="en" data-title="Pyridoxal phosphate" data-language-autonym="English" data-language-local-name="inglese" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Piridoxal_fosfato" title="Piridoxal fosfato - spagnolo" lang="es" hreflang="es" data-title="Piridoxal fosfato" data-language-autonym="Español" data-language-local-name="spagnolo" 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%D8%B1%DB%8C%D8%AF%D9%88%DA%A9%D8%B3%D8%A7%D9%84_%D9%81%D8%B3%D9%81%D8%A7%D8%AA" title="پیریدوکسال فسفات - persiano" lang="fa" hreflang="fa" data-title="پیریدوکسال فسفات" 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/Pyridoksaalifosfaatti" title="Pyridoksaalifosfaatti - finlandese" lang="fi" hreflang="fi" data-title="Pyridoksaalifosfaatti" 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/Phosphate_de_pyridoxal" title="Phosphate de pyridoxal - francese" lang="fr" hreflang="fr" data-title="Phosphate de pyridoxal" data-language-autonym="Français" data-language-local-name="francese" 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/Piridoxal_fosfato" title="Piridoxal fosfato - galiziano" lang="gl" hreflang="gl" data-title="Piridoxal fosfato" data-language-autonym="Galego" data-language-local-name="galiziano" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Piridox%C3%A1l-foszf%C3%A1t" title="Piridoxál-foszfát - ungherese" lang="hu" hreflang="hu" data-title="Piridoxál-foszfát" data-language-autonym="Magyar" data-language-local-name="ungherese" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%94%E3%83%AA%E3%83%89%E3%82%AD%E3%82%B5%E3%83%BC%E3%83%AB%E3%83%AA%E3%83%B3%E9%85%B8" title="ピリドキサールリン酸 - giapponese" lang="ja" hreflang="ja" data-title="ピリドキサールリン酸" 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/%ED%94%BC%EB%A6%AC%EB%8F%85%EC%82%B4_%EC%9D%B8%EC%82%B0" title="피리독살 인산 - coreano" lang="ko" hreflang="ko" data-title="피리독살 인산" 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/Piridoksal_fosfat" title="Piridoksal fosfat - malese" lang="ms" hreflang="ms" data-title="Piridoksal fosfat" 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/Pyridoxaalfosfaat" title="Pyridoxaalfosfaat - olandese" lang="nl" hreflang="nl" data-title="Pyridoxaalfosfaat" 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/Fosforan_pirydoksalu" title="Fosforan pirydoksalu - polacco" lang="pl" hreflang="pl" data-title="Fosforan pirydoksalu" 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/Piridoxal_fosfato" title="Piridoxal fosfato - portoghese" lang="pt" hreflang="pt" data-title="Piridoxal fosfato" 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/Piridoxal_fosfat" title="Piridoxal fosfat - rumeno" lang="ro" hreflang="ro" data-title="Piridoxal fosfat" data-language-autonym="Română" data-language-local-name="rumeno" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru badge-Q70894304 mw-list-item" title=""><a href="https://ru.wikipedia.org/wiki/%D0%9F%D0%B8%D1%80%D0%B8%D0%B4%D0%BE%D0%BA%D1%81%D0%B0%D0%BB%D1%8C%D1%84%D0%BE%D1%81%D1%84%D0%B0%D1%82" title="Пиридоксальфосфат - russo" lang="ru" hreflang="ru" data-title="Пиридоксальфосфат" data-language-autonym="Русский" data-language-local-name="russo" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Piridoksal_fosfat" title="Piridoksal fosfat - serbo-croato" lang="sh" hreflang="sh" data-title="Piridoksal fosfat" 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/Pyridoxalfosf%C3%A1t" title="Pyridoxalfosfát - slovacco" lang="sk" hreflang="sk" data-title="Pyridoxalfosfát" 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/Piridoksal_fosfat" title="Piridoksal fosfat - serbo" lang="sr" hreflang="sr" data-title="Piridoksal fosfat" 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-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%A3%B7%E9%85%B8%E5%90%A1%E5%93%86%E9%86%9B" title="磷酸吡哆醛 - cinese" lang="zh" hreflang="zh" data-title="磷酸吡哆醛" data-language-autonym="中文" data-language-local-name="cinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div 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summary="Tabella sinottica che riassume i principali dati del soggetto" style="width:300px;"><tbody><tr class="sinottico_testata"><th colspan="2" style="background-color:#AADDFF;">Piridossalfosfato</th></tr><tr><td class="sinottico_testo_centrale" colspan="2"><figure class="mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:Pyridoxal-phosphate.svg" class="mw-file-description" title="formula di struttura"><img alt="formula di struttura" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Pyridoxal-phosphate.svg/250px-Pyridoxal-phosphate.svg.png" decoding="async" width="250" height="148" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Pyridoxal-phosphate.svg/375px-Pyridoxal-phosphate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Pyridoxal-phosphate.svg/500px-Pyridoxal-phosphate.svg.png 2x" data-file-width="1224" data-file-height="725" /></a><figcaption>formula di struttura</figcaption></figure> </td></tr><tr><td class="sinottico_testo_centrale" colspan="2"><figure class="mw-halign-center" typeof="mw:File/Frameless"><a href="/wiki/File:PLP_3d.gif" class="mw-file-description" title="modello molecolare"><img alt="modello molecolare" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/PLP_3d.gif/250px-PLP_3d.gif" decoding="async" width="250" height="184" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/5/5f/PLP_3d.gif 1.5x" data-file-width="340" data-file-height="250" /></a><figcaption>modello molecolare</figcaption></figure> </td></tr><tr class="sinottico_divisione"><th colspan="2" style="background-color:#DDEEFF;">Nome <a href="/wiki/Unione_internazionale_di_chimica_pura_e_applicata" title="Unione internazionale di chimica pura e applicata">IUPAC</a></th></tr><tr><td class="sinottico_testo_centrale" colspan="2">Piridossal-5'-Fosfato </td></tr><tr class="sinottico_divisione"><th colspan="2" style="background-color:#DDEEFF;">Nomi alternativi</th></tr><tr><td class="sinottico_testo_centrale" colspan="2">Vitamina B6<br />PALP </td></tr><tr class="sinottico_divisione"><th colspan="2" style="background-color:#AAEEFF;">Caratteristiche generali</th></tr><tr><th><a href="/wiki/Formula_bruta" title="Formula bruta">Formula bruta</a> o <a href="/wiki/Formula_molecolare" title="Formula molecolare">molecolare</a></th><td>C<sub>8</sub>H<sub>10</sub>NO<sub>3</sub>PO<sub>3</sub> </td></tr><tr><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</a>)</th><td>247,144 </td></tr><tr><th><a href="/wiki/Colore" title="Colore">Aspetto</a></th><td>polvere giallo pallido </td></tr><tr><th><a href="/wiki/Numero_CAS" title="Numero CAS">Numero CAS</a></th><td><span class="reflink plainlinksneverexpand"><span class="noarchive"><a class="external text" href="https://iw.toolforge.org/magnustools/cas.php?language=it&cas=54-47-7">54-47-7</a></span></span> </td></tr><tr><th><a href="/wiki/Numero_EINECS" title="Numero EINECS">Numero EINECS</a></th><td>200-208-3 </td></tr><tr><th><a href="/wiki/PubChem" title="PubChem">PubChem</a></th><td><a rel="nofollow" class="external text" href="http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=1051">1051</a> </td></tr><tr><th><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td><a rel="nofollow" class="external text" href="http://www.drugbank.ca/drugs/DBDB00114">DBDB00114</a> </td></tr><tr><th><a href="/wiki/SMILES" title="SMILES">SMILES</a></th><td><div style="word-break: break-all;"><code style="background-color:transparent; border:none">CC1=NC=C(C(=C1O)C=O)COP(=O)(O)O</code></div> </td></tr><tr class="sinottico_divisione"><th colspan="2" style="background-color:#AAEEFF;">Proprietà chimico-fisiche</th></tr><tr><th><a href="/wiki/Densit%C3%A0" title="Densità">Densità</a> (g/cm<sup>3</sup>, in <a href="/wiki/Condizioni_standard" title="Condizioni standard">c.s.</a>)</th><td>  </td></tr><tr><th><a href="/wiki/Solubilit%C3%A0" title="Solubilità">Solubilità</a> in <a href="/wiki/Acqua" title="Acqua">acqua</a></th><td>  5 g/l a 25 °C </td></tr><tr><th><a href="/wiki/Temperatura_di_fusione" class="mw-redirect" title="Temperatura di fusione">Temperatura di fusione</a></th><td>140-143 °C (413-416 K) </td></tr><tr><th><a href="/wiki/Entalpia_di_fusione" title="Entalpia di fusione">Δ<sub>fus</sub>H<sup>0</sup></a> (kJ·mol<sup>−1</sup>)</th><td>  </td></tr><tr><th><a href="/wiki/Entropia_di_fusione" title="Entropia di fusione">Δ<sub>fus</sub>S<sup>0</sup></a> (J·K<sup>−1</sup>mol<sup>−1</sup>)</th><td>  </td></tr><tr class="sinottico_divisione"><th colspan="2" style="background-color:#AAEEFF;">Proprietà termochimiche</th></tr><tr><th><a href="/wiki/Entalpia_standard_di_formazione" title="Entalpia standard di formazione">Δ<sub>f</sub>H<sup>0</sup></a> (kJ·mol<sup>−1</sup>)</th><td>  </td></tr><tr><th><a href="/wiki/Entropia_molare_standard" title="Entropia molare standard">S<sup>0</sup><sub>m</sub></a>(J·K<sup>−1</sup>mol<sup>−1</sup>)</th><td>  </td></tr><tr><th><a href="/wiki/Capacit%C3%A0_termica" title="Capacità termica">C<sup>0</sup><sub>p,m</sub></a>(J·K<sup>−1</sup>mol<sup>−1</sup>)</th><td>  </td></tr><tr class="sinottico_divisione"><th colspan="2" style="background-color:#AAEEFF;">Indicazioni di sicurezza</th></tr><tr><th><a href="/wiki/Frasi_R" title="Frasi R">Frasi R</a></th><td>- </td></tr><tr><th><a href="/wiki/Frasi_S" title="Frasi S">Frasi S</a></th><td>24/25 </td></tr><tr><td class="sinottico_piede2 noprint nomobile metadata" colspan="2"><a href="https://www.wikidata.org/wiki/Q418957" class="extiw" title="d:Q418957"><span title="Modifica i dati della voce Piridossalfosfato su Wikidata">Modifica dati su Wikidata</span></a><b> ·</b> <a href="/wiki/Template:Composto_chimico/man" title="Template:Composto chimico/man"><span title="Manuale del template Composto chimico">Manuale</span></a></td></tr></tbody></table> <p>Il <b>piridossalfosfato</b> o secondo le direttive <a href="/wiki/Unione_internazionale_di_chimica_pura_e_applicata" title="Unione internazionale di chimica pura e applicata">IUPAC</a> <b>piridossal-5'-fosfato</b> (o <b>piridossal fosfato</b> o <b>PL-5'P</b> o <b>PLP</b> o <b>PALP</b>) è la forma attiva della <a href="/wiki/Vitamina_B6" title="Vitamina B6">Vitamina B6</a> ed un coenzima di <a href="/wiki/Enzimi" class="mw-redirect" title="Enzimi">enzimi</a> <a href="/wiki/Transferasi" title="Transferasi">transferasi</a> come le <a href="/wiki/Transaminasi" title="Transaminasi">transaminasi</a>. </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=Piridossalfosfato&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=Piridossalfosfato&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>La molecola è composta da un anello <a href="/wiki/Piridina" title="Piridina">piridinico</a> con 4 sostituenti: un gruppo <a href="/wiki/Gruppo_funzionale" title="Gruppo funzionale">aldeidico</a> (carbonio 4), un <a href="/wiki/Gruppo_funzionale" title="Gruppo funzionale">metile</a> (carbonio 2), un <a href="/wiki/Gruppo_funzionale" title="Gruppo funzionale">idrossimetile</a> fosfato (carbonio 5), un <a href="/wiki/Gruppo_funzionale" title="Gruppo funzionale">ossidrile</a> (carbonio 3). Quest'ultimo ha delle particolarità ed insieme all'azoto e al gruppo aldeidico sono responsabili dell'attività <a href="/wiki/Catalisi" title="Catalisi">catalitica</a> del cofattore. Il <a href="/wiki/Fosfato_organico" title="Fosfato organico">gruppo fosfato</a> invece, nella maggior parte dei casi, ha funzione di appiglio per mezzo di cui la proteina lega la molecola; un'eccezione è rappresentata dall'enzima <a href="/wiki/Glicogeno_fosforilasi" class="mw-redirect" title="Glicogeno fosforilasi">Glicogeno fosforilasi</a> in cui è il fosfato ad esplicare funzione catalitica. </p><p>I 5 carboni dell'anello, l'azoto, il carbonio e l'ossigeno del gruppo aldeidico (-CHO) sono <a href="/wiki/Ibridizzazione" title="Ibridizzazione">ibridati</a> <i>sp<sup>2</sup></i>. La prima conseguenza di questo è che gli atomi succitati giacciono sullo stesso piano; la seconda conseguenza è che ogni atomo di questi ha un orbitale p con un <a href="/wiki/Elettrone_spaiato" title="Elettrone spaiato">elettrone spaiato</a> perpendicolare al piano della molecola, che viene messo in comune con gli altri atomi, creando così un sistema risonante su 8 atomi (responsabile del colore giallo intenso delle soluzioni che contengono la vitamina). </p><p>Essendo molecola planare è possibile individuare due facce (vedi figura 2 a metà pagina), mantenendo il gruppo fosfato verso l'osservatore ed il C4' verso destra; la faccia superiore viene indicata come "si" e quella inferiore come "re". </p> <div class="mw-heading mw-heading2"><h2 id="Ruolo_biologico">Ruolo biologico</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Piridossalfosfato&veaction=edit&section=2" title="Modifica la sezione Ruolo biologico" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Piridossalfosfato&action=edit&section=2" title="Edit section's source code: Ruolo biologico"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r130657691">body:not(.skin-minerva) .mw-parser-output .vedi-anche{font-size:95%}</style><style data-mw-deduplicate="TemplateStyles:r139142988">.mw-parser-output .hatnote-content{align-items:center;display:flex}.mw-parser-output .hatnote-icon{flex-shrink:0}.mw-parser-output .hatnote-icon img{display:flex}.mw-parser-output .hatnote-text{font-style:italic}body:not(.skin-minerva) .mw-parser-output .hatnote{border:1px solid #CCC;display:flex;margin:.5em 0;padding:.2em .5em}body:not(.skin-minerva) .mw-parser-output .hatnote-text{padding-left:.5em}body.skin-minerva .mw-parser-output .hatnote-icon{padding-right:8px}body.skin-minerva .mw-parser-output .hatnote-icon img{height:auto;width:16px}body.skin--responsive .mw-parser-output .hatnote a.new{color:#d73333}body.skin--responsive .mw-parser-output .hatnote a.new:visited{color:#a55858}</style> <div class="hatnote noprint vedi-anche"> <div class="hatnote-content"><span class="noviewer hatnote-icon" typeof="mw:File"><span><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/87/Magnifying_glass_icon_mgx2.svg/18px-Magnifying_glass_icon_mgx2.svg.png" decoding="async" width="18" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/87/Magnifying_glass_icon_mgx2.svg/27px-Magnifying_glass_icon_mgx2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/87/Magnifying_glass_icon_mgx2.svg/36px-Magnifying_glass_icon_mgx2.svg.png 2x" data-file-width="286" data-file-height="280" /></span></span> <span class="hatnote-text">Lo stesso argomento in dettaglio: <b><a href="/wiki/Catalisi_enzimatica_covalente" title="Catalisi enzimatica covalente">Catalisi enzimatica covalente</a></b>.</span></div> </div> <p>Il piridossalfosfato è un <a href="/wiki/Cofattore_(biologia)" title="Cofattore (biologia)">cofattore</a> di <a href="/wiki/Enzimi" class="mw-redirect" title="Enzimi">enzimi</a> <a href="/wiki/Transferasi" title="Transferasi">transferasi</a> come le <a href="/wiki/Transaminasi" title="Transaminasi">transaminasi</a>. </p><p>Funziona con catalisi covalente elettrofila per formazione di una base di Schiff. Il <a href="/wiki/Gruppo_carbonilico" class="mw-redirect" title="Gruppo carbonilico">gruppo carbonilico</a> del piridossalfosfato si lega ad un gruppo ammino-terminale formando un'<a href="/wiki/Immina" class="mw-redirect" title="Immina">immina</a> (base di Schiff). </p> <div class="mw-heading mw-heading2"><h2 id="Proprietà"><span id="Propriet.C3.A0"></span>Proprietà</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Piridossalfosfato&veaction=edit&section=3" title="Modifica la sezione Proprietà" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Piridossalfosfato&action=edit&section=3" title="Edit section's source code: Proprietà"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>L'effetto della risonanza unita all'<a href="/wiki/Elettronegativit%C3%A0" title="Elettronegatività">elettronegatività</a> dell'<a href="/wiki/Azoto" title="Azoto">azoto</a> e dell'<a href="/wiki/Ossigeno" title="Ossigeno">ossigeno</a> al C3 fanno del piridossalfosfato una trappola per elettroni di media capacità; inoltre a <a href="/wiki/PH" title="PH">pH</a> vicino a 7 l'azoto piridinico viene protonato conferendo alla molecola una carica positiva delocalizzata, che accresce questa capacità. </p><p>Pur essendo questa proprietà del PLP importante, la sua peculiare struttura elettronica gli conferisce un'incredibile capacità catalitica che si evidenzia nelle reazioni con gli <a href="/wiki/Amminoacidi" class="mw-redirect" title="Amminoacidi">amminoacidi</a>: unendo ad una <a href="/wiki/Soluzione_(chimica)" title="Soluzione (chimica)">soluzione</a> di un amminoacido una piccola quantità di una soluzione di questa vitamina e analizzando successivamente la composizione, si possono ritrovare il cofattore intatto, il cofattore modificato e una varietà di <a href="/wiki/Molecola" title="Molecola">molecole</a> derivate dall'amminoacido di partenza; si conclude che questo cofattore possiede intrinsecamente attività catalitica per varie reazioni (<a href="/wiki/Decarbossilazione" title="Decarbossilazione">decarbossilazione</a>, <a href="/wiki/Deaminazione" title="Deaminazione">deaminazione</a>, <a href="/w/index.php?title=Racemizzazione&action=edit&redlink=1" class="new" title="Racemizzazione (la pagina non esiste)">racemizzazione</a> etc.) e che la sua capacità ed aspecificità devono essere modulate per svolgere una funzione utile e non recare danni alla cellula. Si può trovare nelle transaminasi, enzimi che trasportano un gruppo NH<sub>2</sub> da un amminoacido su un α-chetoacido. Oppure si può trovare nelle amminoacididecarbossilasi, enzimi che tolgono il gruppo <a href="/wiki/Acidi_carbossilici" title="Acidi carbossilici">-COOH</a> degli amminoacidi, o ancora nelle deidratasi, enzimi che tolgono acqua da certi amminoacidi. </p><p>Vediamo come siano spiegabili queste trasformazioni adottando una versione semplificata della <a href="/wiki/Orbitale_molecolare" title="Orbitale molecolare">teoria degli orbitali molecolari</a>. </p><p>All'atto del legame del piridossalfosfato con l'azoto <a href="/wiki/Gruppo_funzionale" title="Gruppo funzionale">amminico</a> di un amminoacido tramite il suo gruppo aldeidico, si forma una <a href="/wiki/Base_di_Schiff" class="mw-redirect" title="Base di Schiff">Base di Schiff</a> o Aldimina. Essendo divenuto anche quest'azoto ibridato sp<sup>2</sup> il carbonio α si trova a contatto con un esteso <a href="/wiki/Risonanza_(chimica)" title="Risonanza (chimica)">sistema risonante</a>. Gli elettroni che si trovano nell'orbitale di legame di tipo σ che si dispone su un piano perpendicolare al piano della molecola (fig. 3) vengono attirati nel sistema e delocalizzati, cosa che comporta la scissione eterolitica del legame con il <a href="/wiki/Sostituente" title="Sostituente">sostituente</a>, formando un intermedio detto <b>chinonoide</b> instabile in cui anche il carbonio α è ibridato sp<sup>2</sup>. Viene quindi eliminato un sostituente con una carica negativa in meno, da -H si libera H<sup>+</sup> da -COO<sup>-</sup> si libera CO<sub>2</sub> o ancora R (vedi <a href="/wiki/Amminoacidi" class="mw-redirect" title="Amminoacidi">amminoacidi</a>). Essendo instabile il composto tende a stabilizzarsi in vari possibili modi: addizionando al carbonio α un sostituente diverso (reazione per α-sintasi, decarbossilasi, racemasi, etc.), addizionando un H+ al C4' scindendo il legame N-C<sub>α</sub>(aminotrasferasi), sottraendo sostituenti al Cβ o al Cγ ai quali in seguito si possono addizionare gruppi diversi (β o γ sintasi e β eliminazione). La maggior parte delle reazioni elencate è indicativa di un gruppo di reazioni specifiche che dipendono dal substrato e dal gruppo addizionato. Enzimaticamente il contorno proteico modula molte proprietà del cofattore (pK, stabilità di un intermedio piuttosto che un altro) ed indirizza la reazione verso uno o (se non possibile) pochi prodotti specifici. </p> <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:PLP_space.jpg" class="mw-file-description" title="(fig 1) Vista frontale della molecola rappresentata in un modello spaziale"><img alt="(fig 1) Vista frontale della molecola rappresentata in un modello spaziale" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/PLP_space.jpg/120px-PLP_space.jpg" decoding="async" width="120" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ae/PLP_space.jpg/180px-PLP_space.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ae/PLP_space.jpg/240px-PLP_space.jpg 2x" data-file-width="465" data-file-height="336" /></a></span></div> <div class="gallerytext">(fig 1) Vista frontale della molecola rappresentata in un modello spaziale</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:PLP_3d_plane.jpg" class="mw-file-description" title="(fig 2) Vista laterale della molecola rappresentata in un modello a sfere e bastoncini (doppi legami non rappresentati)"><img alt="(fig 2) Vista laterale della molecola rappresentata in un modello a sfere e bastoncini (doppi legami non rappresentati)" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d2/PLP_3d_plane.jpg/120px-PLP_3d_plane.jpg" decoding="async" width="120" height="69" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d2/PLP_3d_plane.jpg/180px-PLP_3d_plane.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d2/PLP_3d_plane.jpg/240px-PLP_3d_plane.jpg 2x" data-file-width="660" data-file-height="380" /></a></span></div> <div class="gallerytext">(fig 2) Vista laterale della molecola rappresentata in un modello a sfere e bastoncini (doppi legami non rappresentati)</div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="Sintesi">Sintesi</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Piridossalfosfato&veaction=edit&section=4" title="Modifica la sezione Sintesi" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Piridossalfosfato&action=edit&section=4" title="Edit section's source code: Sintesi"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Biologica">Biologica</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Piridossalfosfato&veaction=edit&section=5" title="Modifica la sezione Biologica" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Piridossalfosfato&action=edit&section=5" title="Edit section's source code: Biologica"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r139255918">.mw-parser-output .avviso-mini{border:1px solid #aaa;background-color:#fbfbfb;margin-bottom:.5em;padding:0 2px 0 3px;margin:5px 10%;font-size:90%}.mw-parser-output .avviso-mini>div:first-of-type{margin:2px 2px 2px 0}.mw-parser-output .avviso-mini .mw-collapsible-content{padding:2px 0 0 7px}.mw-parser-output .avviso-mini-informazioni{border-left:10px solid #1e90ff}.mw-parser-output .avviso-mini-contenuto{border-left:10px solid #f28500}.mw-parser-output .avviso-mini-stile{border-left:10px solid #f4c430}.mw-parser-output .avviso-mini-statico{border-left:10px solid limegreen}.mw-parser-output .avviso-mini-struttura{border-left:10px solid #9932cc}.mw-parser-output .avviso-mini-generico{border-left:10px solid #bba}body.skin-minerva .mw-parser-output .avviso-mini{border:none;margin-bottom:1px;padding:inherit}body.skin-minerva .mw-parser-output .avviso-mini .mbox-text-div{font-style:normal}html.client-js body.skin-minerva .mw-parser-output .avviso-mini>div{padding:8px 8px 8px 32px!important;position:relative}</style><div class="ambox avviso-mini noprint metadata avviso-mini-informazioni plainlinks"> <div class="mbox-text"> <div class="mbox-text-div" style="display:flex; flex-direction:row; align-items:center; column-gap:5px;"><span class="mbox-image"><span typeof="mw:File"><a href="/wiki/File:Quill-Nuvola.svg" class="mw-file-description" title="Sezione vuota"><img alt="Sezione vuota" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Quill-Nuvola.svg/20px-Quill-Nuvola.svg.png" decoding="async" width="20" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Quill-Nuvola.svg/30px-Quill-Nuvola.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Quill-Nuvola.svg/40px-Quill-Nuvola.svg.png 2x" data-file-width="50" data-file-height="50" /></a></span></span><span style="width:100%"><b>Questa sezione  sull'argomento chimica è ancora vuota</b>. <a class="external text" href="https://it.wikipedia.org/w/index.php?title=Piridossalfosfato&action=edit">Aiutaci</a> a scriverla!</span></div> </div> </div> <div class="mw-heading mw-heading3"><h3 id="Industriale">Industriale</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Piridossalfosfato&veaction=edit&section=6" title="Modifica la sezione Industriale" class="mw-editsection-visualeditor"><span>modifica</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=Piridossalfosfato&action=edit&section=6" title="Edit section's source code: Industriale"><span>modifica wikitesto</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r139255918"><div class="ambox avviso-mini noprint metadata avviso-mini-informazioni plainlinks"> <div class="mbox-text"> <div class="mbox-text-div" style="display:flex; 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Nelson, Michael M. Cox, <span style="font-style:italic;">I Principi di Biochimica di Lehninger</span>, 3ª ed., Bologna, <a href="/wiki/Nicola_Zanichelli_Editore" class="mw-redirect" title="Nicola Zanichelli Editore">Zanichelli</a>, febbraio 2002, <a href="/wiki/ISBN" title="ISBN">ISBN</a> <a href="/wiki/Speciale:RicercaISBN/88-08-09035-3" title="Speciale:RicercaISBN/88-08-09035-3">88-08-09035-3</a>.</cite></li></ul> <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=Piridossalfosfato&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=Piridossalfosfato&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:Pyridoxal phosphate"><a class="external text" href="https://commons.wikimedia.org/wiki/Category:Pyridoxal_phosphate?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:Pyridoxal_phosphate?uselang=it">Piridossalfosfato</a></span></b></li></ul> <style data-mw-deduplicate="TemplateStyles:r141815314">.mw-parser-output .navbox{border:1px solid #aaa;clear:both;margin:auto;padding:2px;width:100%}.mw-parser-output .navbox th{padding-left:1em;padding-right:1em;text-align:center}.mw-parser-output .navbox>tbody>tr:first-child>th{background:#ccf;font-size:90%;width:100%;color:var(--color-base,black)}.mw-parser-output .navbox_navbar{float:left;margin:0;padding:0 10px 0 0;text-align:left;width:6em}.mw-parser-output .navbox_title{font-size:110%}.mw-parser-output .navbox_abovebelow{background:#ddf;font-size:90%;font-weight:normal}.mw-parser-output .navbox_group{background:#ddf;font-size:90%;padding:0 10px;white-space:nowrap}.mw-parser-output .navbox_list{font-size:90%;width:100%}.mw-parser-output .navbox_list a{white-space:nowrap}html:not(.vector-feature-night-mode-enabled) .mw-parser-output .navbox_odd{background:#fdfdfd;color:var(--color-base,black)}html:not(.vector-feature-night-mode-enabled) .mw-parser-output .navbox_even{background:#f7f7f7;color:var(--color-base,black)}.mw-parser-output .navbox a.mw-selflink{color:var(--color-base,black)}.mw-parser-output .navbox_center{text-align:center}.mw-parser-output .navbox .navbox_image{padding-left:7px;vertical-align:middle;width:0}.mw-parser-output .navbox+.navbox{margin-top:-1px}.mw-parser-output .navbox .mw-collapsible-toggle{font-weight:normal;text-align:right;width:7em}body.skin--responsive .mw-parser-output .navbox_image img{max-width:none!important}.mw-parser-output .subnavbox{margin:-3px;width:100%}.mw-parser-output .subnavbox_group{background:#e6e6ff;padding:0 10px}@media screen{html.skin-theme-clientpref-night .mw-parser-output .navbox>tbody>tr:first-child>th{background:var(--background-color-interactive)!important}html.skin-theme-clientpref-night .mw-parser-output .navbox th{color:var(--color-base)!important}html.skin-theme-clientpref-night .mw-parser-output .navbox_abovebelow,html.skin-theme-clientpref-night .mw-parser-output .navbox_group{background:var(--background-color-interactive-subtle)!important}html.skin-theme-clientpref-night .mw-parser-output .subnavbox_group{background:var(--background-color-neutral-subtle)!important}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbox>tbody>tr:first-child>th{background:var(--background-color-interactive)!important}html.skin-theme-clientpref-os .mw-parser-output .navbox th{color:var(--color-base)!important}html.skin-theme-clientpref-os .mw-parser-output .navbox_abovebelow,html.skin-theme-clientpref-os .mw-parser-output .navbox_group{background:var(--background-color-interactive-subtle)!important}html.skin-theme-clientpref-os .mw-parser-output .subnavbox_group{background:var(--background-color-neutral-subtle)!important}}</style><table class="navbox mw-collapsible mw-collapsed noprint metadata" id="navbox-Vitamine"><tbody><tr><th colspan="2"><div class="navbox_navbar"><div class="noprint plainlinks" style="background-color:transparent; padding:0; font-size:xx-small; color:var(--color-base, #000000); white-space:nowrap;"><a href="/wiki/Template:Vitamine" title="Template:Vitamine"><span title="Vai alla pagina del template">V</span></a> · <a href="/w/index.php?title=Discussioni_template:Vitamine&action=edit&redlink=1" class="new" title="Discussioni template:Vitamine (la pagina non esiste)"><span title="Discuti del template">D</span></a> · <a class="external text" href="https://it.wikipedia.org/w/index.php?title=Template:Vitamine&action=edit"><span title="Modifica il template. Usa l'anteprima prima di salvare">M</span></a></div></div><span class="navbox_title"><a href="/wiki/Vitamine" title="Vitamine">Vitamine</a></span></th></tr><tr><th colspan="1" class="navbox_group">Solubili in grasso</th><td colspan="1" class="navbox_list navbox_odd"><table class="subnavbox"><tbody><tr><th class="subnavbox_group"><a href="/wiki/Vitamina_A" class="mw-redirect" title="Vitamina A">A</a></th><td colspan="1"><a href="/wiki/Acido_retinoico" title="Acido retinoico">Acido retinoico</a><b> ·</b> <a href="/wiki/Carotene" title="Carotene">Carotene</a> (<a href="/w/index.php?title=Alfa-carotene&action=edit&redlink=1" class="new" title="Alfa-carotene (la pagina non esiste)">Alfa</a><b> ·</b> <a href="/wiki/Beta-carotene" title="Beta-carotene">Beta</a><b> ·</b> <a href="/w/index.php?title=Gamma-carotene&action=edit&redlink=1" class="new" title="Gamma-carotene (la pagina non esiste)">Gamma</a><b> ·</b> <a href="/w/index.php?title=Delta-carotene&action=edit&redlink=1" class="new" title="Delta-carotene (la pagina non esiste)">Delta</a>)<b> ·</b> <a href="/wiki/Retinale" title="Retinale">Retinale</a><b> ·</b> <a href="/wiki/Retinolo" title="Retinolo">Retinolo</a></td></tr><tr><th class="subnavbox_group"><a href="/wiki/Vitamina_D" title="Vitamina D">D</a></th><td colspan="1">D<sub>2</sub> (<a href="/wiki/Ergosterolo" title="Ergosterolo">Ergosterolo</a><b> ·</b> <a href="/wiki/Ergocalciferolo" title="Ergocalciferolo">Ergocalciferolo</a>)<b> ·</b> D<sub>3</sub> (<a href="/wiki/7-deidrocolesterolo" title="7-deidrocolesterolo">7-deidrocolesterolo</a><b> ·</b> <a href="/wiki/Acido_calcitroico" title="Acido calcitroico">Acido calcitroico</a><b> ·</b> <a href="/wiki/Calcidiolo" title="Calcidiolo">Calcidiolo</a><b> ·</b> <a href="/wiki/Calcitriolo" title="Calcitriolo">Calcitriolo</a><b> ·</b> <a href="/wiki/Colecalciferolo" title="Colecalciferolo">Colecalciferolo</a><b> ·</b> <a href="/w/index.php?title=Previtamina_D3&action=edit&redlink=1" class="new" title="Previtamina D3 (la pagina non esiste)">Previtamina D<sub>3</sub></a>)<b> ·</b> D<sub>4</sub> (<a href="/w/index.php?title=22-deidroergocalciferolo&action=edit&redlink=1" class="new" title="22-deidroergocalciferolo (la pagina non esiste)">22-deidroergocalciferolo</a>)<b> ·</b> <a href="/wiki/Vitamina_D5" title="Vitamina D5">D<sub>5</sub></a><b> ·</b> Altri analoghi (<a href="/wiki/Alfacalcidolo" title="Alfacalcidolo">Alfacalcidolo</a><b> ·</b> <a href="/wiki/Diidrotachisterolo" title="Diidrotachisterolo">Diidrotachisterolo</a><b> ·</b> <a href="/wiki/Calcipotriolo" title="Calcipotriolo">Calcipotriolo</a><b> ·</b> <a href="/wiki/Tacalcitolo" title="Tacalcitolo">Tacalcitolo</a><b> ·</b> <a href="/w/index.php?title=Paricalcitolo&action=edit&redlink=1" class="new" title="Paricalcitolo (la pagina non esiste)">Paricalcitolo</a>)</td></tr><tr><th class="subnavbox_group"><a href="/wiki/Vitamina_E" class="mw-redirect" title="Vitamina E">E</a></th><td colspan="1"><a href="/wiki/Tocoferolo" title="Tocoferolo">Tocoferolo</a> (<a href="/w/index.php?title=Alfa-tocoferolo&action=edit&redlink=1" class="new" title="Alfa-tocoferolo (la pagina non esiste)">Alfa</a><b> ·</b> <a href="/w/index.php?title=Beta-tocoferolo&action=edit&redlink=1" class="new" title="Beta-tocoferolo (la pagina non esiste)">Beta</a><b> ·</b> <a href="/w/index.php?title=Gamma-tocoferolo&action=edit&redlink=1" class="new" title="Gamma-tocoferolo (la pagina non esiste)">Gamma</a><b> ·</b> <a href="/w/index.php?title=Delta-tocoferolo&action=edit&redlink=1" class="new" title="Delta-tocoferolo (la pagina non esiste)">Delta</a>)<b> ·</b> <a href="/w/index.php?title=Tocotrienolo&action=edit&redlink=1" class="new" title="Tocotrienolo (la pagina non esiste)">Tocotrienolo</a> (<a href="/w/index.php?title=Alfa-tocotrienolo&action=edit&redlink=1" class="new" title="Alfa-tocotrienolo (la pagina non esiste)">Alfa</a><b> ·</b> <a href="/w/index.php?title=Beta-tocotrienolo&action=edit&redlink=1" class="new" title="Beta-tocotrienolo (la pagina non esiste)">Beta</a><b> ·</b> <a href="/w/index.php?title=Gamma-tocotrienolo&action=edit&redlink=1" class="new" title="Gamma-tocotrienolo (la pagina non esiste)">Gamma</a><b> ·</b> <a href="/w/index.php?title=Delta-tocotrienolo&action=edit&redlink=1" class="new" title="Delta-tocotrienolo (la pagina non esiste)">Delta</a>)<b> ·</b> <a href="/w/index.php?title=Tocofersolan&action=edit&redlink=1" class="new" title="Tocofersolan (la pagina non esiste)">Tocofersolan</a></td></tr><tr><th class="subnavbox_group"><a href="/wiki/Vitamina_K" title="Vitamina K">K</a></th><td colspan="1"><a href="/wiki/Naftochinone" title="Naftochinone">Naftochinone</a><b> ·</b> K<sub>1</sub> (<a href="/wiki/Fitomenadione" title="Fitomenadione">Fitomenadione</a>)<b> ·</b> K<sub>2</sub> (<a href="/w/index.php?title=Menachinone&action=edit&redlink=1" class="new" title="Menachinone (la pagina non esiste)">Menachinone</a>)<b> ·</b> K<sub>3</sub> (<a href="/w/index.php?title=Menadione&action=edit&redlink=1" class="new" title="Menadione (la pagina non esiste)">Menadione</a>)<b> ·</b> K<sub>4</sub><b> ·</b> K<sub>5</sub> (<a href="/w/index.php?title=4-amino-2-metil-1-naftol&action=edit&redlink=1" class="new" title="4-amino-2-metil-1-naftol (la pagina non esiste)">4-amino-2-metil-1-naftol</a>)<b> ·</b> K<sub>6</sub> (<a href="/w/index.php?title=2-metilnaftalene-1,4-diamine&action=edit&redlink=1" class="new" title="2-metilnaftalene-1,4-diamine (la pagina non esiste)">2-metilnaftalene-1,4-diamine</a>)<b> ·</b> K<sub>7</sub> (<a href="/w/index.php?title=4-amino-3-metil-1-naftol&action=edit&redlink=1" class="new" title="4-amino-3-metil-1-naftol (la pagina non esiste)">4-amino-3-metil-1-naftol</a>)</td></tr></tbody></table></td></tr><tr><th colspan="1" class="navbox_group">Solubili in acqua</th><td colspan="1" class="navbox_list navbox_even"><table class="subnavbox"><tbody><tr><th class="subnavbox_group"><a href="/wiki/Vitamina_B" title="Vitamina B">B</a></th><td colspan="1">B<sub>1</sub> (<a href="/wiki/Tiamina" title="Tiamina">Tiamina</a><b> ·</b> <a href="/w/index.php?title=Acefurtiamina&action=edit&redlink=1" class="new" title="Acefurtiamina (la pagina non esiste)">Acefurtiamina</a><b> ·</b> <a href="/w/index.php?title=Allitiamina&action=edit&redlink=1" class="new" title="Allitiamina (la pagina non esiste)">Allitiamina</a><b> ·</b> <a href="/w/index.php?title=Fursultiamina&action=edit&redlink=1" class="new" title="Fursultiamina (la pagina non esiste)">Fursultiamina</a><b> ·</b> <a href="/w/index.php?title=Octotiamina&action=edit&redlink=1" class="new" title="Octotiamina (la pagina non esiste)">Octotiamina</a><b> ·</b> <a href="/w/index.php?title=Prosultiamina&action=edit&redlink=1" class="new" title="Prosultiamina (la pagina non esiste)">Prosultiamina</a><b> ·</b> <a href="/w/index.php?title=Sulbutiamina&action=edit&redlink=1" class="new" title="Sulbutiamina (la pagina non esiste)">Sulbutiamina</a>)<b> ·</b> B<sub>2</sub> (<a href="/wiki/Riboflavina" title="Riboflavina">Riboflavina</a>)<b> ·</b> B<sub>3</sub> (<a href="/wiki/Niacina" title="Niacina">Niacina</a><b> ·</b> <a href="/wiki/Nicotinamide" title="Nicotinamide">Nicotinamide</a>)<b> ·</b> B<sub>5</sub> (<a href="/wiki/Acido_pantotenico" title="Acido pantotenico">Acido pantotenico</a><b> ·</b> <a href="/wiki/Pantenolo" class="mw-redirect" title="Pantenolo">Pantenolo</a><b> ·</b> <a href="/w/index.php?title=Pantetina&action=edit&redlink=1" class="new" title="Pantetina (la pagina non esiste)">Pantetina</a>)<b> ·</b> <a href="/wiki/Vitamina_B6" title="Vitamina B6">B<sub>6</sub></a> (<a href="/wiki/Piridossale" title="Piridossale">Piridossale</a><b> ·</b> <a href="/wiki/Piridossina" title="Piridossina">Piridossina</a><b> ·</b> <a class="mw-selflink selflink">Piridossalfosfato</a><b> ·</b> <a href="/wiki/Piridossamina" title="Piridossamina">Piridossamina</a><b> ·</b> <a href="/w/index.php?title=Piritinolo&action=edit&redlink=1" class="new" title="Piritinolo (la pagina non esiste)">Piritinolo</a>)<b> ·</b> B<sub>7</sub> (<a href="/wiki/Biotina" title="Biotina">Biotina</a>)<b> ·</b> B<sub>9</sub> (<a href="/wiki/Acido_folico" title="Acido folico">Acido folico</a><b> ·</b> <a href="/wiki/Acido_diidrofolico" title="Acido diidrofolico">Acido diidrofolico</a><b> ·</b> <a href="/wiki/Acido_folinico" title="Acido folinico">Acido folinico</a><b> ·</b> <a href="/wiki/Acido_5-metiltetraidrofolico" title="Acido 5-metiltetraidrofolico">Acido 5-metiltetraidrofolico</a>)<b> ·</b> B<sub>12</sub> (<a href="/wiki/Cobalamina" title="Cobalamina">Cobalamina</a><b> ·</b> <a href="/wiki/Cobamamide" title="Cobamamide">Cobamamide</a><b> ·</b> <a href="/wiki/Cianocobalamina" class="mw-redirect" title="Cianocobalamina">Cianocobalamina</a><b> ·</b> <a href="/w/index.php?title=Idrossocobalamina&action=edit&redlink=1" class="new" title="Idrossocobalamina (la pagina non esiste)">Idrossocobalamina</a><b> ·</b> <a href="/w/index.php?title=Metilcobalamina&action=edit&redlink=1" class="new" title="Metilcobalamina (la pagina non esiste)">Metilcobalamina</a>)</td></tr><tr><th class="subnavbox_group"><a href="/wiki/Vitamina_C" class="mw-redirect" title="Vitamina C">C</a></th><td colspan="1"><a href="/wiki/Acido_ascorbico" title="Acido ascorbico">Acido ascorbico</a><b> ·</b> <a href="/w/index.php?title=Acido_deidroascorbico&action=edit&redlink=1" class="new" title="Acido deidroascorbico (la pagina non esiste)">Acido deidroascorbico</a><b> ·</b> <a href="/wiki/Ascorbato_di_sodio" title="Ascorbato di sodio">Ascorbato di sodio</a></td></tr></tbody></table></td></tr></tbody></table> <div class="noprint" style="width:100%; padding: 3px 0; display: flex; flex-wrap: wrap; row-gap: 4px; column-gap: 8px; box-sizing: border-box;"><div style="flex-basis: calc( 100% / 2 - 8px / 2 );"><style data-mw-deduplicate="TemplateStyles:r140555418">.mw-parser-output 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