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class="mw-page-title-main">Phenylalanine</span></h1> <div class="tagline"></div> </div> <ul id="p-associated-pages" class="minerva__tab-container"> <li class="minerva__tab selected"> <a class="minerva__tab-text" href="/wiki/Phenylalanine" rel="" data-event-name="tabs.subject">Article</a> </li> <li class="minerva__tab "> <a class="minerva__tab-text" href="/wiki/Talk:Phenylalanine" rel="discussion" data-event-name="tabs.talk">Talk</a> </li> </ul> <nav class="page-actions-menu"> <ul id="p-views" class="page-actions-menu__list"> <li id="language-selector" class="page-actions-menu__list-item"> <a role="button" href="#p-lang" data-mw="interface" data-event-name="menu.languages" title="Language" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet language-selector"> <span class="minerva-icon minerva-icon--language"></span> <span>Language</span> </a> </li> <li id="page-actions-watch" 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id="mw-content-text" class="mw-body-content"><script>function mfTempOpenSection(id){var block=document.getElementById("mf-section-"+id);block.className+=" open-block";block.previousSibling.className+=" open-block";}</script><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><section class="mf-section-0" id="mf-section-0"> <p> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> </p> <p><b>Phenylalanine</b> (symbol <b>Phe</b> or <b>F</b>)<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> is an essential α-<a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> with the <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> <span class="chemf nowrap">C<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">9</sub></span></span>H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">11</sub></span></span>NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span>. It can be viewed as a <a href="/wiki/Benzyl" class="mw-redirect" title="Benzyl">benzyl</a> group <a href="/wiki/Substituent" title="Substituent">substituted</a> for the <a href="/wiki/Methyl_group" title="Methyl group">methyl group</a> of <a href="/wiki/Alanine" title="Alanine">alanine</a>, or a <a href="/wiki/Phenyl" class="mw-redirect" title="Phenyl">phenyl</a> group in place of a terminal hydrogen of alanine. This <a href="/wiki/Essential_amino_acid" title="Essential amino acid">essential amino acid</a> is classified as neutral, and <a href="/wiki/Chemical_polarity" title="Chemical polarity">nonpolar</a> because of the inert and <a href="/wiki/Hydrophobic" class="mw-redirect" title="Hydrophobic">hydrophobic</a> nature of the <a href="/wiki/Benzyl" class="mw-redirect" title="Benzyl">benzyl</a> side chain. The <a href="/wiki/Chirality_(chemistry)#Naming_conventions" title="Chirality (chemistry)"><small>L</small>-isomer</a> is used to biochemically form <a href="/wiki/Protein" title="Protein">proteins</a> coded for by <a href="/wiki/DNA" title="DNA">DNA</a>. Phenylalanine is a precursor for <a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a>, the <a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">monoamine neurotransmitters</a> <a href="/wiki/Dopamine" title="Dopamine">dopamine</a>, <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a> (noradrenaline), and <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a> (adrenaline), and the <a href="/wiki/Biological_pigment" title="Biological pigment">biological pigment</a> <a href="/wiki/Melanin" title="Melanin">melanin</a>. It is <a href="/wiki/Genetic_code" title="Genetic code">encoded</a> by the <a href="/wiki/Messenger_RNA" title="Messenger RNA">messenger RNA</a> <a href="/wiki/Codons" class="mw-redirect" title="Codons">codons</a> UUU and UUC. </p><table class="infobox ib-chembox"> <caption>Phenylalanine </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:L-Phenylalanin_-_L-Phenylalanine.svg" class="mw-file-description" title="Skeletal formula"><img alt="Skeletal formula" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/L-Phenylalanin_-_L-Phenylalanine.svg/220px-L-Phenylalanin_-_L-Phenylalanine.svg.png" decoding="async" width="220" height="121" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/L-Phenylalanin_-_L-Phenylalanine.svg/330px-L-Phenylalanin_-_L-Phenylalanine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7a/L-Phenylalanin_-_L-Phenylalanine.svg/440px-L-Phenylalanin_-_L-Phenylalanine.svg.png 2x" data-file-width="232" data-file-height="128"></a></span><br><div style="text-align:center;"><a href="/wiki/Skeletal_formula" title="Skeletal formula">Skeletal formula</a> of <small>L</small>-phenylalanine</div> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:1PhenylalanineAtPhysiologicalpH.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/1PhenylalanineAtPhysiologicalpH.svg/180px-1PhenylalanineAtPhysiologicalpH.svg.png" decoding="async" width="180" height="99" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/1PhenylalanineAtPhysiologicalpH.svg/270px-1PhenylalanineAtPhysiologicalpH.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/1PhenylalanineAtPhysiologicalpH.svg/360px-1PhenylalanineAtPhysiologicalpH.svg.png 2x" data-file-width="232" data-file-height="128"></a></span><br><div style="text-align:center;"><small>L</small>-Phenylalanine at physiological pH</div> </td></tr> <tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Phenylalanine-from-xtal-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Phenylalanine-from-xtal-3D-bs-17.png/120px-Phenylalanine-from-xtal-3D-bs-17.png" decoding="async" width="120" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Phenylalanine-from-xtal-3D-bs-17.png/180px-Phenylalanine-from-xtal-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1c/Phenylalanine-from-xtal-3D-bs-17.png/240px-Phenylalanine-from-xtal-3D-bs-17.png 2x" data-file-width="2000" data-file-height="1935"></a><figcaption></figcaption></figure><div style="text-align:center"><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Ball-and-stick model</a><sup id="cite_ref-Ihlefeldt_1-0" class="reference"><a href="#cite_note-Ihlefeldt-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Phenylalanine-from-xtal-3D-sf.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Phenylalanine-from-xtal-3D-sf.png/120px-Phenylalanine-from-xtal-3D-sf.png" decoding="async" width="120" height="121" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Phenylalanine-from-xtal-3D-sf.png/180px-Phenylalanine-from-xtal-3D-sf.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Phenylalanine-from-xtal-3D-sf.png/240px-Phenylalanine-from-xtal-3D-sf.png 2x" data-file-width="1985" data-file-height="2000"></a><figcaption></figcaption></figure><div style="text-align:center"><a href="/wiki/Space-filling_model" title="Space-filling model">Space-filling model</a><sup id="cite_ref-Ihlefeldt_1-1" class="reference"><a href="#cite_note-Ihlefeldt-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div> </td></tr></tbody></table> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td>Pronunciation </td> <td><span class="rt-commentedText nowrap"><style data-mw-deduplicate="TemplateStyles:r1177148991">.mw-parser-output .IPA-label-small{font-size:85%}.mw-parser-output .references .IPA-label-small,.mw-parser-output .infobox .IPA-label-small,.mw-parser-output .navbox .IPA-label-small{font-size:100%}</style><span class="IPA-label IPA-label-small"><a href="/wiki/American_English" title="American English">US</a>: </span><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˌ/: secondary stress follows">ˌ</span><span title="'f' in 'find'">f</span><span title="/ɛ/: 'e' in 'dress'">ɛ</span><span title="'n' in 'nigh'">n</span><span title="/əl/: 'le' in 'bottle'">əl</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="/æ/: 'a' in 'bad'">æ</span><span title="'l' in 'lie'">l</span><span title="/ə/: 'a' in 'about'">ə</span><span title="'n' in 'nigh'">n</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span>; <span class="rt-commentedText nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1177148991"><span class="IPA-label IPA-label-small"><a href="/wiki/British_English" title="British English">UK</a>: </span><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˌ/: secondary stress follows">ˌ</span><span title="'f' in 'find'">f</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span><span title="/aɪ/: 'i' in 'tide'">aɪ</span><span title="'l' in 'lie'">l</span></span>-/</a></span></span> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Phenylalanine</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">(<i>S</i>)-2-Amino-3-phenylpropanoic acid</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li>L: <span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=63-91-2">63-91-2</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li><li>D/L: <span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=150-30-1">150-30-1</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li><li>D: <span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=673-06-3">673-06-3</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>L: <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=c1ccc%28cc1%29C%5BC%40%40H%5D%28C%28%3DO%29O%29N">Interactive image</a></span></li><li>D: <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=c1ccc%28cc1%29C%5BC%40H%5D%28C%28%3DO%29O%29N">Interactive image</a></span></li><li>L <a href="/wiki/Zwitterion" title="Zwitterion">Zwitterion</a>: <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=%5BNH3%2B%5D%5BC%40%40H%5D%28CC1%3DCC%3DCC%3DC1%29C%28%5BO-%5D%29%3DO">Interactive image</a></span></li><li>D <a href="/wiki/Zwitterion" title="Zwitterion">Zwitterion</a>: <span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=%5BNH3%2B%5D%5BC%40H%5D%28CC1%3DCC%3DCC%3DC1%29C%28%5BO-%5D%29%3DO">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>L: <span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=17295">CHEBI:17295</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li><li>D/L: <span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=28044">CHEBI:28044</a></span></li><li>D: <span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=16998">CHEBI:16998</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>L: <span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL301523">ChEMBL301523</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>L: <span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.5910.html">5910</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li><li>D/L: <span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.969.html">969</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li><li>D: <span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.64639.html">64639</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>L: <span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00120">DB00120</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.517">100.000.517</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q170545#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20"></a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>L: <span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=3313">3313</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>L: <span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00021">D00021</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>L: <span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6140">6140</a></span></li><li>D/L: <span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/994">994</a></span></li><li>D: <span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/71567">71567</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>L: <span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/47E5O17Y3R">47E5O17Y3R</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li><li>D/L: <span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/8P946UF12S">8P946UF12S</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li><li>D: <span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/032K16VRCU">032K16VRCU</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>L: <span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID4040763">DTXSID4040763</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q170545#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20"></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)/t8-/m0/s1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: COLNVLDHVKWLRT-QMMMGPOBSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600"></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">L: Key: COLNVLDHVKWLRT-QMMMGPOBBC</div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">D/L: Key: COLNVLDHVKWLRT-UHFFFAOYSA-N</div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">D: Key: COLNVLDHVKWLRT-MRVPVSSYSA-N</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">L: c1ccc(cc1)C[C@@H](C(=O)O)N</div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">D: c1ccc(cc1)C[C@H](C(=O)O)N</div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">L <a href="/wiki/Zwitterion" title="Zwitterion">Zwitterion</a>: [NH3+][C@@H](CC1=CC=CC=C1)C([O-])=O</div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">D <a href="/wiki/Zwitterion" title="Zwitterion">Zwitterion</a>: [NH3+][C@H](CC1=CC=CC=C1)C([O-])=O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>9</sub><span title="Hydrogen">H</span><sub>11</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002165192000000000♠"></span>165.192</span> g·mol<sup>−1</sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>9.97 g/L at 0 °C <br> <p>14.11 g/L at 25 °C <br> 21.87 g/L at 50 °C <br> 37.08 g/L at 75 °C <br> 68.9 g/L at 100 °C </p> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td>1.83 (carboxyl), 9.13 (amino)<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> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_482e25fdfe95519d"></span><map name="ImageMap_482e25fdfe95519d"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform"><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil"><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen"><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code"></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Supplementary data page </th></tr> <tr> <td colspan="2" style="text-align:center"><a href="/wiki/Phenylalanine_(data_page)" title="Phenylalanine (data page)">Phenylalanine (data page)</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table> <p>Phenylalanine is found naturally in the milk of <a href="/wiki/Mammal" title="Mammal">mammals</a>. It is used in the manufacture of food and drink products and sold as a nutritional supplement as it is a direct precursor to the <a href="/wiki/Neuromodulation" title="Neuromodulation">neuromodulator</a> <a href="/wiki/Phenethylamine" title="Phenethylamine">phenethylamine</a>. As an essential amino acid, phenylalanine is not synthesized <a href="/wiki/De_novo_synthesis" title="De novo synthesis">de novo</a> in humans and other animals, who must ingest phenylalanine or phenylalanine-containing proteins. </p><p>The one-letter symbol F was assigned to phenylalanine for its phonetic similarity.<sup id="cite_ref-:0_4-0" class="reference"><a href="#cite_note-:0-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div id="toc" class="toc" role="navigation" aria-labelledby="mw-toc-heading"><input type="checkbox" role="button" id="toctogglecheckbox" class="toctogglecheckbox" style="display:none"><div class="toctitle" lang="en" dir="ltr"><h2 id="mw-toc-heading">Contents</h2><span class="toctogglespan"><label class="toctogglelabel" for="toctogglecheckbox"></label></span></div> <ul> <li class="toclevel-1 tocsection-1"><a href="#History"><span class="tocnumber">1</span> <span class="toctext">History</span></a></li> <li class="toclevel-1 tocsection-2"><a href="#Dietary_sources"><span class="tocnumber">2</span> <span class="toctext">Dietary sources</span></a></li> <li class="toclevel-1 tocsection-3"><a href="#Dietary_recommendations"><span class="tocnumber">3</span> <span class="toctext">Dietary recommendations</span></a></li> <li class="toclevel-1 tocsection-4"><a href="#Other_biological_roles"><span class="tocnumber">4</span> <span class="toctext">Other biological roles</span></a> <ul> <li class="toclevel-2 tocsection-5"><a href="#In_plants"><span class="tocnumber">4.1</span> <span class="toctext">In plants</span></a></li> </ul> </li> <li class="toclevel-1 tocsection-6"><a href="#Biosynthesis"><span class="tocnumber">5</span> <span class="toctext">Biosynthesis</span></a></li> <li class="toclevel-1 tocsection-7"><a href="#Phenylketonuria"><span class="tocnumber">6</span> <span class="toctext">Phenylketonuria</span></a></li> <li class="toclevel-1 tocsection-8"><a href="#D-,_L-_and_DL-phenylalanine"><span class="tocnumber">7</span> <span class="toctext">D-, L- and DL-phenylalanine</span></a></li> <li class="toclevel-1 tocsection-9"><a href="#Commercial_synthesis"><span class="tocnumber">8</span> <span class="toctext">Commercial synthesis</span></a></li> <li class="toclevel-1 tocsection-10"><a href="#Derivatives"><span class="tocnumber">9</span> <span class="toctext">Derivatives</span></a></li> <li class="toclevel-1 tocsection-11"><a href="#References"><span class="tocnumber">10</span> <span class="toctext">References</span></a></li> <li class="toclevel-1 tocsection-12"><a href="#External_links"><span class="tocnumber">11</span> <span class="toctext">External links</span></a></li> </ul> </div> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(1)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="History">History</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Phenylalanine&action=edit&section=1" title="Edit section: History" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-1 collapsible-block" id="mf-section-1"> <p>The first description of phenylalanine was made in 1879, when <a href="/wiki/Ernst_Schulze_(chemist)" title="Ernst Schulze (chemist)">Schulze</a> and Barbieri identified a compound with the <a href="/wiki/Empirical_formula" title="Empirical formula">empirical formula</a>, C<sub>9</sub>H<sub>11</sub>NO<sub>2</sub>, in <a href="/wiki/Lupinus_luteus" title="Lupinus luteus">yellow lupine</a> (<i>Lupinus luteus</i>) seedlings. In 1882, <a href="/wiki/Emil_Erlenmeyer" title="Emil Erlenmeyer">Erlenmeyer</a> and Lipp first synthesized phenylalanine from <a href="/wiki/Phenylacetaldehyde" title="Phenylacetaldehyde">phenylacetaldehyde</a>, <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a>, and <a href="/wiki/Ammonia" title="Ammonia">ammonia</a>.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>The genetic <a href="/wiki/Codon" class="mw-redirect" title="Codon">codon</a> for phenylalanine was first discovered by <a href="/wiki/J._Heinrich_Matthaei" title="J. Heinrich Matthaei">J. Heinrich Matthaei</a> and <a href="/wiki/Marshall_W._Nirenberg" class="mw-redirect" title="Marshall W. Nirenberg">Marshall W. Nirenberg</a> in 1961. They showed that by using <a href="/wiki/Messenger_RNA" title="Messenger RNA">mRNA</a> to insert multiple <a href="/wiki/Uracil" title="Uracil">uracil</a> repeats into the <a href="/wiki/Genome" title="Genome">genome</a> of the <a href="/wiki/Bacterium" class="mw-redirect" title="Bacterium">bacterium</a> <i><a href="/wiki/Escherichia_coli" title="Escherichia coli">E. coli</a></i>, they could cause the bacterium to produce a <a href="/wiki/Peptide" title="Peptide">polypeptide</a> consisting solely of repeated phenylalanine amino acids. This discovery helped to establish the nature of the <a href="/wiki/Coding_strand" title="Coding strand">coding</a> relationship that links information stored in <a href="/wiki/Genome" title="Genome">genomic</a> nucleic acid with <a href="/wiki/Proteome" title="Proteome">protein expression</a> in the living cell. </p> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(2)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Dietary_sources">Dietary sources</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Phenylalanine&action=edit&section=2" title="Edit section: Dietary sources" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-2 collapsible-block" id="mf-section-2"> <p>Good sources of phenylalanine are eggs, chicken, liver, beef, milk, and soybeans.<sup id="cite_ref-RossRoth1991_7-0" class="reference"><a href="#cite_note-RossRoth1991-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Another common source of phenylalanine is anything sweetened with the artificial sweetener <a href="/wiki/Aspartame" title="Aspartame">aspartame</a>, such as <a href="/wiki/Diet_drink" class="mw-redirect" title="Diet drink">diet drinks</a>, <a href="/wiki/Diet_food" title="Diet food">diet foods</a> and medication; the metabolism of aspartame produces phenylalanine as one of the compound's <a href="/wiki/Metabolite" title="Metabolite">metabolites</a>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(3)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Dietary_recommendations">Dietary recommendations</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Phenylalanine&action=edit&section=3" title="Edit section: Dietary recommendations" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-3 collapsible-block" id="mf-section-3"> <p>The Food and Nutrition Board (FNB) of the U.S. Institute of Medicine set Recommended Dietary Allowances (RDAs) for <a href="/wiki/Essential_amino_acid" title="Essential amino acid">essential amino acids</a> in 2002. For phenylalanine plus tyrosine, for adults 19 years and older, 33 mg/kg body weight/day.<sup id="cite_ref-DRItext_9-0" class="reference"><a href="#cite_note-DRItext-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> In 2005 the DRI is set to 27 mg/kg per day (with no tyrosine), the <a href="/wiki/Food_and_Agriculture_Organization" title="Food and Agriculture Organization">FAO</a>/<a href="/wiki/World_Health_Organization" title="World Health Organization">WHO</a>/<a href="/wiki/United_Nations_University" title="United Nations University">UNU</a> recommendation of 2007 is 25 mg/kg per day (with no tyrosine).<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(4)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Other_biological_roles">Other biological roles</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Phenylalanine&action=edit&section=4" title="Edit section: Other biological roles" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-4 collapsible-block" id="mf-section-4"> <p><small>L</small>-Phenylalanine is biologically converted into <small>L</small>-<a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a>, another one of the DNA-encoded amino acids. <small>L</small>-tyrosine in turn is converted into <a href="/wiki/L-DOPA" title="L-DOPA"><small>L</small>-DOPA</a>, which is further converted into <a href="/wiki/Dopamine" title="Dopamine">dopamine</a>, <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a> (noradrenaline), and <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a> (adrenaline). The latter three are known as the <a href="/wiki/Catecholamines" class="mw-redirect" title="Catecholamines">catecholamines</a>. </p><p> Phenylalanine uses the same active transport channel as <a href="/wiki/Tryptophan" title="Tryptophan">tryptophan</a> to cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a>. In excessive quantities, supplementation can interfere with the production of <a href="/wiki/Serotonin" title="Serotonin">serotonin</a> and other <a href="/wiki/Aromatic_amino_acid" title="Aromatic amino acid">aromatic amino acids</a><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> as well as <a href="/wiki/Nitric_oxide" title="Nitric oxide">nitric oxide</a> due to the overuse (eventually, limited availability) of the associated cofactors, <a href="/wiki/Iron" title="Iron">iron</a> or <a href="/wiki/Tetrahydrobiopterin" title="Tetrahydrobiopterin">tetrahydrobiopterin</a>. <sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (December 2018)">citation needed</span></a></i>]</sup> The corresponding enzymes for those compounds are the <a href="/wiki/Aromatic_amino_acid_hydroxylase" class="mw-redirect" title="Aromatic amino acid hydroxylase">aromatic amino acid hydroxylase</a> family and <a href="/wiki/Nitric_oxide_synthase" title="Nitric oxide synthase">nitric oxide synthase</a>.</p><div class="skin-invert-image"> <table role="presentation" cellpadding="0" style="border-spacing:0; margin-left: auto; margin-right: auto; border: none;"> <tbody><tr> <td><div class="thumb center" style="margin: 1em auto;"> <div class="thumbinner" style="width:592px;"> <div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: #F0F8FF;margin-bottom:3px;">Biosynthetic pathways for <a href="/wiki/Catecholamine" title="Catecholamine">catecholamines</a> and <a href="/wiki/Trace_amine" title="Trace amine">trace amines</a> in the <a href="/wiki/Human_brain" title="Human brain">human brain</a><sup id="cite_ref-Trace_amine_template_1_12-0" class="reference"><a href="#cite_note-Trace_amine_template_1-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Trace_amine_template_2_13-0" class="reference"><a href="#cite_note-Trace_amine_template_2-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CYP2D6_tyramine-dopamine_metabolism_14-0" class="reference"><a href="#cite_note-CYP2D6_tyramine-dopamine_metabolism-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup></div> <div style="position:relative; width:590px; height:465px; overflow:hidden; border:solid #ccc 1px; background-color:white;"> <div style="left:5px; top:0px; width:580px; position:absolute"> <span typeof="mw:File"><a href="https://commons.wikimedia.org/wiki/File:Catecholamine_and_trace_amine_biosynthesis.svg" title="commons:File:Catecholamine and trace amine biosynthesis.svg"><noscript><img alt="Graphic of catecholamine and trace amine biosynthesis" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Catecholamine_and_trace_amine_biosynthesis.svg/580px-Catecholamine_and_trace_amine_biosynthesis.svg.png" decoding="async" width="580" height="458" class="mw-file-element" data-file-width="512" data-file-height="404"></noscript><span class="lazy-image-placeholder" style="width: 580px;height: 458px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Catecholamine_and_trace_amine_biosynthesis.svg/580px-Catecholamine_and_trace_amine_biosynthesis.svg.png" data-alt="Graphic of catecholamine and trace amine biosynthesis" data-width="580" data-height="458" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Catecholamine_and_trace_amine_biosynthesis.svg/870px-Catecholamine_and_trace_amine_biosynthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/46/Catecholamine_and_trace_amine_biosynthesis.svg/1160px-Catecholamine_and_trace_amine_biosynthesis.svg.png 2x" data-class="mw-file-element"> </span></a></span> </div> <div style="text-align:center; font-size:14px; line-height:110%"> <div style="background-color:transparent; color:black"><div id="annotation_40x60" style="position:absolute; left:40px; top:60px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><span style="color:black;background:yellow"><b><small>L</small>-Phenylalanine</b></span></span></div> <div id="annotation_50x185" style="position:absolute; left:50px; top:185px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Tyrosine" title="Tyrosine"><small>L</small>-Tyrosine</a></span></div> <div id="annotation_60x315" style="position:absolute; left:60px; top:315px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/L-DOPA" title="L-DOPA"><small>L</small>-DOPA</a></span></div> <div id="annotation_50x445" style="position:absolute; left:50px; top:445px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Adrenaline" title="Adrenaline">Epinephrine</a></span></div> <div id="annotation_245x60" style="position:absolute; left:245px; top:60px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></span></div> <div id="annotation_245x185" style="position:absolute; left:245px; top:185px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Tyramine" title="Tyramine"><i>p</i>-Tyramine</a></span></div> <div id="annotation_245x315" style="position:absolute; left:245px; top:315px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></span></div> <div id="annotation_245x445" style="position:absolute; left:245px; top:445px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a></span></div> <div id="annotation_415x60" style="position:absolute; left:415px; top:60px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/N-Methylphenethylamine" title="N-Methylphenethylamine"><i>N</i>-Methylphenethylamine</a></span></div> <div id="annotation_440x138" style="position:absolute; left:440px; top:138px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/N-Methyltyramine" title="N-Methyltyramine"><i>N</i>-Methyltyramine</a></span></div> <div id="annotation_440x228" style="position:absolute; left:440px; top:228px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Octopamine" title="Octopamine"><i>p</i>-Octopamine</a></span></div> <div id="annotation_455x350" style="position:absolute; left:455px; top:350px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Synephrine" title="Synephrine">Synephrine</a></span></div> <div id="annotation_445x445" style="position:absolute; left:445px; top:445px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a></span></div> <div id="annotation_167x16" style="position:absolute; left:167px; top:16px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">AADC</a></span></div> <div id="annotation_167x145" style="position:absolute; left:167px; top:145px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">AADC</a></span></div> <div id="annotation_167x275" style="position:absolute; left:167px; top:275px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase">AADC</a></span></div> <div id="annotation_164x295" style="position:absolute; left:164px; top:295px; font-size:12px; font-size:12; line-height:14px;"><span style="background-color:transparent; color:inherit;">primary<br>pathway</span></div> <div id="annotation_370x17" style="position:absolute; left:370px; top:17px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></span></div> <div id="annotation_360x120" style="position:absolute; left:360px; top:120px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></span></div> <div id="annotation_445x255" style="position:absolute; left:445px; top:255px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></span></div> <div id="annotation_176x407" style="position:absolute; left:176px; top:407px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase">PNMT</a></span></div> <div id="annotation_40x90" style="position:absolute; left:40px; top:90px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Biopterin-dependent_aromatic_amino_acid_hydroxylase" title="Biopterin-dependent aromatic amino acid hydroxylase">AAAH</a></span></div> <div id="annotation_40x220" style="position:absolute; left:40px; top:220px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Biopterin-dependent_aromatic_amino_acid_hydroxylase" title="Biopterin-dependent aromatic amino acid hydroxylase">AAAH</a></span></div> <div id="annotation_225x215" style="position:absolute; left:225px; top:215px; line-height:110%;"><span style="background-color:transparent; color:inherit;">brain<br><a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a></span></div> <div id="annotation_291x217" style="position:absolute; left:291px; top:217px; font-size:12px; font-size:12; line-height:14px; text-align:left;"><span style="background-color:transparent; color:inherit;">minor<br>pathway</span></div> <div id="annotation_325x350" style="position:absolute; left:325px; top:350px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Catechol-O-methyltransferase" title="Catechol-O-methyltransferase">COMT</a></span></div> <div id="annotation_250x350" style="position:absolute; left:250px; top:350px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Dopamine_beta-hydroxylase" title="Dopamine beta-hydroxylase">DBH</a></span></div> <div id="annotation_360x185" style="position:absolute; left:360px; top:185px; line-height:110%;"><span style="background-color:transparent; color:inherit;"><a href="/wiki/Dopamine_beta-hydroxylase" title="Dopamine beta-hydroxylase">DBH</a></span></div></div> </div> </div> <div class="thumbcaption" style="clear:left"><div style="float:left;margin-right:0.5em"><span typeof="mw:File"><span title="The image above contains clickable links"><noscript><img alt="The image above contains clickable links" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/18px-Interactive_icon.svg.png" decoding="async" width="18" height="27" class="mw-file-element" data-file-width="133" data-file-height="200"></noscript><span class="lazy-image-placeholder" style="width: 18px;height: 27px;" data-src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/18px-Interactive_icon.svg.png" data-alt="The image above contains clickable links" data-width="18" data-height="27" data-srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/27px-Interactive_icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/36px-Interactive_icon.svg.png 2x" data-class="mw-file-element"> </span></span></span></div>Phenylalanine in humans may ultimately be metabolized into a range of different substances.</div> </div> </div> </td></tr></tbody></table> </div> <p><br> </p> <div class="mw-heading mw-heading3"><h3 id="In_plants">In plants</h3><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Phenylalanine&action=edit&section=5" title="Edit section: In plants" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div> <p>Phenylalanine is the starting compound used in the <a href="/wiki/Biosynthesis" title="Biosynthesis">synthesis</a> of <a href="/wiki/Flavonoid" title="Flavonoid">flavonoids</a>. <a href="/wiki/Lignan" title="Lignan">Lignan</a> is derived from phenylalanine and from <a href="/wiki/Tyrosine" title="Tyrosine">tyrosine</a>. Phenylalanine is converted to <a href="/wiki/Cinnamic_acid" title="Cinnamic acid">cinnamic acid</a> by the enzyme <a href="/wiki/Phenylalanine_ammonia-lyase" title="Phenylalanine ammonia-lyase">phenylalanine ammonia-lyase</a>.<sup id="cite_ref-Nelson_15-0" class="reference"><a href="#cite_note-Nelson-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(5)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Phenylalanine&action=edit&section=6" title="Edit section: Biosynthesis" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-5 collapsible-block" id="mf-section-5"> <p>Phenylalanine is biosynthesized via the <a href="/wiki/Shikimate_pathway" title="Shikimate pathway">shikimate pathway</a>. </p> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(6)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Phenylketonuria">Phenylketonuria</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Phenylalanine&action=edit&section=7" title="Edit section: Phenylketonuria" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-6 collapsible-block" id="mf-section-6"> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Phenylketonuria" title="Phenylketonuria">Phenylketonuria</a></div> <p>The genetic disorder <a href="/wiki/Phenylketonuria" title="Phenylketonuria">phenylketonuria</a> (PKU) is the inability to metabolize phenylalanine because of a lack of the enzyme <a href="/wiki/Phenylalanine_hydroxylase" title="Phenylalanine hydroxylase">phenylalanine hydroxylase</a>. Individuals with this disorder are known as "phenylketonurics" and must regulate their intake of phenylalanine. Phenylketonurics often use blood tests to monitor the amount of phenylalanine in their blood. Lab results may report phenylalanine levels using either mg/dL and μmol/L. One mg/dL of phenylalanine is approximately equivalent to 60 μmol/L. </p><p>A (rare) "variant form" of phenylketonuria called <a href="/wiki/Hyperphenylalaninemia" title="Hyperphenylalaninemia">hyperphenylalaninemia</a> is caused by the inability to synthesize a <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactor</a> called <a href="/wiki/Tetrahydrobiopterin" title="Tetrahydrobiopterin">tetrahydrobiopterin</a>, which can be supplemented. Pregnant women with hyperphenylalaninemia may show similar symptoms of the disorder (high levels of phenylalanine in blood), but these indicators will usually disappear at the end of gestation. Pregnant women with PKU must control their blood phenylalanine levels even if the fetus is heterozygous for the defective gene because the fetus could be adversely affected due to hepatic immaturity.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (April 2016)">medical citation needed</span></a></i>]</sup> </p><p>A non-food source of phenylalanine is the artificial sweetener <a href="/wiki/Aspartame" title="Aspartame">aspartame</a>. This compound is metabolized by the body into several chemical byproducts including phenylalanine. The breakdown problems phenylketonurics have with the buildup of phenylalanine in the body also occurs with the ingestion of aspartame, although to a lesser degree. Accordingly, all products in Australia, the U.S. and Canada that contain aspartame must be labeled: "Phenylketonurics: Contains phenylalanine." In the UK, foods containing aspartame must carry ingredient panels that refer to the presence of "aspartame or E951"<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> and they must be labeled with a warning "Contains a source of phenylalanine." In Brazil, the label "Contém Fenilalanina" (Portuguese for "Contains Phenylalanine") is also mandatory in products which contain it. These warnings are placed to help individuals avoid such foods. </p> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(7)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="D-,_L-_and_DL-phenylalanine"><span id="D-.2C_L-_and_DL-phenylalanine"></span><small>D</small>-, <small>L</small>- and <small>DL</small>-phenylalanine</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Phenylalanine&action=edit&section=8" title="Edit section: D-, L- and DL-phenylalanine" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-7 collapsible-block" id="mf-section-7"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/D-Phenylalanine" title="D-Phenylalanine">D-Phenylalanine</a></div> <p>The <a href="/wiki/Stereoisomer" class="mw-redirect" title="Stereoisomer">stereoisomer</a> <a href="/wiki/D-phenylalanine" class="mw-redirect" title="D-phenylalanine"><small>D</small>-phenylalanine</a> (DPA) can be produced by conventional <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a>, either as a single <a href="/wiki/Enantiomer" title="Enantiomer">enantiomer</a> or as a component of the <a href="/wiki/Racemic" class="mw-redirect" title="Racemic">racemic</a> mixture. It does not participate in <a href="/wiki/Protein_biosynthesis" title="Protein biosynthesis">protein biosynthesis</a> although it is found in proteins in small amounts - particularly aged proteins and food proteins that have been <a href="/wiki/Food_processing" title="Food processing">processed</a>. The biological functions of <small>D</small>-amino acids remain unclear, although <small>D</small>-phenylalanine has <a href="/wiki/Pharmacological_activity" class="mw-redirect" title="Pharmacological activity">pharmacological activity</a> at <a href="/wiki/Niacin_receptor_2" class="mw-redirect" title="Niacin receptor 2">niacin receptor 2</a>.<sup id="cite_ref-IUPHAR/BPS-bio_17-0" class="reference"><a href="#cite_note-IUPHAR/BPS-bio-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p><small>DL</small>-Phenylalanine (DLPA) is marketed as a nutritional supplement for its purported <a href="/wiki/Analgesic" title="Analgesic">analgesic</a> and <a href="/wiki/Antidepressant" title="Antidepressant">antidepressant</a> activities, which have been supported by clinical trials.<sup id="cite_ref-Wood_Reimherr_Wender_1985_pp._21–26_18-0" class="reference"><a href="#cite_note-Wood_Reimherr_Wender_1985_pp._21%E2%80%9326-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Beckmann_Strauss_Ludolph_1977_pp._123–134_19-0" class="reference"><a href="#cite_note-Beckmann_Strauss_Ludolph_1977_pp._123%E2%80%93134-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Beckmann_Athen_Olteanu_Zimmer_1979_pp._49–58_20-0" class="reference"><a href="#cite_note-Beckmann_Athen_Olteanu_Zimmer_1979_pp._49%E2%80%9358-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> <small>DL</small>-Phenylalanine is a mixture of <small>D</small>-phenylalanine and <small>L</small>-phenylalanine. The reputed analgesic activity of <small>DL</small>-phenylalanine may be explained by the possible blockage by <small>D</small>-phenylalanine of <a href="/wiki/Enkephalin" title="Enkephalin">enkephalin</a> <a href="/wiki/Chemical_decomposition" title="Chemical decomposition">degradation</a> by the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Carboxypeptidase_A" title="Carboxypeptidase A">carboxypeptidase A</a>.<sup id="cite_ref-IUPHAR/BPS-clinical_21-0" class="reference"><a href="#cite_note-IUPHAR/BPS-clinical-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Enkephalins act as agonists of the <a href="/wiki/Mu_opioid_receptor" class="mw-redirect" title="Mu opioid receptor">mu</a> and <a href="/wiki/Delta_opioid_receptor" class="mw-redirect" title="Delta opioid receptor">delta opioid receptors</a>, and agonists of these receptors are known to produce antidepressant effects.<sup id="cite_ref-Jelen_Stone_Young_Mehta_2022_p=104800_23-0" class="reference"><a href="#cite_note-Jelen_Stone_Young_Mehta_2022_p=104800-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> The mechanism of <small>DL</small>-phenylalanine's supposed antidepressant activity may also be accounted for in part by the <a href="/wiki/Protein_precursor" title="Protein precursor">precursor</a> role of <small>L</small>-phenylalanine in the synthesis of the <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitters</a> <a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a> and <a href="/wiki/Dopamine" title="Dopamine">dopamine</a>, though clinical trials have not found an antidepressant effect from <small>L</small>-phenylalanine alone.<sup id="cite_ref-Wood_Reimherr_Wender_1985_pp._21–26_18-1" class="reference"><a href="#cite_note-Wood_Reimherr_Wender_1985_pp._21%E2%80%9326-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Elevated brain levels of norepinephrine and dopamine are thought to have an antidepressant effect. <small>D</small>-Phenylalanine is absorbed from the <a href="/wiki/Small_intestine" title="Small intestine">small intestine</a> and transported to the liver via the <a href="/wiki/Portal_circulation" class="mw-redirect" title="Portal circulation">portal circulation</a>. A small amount of <small>D</small>-phenylalanine appears to be converted to <small>L</small>-phenylalanine. <small>D</small>-Phenylalanine is distributed to the various tissues of the body via the <a href="/wiki/Systemic_circulation" class="mw-redirect" title="Systemic circulation">systemic circulation</a>. It appears to cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> less efficiently than <small>L</small>-phenylalanine, and so a small amount of an ingested dose of <small>D</small>-phenylalanine is excreted in the <a href="/wiki/Urine" title="Urine">urine</a> without penetrating the central nervous system.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p><small>L</small>-Phenylalanine is an antagonist at <a href="/wiki/Voltage-gated_calcium_channel" title="Voltage-gated calcium channel">α<sub>2</sub>δ Ca<sup>2+</sup> calcium channels</a> with a K<sub>i</sub> of 980 nM.<sup id="cite_ref-pmid16380257_25-0" class="reference"><a href="#cite_note-pmid16380257-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>In the brain, <small>L</small>-phenylalanine is a <a href="/wiki/Competitive_antagonist" class="mw-redirect" title="Competitive antagonist">competitive antagonist</a> at the <a href="/wiki/Glycine" title="Glycine">glycine</a> binding site of <a href="/wiki/NMDA_receptor" title="NMDA receptor">NMDA receptor</a><sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> and at the <a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a> binding site of <a href="/wiki/AMPA_receptor" title="AMPA receptor">AMPA receptor</a>.<sup id="cite_ref-Glushakov_116–24_27-0" class="reference"><a href="#cite_note-Glushakov_116%E2%80%9324-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> At the <a href="/wiki/Glycine" title="Glycine">glycine</a> binding site of <a href="/wiki/NMDA_receptor" title="NMDA receptor">NMDA receptor</a> <small>L</small>-phenylalanine has an apparent equilibrium dissociation constant (K<sub>B</sub>) of 573 μM estimated by <a href="/wiki/Schild_regression" class="mw-redirect" title="Schild regression">Schild regression</a><sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> which is considerably lower than brain <small>L</small>-phenylalanine concentration observed in untreated human <a href="/wiki/Phenylketonuria" title="Phenylketonuria">phenylketonuria</a>.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> <small>L</small>-Phenylalanine also inhibits <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> release at <a href="/wiki/Glutamatergic" title="Glutamatergic">glutamatergic</a> <a href="/wiki/Synapses" class="mw-redirect" title="Synapses">synapses</a> in <a href="/wiki/Hippocampus" title="Hippocampus">hippocampus</a> and <a href="/wiki/Cerebral_cortex" title="Cerebral cortex">cortex</a> with <a href="/wiki/IC50" title="IC50">IC<sub>50</sub></a> of 980 μM, a brain concentration seen in classical <a href="/wiki/Phenylketonuria" title="Phenylketonuria">phenylketonuria</a>, whereas <small>D</small>-phenylalanine has a significantly smaller effect.<sup id="cite_ref-Glushakov_116–24_27-1" class="reference"><a href="#cite_note-Glushakov_116%E2%80%9324-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(8)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Commercial_synthesis">Commercial synthesis</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Phenylalanine&action=edit&section=9" title="Edit section: Commercial synthesis" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-8 collapsible-block" id="mf-section-8"> <p><small>L</small>-Phenylalanine is produced for medical, feed, and nutritional applications, such as <a href="/wiki/Aspartame" title="Aspartame">aspartame</a>, in large quantities by utilizing the bacterium <i><a href="/wiki/Escherichia_coli" title="Escherichia coli">Escherichia coli</a></i>, which naturally produces <a href="/wiki/Aromatic_amino_acids" class="mw-redirect" title="Aromatic amino acids">aromatic amino acids</a> like phenylalanine. The quantity of <small>L</small>-phenylalanine produced commercially has been increased by <a href="/wiki/Genetic_engineering" title="Genetic engineering">genetically engineering</a> <i>E. coli</i>, such as by altering the regulatory <a href="/wiki/Promoter_(biology)" class="mw-redirect" title="Promoter (biology)">promoters</a> or amplifying the number of <a href="/wiki/Genes" class="mw-redirect" title="Genes">genes</a> controlling enzymes responsible for the synthesis of the amino acid.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(9)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="Derivatives">Derivatives</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Phenylalanine&action=edit&section=10" title="Edit section: Derivatives" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-9 collapsible-block" id="mf-section-9"> <p><b>Boronophenylalanine</b> (BPA) is a dihydroxyboryl derivative of phenylalanine, used in <a href="/wiki/Neutron_capture_therapy" class="mw-redirect" title="Neutron capture therapy">neutron capture therapy</a>. </p><p><b>4-Azido-<small>L</small>-phenylalanine</b> is a protein-incorporated unnatural amino acid used as a tool for <a href="/wiki/Bioconjugation" title="Bioconjugation">bioconjugation</a> in the field of <a href="/wiki/Chemical_biology" title="Chemical biology">chemical biology</a>. </p> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(10)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="References">References</h2><span class="mw-editsection"> <a role="button" href="/w/index.php?title=Phenylalanine&action=edit&section=11" title="Edit section: References" class="cdx-button cdx-button--size-large cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--icon-only cdx-button--weight-quiet "> <span class="minerva-icon minerva-icon--edit"></span> <span>edit</span> </a> </span> </div><section class="mf-section-10 collapsible-block" id="mf-section-10"> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-Ihlefeldt-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ihlefeldt_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ihlefeldt_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite 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Ed.</a></i> <b>53</b> (49): 13600–13604. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.201406886">10.1002/anie.201406886</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/25336255">25336255</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angew.+Chem.+Int.+Ed.&rft.atitle=The+Polymorphs+of+L-Phenylalanine&rft.volume=53&rft.issue=49&rft.pages=13600-13604&rft.date=2014&rft_id=info%3Adoi%2F10.1002%2Fanie.201406886&rft_id=info%3Apmid%2F25336255&rft.aulast=Ihlefeldt&rft.aufirst=Franziska+Stefanie&rft.au=Pettersen%2C+Fredrik+Bjarte&rft.au=von+Bonin%2C+Aidan&rft.au=Zawadzka%2C+Malgorzata&rft.au=G%C3%B6rbitz%2C+Prof.+Carl+Henrik&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenylalanine" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDawson1959" class="citation book cs1">Dawson RM, et al. 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(February 2005). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fbrain%2Fawh354">"Long-term changes in glutamatergic synaptic transmission in phenylketonuria"</a>. <i>Brain</i>. <b>128</b> (Pt 2): 300–307. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fbrain%2Fawh354">10.1093/brain/awh354</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15634735">15634735</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Brain&rft.atitle=Long-term+changes+in+glutamatergic+synaptic+transmission+in+phenylketonuria&rft.volume=128&rft.issue=Pt+2&rft.pages=300-307&rft.date=2005-02&rft_id=info%3Adoi%2F10.1093%2Fbrain%2Fawh354&rft_id=info%3Apmid%2F15634735&rft.aulast=Glushakov&rft.aufirst=AV&rft.au=Glushakova%2C+O&rft.au=Varshney%2C+M&rft.au=Bajpai%2C+LK&rft.au=Sumners%2C+C&rft.au=Laipis%2C+PJ&rft.au=Embury%2C+JE&rft.au=Baker%2C+SP&rft.au=Otero%2C+DH&rft.au=Dennis%2C+DM&rft.au=Seubert%2C+CN&rft.au=Martynyuk%2C+AE&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Fbrain%252Fawh354&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenylalanine" class="Z3988"></span></span> </li> <li id="cite_note-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-29">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMöllerWeglageBickWiedermann2003" class="citation journal cs1">Möller HE, Weglage J, Bick U, Wiedermann D, Feldmann R, Ullrich K (December 2003). "Brain imaging and proton magnetic resonance spectroscopy in patients with phenylketonuria". <i>Pediatrics</i>. <b>112</b> (6 Pt 2): 1580–1583. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1542%2Fpeds.112.S4.1580">10.1542/peds.112.S4.1580</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/11858%2F00-001M-0000-0010-A24A-C">11858/00-001M-0000-0010-A24A-C</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/14654669">14654669</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:2198040">2198040</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pediatrics&rft.atitle=Brain+imaging+and+proton+magnetic+resonance+spectroscopy+in+patients+with+phenylketonuria&rft.volume=112&rft.issue=6+Pt+2&rft.pages=1580-1583&rft.date=2003-12&rft_id=info%3Ahdl%2F11858%2F00-001M-0000-0010-A24A-C&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A2198040%23id-name%3DS2CID&rft_id=info%3Apmid%2F14654669&rft_id=info%3Adoi%2F10.1542%2Fpeds.112.S4.1580&rft.aulast=M%C3%B6ller&rft.aufirst=HE&rft.au=Weglage%2C+J&rft.au=Bick%2C+U&rft.au=Wiedermann%2C+D&rft.au=Feldmann%2C+R&rft.au=Ullrich%2C+K&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenylalanine" class="Z3988"></span></span> </li> <li id="cite_note-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-30">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSprenger2007" class="citation book cs1">Sprenger GA (2007). "Aromatic Amino Acids". <i>Amino Acid Biosynthesis: Pathways, Regulation and Metabolic Engineering</i> (1st ed.). Springer. pp. 106–113. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-48595-7" title="Special:BookSources/978-3-540-48595-7"><bdi>978-3-540-48595-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Aromatic+Amino+Acids&rft.btitle=Amino+Acid+Biosynthesis%3A+Pathways%2C+Regulation+and+Metabolic+Engineering&rft.pages=106-113&rft.edition=1st&rft.pub=Springer&rft.date=2007&rft.isbn=978-3-540-48595-7&rft.aulast=Sprenger&rft.aufirst=G.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenylalanine" class="Z3988"></span></span> </li> </ol></div> </section><div class="mw-heading mw-heading2 section-heading" onclick="mfTempOpenSection(11)"><span class="indicator mf-icon mf-icon-expand mf-icon--small"></span><h2 id="External_links">External links</h2><span class="mw-editsection"> <a role="button" 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minerva-icon--modified-history"></span> <span class="last-modified-bar__text modified-enhancement" data-user-name="98.191.202.231" data-user-gender="unknown" data-timestamp="1721942761"> <span>Last edited on 25 July 2024, at 21:26</span> </span> <span class="minerva-icon minerva-icon-size-small minerva-icon--expand"></span> </div> </a> <div class="post-content footer-content"> <div id='mw-data-after-content'> <div class="read-more-container"></div> </div> <div id="p-lang"> <h4>Languages</h4> <section> <ul id="p-variants" class="minerva-languages"></ul> <ul class="minerva-languages"><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%81%D9%8A%D9%86%D9%8A%D9%84_%D8%A3%D9%84%D8%A7%D9%86%D9%8A%D9%86" title="فينيل ألانين – Arabic" lang="ar" hreflang="ar" data-title="فينيل ألانين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Fenilalanin" title="Fenilalanin – Azerbaijani" lang="az" hreflang="az" data-title="Fenilalanin" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%81%D9%86%DB%8C%D9%84%E2%80%8C%D8%A2%D9%84%D8%A7%D9%86%DB%8C%D9%86" title="فنیل‌آلانین – South Azerbaijani" lang="azb" hreflang="azb" data-title="فنیل‌آلانین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/Phenylalanin" title="Phenylalanin – Minnan" lang="nan" hreflang="nan" data-title="Phenylalanin" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D1%96%D0%BB%D0%B0%D0%BB%D0%B0%D0%BD%D1%96%D0%BD" title="Фенілаланін – Belarusian" lang="be" hreflang="be" data-title="Фенілаланін" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%B8%D0%BB%D0%B0%D0%BB%D0%B0%D0%BD%D0%B8%D0%BD" title="Фенилаланин – Bulgarian" lang="bg" hreflang="bg" data-title="Фенилаланин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Fenilalanin" title="Fenilalanin – Bosnian" lang="bs" hreflang="bs" data-title="Fenilalanin" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Fenilalanina" title="Fenilalanina – Catalan" lang="ca" hreflang="ca" data-title="Fenilalanina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Fenylalanin" title="Fenylalanin – Czech" lang="cs" hreflang="cs" data-title="Fenylalanin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Fenylalanin" title="Fenylalanin – Danish" lang="da" hreflang="da" data-title="Fenylalanin" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Phenylalanin" title="Phenylalanin – German" lang="de" hreflang="de" data-title="Phenylalanin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Fen%C3%BC%C3%BClalaniin" title="Fenüülalaniin – Estonian" lang="et" hreflang="et" data-title="Fenüülalaniin" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A6%CE%B1%CE%B9%CE%BD%CF%85%CE%BB%CE%B1%CE%BB%CE%B1%CE%BD%CE%AF%CE%BD%CE%B7" title="Φαινυλαλανίνη – Greek" lang="el" hreflang="el" data-title="Φαινυλαλανίνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Fenilalanina" title="Fenilalanina – Spanish" lang="es" hreflang="es" data-title="Fenilalanina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Fenilalanino" title="Fenilalanino – Esperanto" lang="eo" hreflang="eo" data-title="Fenilalanino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Fenilalanina" title="Fenilalanina – Basque" lang="eu" hreflang="eu" data-title="Fenilalanina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%81%D9%86%DB%8C%D9%84%E2%80%8C%D8%A2%D9%84%D8%A7%D9%86%DB%8C%D9%86" title="فنیل‌آلانین – Persian" lang="fa" hreflang="fa" data-title="فنیل‌آلانین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Ph%C3%A9nylalanine" title="Phénylalanine – French" lang="fr" hreflang="fr" data-title="Phénylalanine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Fenilalanina" title="Fenilalanina – Galician" lang="gl" hreflang="gl" data-title="Fenilalanina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8E%98%EB%8B%90%EC%95%8C%EB%9D%BC%EB%8B%8C" title="페닐알라닌 – Korean" lang="ko" hreflang="ko" data-title="페닐알라닌" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%96%D5%A5%D5%B6%D5%AB%D5%AC%D5%A1%D5%AC%D5%A1%D5%B6%D5%AB%D5%B6" title="Ֆենիլալանին – Armenian" lang="hy" hreflang="hy" data-title="Ֆենիլալանին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Fenilalanin" title="Fenilalanin – Croatian" lang="hr" hreflang="hr" data-title="Fenilalanin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Fenilalanina" title="Fenilalanina – Indonesian" lang="id" hreflang="id" data-title="Fenilalanina" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Fenilalanina" title="Fenilalanina – Italian" lang="it" hreflang="it" data-title="Fenilalanina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A4%D7%A0%D7%99%D7%9C%D7%90%D7%9C%D7%A0%D7%99%D7%9F" title="פנילאלנין – Hebrew" lang="he" hreflang="he" data-title="פנילאלנין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%B8%D0%BB%D0%B0%D0%BB%D0%B0%D0%BD%D0%B8%D0%BD" title="Фенилаланин – Kazakh" lang="kk" hreflang="kk" data-title="Фенилаланин" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ku mw-list-item"><a href="https://ku.wikipedia.org/wiki/F%C3%AAn%C3%AElalan%C3%AEn" title="Fênîlalanîn – Kurdish" lang="ku" hreflang="ku" data-title="Fênîlalanîn" data-language-autonym="Kurdî" data-language-local-name="Kurdish" class="interlanguage-link-target"><span>Kurdî</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Fenilalan%C4%ABns" title="Fenilalanīns – Latvian" lang="lv" hreflang="lv" data-title="Fenilalanīns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Phenylalanin" title="Phenylalanin – Luxembourgish" lang="lb" hreflang="lb" data-title="Phenylalanin" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target"><span>Lëtzebuergesch</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Fenilalaninas" title="Fenilalaninas – Lithuanian" lang="lt" hreflang="lt" data-title="Fenilalaninas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Fenilalanin" title="Fenilalanin – Hungarian" lang="hu" hreflang="hu" data-title="Fenilalanin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%B8%D0%BB%D0%B0%D0%BB%D0%B0%D0%BD%D0%B8%D0%BD" title="Фенилаланин – Macedonian" lang="mk" hreflang="mk" data-title="Фенилаланин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-arz mw-list-item"><a href="https://arz.wikipedia.org/wiki/%D9%81%D9%8A%D9%86%D9%8A%D9%84_%D8%A3%D9%84%D8%A7%D9%86%D9%8A%D9%86" title="فينيل ألانين – Egyptian Arabic" lang="arz" hreflang="arz" data-title="فينيل ألانين" data-language-autonym="مصرى" data-language-local-name="Egyptian Arabic" class="interlanguage-link-target"><span>مصرى</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Fenilalanina" title="Fenilalanina – Malay" lang="ms" hreflang="ms" data-title="Fenilalanina" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%B8%D0%BB%D0%B0%D0%BB%D0%B0%D0%BD%D0%B8%D0%BD" title="Фенилаланин – Mongolian" lang="mn" hreflang="mn" data-title="Фенилаланин" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Fenylalanine" title="Fenylalanine – Dutch" lang="nl" hreflang="nl" data-title="Fenylalanine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%95%E3%82%A7%E3%83%8B%E3%83%AB%E3%82%A2%E3%83%A9%E3%83%8B%E3%83%B3" title="フェニルアラニン – Japanese" lang="ja" hreflang="ja" data-title="フェニルアラニン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Fenylalanin" title="Fenylalanin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Fenylalanin" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Fenylalanin" title="Fenylalanin – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Fenylalanin" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Fenilalanina" title="Fenilalanina – Occitan" lang="oc" hreflang="oc" data-title="Fenilalanina" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Fenyloalanina" title="Fenyloalanina – Polish" lang="pl" hreflang="pl" data-title="Fenyloalanina" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Fenilalanina" title="Fenilalanina – Portuguese" lang="pt" hreflang="pt" data-title="Fenilalanina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Fenilalanin%C4%83" title="Fenilalanină – Romanian" lang="ro" hreflang="ro" data-title="Fenilalanină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%B8%D0%BB%D0%B0%D0%BB%D0%B0%D0%BD%D0%B8%D0%BD" title="Фенилаланин – Russian" lang="ru" hreflang="ru" data-title="Фенилаланин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Phenylalanine" title="Phenylalanine – Simple English" lang="en-simple" hreflang="en-simple" data-title="Phenylalanine" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Fenylalan%C3%ADn" title="Fenylalanín – Slovak" lang="sk" hreflang="sk" data-title="Fenylalanín" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Fenilalanin" title="Fenilalanin – Slovenian" lang="sl" hreflang="sl" data-title="Fenilalanin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%B8%D0%BB%D0%B0%D0%BB%D0%B0%D0%BD%D0%B8%D0%BD" title="Фенилаланин – Serbian" lang="sr" hreflang="sr" data-title="Фенилаланин" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Fenilalanin" title="Fenilalanin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Fenilalanin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Fenyylialaniini" title="Fenyylialaniini – Finnish" lang="fi" hreflang="fi" data-title="Fenyylialaniini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Fenylalanin" title="Fenylalanin – Swedish" lang="sv" hreflang="sv" data-title="Fenylalanin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%AA%E0%AE%BF%E0%AE%A9%E0%AF%88%E0%AE%B2%E0%AF%8D%E0%AE%85%E0%AE%B2%E0%AE%A9%E0%AE%BF%E0%AE%A9%E0%AF%8D" title="பினைல்அலனின் – Tamil" lang="ta" hreflang="ta" data-title="பினைல்அலனின்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%9F%E0%B8%B5%E0%B8%99%E0%B8%B4%E0%B8%A5%E0%B8%AD%E0%B8%B0%E0%B8%A5%E0%B8%B2%E0%B8%99%E0%B8%B5%E0%B8%99" title="ฟีนิลอะลานีน – Thai" lang="th" hreflang="th" data-title="ฟีนิลอะลานีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Fenilalanin" title="Fenilalanin – Turkish" lang="tr" hreflang="tr" data-title="Fenilalanin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D1%96%D0%BB%D0%B0%D0%BB%D0%B0%D0%BD%D1%96%D0%BD" title="Фенілаланін – Ukrainian" lang="uk" hreflang="uk" data-title="Фенілаланін" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vec mw-list-item"><a href="https://vec.wikipedia.org/wiki/Fenilalanina" title="Fenilalanina – Venetian" lang="vec" hreflang="vec" data-title="Fenilalanina" data-language-autonym="Vèneto" data-language-local-name="Venetian" class="interlanguage-link-target"><span>Vèneto</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Phenylalanin" title="Phenylalanin – Vietnamese" lang="vi" hreflang="vi" data-title="Phenylalanin" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%8B%AF%E4%B8%99%E6%B0%A8%E9%85%B8" title="苯丙氨酸 – Wu" lang="wuu" hreflang="wuu" data-title="苯丙氨酸" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E8%8B%AF%E4%B8%99%E6%B0%A8%E9%85%B8" title="苯丙氨酸 – Cantonese" lang="yue" hreflang="yue" data-title="苯丙氨酸" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%8B%AF%E4%B8%99%E6%B0%A8%E9%85%B8" title="苯丙氨酸 – Chinese" lang="zh" hreflang="zh" data-title="苯丙氨酸" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li></ul> </section> </div> <div class="minerva-footer-logo"><img src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" alt="Wikipedia" width="120" height="18" style="width: 7.5em; height: 1.125em;"/> </div> <ul id="footer-info" class="footer-info hlist hlist-separated"> <li 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