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二硫苏糖醇 - 维基百科,自由的百科全书
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class="vector-toc-list"> </ul> </li> <li id="toc-参考文献" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#参考文献"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>参考文献</span> </div> </a> <ul id="toc-参考文献-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="目录" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="开关目录" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">开关目录</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">二硫苏糖醇</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="前往另一种语言写成的文章。18种语言可用" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-18" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">18种语言</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%AF%DB%8C%E2%80%8C%D8%AA%DB%8C%D9%88%D8%AA%D8%B1%DB%8C%D8%AA%D9%88%D9%84" title="دیتیوتریتول – South Azerbaijani" lang="azb" hreflang="azb" data-title="دیتیوتریتول" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Dithiotreitol" title="Dithiotreitol – 捷克语" lang="cs" hreflang="cs" data-title="Dithiotreitol" data-language-autonym="Čeština" data-language-local-name="捷克语" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Dithiothreitol" title="Dithiothreitol – 德语" lang="de" hreflang="de" data-title="Dithiothreitol" data-language-autonym="Deutsch" data-language-local-name="德语" 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/Dithiothreitol" title="Dithiothreitol – 英语" lang="en" hreflang="en" data-title="Dithiothreitol" data-language-autonym="English" data-language-local-name="英语" class="interlanguage-link-target"><span>English</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AF%DB%8C%E2%80%8C%D8%AA%DB%8C%D9%88%D8%AA%D8%B1%DB%8C%D8%AA%D9%88%D9%84" title="دیتیوتریتول – 波斯语" lang="fa" hreflang="fa" data-title="دیتیوتریتول" data-language-autonym="فارسی" data-language-local-name="波斯语" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Ditiotreitoli" title="Ditiotreitoli – 芬兰语" lang="fi" hreflang="fi" data-title="Ditiotreitoli" data-language-autonym="Suomi" data-language-local-name="芬兰语" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Dithiothr%C3%A9itol" title="Dithiothréitol – 法语" lang="fr" hreflang="fr" data-title="Dithiothréitol" data-language-autonym="Français" data-language-local-name="法语" 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/Ditiotreitol" title="Ditiotreitol – 加利西亚语" lang="gl" hreflang="gl" data-title="Ditiotreitol" data-language-autonym="Galego" data-language-local-name="加利西亚语" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/DTT" title="DTT – 匈牙利语" lang="hu" hreflang="hu" data-title="DTT" data-language-autonym="Magyar" data-language-local-name="匈牙利语" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Ditiotreitolo" title="Ditiotreitolo – 意大利语" lang="it" hreflang="it" data-title="Ditiotreitolo" data-language-autonym="Italiano" data-language-local-name="意大利语" 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%82%B8%E3%83%81%E3%82%AA%E3%83%88%E3%83%AC%E3%82%A4%E3%83%88%E3%83%BC%E3%83%AB" title="ジチオトレイトール – 日语" lang="ja" hreflang="ja" data-title="ジチオトレイトール" data-language-autonym="日本語" data-language-local-name="日语" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Ditiotreitol" title="Ditiotreitol – 波兰语" lang="pl" hreflang="pl" data-title="Ditiotreitol" data-language-autonym="Polski" data-language-local-name="波兰语" 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/Ditiotreitol" title="Ditiotreitol – 葡萄牙语" lang="pt" hreflang="pt" data-title="Ditiotreitol" data-language-autonym="Português" data-language-local-name="葡萄牙语" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%94%D0%B8%D1%82%D0%B8%D0%BE%D1%82%D1%80%D0%B5%D0%B8%D1%82%D0%BE%D0%BB" title="Дитиотреитол – 俄语" lang="ru" hreflang="ru" data-title="Дитиотреитол" data-language-autonym="Русский" data-language-local-name="俄语" 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/Ditiotreitol" title="Ditiotreitol – 塞尔维亚-克罗地亚语" lang="sh" hreflang="sh" data-title="Ditiotreitol" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="塞尔维亚-克罗地亚语" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Ditiotreitol" title="Ditiotreitol – 斯洛伐克语" lang="sk" hreflang="sk" data-title="Ditiotreitol" data-language-autonym="Slovenčina" data-language-local-name="斯洛伐克语" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Ditiotreitol" title="Ditiotreitol – 塞尔维亚语" lang="sr" hreflang="sr" 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font-size:90%;"> <tbody><tr> <th colspan="2" style="font-size:120%; text-align:center; background:#d6e0dc;">二硫苏糖醇<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <td colspan="2" style="background:#ffffff; text-align:center;"><span typeof="mw:File"><a href="/wiki/File:Dithiothreitol.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Dithiothreitol.png/219px-Dithiothreitol.png" decoding="async" width="219" height="115" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Dithiothreitol.png/329px-Dithiothreitol.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2e/Dithiothreitol.png/438px-Dithiothreitol.png 2x" data-file-width="1751" data-file-height="920" /></a></span> </td></tr> <tr> <td colspan="2" style="max-width:305px; word-wrap: break-word; text-align: center;"><a href="/wiki/IUPAC%E5%91%BD%E5%90%8D%E6%B3%95" title="IUPAC命名法">IUPAC名</a><br />(<i>2S,3S</i>)-1,4-Bis-sulfanylbutane-2,3-diol </td></tr> <tr> <td>别名 </td> <td>1,4-二硫苏糖醇、二硫代苏糖醇、Cleland试剂 </td></tr> <tr> <th style="background:#D6E0DC; text-align:center;" colspan="2">识别 </th></tr> <tr> <td><a href="/wiki/CAS%E5%8F%B7" title="CAS号">CAS号</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=3483-12-3">3483-12-3</a></span> <sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/commons/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/commons/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/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> </td></tr> <tr> <td><a href="/wiki/PubChem" title="PubChem">PubChem</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/446094">446094</a></span> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="http://www.chemspider.com/393541">393541</a></span> </td></tr> <tr> <td><a href="/wiki/SMILES" class="mw-redirect" title="SMILES">SMILES</a> </td> <td><div style="word-break:break-all;"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div> </div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0;"><li style="line-height: inherit; margin: 0"><span lang="en">C([C@H]([C@@H](CS)O)O)S</span></li></ul> </div></div> </td></tr> <tr> <td><a href="/wiki/%E5%9B%BD%E9%99%85%E5%8C%96%E5%90%88%E7%89%A9%E6%A0%87%E8%AF%86" title="国际化合物标识">InChI</a> </td> <td><div style="word-break:break-all;"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div> </div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0;"><li style="line-height: inherit; margin: 0">1/C4H10O2S2/c5-3(1-7)4(6)2-8/h3-8H,1-2H2/t3-,4-/m1/s1</li></ul> </div></div> </td></tr> <tr> <td><a href="/wiki/%E5%9B%BD%E9%99%85%E5%8C%96%E5%90%88%E7%89%A9%E6%A0%87%E8%AF%86" title="国际化合物标识">InChIKey</a> </td> <td><small>VHJLVAABSRFDPM-QWWZWVQMBU</small> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:42170">42170</a></span> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="http://www.drugbank.ca/cgi-bin/show_drug.cgi?CARD=DB04447">DB04447</a></span> </td></tr> <tr> <th style="background:#D6E0DC; text-align:center;" colspan="2">性质 </th></tr> <tr> <td><a href="/wiki/%E5%8C%96%E5%AD%A6%E5%BC%8F" title="化学式">化学式</a> </td> <td><span lang="en">C<sub>4</sub>H<sub>10</sub>O<sub>2</sub>S<sub>2</sub></span> </td></tr> <tr> <td><a href="/wiki/%E6%91%A9%E5%B0%94%E8%B4%A8%E9%87%8F" title="摩尔质量">摩尔质量</a> </td> <td>154.253 g·mol⁻¹ </td></tr> <tr> <td>外观 </td> <td>白色固体 </td></tr> <tr> <td><a href="/wiki/%E7%86%94%E7%82%B9" title="熔点">熔点</a> </td> <td>42-43 °C </td></tr> <tr> <td><a href="/wiki/%E6%B2%B8%E7%82%B9" title="沸点">沸点</a> </td> <td>125-130 °C (2 mmHg压力下) </td></tr> <tr> <td><a href="/wiki/%E6%BA%B6%E8%A7%A3%E6%80%A7" class="mw-redirect" title="溶解性">溶解性</a>(<a href="/wiki/%E6%B0%B4" title="水">水</a>) </td> <td>可溶 </td></tr> <tr> <td style="background:#D6E0DC; text-align:center;" colspan="2">若非注明,所有数据均出自<a href="/wiki/%E6%A0%87%E5%87%86%E7%8A%B6%E6%80%81" title="标准状态">标准状态(25 ℃,100 kPa)</a>下。 </td></tr></tbody></table> <p><b>二硫苏糖醇</b>(Dithiothreitol,简称为<b>DTT</b>)是一种小分子<a href="/wiki/%E6%9C%89%E6%9C%BA%E5%8C%96%E5%90%88%E7%89%A9" title="有机化合物">有机</a><a href="/wiki/%E8%BF%98%E5%8E%9F%E5%89%82" title="还原剂">还原剂</a>,<a href="/wiki/%E5%8C%96%E5%AD%A6%E5%BC%8F" title="化学式">化学式</a>为C<sub>4</sub>H<sub>10</sub>O<sub>2</sub>S<sub>2</sub>。其还原状态下为线性分子,被氧化后变为包含<a href="/wiki/%E4%BA%8C%E7%A1%AB%E9%8D%B5" class="mw-redirect" title="二硫鍵">二硫键</a>的六元环状结构。二硫苏糖醇的名字衍生自<a href="/wiki/%E8%8B%8F%E7%B3%96" title="苏糖">苏糖</a>(一种四碳<a href="/wiki/%E5%8D%95%E7%B3%96" class="mw-redirect" title="单糖">单糖</a>)。DTT的<a href="/wiki/%E5%BC%82%E6%9E%84%E4%BD%93" class="mw-redirect" title="异构体">异构体</a>为<a href="/wiki/%E4%BA%8C%E7%A1%AB%E8%B5%A4%E7%B3%96%E9%86%87" title="二硫赤糖醇">二硫赤糖醇</a>(DTE),即DTT的C3-差向异构体。 </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="还原性"><span id=".E8.BF.98.E5.8E.9F.E6.80.A7"></span>还原性</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E4%BA%8C%E7%A1%AB%E8%8B%8F%E7%B3%96%E9%86%87&action=edit&section=1" title="编辑章节:还原性"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>DTT是一种很强的还原剂,其还原性很大程度上是由于其氧化状态六元环(含二硫键)的构象稳定性。它的<a href="/wiki/%E6%B0%A7%E5%8C%96%E8%BF%98%E5%8E%9F" class="mw-redirect" title="氧化还原">氧化还原</a>电势在<a href="/wiki/PH" class="mw-redirect" title="PH">pH</a>为7时为-0.33<a href="/wiki/%E4%BC%8F%E7%89%B9" title="伏特">伏</a>。二硫苏糖醇对一个典型的二硫键的还原是由两步连续的<a href="/w/index.php?title=%E5%B7%AF%E5%9F%BA-%E4%BA%8C%E7%A1%AB%E9%94%AE%E4%BA%A4%E6%8D%A2&action=edit&redlink=1" class="new" title="巯基-二硫键交换(页面不存在)">巯基-二硫键交换</a>反应所组成: </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Disulfide_reduction_by_DTT-2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/Disulfide_reduction_by_DTT-2.png/400px-Disulfide_reduction_by_DTT-2.png" decoding="async" width="400" height="169" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/Disulfide_reduction_by_DTT-2.png/600px-Disulfide_reduction_by_DTT-2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/61/Disulfide_reduction_by_DTT-2.png/800px-Disulfide_reduction_by_DTT-2.png 2x" data-file-width="1288" data-file-height="544" /></a></span></dd></dl> <p>其中,第一步反应所形成的中间态很不稳定,因为DTT上的第二个<a href="/wiki/%E5%B7%AF%E5%9F%BA" class="mw-redirect" title="巯基">巯基</a>趋向于与被氧化的硫原子连接,使中间态很快被转化为DTT的环状氧化结构,从而完成对二硫键的还原。 </p><p>DTT的还原力受pH值的影响,只在pH值大于7的情况下能够发挥还原作用。这是因为只有脱去质子的<a href="/w/index.php?title=%E7%A1%AB%E9%86%87%E7%9B%90&action=edit&redlink=1" class="new" title="硫醇盐(页面不存在)">硫醇盐</a>负离子(-S<sup>–</sup>)才具有反应活性,<a href="/wiki/%E7%A1%AB%E9%86%87" title="硫醇">硫醇</a>(-SH)则没有;而巯基的<a href="/wiki/PKa" class="mw-redirect" title="PKa">pKa</a>一般为~8.3。 </p> <div class="mw-heading mw-heading2"><h2 id="应用"><span id=".E5.BA.94.E7.94.A8"></span>应用</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E4%BA%8C%E7%A1%AB%E8%8B%8F%E7%B3%96%E9%86%87&action=edit&section=2" title="编辑章节:应用"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>DTT的用途之一是作为巯基化<a href="/wiki/DNA" class="mw-redirect" title="DNA">DNA</a>的还原剂和去保护剂。巯基化DNA末端硫原子在溶液中趋向于形成<a href="/wiki/%E4%BA%8C%E8%81%9A%E4%BD%93" class="mw-redirect" title="二聚体">二聚体</a>,特别是在存在氧气的情况下。这种二聚化大大降低了一些偶联反应实验(如DNA在生物感应器中的固定)的效率;而在DNA溶液中加入DTT,反应一段时间后除去,就可以降低DNA的二聚化。 </p><p>DTT也常常被用于<a href="/wiki/%E8%9B%8B%E7%99%BD%E8%B4%A8" title="蛋白质">蛋白质</a>中雙硫键的还原,可用于阻止蛋白质中的<a href="/wiki/%E5%8D%8A%E8%83%B1%E6%B0%A8%E9%85%B8" title="半胱氨酸">半胱氨酸</a>之间所形成的蛋白质分子内或分子间雙硫键。但DTT往往无法还原包埋于蛋白质结构内部(溶剂不可及)的雙硫键,这类雙硫键的还原常常需要先将蛋白质<a href="/wiki/%E5%8F%98%E6%80%A7_(%E7%94%9F%E7%89%A9%E5%8C%96%E5%AD%A6)" title="变性 (生物化学)">变性</a>(高温加热或加入变性剂,如6M <a href="/wiki/%E8%83%8D" title="胍">盐酸胍</a>、8M <a href="/wiki/%E5%B0%BF%E7%B4%A0" title="尿素">尿素</a>或1% <a href="/wiki/SDS" class="mw-redirect" title="SDS">SDS</a>)。反之,根据DTT存在情况下,雙硫键还原速度的不同,可以判断其包埋程度的深浅。 </p> <div class="mw-heading mw-heading2"><h2 id="特点"><span id=".E7.89.B9.E7.82.B9"></span>特点</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E4%BA%8C%E7%A1%AB%E8%8B%8F%E7%B3%96%E9%86%87&action=edit&section=3" title="编辑章节:特点"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>由于容易被空气<a href="/wiki/%E6%B0%A7%E5%8C%96" title="氧化">氧化</a>,因此DTT的稳定性较差;但冷冻保存或在<a href="/wiki/%E9%9D%9E%E6%B4%BB%E6%80%A7%E6%B0%A3%E9%AB%94" title="非活性氣體">惰性气体</a>中处理能够延长它的使用寿命。由于质子化的硫的亲核性较低,随着pH值的降低,DTT的有效还原性也随之降低;而Tris(2-carboxyethyl)phosphine HCl(TCEP盐酸盐)可以作为低pH值条件下DTT的替代品,而且也比DTT更为稳定。 </p> <div class="mw-heading mw-heading2"><h2 id="参考文献"><span id=".E5.8F.82.E8.80.83.E6.96.87.E7.8C.AE"></span>参考文献</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=%E4%BA%8C%E7%A1%AB%E8%8B%8F%E7%B3%96%E9%86%87&action=edit&section=4" title="编辑章节:参考文献"><span>编辑</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="reflist" style="list-style-type: decimal;"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><i>Merck Index</i>, 11th Edition, <b>3382</b>.</span> </li> </ol></div> <style data-mw-deduplicate="TemplateStyles:r80540462">.mw-parser-output .refbegin{font-size:90%;margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li{margin-left:0;padding-left:3.2em;text-indent:-3.2em}.mw-parser-output .refbegin-hanging-indents ul,.mw-parser-output .refbegin-hanging-indents ul li{list-style:none}@media(max-width:720px){.mw-parser-output .refbegin-hanging-indents>ul>li{padding-left:1.6em;text-indent:-1.6em}}.mw-parser-output .refbegin-columns{margin-top:0.3em}.mw-parser-output .refbegin-columns ul{margin-top:0}.mw-parser-output .refbegin-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .refbegin-100{font-size:100%}</style><div class="refbegin" style=""> <ul><li>Cleland WW. (1964) "Dithiothreitol, A New Protective Reagent for SH Groups", <i>Biochemistry</i>, <b>3</b>, 480-482.</li> <li>Ruegg UT and Rudinger J. (1977) "Cleavage of disulfide bonds in proteins", <i>Methods Enzymol.</i>, <b>47</b>, 111.</li></ul> </div> <!-- NewPP limit report Parsed by mw‐web.codfw.main‐f69cdc8f6‐b5stz Cached time: 20241123181248 Cache expiry: 2592000 Reduced expiry: false Complications: [show‐toc] CPU time usage: 0.187 seconds Real time usage: 0.257 seconds Preprocessor visited node count: 3045/1000000 Post‐expand include size: 22679/2097152 bytes Template argument size: 5541/2097152 bytes Highest expansion depth: 16/100 Expensive parser function count: 6/500 Unstrip recursion depth: 0/20 Unstrip post‐expand size: 1481/5000000 bytes Lua time usage: 0.026/10.000 seconds Lua memory usage: 1026147/52428800 bytes Number of Wikibase entities loaded: 0/400 --> <!-- Transclusion expansion time report (%,ms,calls,template) 100.00% 195.803 1 -total 91.52% 179.199 1 Template:Chembox 50.62% 99.107 1 Template:Chembox_Identifiers 19.37% 37.931 63 Template:Chembox_entry 15.76% 30.849 1 Template:Chembox_Properties 6.67% 13.054 11 Template:Chembox_CASCheck 5.39% 10.556 1 Template:Refbegin 4.68% 9.157 2 Template:Ebicite 3.47% 6.795 1 Template:Cross 3.01% 5.897 1 Template:Chembox_SMILES --> <!-- Saved in parser cache with key zhwiki:pcache:idhash:772472-0!canonical!zh and timestamp 20241123181248 and revision id 56469130. 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