Highly Efficient Cyclic Dinucleotide Based Artificial Metalloribozymes for Enantioselective Friedel–Crafts Reactions in Water

Wang Changhao; Hao Min; Qi Qianqian; Dang Jingshuang; Dong Xingchen; Lv Shuting; Xiong Ling; Gao Huanhuan; Jia Guoqing; Chen Yashao; Hartig J?rg S.; Li Can

摘要

Abstract > The diverse secondary structures of nucleic acids are emerging as attractive chiral scaffolds to construct artificial metalloenzymes (ArMs) for enantioselective catalysis. DNA‐based ArMs containing duplex and G‐quadruplex scaffolds have been widely investigated, yet RNA‐based ArMs are scarce. Here we report that a cyclic dinucleotide of c‐di‐AMP and Cu 2+ ions assemble into an artificial metalloribozyme (c‐di‐AMP?Cu 2+ ) that enables catalysis of enantioselective Friedel–Crafts reactions in aqueous media with high reactivity and excellent enantioselectivity of up to 97?% ee . The assembly of c‐di‐AMP?Cu 2+ gives rise to a 20‐fold rate acceleration compared to Cu 2+ ions. Based on various biophysical techniques and density function theory (DFT) calculations, a fine coordination structure of c‐di‐AMP?Cu 2+ metalloribozyme is suggested in which two c‐di‐AMP form a dimer scaffold and the Cu 2+ ion is located in the center of an adenine‐adenine plane through binding to two N7 nitrogen atoms and one phosphate oxygen atom. </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> > 核酸的各种二级结构是有吸引力的手性支架，以构建用于对映选择性催化的人工金属酶（臂）。含有双相和G-QuadrupleS支架的DNA的臂已被广泛研究，但基于RNA的臂稀缺。在这里，我们报告称C-Di-AMP和Cu的循环二核苷酸 2 + </ sup> 离子组装成人工金属键（C-Di-AMP？Cu 2 + </ sup> ）这使得能够在水性介质中催化映射式Friedel-Crafts反应，其具有高反应性和优异的对映选择性高达97Ω％ ee </ i> 。 C-Di-AMP的组装？Cu 2 + </ sup> 与Cu相比产生20倍的速率加速度 2 + </ sup> 离子。基于各种生物物理技术和密度函数理论（DFT）计算，C-Di-AMP的精细配位结构 2 + </ sup> 建议其中两种C-Di-AMP形成二聚体支架和Cu的金属吡啶酶 2 + </ sup> 离子位于腺嘌呤 - 腺嘌呤平面的中心，通过结合两个N7氮原子和一种磷酸盐氧原子。 </ 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9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=Wang Changhao&option=202" target="_blank" rel="nofollow">Wang Changhao;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Hao Min&option=202" target="_blank" rel="nofollow">Hao Min;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Qi Qianqian&option=202" target="_blank" rel="nofollow">Qi Qianqian;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Dang Jingshuang&option=202" target="_blank" rel="nofollow">Dang Jingshuang;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Dong Xingchen&option=202" target="_blank" rel="nofollow">Dong Xingchen;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lv Shuting&option=202" target="_blank" rel="nofollow">Lv Shuting;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Xiong Ling&option=202" target="_blank" rel="nofollow">Xiong Ling;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Gao Huanhuan&option=202" target="_blank" rel="nofollow">Gao Huanhuan;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Jia Guoqing&option=202" target="_blank" rel="nofollow">Jia Guoqing;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chen Yashao&option=202" target="_blank" rel="nofollow">Chen Yashao;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Hartig J?rg S.&option=202" target="_blank" rel="nofollow">Hartig J?rg S.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Li Can&option=202" target="_blank" rel="nofollow">Li Can;</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>Key Laboratory of Applied Surface and Colloid ChemistryMinistry of EducationXi'an 710119 China;</p> <p>Key Laboratory of Applied Surface and Colloid ChemistryMinistry of EducationXi'an 710119 China;</p> <p>Key Laboratory of Applied Surface and Colloid ChemistryMinistry of EducationXi'an 710119 China;</p> <p>Key Laboratory of Applied Surface and Colloid ChemistryMinistry of EducationXi'an 710119 China;</p> <p>Key Laboratory of Applied Surface and Colloid ChemistryMinistry of EducationXi'an 710119 China;</p> <p>Key Laboratory of Applied Surface and Colloid ChemistryMinistry of EducationXi'an 710119 China;</p> <p>Key Laboratory of Applied Surface and Colloid ChemistryMinistry of EducationXi'an 710119 China;</p> <p>Key Laboratory of Applied Surface and Colloid ChemistryMinistry of EducationXi'an 710119 China;</p> <p>State Key Laboratory of CatalysisChinese Academy of SciencesDalian 116023 China;</p> <p>Key Laboratory of Applied Surface and Colloid ChemistryMinistry of EducationXi'an 710119 China;</p> <p>Department of ChemistryUniversity of Konstanz78457 Konstanz Germany;</p> <p>State Key Laboratory of CatalysisChinese Academy of SciencesDalian 116023 China;</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=artificial metalloribozymes&option=203" rel="nofollow">artificial metalloribozymes;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=c-di-AMP&option=203" rel="nofollow">c-di-AMP;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=cyclic dinucleotides&option=203" rel="nofollow">cyclic dinucleotides;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=homogeneous catalysis&option=203" rel="nofollow">homogeneous catalysis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=nucleic acid based catalysts&option=203" rel="nofollow">nucleic acid based catalysts;</a> </p> <div class="translation"> 机译：人工金属键;C-Di-AMP;循环二核苷酸;均匀催化;核酸基催化剂; </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/0704028161055.html">Highly Efficient Cyclic Dinucleotide Based Artificial Metalloribozymes for Enantioselective Friedel–Crafts Reactions in Water</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wang Changhao&option=202" target="_blank" rel="nofollow" class="tuijian_auth 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href="/academic-journal-cn_chemical-research-application_thesis/0201235519986.html">FeCl3作用下α-羰基二硫缩烯酮的Friedel-Crafts酰基化反应</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=赵辉&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 赵辉</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=于海丰&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,于海丰</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=李铁纯&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,李铁纯</a> <span> <a href="/journal-cn-12032/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 化学研究与应用 </a> </span> <span> . 2016</span><span>,第004期</span> </span> </div> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/academic-journal-cn_gansu-petroleum-chemical-industry_thesis/0201245881584.html">Friedel－Crafts反应合成单苯基二氯化磷工艺探讨</a> <b>[J]</b> <span> <a 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