Total Synthesis of a Mycolic Acid from Mycobacterium tuberculosis

Tahiri Nabil; Fodran Peter; Jayaraman Dhineshkumar; Buter Jeffrey; Witte Martin D.; Ocampo Tonatiuh A.; Moody D. Branch; Van Rhijn Ildiko; Minnaard Adriaan J.

摘要

Abstract > In Mycobacterium tuberculosis, mycolic acids and their glycerol, glucose, and trehalose esters (“cord factor”) form the main part of the mycomembrane. Despite their first isolation almost a century ago, full stereochemical evaluation is lacking, as is a scalable synthesis required for accurate immunological, including vaccination, studies. Herein, we report an efficient, convergent, gram‐scale synthesis of four stereo‐isomers of a mycolic acid and its glucose ester. Binding to the antigen presenting protein CD1b and T cell activation studies are used to confirm the antigenicity of the synthetic material. The absolute stereochemistry of the syn ‐methoxy methyl moiety in natural material is evaluated by comparing its optical rotation with that of synthetic material. </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> > 在结核分枝杆菌，</ i> 氰酸和它们的甘油，葡萄糖和海藻糖酯（“脐带因子”）形成MyComembrane的主要部分。尽管近一个世纪前的第一次隔离，但缺乏完全立体化学评价，这是一种准确的免疫学，包括疫苗接种，研究所需的可扩展合成。在此，我们报告了氰酸及其葡萄糖酯的四个立体异构体的有效，会聚，革兰级合成。与蛋白CD1B和T细胞活化研究的抗原结合用于确认合成材料的抗原性。绝对立体化学 syn </ i> 通过将其光学旋转与合成材料的光学旋转进行比较来评价天然材料中的甲氧基甲基部分。 </ 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6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=Tahiri Nabil&option=202" target="_blank" rel="nofollow">Tahiri Nabil;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Fodran Peter&option=202" target="_blank" rel="nofollow">Fodran Peter;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Jayaraman Dhineshkumar&option=202" target="_blank" rel="nofollow">Jayaraman Dhineshkumar;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Buter Jeffrey&option=202" target="_blank" rel="nofollow">Buter Jeffrey;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Witte Martin D.&option=202" target="_blank" rel="nofollow">Witte Martin D.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ocampo Tonatiuh A.&option=202" target="_blank" rel="nofollow">Ocampo Tonatiuh A.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Moody D. Branch&option=202" target="_blank" rel="nofollow">Moody D. Branch;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Van Rhijn Ildiko&option=202" target="_blank" rel="nofollow">Van Rhijn Ildiko;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Minnaard Adriaan J.&option=202" target="_blank" rel="nofollow">Minnaard Adriaan J.;</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>Stratingh Institute for ChemistryUniversity of GroningenNijenborgh 7 9747 AG Groningen The Netherlands;</p> <p>Stratingh Institute for ChemistryUniversity of GroningenNijenborgh 7 9747 AG Groningen The Netherlands;</p> <p>Stratingh Institute for ChemistryUniversity of GroningenNijenborgh 7 9747 AG Groningen The Netherlands;</p> <p>Stratingh Institute for ChemistryUniversity of GroningenNijenborgh 7 9747 AG Groningen The Netherlands;</p> <p>Stratingh Institute for ChemistryUniversity of GroningenNijenborgh 7 9747 AG Groningen The Netherlands;</p> <p>Brigham and Women's Hospital Division of Rheumatology Inflammation and ImmunityHarvard Medical School Hale BTM60 Fenwood Road Boston MA 02115 USA;</p> <p>Brigham and Women's Hospital Division of Rheumatology Inflammation and ImmunityHarvard Medical School Hale BTM60 Fenwood Road Boston MA 02115 USA;</p> <p>Brigham and Women's Hospital Division of Rheumatology Inflammation and ImmunityHarvard Medical School Hale BTM60 Fenwood Road Boston MA 02115 USA;</p> <p>Stratingh Institute for ChemistryUniversity of GroningenNijenborgh 7 9747 AG Groningen The Netherlands;</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=CD1b&option=203" rel="nofollow">CD1b;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=cross coupling&option=203" rel="nofollow">cross coupling;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=mycolic acid&option=203" rel="nofollow">mycolic acid;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=total synthesis&option=203" rel="nofollow">total synthesis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=tuberculosis&option=203" rel="nofollow">tuberculosis;</a> </p> <div class="translation"> 机译：CD1B;交叉偶联;氰酸;总合成;结核病; </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/0704028160703.html">Total Synthesis of a Mycolic Acid from Mycobacterium tuberculosis</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Tahiri Nabil&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Tahiri Nabil,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Fodran Peter&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Fodran Peter,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Jayaraman Dhineshkumar&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Jayaraman Dhineshkumar,</a> <a href="/journal-foreign-19011/" target="_blank" rel="nofollow" class="tuijian_authcolor">Angewandte Chemie .</a> <span>2020</span><span>,第19期</span> </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：来自结核分枝杆菌的霉菌酸的总合成</span> </p> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/academic-journal-foreign_detail_thesis/0204118496020.html">Function of Heterologous Mycobacterium tuberculosis InhA, a Type 2 Fatty Acid Synthase Enzyme Involved in Extending C20 Fatty Acids to C60-to-C90 Mycolic Acids, during De Novo Lipoic Acid Synthesis in Saccharomyces cerevisiae</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Aner Gurvitz&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Aner Gurvitz,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=J. 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href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=黄喜桂&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,黄喜桂</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=等&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,等</a> <span> <a href="/journal-cn-6415/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 中国抗生素杂志 </a> </span> <span> . 1999</span><span>,第001期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-49766_thesis/020222874733.html">铜氨液中总氨总酸总铜含量快速测定</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=王贵清&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 王贵清</a> <span> <a href="/conference-cn-49766/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 中小型氮肥厂节能设备技术交流会 </a> <span> <span> . 1986</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020315272247.html">黄花蒿内生草酸青霉菌(Penicillium oxalicum B4)促进青蒿素合成、转化青蒿酸和降解三氯生的研究</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=田浩&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 田浩</a> <span> . 2019</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120102159363.html">来自结核分枝杆菌的氨基酸序列或其相应核酸在诊断和预防结核感染、诊断试剂盒及其疫苗中的应用</a> <b>[P]</b> . <span> 中国专利： CN103402533A </span> <span> . 2013-11-20</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/061201431074.html">来自辣椒疫霉菌的阿魏酸酯酶PCFAE2及其编码基因与应用</a> <b>[P]</b> . <span> 中国专利： CN102676468B </span> <span> . 2014.07.16</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130455759356.html">Cloning and expression of dna involved in the biosynthesis o f cyclopropanated mycolic acids in mycobacterium tuberculosi s</a> <b>[P]</b> . <span> 外国专利：  AU5881496A </span> <span> . 1996-12-18</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：结核分枝杆菌中环丙烷化霉菌酸生物合成中涉及的dna的克隆与表达 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130455721937.html">CLONING AND EXPRESSION OF DNA INVOLVED IN THE BIOSYNTHESIS OF CYCLOPROPANATED MYCOLIC ACIDS IN MYCOBACTERIUM TUBERCULOSIS</a> <b>[P]</b> . <span> 外国专利：  WO9638581A1 </span> <span> . 1996-12-05</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：结核分枝杆菌环丙醇酸生物合成中涉及DNA的克隆与表达 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130410364846.html">Use of Mycobacterium tuberculosis-derived amino acid sequences or their corresponding nucleic acids for diagnosis and prevention of Mycobacterium tuberculosis infection, and diagnostic kits and vaccines derived therefrom</a> <b>[P]</b> . <span> 外国专利：  JP6150842B2 </span> <span> . 2017-06-21</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：结核分枝杆菌衍生的氨基酸序列或其相应核酸在诊断和预防结核分枝杆菌感染中的用途，以及由此衍生的诊断试剂盒和疫苗 </span> </p> </li> </ul> </div> </div> </div> <div class="theme cardcommon" style="overflow: auto;display:none"> <h3 class="all_title" id="enpatent55">相关主题</h3> <ul id="subject"> </ul> </div> </div> </div> </div> <div class="right rightcon"> <div class="details_img cardcommon clearfix" style="margin-bottom: 10px;display:none;" > </div> </div> </div> <div id="thesis_get_original1" class="downloadBth" style="bottom: 19px;z-index: 999;" onclick="ywcd('0704028160703','4',7,2,1,'',this,24)" 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