Pathway from N‐Alkylglycine to Alkylisonitrile Catalyzed by Iron(II) and 2‐Oxoglutarate‐Dependent Oxygenases

Chen Tzu‐Yu; Chen Jinfeng; Tang Yijie; Zhou Jiahai; Guo Yisong; Chang Wei‐chen

摘要

Abstract > N‐alkylisonitrile, a precursor to isonitrile‐containing lipopeptides, is biosynthesized by decarboxylation‐assisted ‐N≡C group (isonitrile) formation by using N‐alkylglycine as the substrate. This reaction is catalyzed by iron(II) and 2‐oxoglutarate (Fe/2OG) dependent enzymes. Distinct from typical oxygenation or halogenation reactions catalyzed by this class of enzymes, installation of the isonitrile group represents a novel reaction type for Fe/2OG enzymes that involves a four‐electron oxidative process. Reported here is a plausible mechanism of three Fe/2OG enzymes, Sav607, ScoE and SfaA, which catalyze isonitrile formation. The X‐ray structures of iron‐loaded ScoE in complex with its substrate and the intermediate, along with biochemical and biophysical data reveal that ‐N≡C bond formation involves two cycles of Fe/2OG enzyme catalysis. The reaction starts with an Fe IV ‐oxo‐catalyzed hydroxylation. It is likely followed by decarboxylation‐assisted desaturation to complete isonitrile installation. </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><Abstract Type =“Main”XML：Lang =“en”> <标题类型=“main”>抽象</ title> > N-烷基硅二腈，一种含异腈的脂肽的前体，通过使用N-烷基甘氨酸作为基材来通过脱羧辅助-NI≡C组（异腈）形成生物合成。该反应由铁（II）和2-氧氧化或Fe / 2g）依赖性酶催化。不同于该类酶催化的典型氧合或卤化反应，载异腈基的安装代表了用于Fe / 2g酶的新型反应类型，其涉及四电子氧化过程。据报道，这是三种Fe / 2g酶，SAV607，SCOE和SFAA的合理机制，其催化了异腈形成。与其基材和中间体复合物中的铁载体X射线结构以及生物化学和生物物理数据揭示了-N≡C键形成涉及两种Fe / 2g酶催化的循环。反应从一个fe开始 iv </ sup> - 催化羟基化。其次是脱羧辅助的去饱和以完成异腈装置。 </ p> </摘要> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" >著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-19011/'>《Angewandte Chemie》</a> <b style="margin: 0 2px;">|</b><span>2020年第19期</span><b style="margin: 0 2px;">|</b><span>共5页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chen Tzu‐Yu&option=202" target="_blank" rel="nofollow">Chen Tzu‐Yu;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chen Jinfeng&option=202" target="_blank" rel="nofollow">Chen Jinfeng;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Tang Yijie&option=202" target="_blank" rel="nofollow">Tang Yijie;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhou Jiahai&option=202" target="_blank" rel="nofollow">Zhou Jiahai;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Guo Yisong&option=202" target="_blank" rel="nofollow">Guo Yisong;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chang Wei‐chen&option=202" target="_blank" rel="nofollow">Chang Wei‐chen;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>Department of ChemistryNorth Carolina State UniversityRaleigh NC 27695 USA;</p> <p>State Key Laboratory of Bio-organic and Natural Products ChemistryUniversity of Chinese Academy of SciencesShanghai 200032 China;</p> <p>Department of ChemistryCarnegie Mellon UniversityPittsburgh PA 15213 USA;</p> <p>State Key Laboratory of Bio-organic and Natural Products ChemistryUniversity of Chinese Academy of SciencesShanghai 200032 China;</p> <p>Department of ChemistryCarnegie Mellon UniversityPittsburgh PA 15213 USA;</p> <p>Department of ChemistryNorth Carolina State UniversityRaleigh NC 27695 USA;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li > <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span><a href="https://www.zhangqiaokeyan.com/clc/1188.html" title="应用化学">应用化学;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=catalysis&option=203" rel="nofollow">catalysis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=decarboxylation&option=203" rel="nofollow">decarboxylation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=enzymes&option=203" rel="nofollow">enzymes;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=iron&option=203" rel="nofollow">iron;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=reaction mechanisms&option=203" rel="nofollow">reaction mechanisms;</a> </p> <div class="translation"> 机译：催化;脱羧;酶;铁;反应机制; </div> </li> </ul> </div> </div> <div class="literature cardcommon"> <div class="similarity "> <h3 class="all_title" id="enpatent66">相似文献</h3> <div class="similaritytab clearfix"> <ul> <li class="active" >外文文献</li> <li >中文文献</li> <li >专利</li> </ul> </div> <div class="similarity_details"> <ul > <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704028162808.html">Pathway from N‐Alkylglycine to Alkylisonitrile Catalyzed by Iron(II) and 2‐Oxoglutarate‐Dependent Oxygenases</a> <b>[J]</b> . <span> <a 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href="/academic-degree-domestic_mphd_thesis/02031379497.html">1.氟化N-（3-长链烷氧-2-羟）丙基-N，N，N-三烷基铵的合成及性质;2.手性氨基烷基酚的合成及不对称催化</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=常建国&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 常建国</a> <span> . 2004</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/061201125374.html">合成N-[3-[(2-甲氧基苯基)硫烷基]-2-甲基丙基]-3,4-二氢-2H-1,5-苯并氧硫杂*-3-胺的方法</a> <b>[P]</b> . <span> 中国专利： CN101535287B </span> <span> . 2013.02.27</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120693424.html">[2-(8,9-二氧代-2,6-二氮杂二环[5.2.0]壬-1(7)-烯-2-基)烷基]膦酸衍生物及其作为N-甲基-D-天冬氨酸(NMDA)受体拮抗剂的应用</a> <b>[P]</b> . <span> 中国专利： CN1863810B </span> <span> . 2010.12.01</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130419893403.html">A METHOD FOR ASSAYING FTO 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