A Biocatalytic Synthesis of Heteroaromatic N‐Oxides by Whole Cells of Escherichia coli Expressing the Multicomponent, Soluble Di‐Iron Monooxygenase (SDIMO) PmlABCDEF

Petkevi?ius Vytautas; Vaitekūnas Justas; Taurait? Daiva; Stankevi?iūt? Jonita; ?arlauskas Jonas; ??nas Narimantas; Me?kys Rolandas

摘要

Abstract > Aromatic N ‐oxides (ArN?OX) are desirable biologically active compounds with a potential for application in pharmacy and agriculture industries. As biocatalysis is making a great impact in organic synthesis, there is still a lack of efficient and convenient enzyme‐based techniques for the production of aromatic N ‐oxides. In this study, a recombinant soluble di‐iron monooxygenase (SDIMO) PmlABCDEF overexpressed in Escherichia coli was showed to produce various aromatic N‐ oxides. Out of 98 tested N ‐heterocycles, seventy were converted to the corresponding N ‐oxides without any side oxidation products. This whole‐cell biocatalyst showed a high activity towards pyridines, pyrazines, and pyrimidines. It was also capable of oxidizing bulky N ‐heterocycles with two or even three aromatic rings. Being entirely biocatalytic, our approach provides an environmentally friendly and mild method for the production of aromatic N ‐oxides avoiding the use of strong oxidants, organometallic catalysts, undesirable solvents, or other environment unfriendly reagents. > <blockFixed type="graphic"> <mediaResourceGroup> <mediaResource alt="image" href="urn:x-wiley:16154150:media:adsc201801491:adsc201801491-toc-0001"/> </mediaResourceGroup> </blockFixed> </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> > 芳香 n </ i> - 氧化物（ARNαOX）是理想的生物活性化合物，具有在药房和农业产业中的应用潜力。作为生物催化在有机合成产生重大影响，仍然缺乏缺乏有效和方便的基于酶的生产的芳香族技术 n </ i> 过氧化物。在该研究中，一种重组可溶性二 - 铁单氧化酶（Sdimo）Pmlabcdef在过表达中大肠杆菌</ i> 显示出生产各种芳香族 n - </ i> 氧化物。在98个测试中 n </ i> - 六十年代，转换为相应的速度 n </ i> - 氧化物没有任何侧氧化物产物。这种全细胞生物催化剂向吡啶，吡嗪和嘧啶呈现出高活性。它也能够氧化笨重 n </ i> - 用两个甚至三个芳香环的克莱切笼。我们的方法完全是生物催化，为芳香的生产提供了一种环保和温和的方法 n </ i> - 避免使用强氧化剂，有机金属催化剂，不希望的溶剂或其他环境不友好的试剂。 </ p> > <blockfixed type =“图形”> <mediaresourcegroup> <MediareSource Alt =“图像”HREF =“URN：X-Wiley：16154150：介质：ADSC201801491：ADSC201801491-TOC-0001”/> </ mediaresourcegroup> </ blockfixed> </ 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-19407/'>《Advanced synthesis & catalysis》</a> <b style="margin: 0 2px;">|</b><span>2019年第11期</span><b style="margin: 0 2px;">|</b><span>共10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=Petkevi?ius Vytautas&option=202" target="_blank" rel="nofollow">Petkevi?ius Vytautas;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Vaitekūnas Justas&option=202" target="_blank" rel="nofollow">Vaitekūnas Justas;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Taurait? Daiva&option=202" target="_blank" rel="nofollow">Taurait? Daiva;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Stankevi?iūt? Jonita&option=202" target="_blank" rel="nofollow">Stankevi?iūt? Jonita;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=?arlauskas Jonas&option=202" target="_blank" rel="nofollow">?arlauskas Jonas;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=??nas Narimantas&option=202" target="_blank" rel="nofollow">??nas Narimantas;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Me?kys Rolandas&option=202" target="_blank" rel="nofollow">Me?kys Rolandas;</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 Molecular Microbiology and Biotechnology Institute of Biochemistry Life Sciences CenterVilnius UniversitySaul?tekio 7 Vilnius LT-10257 Lithuania;</p> <p>Department of Molecular Microbiology and Biotechnology Institute of Biochemistry Life Sciences CenterVilnius UniversitySaul?tekio 7 Vilnius LT-10257 Lithuania;</p> <p>Department of Molecular Microbiology and Biotechnology Institute of Biochemistry Life Sciences CenterVilnius UniversitySaul?tekio 7 Vilnius LT-10257 Lithuania;</p> <p>Department of Molecular Microbiology and Biotechnology Institute of Biochemistry Life Sciences CenterVilnius UniversitySaul?tekio 7 Vilnius LT-10257 Lithuania;</p> <p>Department of Xenobiotics Biochemistry Institute of Biochemistry Life Sciences CenterVilnius UniversitySaul?tekio 7 Vilnius LT-10257 Lithuania;</p> <p>Department of Xenobiotics Biochemistry Institute of Biochemistry Life Sciences CenterVilnius UniversitySaul?tekio 7 Vilnius LT-10257 Lithuania;</p> <p>Department of Molecular Microbiology and Biotechnology Institute of Biochemistry Life Sciences CenterVilnius UniversitySaul?tekio 7 Vilnius LT-10257 Lithuania;</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/238.html" title="化学工业">化学工业;</a><a href="https://www.zhangqiaokeyan.com/clc/1186.html" title="物理化学（理论化学）、化学物理学">物理化学（理论化学）、化学物理学;</a><a href="https://www.zhangqiaokeyan.com/clc/7777.html" title="化学反应过程">化学反应过程;</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=Biocatalysis&option=203" rel="nofollow">Biocatalysis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=chemoselectivity&option=203" rel="nofollow">chemoselectivity;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=nitrogen heterocycles&option=203" rel="nofollow">nitrogen heterocycles;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=oxidation&option=203" rel="nofollow">oxidation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=regioselectivity&option=203" rel="nofollow">regioselectivity;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=soluble di-iron monooxygenase&option=203" rel="nofollow">soluble di-iron monooxygenase;</a> </p> <div class="translation"> 机译：生物催化;化学选择性;氮杂环;氧化;区域选择性;可溶性二铁单氧酶; </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/0704022693832.html">Front Cover Picture: A Biocatalytic Synthesis of Heteroaromatic N‐Oxides by Whole Cells of Escherichia coli Expressing the Multicomponent, Soluble Di‐Iron Monooxygenase (SDIMO) PmlABCDEF (Adv. 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initial;text-overflow: initial;overflow: initial;"> <span>机译：酯生物合成和ω-氧化的组合，用于在大肠杆菌的全细胞生物催化装置中生产单乙基二羧酸和二乙基酯</span> </p> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/academic-journal-cn_chemical-journal-chinese-universities_thesis/0201293921389.html">N－（1－氧代－1－磷杂－2，6，7－三氧杂双环［2．2．2］－辛烷－4－羰基）－N＇－芳（烷）基硫脲的合成及结构研究</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=李玉桂&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 李玉桂</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=朱雪峰&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,朱雪峰</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=黄芹&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,黄芹</a> <span> <a href="/journal-cn-10958/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 高等学校化学学报 </a> </span> <span> . 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href="/academic-journal-cn_detail_thesis/0201295856074.html">N-{5-1-(2′,4′-二氯苯氧)乙基-1,3,4-噻二唑-2-基}-N′-芳氧乙酰基硫脲的合成与生物活性</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=龚银香&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 龚银香</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=王胜&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,王胜</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=汪焱钢&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,汪焱钢</a> <span> <a href="/journal-cn-57029/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 化学试剂 </a> </span> <span> . 2005</span><span>,第11期</span> </span> </div> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/academic-journal-cn_industrial-catalysis_thesis/0201246448495.html">聚乙二醇及其衍生物催化合成苯并呋咱-N-氧化物的研究</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=范磊刚&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 范磊刚</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=杨晓慧&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,杨晓慧</a> <span> <a href="/journal-cn-9123/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 工业催化 </a> </span> <span> . 2005</span><span>,第012期</span> </span> </div> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/academic-journal-cn_chinese-journal-inorganic-chemistry_thesis/0201250733559.html">含取代芳酰腙和单齿N-杂环分子铜(Ⅱ)配合物的合成、结构及荧光性质</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=刘会艳&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 刘会艳</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=王海营&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,王海营</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=牛德仲&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,牛德仲</a> <span> <a href="/journal-cn-15070/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 无机化学学报 </a> </span> <span> . 2007</span><span>,第004期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-4273_thesis/020221024757.html">9,10-二氢-9-氧杂-10-N,N-二(羟乙基氨甲基)-10-膦酰杂菲-10-氧化物合成</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=WANG Hao&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . WANG Hao</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=王浩&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,王浩</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=SU Haixiao&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,SU Haixiao</a> <span> <a href="/conference-cn-4273/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 2013年全国阻燃学术年会 </a> <span> <span> . 2013</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020311918011.html">无溶剂合成氧杂蒽二酮类化合物、N-羧甲基氮杂蒽二酮类化合物和喹唑啉二酮类化合物的研究</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=何璇&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 何璇</a> <span> . 2010</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120105322643.html">新的果糖1,6－二磷酸酶的杂芳族抑制剂</a> <b>[P]</b> . <span> 中国专利： CN101125864A </span> <span> . 2008-02-20</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120344833.html">新的果糖1,6－二磷酸酶的杂芳族抑制剂</a> <b>[P]</b> . <span> 中国专利： CN100349904C </span> <span> . 2007.11.21</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130403024846.html">GENE-THERAPEUTIC DNA VECTOR BASED ON THE GENE-THERAPEUTIC DNA VECTOR VTvaf17, CARRYING THE TARGET GENE CFTR, OR NOS1, OR AQ1, OR AQ3, OR AQ5, FOR TREATING DISEASES ASSOCIATED WITH THE NEED TO INCREASE THE LEVEL OF EXPRESSION OF THESE TARGET GENES, A METHOD FOR PRODUCING AND USING IT, ESCHERICHIA COLI SCS110-AF/VTvaf17-CFTR STRAIN, OR ESCHERICHIA COLI SCS110-AF/VTvaf17-NOS1, OR ESCHERICHIA COLI SCS110-AF/VTvaf17-AQ1, OR ESCHERICHIA COLI SCS110-AF/VTvaf17-AQ3, OR ESCHERICHIA COLI SCS110-AF/VTvaf17-AQ5, CARRYING A GENE-THERAPEUTIC DNA VECTOR, METHOD FOR PRODUCTION THEREOF, A METHOD FOR INDUSTRIAL PRODUCTION OF A GENE-THERAPEUTIC DNA VECTOR</a> <b>[P]</b> . <span> 外国专利：  RU2705252C1 </span> <span> . 2019-11-06</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：基于基因治疗DNA矢量VTvaf17的基因治疗DNA矢量，携带目标基因CFTR或NOS1，AQ1，AQ3或AQ5，以治疗与需要增加表达水平相关的疾病，其生产和使用方法，大肠埃希氏菌SCS110-AF / VTvaf17-CFTR应变或大肠埃希氏菌SCS110-AF / VTvaf17-NOS1或大肠埃希氏菌SCS110-AF / VTvaf17-AQ1或大肠埃希氏菌SCS110-AF / VTvaf17 -AQ3或大肠埃希氏菌SCS110-AF / VTvaf17-AQ5，携带基因治疗性DNA矢量，其生产方法，工业生产基因治疗性DNA矢量的方法 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130400520078.html">RECOMBINANT PLASMID DNA OF PQE-30_P36GP12_GP57, PROVIDING SYNTHESIS OF RECOMBINANT PROTEIN P36GP12 IN CELLS OF ESCHERICHIA COLI, A STRAIN OF BACTERIA ESCHERICHIA COLI - PRODUCER OF RECOMBINANT PROTEIN P36GP12, RECOMBINANT PROTEIN P36GP12, CAPABLE TO BIND LIPOPOLYSACCHARIDES ESCHERICHIA COLI</a> <b>[P]</b> . <span> 外国专利：  RU2707922C1 </span> <span> . 2019-12-02</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：PQE-30_P36GP12_GP57的重组质粒DNA，提供了在大肠杆菌中的重组蛋白P36GP12的合成，该菌株是一株大肠杆菌，重组蛋白P36GP12的产生，重组蛋白蛋白酶B3的产生，该蛋白质为蛋白酶体。 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130431763281.html">BACTERIOPHAGE N15 REPLICON-BASE VECTOR AND RECOMBINANT VECTOR FOR REGULATED EXPRESSION OF TARGET GENE IN ESCHERICHIA COLI CELLS, STRAIN ESCHERICHIA COLI PROVIDING POSSIBILITY FOR REGULATION OF VECTOR COPY NUMBER AND EXPRESSION SYSTEM</a> <b>[P]</b> . <span> 外国专利：  RU2312146C1 </span> <span> . 2007-12-10</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> 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