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text-align: left; font-size: 88%; line-height: 1.5em;"><tbody><tr><td colspan="2" class="" style="text-align:center; font-size: 125%; font-weight: bold; background:#F0F0C0;">Гипоглицин</td></tr><tr><td colspan="2" class="" style="text-align:center;"> <table><tbody><tr> <td style="width:50%; padding:0 4px 0 0; vertical-align:bottom;"><span typeof="mw:File"><a href="/wiki/%D0%A1%D1%83%D1%80%D0%B5%D1%82:Hypoglycin_A.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/Hypoglycin_A.svg/120px-Hypoglycin_A.svg.png" decoding="async" width="120" height="67" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/Hypoglycin_A.svg/180px-Hypoglycin_A.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/34/Hypoglycin_A.svg/240px-Hypoglycin_A.svg.png 2x" data-file-width="440" data-file-height="245" /></a></span></td> </tr></tbody></table> </td></tr><tr><th colspan="2" style="text-align:center; background:#F0F0C0;">Жалпы мәліметтері</th></tr><tr><th style="">IUPAC атауы</th><td class="" style=""> <p>Гипоглицин </p> </td></tr><tr><th style="">Басқа атаулары</th><td class="" style=""> <p>Гипоглицин,<br /> гипоглицин А,<br /> β-метилциклопропил-L-аланин </p> </td></tr><tr><th style=""><a href="/wiki/%D0%A5%D0%B8%D0%BC%D0%B8%D1%8F%D0%BB%D1%8B%D2%9B_%D1%84%D0%BE%D1%80%D0%BC%D1%83%D0%BB%D0%B0" title="Химиялық формула">Химиялық формуласы</a></th><td class="" style=""> <p>C<sub>7</sub>H<sub>11</sub>NO<sub>2</sub> </p> </td></tr><tr><th colspan="2" style="text-align:center; background:#F0F0C0;">Физикалық қасиеттері</th></tr><tr><th style=""><a href="/wiki/%D0%90%D0%B3%D1%80%D0%B5%D0%B3%D0%B0%D1%82%D1%82%D1%8B%D2%9B_%D0%BA%D2%AF%D0%B9" title="Агрегаттық күй">Күйі</a></th><td class="" style=""> <p>қатты кристалды зат </p> </td></tr><tr><th style=""><a href="/wiki/%D0%9C%D0%BE%D0%BB%D1%8C%D0%B4%D1%96%D0%BA_%D0%BC%D0%B0%D1%81%D1%81%D0%B0" title="Мольдік масса">Мольдік массасы</a></th><td class="" style=""> <p>141,17 г/<a href="/wiki/%D0%9C%D0%BE%D0%BB%D1%8C" title="Моль">моль</a> </p> </td></tr><tr><th colspan="2" style="text-align:center; background:#F0F0C0;">Жылу қасиеттері</th></tr><tr><th style=""><a href="/wiki/%D0%91%D0%B0%D0%BB%D2%9B%D1%83_%D1%82%D0%B5%D0%BC%D0%BF%D0%B5%D1%80%D0%B0%D1%82%D1%83%D1%80%D0%B0%D1%81%D1%8B" title="Балқу температурасы">Балқу t</a></th><td class="" style=""> <p>280-284 °C </p> </td></tr><tr><th style=""><a href="/wiki/%D0%91%D1%83%D0%BB%D0%B0%D0%BD%D1%83_%D0%B6%D1%8B%D0%BB%D1%83%D1%8B" title="Булану жылуы">Булану жылулығы</a></th><td class="" style=""> <p>510 кДж/кг </p> </td></tr><tr><th colspan="2" style="text-align:center; background:#F0F0C0;">Химиялық қасиеттері</th></tr><tr><th style=""><a href="/wiki/%D0%95%D1%80%D1%96%D0%B3%D1%96%D1%88%D1%82%D1%96%D0%BA" title="Ерігіштік">Ерігіштігі</a></th><td class="" style=""> <p><a href="/wiki/%D0%A1%D1%83" title="Су">суда</a>: 20 г/100 мл </p> </td></tr><tr><th colspan="2" style="text-align:center; background:#F0F0C0;">Классификациясы</th></tr><tr><th style=""><a href="/w/index.php?title=CAS_%D1%82%D1%96%D1%80%D0%BA%D0%B5%D1%83_%D0%BD%D3%A9%D0%BC%D1%96%D1%80%D1%96&action=edit&redlink=1" class="new" title="CAS тіркеу нөмірі (мұндай бет жоқ)">CAS нөмірі</a></th><td class="" style=""> <p>156-56-9 </p> </td></tr><tr><th style=""><a href="/wiki/PubChem" title="PubChem">PubChem</a></th><td class="" style=""> <p><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/11768666">11768666</a> </p> </td></tr><tr><th style=""><a href="/w/index.php?title=SMILES&action=edit&redlink=1" class="new" title="SMILES (мұндай бет жоқ)">SMILES</a></th><td class="" style=""> <div class="mw-collapsible mw-collapsed plainlist" style="border:none;padding:0;"> <div style="font-weight:bold;"> </div> <div class="mw-collapsible-content" style="text-align:left;">O=C(O)[C@@H](N)C[C@@H]1C(=C)C1 (<a rel="nofollow" class="external text" href="http://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28O%29%5BC%40%40H%5D%28N%29C%5BC%40%40H%5D1C%28%3DC%29C1">3D-моделі</a>)</div> </div> </td></tr><tr><th colspan="2" style="text-align:center; background:#F0F0C0;">Қауіпсіздігі</th></tr><tr><th style=""><a href="https://en.wikipedia.org/wiki/%D0%9B%D0%9450" class="extiw" title="en:ЛД50">ӨД<sub>50</sub></a><span style="white-space: nowrap"><span class="noprint" style="font-size:95%; position: relative; top: .4em;"> <span class="ref-info" title="ағылшын тілінде" style="font-size:85%; cursor:help; color:#888;">(ағыл.)</span></span><span class="link-ru metadata noprint" style="font-size:80%; margin-left:-1.7em; position: relative; top: -.4em;"><a href="/w/index.php?title=%D0%9B%D0%9450&action=edit&redlink=1" class="new" title="ЛД50 (мұндай бет жоқ)">қаз.</a></span></span></th><td class="" style=""> <p>40 мг/кг (тышқандар, ауыз арқылы) </p> </td></tr><tr><td colspan="2" class="" style="text-align:center;">Егер басқаша көрсетілмесе, деректер стандартты жағдайлар (25 °C, 100 кПа) үшін беріледі.</td></tr><tr><td colspan="2" class="" style="text-align:center; background:#F0F0C0;"><div><b><a href="https://commons.wikimedia.org/wiki/Category:%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD" class="extiw" title="commons:Category:Гипоглицин">Гипоглицин</a></b> <a href="/wiki/%D0%9E%D1%80%D1%82%D0%B0%D2%9B%D2%9B%D0%BE%D1%80" title="Ортаққор">Ортаққорда</a></div></td></tr><tr><td style="text-align:right;" colspan="2"> <div class="noprint plainlinks" style="background-color:transparent; padding:0; white-space:nowrap; font-weight:normal; font-size:xx-small; ;">Бұл үлгіні: <a href="/wiki/%D2%AE%D0%BB%D0%B3%D1%96:%D0%A5%D0%B8%D0%BC%D0%B8%D1%8F%D0%BB%D1%8B%D2%9B_%D0%B7%D0%B0%D1%82" title="Үлгі:Химиялық зат"><span title="Бұл үлгіні көру" style=";">көру</span></a> <span style="font-size:80%;">•</span> <a href="/w/index.php?title=%D2%AE%D0%BB%D0%B3%D1%96_%D1%82%D0%B0%D0%BB%D2%9B%D1%8B%D0%BB%D0%B0%D1%83%D1%8B:%D0%A5%D0%B8%D0%BC%D0%B8%D1%8F%D0%BB%D1%8B%D2%9B_%D0%B7%D0%B0%D1%82&action=edit&redlink=1" class="new" title="Үлгі талқылауы:Химиялық зат (мұндай бет жоқ)"><span style="color:#002bb8;;" title="Осы үлгінің талқылауы">талқылау</span></a> <span style="font-size:80%;">•</span> <a class="external text" href="https://kk.wikipedia.org/w/index.php?title=%D2%AE%D0%BB%D0%B3%D1%96:%D0%A5%D0%B8%D0%BC%D0%B8%D1%8F%D0%BB%D1%8B%D2%9B_%D0%B7%D0%B0%D1%82&action=edit"><span style="color:#002bb8;;" title="Бұл үлгіні өңдей аласыз. Сақтаудың алдынан Қарап шығу батырмасын қолданыңыз.">өңдеу</span></a></div> </td></tr> </tbody></table> <p><b>Гипоглицин</b> (сондай-ақ Гипоглицин А) – табиғи түрде кездесетін <a href="/wiki/%D0%90%D0%BC%D0%B8%D0%BD%D2%9B%D1%8B%D1%88%D2%9B%D1%8B%D0%BB%D0%B4%D0%B0%D1%80" title="Аминқышқылдар">аминқышқылдарының</a> туындысы, <a href="/wiki/%D0%90%D0%BA%D0%B8" title="Аки">Аки</a> ағашының (<i><a href="/wiki/%D0%90%D0%BA%D0%B8" title="Аки">Blighia sapida</a></i>) піспеген жемісінде<sup id="cite_ref-medscape_1-0" class="reference"><a href="#cite_note-medscape-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> және қорапты ақсақал ағашының (<i>Acer negundo</i>) тұқымында кездеседі.<sup id="cite_ref-Valberg2013_2-0" class="reference"><a href="#cite_note-Valberg2013-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Ол ішке қабылданса улы және ямайкалық құсу ауруының қоздырғышы болып табылады.<sup id="cite_ref-medscape_1-1" class="reference"><a href="#cite_note-medscape-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> 2017 жылы Lancet есебінде гипогликемияға және жедел токсикалық энцефалопатиядан өлімге әкелетін піспеген личилерді (құрамында гипоглицин А немесе метиленциклопропилглицин (MCPG)) тұтыну арасындағы байланыс анықталды.<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> </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="kk" dir="ltr"><h2 id="mw-toc-heading">Мазмұны</h2><span class="toctogglespan"><label class="toctogglelabel" for="toctogglecheckbox"></label></span></div> <ul> <li class="toclevel-1 tocsection-1"><a href="#Табиғатта_болу"><span class="tocnumber">1</span> <span class="toctext">Табиғатта болу</span></a></li> <li class="toclevel-1 tocsection-2"><a href="#Уыттылық"><span class="tocnumber">2</span> <span class="toctext">Уыттылық</span></a></li> <li class="toclevel-1 tocsection-3"><a href="#Синтез"><span class="tocnumber">3</span> <span class="toctext">Синтез</span></a></li> <li class="toclevel-1 tocsection-4"><a href="#Дереккөздер"><span class="tocnumber">4</span> <span class="toctext">Дереккөздер</span></a></li> </ul> </div> <div class="mw-heading mw-heading2"><h2 id="Табиғатта_болу"><span id=".D0.A2.D0.B0.D0.B1.D0.B8.D2.93.D0.B0.D1.82.D1.82.D0.B0_.D0.B1.D0.BE.D0.BB.D1.83"></span>Табиғатта болу</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD&veaction=edit&section=1" title="Бөлімді өңдеу: Табиғатта болу" class="mw-editsection-visualeditor"><span>өңдеу</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD&action=edit&section=1" title="Edit section's source code: Табиғатта болу"><span>қайнарын өңдеу</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Піспеген Аки жемісінің барлығы улы және көп мөлшерде гипоглицинді қамтиды. Жеміс ағашта болған кезде жемістер толығымен ашылып, үлкен қара тұқымдарды шығаруға рұқсат етілгенде ғана жеуге қауіпсіз. Уақыт өте келе токсиннің деңгейі төмендейді, бірақ жетілген жемісте шамамен 1000 ppm-ден 0,1 ppm-ге дейін.<sup id="cite_ref-scq_4-0" class="reference"><a href="#cite_note-scq-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Аки туыстары, соның ішінде личи, лонган және рамбутан, олардың жемістерінде гипоглицин А гомологы α-(метиленциклопропил)глицин жеткілікті мөлшерде болуы мүмкін, олар көп мөлшерде тұтынылған кезде, тамақтанбаған балаларда <a href="/wiki/%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D0%BA%D0%B5%D0%BC%D0%B8%D1%8F" title="Гипогликемия">гипогликемиялық</a> энцефалопатияны тудыруы мүмкін.<sup id="cite_ref-EID_5-0" class="reference"><a href="#cite_note-EID-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Уыттылық"><span id=".D0.A3.D1.8B.D1.82.D1.82.D1.8B.D0.BB.D1.8B.D2.9B"></span>Уыттылық</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD&veaction=edit&section=2" title="Бөлімді өңдеу: Уыттылық" class="mw-editsection-visualeditor"><span>өңдеу</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD&action=edit&section=2" title="Edit section's source code: Уыттылық"><span>қайнарын өңдеу</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Гипоглицин А протоксин болып табылады, яғни молекула өздігінен улы емес, бірақ жұтқан кезде улы өнімдерге ыдырайды. Әдетте лейцинді, изолейцинді немесе <a href="/wiki/%D0%92%D0%B0%D0%BB%D0%B8%D0%BD" title="Валин">валинді</a> ацил-КоА туындыларына түрлендіретін тармақталған тізбекті альфа-кетоқышқылды дегидрогеназа кешені гипоглицин А-ны жоғары уытты MCPA-CoA -ға айналдырады. <a href="/wiki/%D0%9C%D0%B0%D0%B9%D0%BB%D1%8B_%D2%9B%D1%8B%D1%88%D2%9B%D1%8B%D0%BB%D0%B4%D0%B0%D1%80" title="Майлы қышқылдар">Май қышқылдарының</a> бета тотығуына қажетті <a href="/wiki/%D0%A4%D0%BB%D0%B0%D0%B2%D0%B8%D0%BD%D0%B0%D0%B4%D0%B5%D0%BD%D0%B8%D0%BD%D0%B4%D0%B8%D0%BD%D1%83%D0%BA%D0%BB%D0%B5%D0%BE%D1%82%D0%B8%D0%B4" title="Флавинадениндинуклеотид">FAD</a> кофакторы MCPA-CoA альфа көміртегімен байланысып, ферментті тоқтататын қайтымсыз кешен жасайды. Сонымен қатар, MCPA-CoA <a href="/wiki/%D0%93%D0%BB%D1%8E%D0%BA%D0%BE%D0%BD%D0%B5%D0%BE%D0%B3%D0%B5%D0%BD%D0%B5%D0%B7" title="Глюконеогенез">глюконеогенезге</a> қажетті кейбір ферменттерді блоктайды.<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>Глюконеогенездің төмендеуі және май қышқылының тотығуының төмендеуі ямайкалық құсу ауруының көптеген белгілерінің себебі болып табылады. Май қышқылдарының метаболизмін тежеу жасушаларды энергия үшін гликогенді пайдалана бастайды. Гликоген таусылғаннан кейін дене одан да көп өндіре алмайды, бұл ауыр гипогликемияға әкеледі. Бұл биохимиялық әсерлер несеп пен <a href="/wiki/%D0%90%D1%86%D0%B8%D0%B4%D0%BE%D0%B7" title="Ацидоз">ацидозда</a> орташа тізбекті май қышқылдарының артық болуымен анықталады . Негізгі емдеу биохимиялық өзгерістерді айналып өтуге немесе оларға қарсы тұруға бағытталған және бүйрек жеткіліксіздігі жағдайында веналық сұйықтықтар мен <a href="/wiki/%D0%93%D0%BB%D1%8E%D0%BA%D0%BE%D0%B7%D0%B0" title="Глюкоза">глюкозаны</a> және <a href="/wiki/%D0%93%D0%B5%D0%BC%D0%BE%D0%B4%D0%B8%D0%B0%D0%BB%D0%B8%D0%B7" title="Гемодиализ">гемодиализді</a> қамтиды.<sup id="cite_ref-nih_7-0" class="reference"><a href="#cite_note-nih-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Синтез"><span id=".D0.A1.D0.B8.D0.BD.D1.82.D0.B5.D0.B7"></span>Синтез</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD&veaction=edit&section=3" title="Бөлімді өңдеу: Синтез" class="mw-editsection-visualeditor"><span>өңдеу</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD&action=edit&section=3" title="Edit section's source code: Синтез"><span>қайнарын өңдеу</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>1958 жылы Джон Карбон, Уильям Мартин және Лео Светт циклопропан сақинасын құру үшін 2-бромопропен мен этил диазоацетаттан бастап, <a href="/wiki/%D0%A0%D0%B0%D1%86%D0%B5%D0%BC%D0%B0%D1%82" title="Рацемат">рацемиялық</a> түрде А гипоглицинді синтездеді.<sup id="cite_ref-NAME_HERE_8-0" class="reference"><a href="#cite_note-NAME_HERE-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="//upload.wikimedia.org/wikipedia/commons/thumb/4/48/Hypoglycin_A_synthesis%27.png/550px-Hypoglycin_A_synthesis%27.png"><img resource="/wiki/%D0%A1%D1%83%D1%80%D0%B5%D1%82:Hypoglycin_A_synthesis%27.png" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/48/Hypoglycin_A_synthesis%27.png/550px-Hypoglycin_A_synthesis%27.png" decoding="async" width="550" height="144" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/48/Hypoglycin_A_synthesis%27.png/825px-Hypoglycin_A_synthesis%27.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/48/Hypoglycin_A_synthesis%27.png/1100px-Hypoglycin_A_synthesis%27.png 2x" data-file-width="2605" data-file-height="682" /></a><figcaption> Джон Карбонның гипоглицин А синтезі</figcaption></figure> <p>1992 жылы Джек Болдуин, Роберт Адлингтон, Дэвид Беббингтон және Эндрю Рассел асимметриялық метилен циклопропан синтезіне мүмкіндік беру үшін Sharpless эпоксидациясы арқылы гипоглицин А жеке диастереоизомерлерінің бірінші асимметриялық толық синтезін орындады.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> <sup>1</sup>H ЯМР және айналмалы дихроизм зерттеулері табиғи гипогицин А негізгі диастереоизомерін (2<i>S</i>, 4<i>R</i>) және кіші диастереоизомері (2<i>S</i>, 4<i>S</i>) ретінде анықтайды. </p> <div class="mw-heading mw-heading2"><h2 id="Дереккөздер"><span id=".D0.94.D0.B5.D1.80.D0.B5.D0.BA.D0.BA.D3.A9.D0.B7.D0.B4.D0.B5.D1.80"></span>Дереккөздер</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD&veaction=edit&section=4" title="Бөлімді өңдеу: Дереккөздер" class="mw-editsection-visualeditor"><span>өңдеу</span></a><span class="mw-editsection-divider"> | </span><a href="/w/index.php?title=%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD&action=edit&section=4" title="Edit section's source code: Дереккөздер"><span>қайнарын өңдеу</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="reflist columns" style="list-style-type: decimal;"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-medscape-1"><span class="mw-cite-backlink">↑ <a href="#cite_ref-medscape_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-medscape_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><span class="citation Journal"> <a rel="nofollow" class="external text" href="http://emedicine.medscape.com/article/1008792-overview"><i>Ackee Fruit Toxicity</i></a>. 2018-06-13<span class="printonly">. <a rel="nofollow" class="external free" href="http://emedicine.medscape.com/article/1008792-overview">http://emedicine.medscape.com/article/1008792-overview</a></span>.</span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Ackee+Fruit+Toxicity&rft.date=2018-06-13&rft_id=http%3A%2F%2Femedicine.medscape.com%2Farticle%2F1008792-overview&rfr_id=info:sid/en.wikipedia.org:%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD"><span style="display: none;"> </span></span></span> </li> <li id="cite_note-Valberg2013-2"><span class="mw-cite-backlink"><a href="#cite_ref-Valberg2013_2-0">↑</a></span> <span class="reference-text"><span class="citation Journal"> <i>Seasonal pasture myopathy/atypical myopathy in North America associated with ingestion of hypoglycin A within seeds of the box elder tree</i>. 2013-07-01.</span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Seasonal+pasture+myopathy%2Fatypical+myopathy+in+North+America+associated+with+ingestion+of+hypoglycin+A+within+seeds+of+the+box+elder+tree&rft.date=2013-07-01&rfr_id=info:sid/en.wikipedia.org:%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD"><span style="display: none;"> </span></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text"><span class="citation Journal"> <i>Association of acute toxic encephalopathy with litchi consumption in an outbreak in Muzaffarpur, India, 2014: a case-control study</i>.</span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Association+of+acute+toxic+encephalopathy+with+litchi+consumption+in+an+outbreak+in+Muzaffarpur%2C+India%2C+2014%3A+a+case-control+study&rfr_id=info:sid/en.wikipedia.org:%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD"><span style="display: none;"> </span></span></span> </li> <li id="cite_note-scq-4"><span class="mw-cite-backlink"><a href="#cite_ref-scq_4-0">↑</a></span> <span class="reference-text"><span class="citation"><a rel="nofollow" class="external text" href="http://www.scq.ubc.ca/the-ackee-fruit-blighia-sapida-and-its-associated-toxic-effects/">THE ACKEE FRUIT (BLIGHIA SAPIDA) AND ITS ASSOCIATED TOXIC EFFECTS</a>.  <a href="/w/index.php?title=University_of_British_Columbia&action=edit&redlink=1" class="new" title="University of British Columbia (мұндай бет жоқ)">University of British Columbia</a> (17 қараша 2005).</span></span> </li> <li id="cite_note-EID-5"><span class="mw-cite-backlink"><a href="#cite_ref-EID_5-0">↑</a></span> <span class="reference-text"><span class="citation">Spencer, P. S. (2015), <i>Probable Toxic Cause for Suspected Lychee-Linked Viral Encephalitis</i>, pp. 904–5, <a href="/w/index.php?title=Digital_object_identifier&action=edit&redlink=1" class="new" title="Digital object identifier (мұндай бет жоқ)">doi</a>:<a href="//doi.org/10.3201/eid2105.141650" class="extiw" title="doi:10.3201/eid2105.141650">10.3201/eid2105.141650</a></span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Probable+Toxic+Cause+for+Suspected+Lychee-Linked+Viral+Encephalitis&rft.aulast=Spencer%2C+P.+S.&rft.au=Spencer%2C+P.+S.&rft.date=2015&rft.pages=pp.+904%E2%80%935&rft_id=info:doi/10.3201%2Feid2105.141650&rfr_id=info:sid/en.wikipedia.org:%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD"><span style="display: none;"> </span></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><a href="#cite_ref-6">↑</a></span> <span class="reference-text"><span class="citation"><a rel="nofollow" class="external text" href="http://www.scq.ubc.ca/the-ackee-fruit-blighia-sapida-and-its-associated-toxic-effects/">THE ACKEE FRUIT (BLIGHIA SAPIDA) AND ITS ASSOCIATED TOXIC EFFECTS</a>.  <a href="/w/index.php?title=University_of_British_Columbia&action=edit&redlink=1" class="new" title="University of British Columbia (мұндай бет жоқ)">University of British Columbia</a> (17 қараша 2005).</span><cite class="citation web cs1" data-ve-ignore="true"><a rel="nofollow" class="external text" href="http://www.scq.ubc.ca/the-ackee-fruit-blighia-sapida-and-its-associated-toxic-effects/">"THE ACKEE FRUIT (BLIGHIA SAPIDA) AND ITS ASSOCIATED TOXIC EFFECTS"</a>. <a href="/w/index.php?title=%D0%91%D1%80%D0%B8%D1%82%D0%B0%D0%BD%D0%B4%D1%8B%D2%9B_%D0%9A%D0%BE%D0%BB%D1%83%D0%BC%D0%B1%D0%B8%D1%8F_%D1%83%D0%BD%D0%B8%D0%B2%D0%B5%D1%80%D1%81%D0%B8%D1%82%D0%B5%D1%82%D1%96&action=edit&redlink=1" class="new" title="Британдық Колумбия университеті (мұндай бет жоқ)">University of British Columbia</a>. 2005-11-17.</cite></span> </li> <li id="cite_note-nih-7"><span class="mw-cite-backlink"><a href="#cite_ref-nih_7-0">↑</a></span> <span class="reference-text"><span class="citation"><a rel="nofollow" class="external text" href="http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+3496">Hypoglycin</a>.  <a href="/w/index.php?title=TOXNET&action=edit&redlink=1" class="new" title="TOXNET (мұндай бет жоқ)">TOXNET</a>.</span></span> </li> <li id="cite_note-NAME_HERE-8"><span class="mw-cite-backlink"><a href="#cite_ref-NAME_HERE_8-0">↑</a></span> <span class="reference-text"><span class="citation">Carbon, J. A. (1958), <i>SYNTHESIS OF α-AMINO- METHYLENECYCLOPROPANEPROPIONIC ACID (HYPOGLYCIN A)</i>, pp. 1002, <a href="/w/index.php?title=Digital_object_identifier&action=edit&redlink=1" class="new" title="Digital object identifier (мұндай бет жоқ)">doi</a>:<a href="//doi.org/10.1021/ja01537a066" class="extiw" title="doi:10.1021/ja01537a066">10.1021/ja01537a066</a></span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=SYNTHESIS+OF+%CE%B1-AMINO-+METHYLENECYCLOPROPANEPROPIONIC+ACID+%28HYPOGLYCIN+A%29&rft.aulast=Carbon%2C+J.+A.&rft.au=Carbon%2C+J.+A.&rft.date=1958&rft.pages=pp.+1002&rft_id=info:doi/10.1021%2Fja01537a066&rfr_id=info:sid/en.wikipedia.org:%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD"><span style="display: none;"> </span></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><a href="#cite_ref-9">↑</a></span> <span class="reference-text"><span class="citation Journal">Baldwin; Adlington; Bebbington. "Asymmetric total synthesis of the individual diastereoisomers of hypoglycin A". <i>Journal of the Chemical Society, Chemical Communications</i> (17): 1249. <a href="/w/index.php?title=Digital_object_identifier&action=edit&redlink=1" class="new" title="Digital object identifier (мұндай бет жоқ)">doi</a>:<a href="//doi.org/10.1039/c39920001249" class="extiw" title="doi:10.1039/c39920001249">10.1039/c39920001249</a>.</span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Asymmetric+total+synthesis+of+the+individual+diastereoisomers+of+hypoglycin+A&rft.jtitle=Journal+of+the+Chemical+Society%2C+Chemical+Communications&rft.aulast=Baldwin&rft.au=Baldwin&rft.au=Adlington&rft.au=Bebbington&rft.issue=17&rft.pages=1249&rft_id=info:doi/10.1039%2Fc39920001249&rfr_id=info:sid/en.wikipedia.org:%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD"><span style="display: none;"> </span></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><a href="#cite_ref-10">↑</a></span> <span class="reference-text"><span class="citation Journal">Baldwin; Adlington; Bebbington. "Asymmetric total synthesis of the individual diastereoisomers of hypoglycin A.". <i>Tetrahedron</i> <b>50</b> (41): 12015–12028. <a href="/w/index.php?title=Digital_object_identifier&action=edit&redlink=1" class="new" title="Digital object identifier (мұндай бет жоқ)">doi</a>:<a href="//doi.org/10.1016/s0040-4020(01)89313-3" class="extiw" title="doi:10.1016/s0040-4020(01)89313-3">10.1016/s0040-4020(01)89313-3</a>.</span><span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Asymmetric+total+synthesis+of+the+individual+diastereoisomers+of+hypoglycin+A.&rft.jtitle=Tetrahedron&rft.aulast=Baldwin&rft.au=Baldwin&rft.au=Adlington&rft.au=Bebbington&rft.volume=50&rft.issue=41&rft.pages=12015%E2%80%9312028&rft_id=info:doi/10.1016%2Fs0040-4020%2801%2989313-3&rfr_id=info:sid/en.wikipedia.org:%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD"><span style="display: none;"> </span></span></span> </li> </ol></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">«<a dir="ltr" href="https://kk.wikipedia.org/w/index.php?title=Гипоглицин&oldid=3066467">https://kk.wikipedia.org/w/index.php?title=Гипоглицин&oldid=3066467</a>» бетінен алынған</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/%D0%90%D1%80%D0%BD%D0%B0%D0%B9%D1%8B:%D0%A1%D0%B0%D0%BD%D0%B0%D1%82%D1%82%D0%B0%D1%80" title="Арнайы:Санаттар">Санаттар</a>: <ul><li><a href="/wiki/%D0%A1%D0%B0%D0%BD%D0%B0%D1%82:%D0%90%D0%BC%D0%B8%D0%BD%D2%9B%D1%8B%D1%88%D2%9B%D1%8B%D0%BB%D0%B4%D0%B0%D1%80" title="Санат:Аминқышқылдар">Аминқышқылдар</a></li><li><a href="/wiki/%D0%A1%D0%B0%D0%BD%D0%B0%D1%82:%D0%A3%D0%BB%D1%8B_%D0%B7%D0%B0%D1%82%D1%82%D0%B0%D1%80" title="Санат:Улы заттар">Улы заттар</a></li><li><a href="/w/index.php?title=%D0%A1%D0%B0%D0%BD%D0%B0%D1%82:%D0%A6%D0%B8%D0%BA%D0%BB%D0%BE%D0%BF%D1%80%D0%BE%D0%BF%D0%B0%D0%BD%D0%B4%D0%B0%D1%80&action=edit&redlink=1" class="new" title="Санат:Циклопропандар (мұндай бет жоқ)">Циклопропандар</a></li></ul></div></div> </div> </div> <div id="mw-navigation"> <h2>Навигация мәзірі</h2> <div id="mw-head"> <nav id="p-personal" class="mw-portlet mw-portlet-personal vector-user-menu-legacy vector-menu" aria-labelledby="p-personal-label" > <h3 id="p-personal-label" class="vector-menu-heading " > <span class="vector-menu-heading-label">Жеке құралдар</span> </h3> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anonuserpage" class="mw-list-item"><span title="Бұл IP мекенжайдың жеке беті">Кірмегенсіз</span></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/%D0%90%D1%80%D0%BD%D0%B0%D0%B9%D1%8B:%D0%A2%D0%B0%D0%BB%D2%9B%D1%8B%D0%BB%D0%B0%D1%83%D1%8B%D0%BC" title="Бұл IP мекенжай өңдемелерін талқылау [n]" accesskey="n"><span>Талқылау</span></a></li><li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/%D0%90%D1%80%D0%BD%D0%B0%D0%B9%D1%8B:%D2%AE%D0%BB%D0%B5%D1%81%D1%96%D0%BC" title="Бұл IP мекенжаймен жасаған өңдемелер тізімі [y]" accesskey="y"><span>Үлесім</span></a></li><li id="pt-createaccount" class="mw-list-item"><a href="/w/index.php?title=%D0%90%D1%80%D0%BD%D0%B0%D0%B9%D1%8B:%D0%96%D0%B0%D2%A3%D0%B0_%D1%82%D1%96%D1%80%D0%BA%D0%B5%D0%BB%D0%B3%D1%96&returnto=%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD" title="Біз сізге есептік жазба бастауды және кіруді ұсынамыз,ол міндетті емес."><span>Тіркелу</span></a></li><li id="pt-login" class="mw-list-item"><a href="/w/index.php?title=%D0%90%D1%80%D0%BD%D0%B0%D0%B9%D1%8B:%D2%9A%D0%B0%D1%82%D1%8B%D1%81%D1%83%D1%88%D1%8B_%D0%BA%D1%96%D1%80%D1%83%D1%96&returnto=%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD" title="Кіруіңізді ұсынамыз, ол міндетті емес. 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data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Hypoglycin" title="Hypoglycin – неміс тілі" lang="de" hreflang="de" data-title="Hypoglycin" data-language-autonym="Deutsch" data-language-local-name="неміс тілі" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-en mw-list-item"><a href="https://en.wikipedia.org/wiki/Hypoglycin_A" title="Hypoglycin A – ағылшын тілі" lang="en" hreflang="en" data-title="Hypoglycin A" data-language-autonym="English" data-language-local-name="ағылшын тілі" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Hipoglicina_A" title="Hipoglicina A – испан тілі" lang="es" hreflang="es" data-title="Hipoglicina A" data-language-autonym="Español" data-language-local-name="испан тілі" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%87%DB%8C%D9%BE%D9%88%DA%AF%D9%84%DB%8C%D8%B3%DB%8C%D9%86" title="هیپوگلیسین – парсы тілі" lang="fa" hreflang="fa" data-title="هیپوگلیسین" data-language-autonym="فارسی" data-language-local-name="парсы тілі" 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/Hypoglycine_A" title="Hypoglycine A – француз тілі" lang="fr" hreflang="fr" data-title="Hypoglycine A" data-language-autonym="Français" data-language-local-name="француз тілі" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Ipoglicina" title="Ipoglicina – итальян тілі" lang="it" hreflang="it" data-title="Ipoglicina" data-language-autonym="Italiano" data-language-local-name="итальян тілі" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%92%E3%83%9D%E3%82%B0%E3%83%AA%E3%82%B7%E3%83%B3" title="ヒポグリシン – жапон тілі" lang="ja" hreflang="ja" data-title="ヒポグリシン" data-language-autonym="日本語" data-language-local-name="жапон тілі" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%93%D0%B8%D0%BF%D0%BE%D0%B3%D0%BB%D0%B8%D1%86%D0%B8%D0%BD" title="Гипоглицин – орыс тілі" lang="ru" hreflang="ru" data-title="Гипоглицин" data-language-autonym="Русский" data-language-local-name="орыс тілі" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Hipoglicin" title="Hipoglicin – серб-хорват тілі" lang="sh" hreflang="sh" data-title="Hipoglicin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="серб-хорват тілі" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Hipoglicin" title="Hipoglicin – серб тілі" lang="sr" hreflang="sr" data-title="Hipoglicin" data-language-autonym="Српски / srpski" data-language-local-name="серб тілі" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E6%AC%A1%E7%94%98%E6%B0%A8%E9%85%B8A" title="次甘氨酸A – қытай тілі" lang="zh" hreflang="zh" data-title="次甘氨酸A" data-language-autonym="中文" data-language-local-name="қытай тілі" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span 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