Detection and Chiral Recognition of α‐Hydroxyl Acid through 1H and CEST NMR Spectroscopy Using a Ytterbium Macrocyclic Complex

He Haonan; Zhao Kelu; Xiao Long; Zhang Yi; Cheng Yi; Wan Sikang; Chen Shizhen; Zhang Lei; Zhou Xin; Liu Kai; Zhang Hongjie

摘要

Abstract > Chiral α‐hydroxyl acids are of great importance in chemical synthesis. Current methods for recognizing their chirality by 1 H?NMR are limited by their small chemical shift differences and intrinsic solubility problem in organic solvents. Herein, we developed three YbDO3A(ala) <sub>3</sub> derivatives to recognize four different commercially available chiral α‐hydroxyl acids in aqueous solution through 1 H?NMR and chemical exchange saturation transfer (CEST) spectroscopy. The shift difference between chiral α‐hydroxyl acid observed by proton and CEST NMR ranged from 15–40 and 20–40?ppm, respectively. Our work demonstrates for first time, that even one chiral center on the side‐arm chain of cyclen could set the stage for rotation of the other two non‐chiral side chains into a preferred position. This is ascribed to the lower energy state of the structure. The results show that chiral YbDO3A‐like complexes can be used to discriminate chiral α‐hydroxyl acids with a distinct signal difference. </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> > 手性α-羟基酸在化学合成方面具有重要意义。识别他们的手性的目前的方法 1 </ sup> H = NMR受到它们在有机溶剂中的小化学变形差和内在溶解性问题的限制。在此，我们开发了三个YBDO3A（ALA） <sub> 3 </ sub> 衍生物在水溶液中识别四种不同的市售手性α-羟基酸 1 </ sup> H？NMR和化学交换饱和度转移（CEST）光谱。通过质子和CEST NMR观察到的手性α-羟基酸之间的换档差异分别为15-40和20-40μlppm。我们的工作首次演示，即侧臂环的一个手平中心甚至可以将其他两个非手性侧链旋转的阶段设置为优选位置。这归因于结构的较低能量状态。结果表明，手性YBDO3A样复合物可用于区分具有不同信号差的手性α-羟基酸。 </ 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>2019年第50期</span><b style="margin: 0 2px;">|</b> <span>共4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=He Haonan&option=202" target="_blank" rel="nofollow">He Haonan;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhao Kelu&option=202" target="_blank" rel="nofollow">Zhao Kelu;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Xiao Long&option=202" target="_blank" rel="nofollow">Xiao Long;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhang Yi&option=202" target="_blank" rel="nofollow">Zhang Yi;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Cheng Yi&option=202" target="_blank" rel="nofollow">Cheng Yi;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wan Sikang&option=202" target="_blank" rel="nofollow">Wan Sikang;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chen Shizhen&option=202" target="_blank" rel="nofollow">Chen Shizhen;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhang Lei&option=202" target="_blank" rel="nofollow">Zhang Lei;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhou Xin&option=202" target="_blank" rel="nofollow">Zhou Xin;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Liu Kai&option=202" target="_blank" rel="nofollow">Liu Kai;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhang Hongjie&option=202" target="_blank" rel="nofollow">Zhang Hongjie;</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>State Key Laboratory of Rare Earth Resource UtilizationChangchun Institute of Applied ChemistryChangchun 130022 P. R. China;</p> <p>State Key Laboratory of Rare Earth Resource UtilizationChangchun Institute of Applied ChemistryChangchun 130022 P. R. China;</p> <p>State Key Laboratory for Magnetic Resonance and Atomic and Molecular PhysicsChinese Academy of SciencesWuhan 430071 China;</p> <p>State Key Laboratory of Rare Earth Resource UtilizationChangchun Institute of Applied ChemistryChangchun 130022 P. R. China;</p> <p>State Key Laboratory of Rare Earth Resource UtilizationChangchun Institute of Applied ChemistryChangchun 130022 P. R. China;</p> <p>State Key Laboratory of Rare Earth Resource UtilizationChangchun Institute of Applied ChemistryChangchun 130022 P. R. China;</p> <p>State Key Laboratory for Magnetic Resonance and Atomic and Molecular PhysicsChinese Academy of SciencesWuhan 430071 China;</p> <p>State Key Laboratory of Rare Earth Resource UtilizationChangchun Institute of Applied ChemistryChangchun 130022 P. R. China;</p> <p>State Key Laboratory for Magnetic Resonance and Atomic and Molecular PhysicsChinese Academy of SciencesWuhan 430071 China;</p> <p>State Key Laboratory of Rare Earth Resource UtilizationChangchun Institute of Applied ChemistryChangchun 130022 P. R. China;</p> <p>State Key Laboratory of Rare Earth Resource UtilizationChangchun Institute of Applied ChemistryChangchun 130022 P. R. 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=alpha hydroxyl acids&option=203" rel="nofollow">alpha hydroxyl acids;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=CEST&option=203" rel="nofollow">CEST;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=chiral recognition&option=203" rel="nofollow">chiral recognition;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=NMR spectroscopy&option=203" rel="nofollow">NMR spectroscopy;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yb complexes&option=203" rel="nofollow">Yb complexes;</a> </p> <div class="translation"> 机译：α羟基酸;CEST;手性识别;NMR光谱;YB复合物; </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/0704028163096.html">Detection and Chiral Recognition of α‐Hydroxyl Acid through 1H and CEST NMR Spectroscopy Using a Ytterbium Macrocyclic Complex</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=He Haonan&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">He Haonan,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhao Kelu&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Zhao Kelu,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Xiao Long&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Xiao Long,</a> <a href="/journal-foreign-19011/" target="_blank" rel="nofollow" class="tuijian_authcolor">Angewandte Chemie .</a> <span>2019</span> <span>,第50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：使用YTTerbium大环复合物通过1H和CEST NMR光谱检测和手性识别1H和CEST NMR光谱法</span> </p> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/academic-journal-foreign_organic-and-biomolecular-chemistry_thesis/0204111643628.html">Chiral discrimination of α-hydroxy acids and W-Ts-α-amino acids induced by tetraaza macrocyclic chiral solvating agents by using ~1H NMR spectroscopy</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Caixia Lv&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Caixia Lv,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lei Feng&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Lei Feng,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Hongmei Zhao&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Hongmei Zhao,</a> <a href="/journal-foreign-696/" target="_blank" rel="nofollow" class="tuijian_authcolor">Organic & biomolecular chemistry .</a> <span>2017</span> <span>,第7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：四氮杂大环手性溶剂化剂诱导的α-羟基酸和W-Ts-α-氨基酸的手性鉴别（〜1H NMR）</span> </p> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/070402861492.html">Chiral recognition in NMR spectroscopy using crown ethers and their ytterbium(III) complexes</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Thomas J. 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href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=舒兴田&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,舒兴田</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=汪燮卿&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,汪燮卿</a> <span> <a href="/journal-cn-7903/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 石油学报（石油加工） </a> </span> <span> . 2003</span><span> ,第003期</span> </span> </div> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/academic-journal-cn_chinese-journal-magnetic-resonance_thesis/0201294446453.html">含羟基的3—苯基—4—（1H）—喹啉酮衍生物的^1H NMR</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=徐鸣夏&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 徐鸣夏</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=王晓莉&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,王晓莉</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=郑虎&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,郑虎</a> <span> <a href="/journal-cn-26656/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 波谱学杂志 </a> </span> <span> . 1999</span><span> ,第2期</span> </span> </div> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/academic-journal-cn_chinese-journal-magnetic-resonance_thesis/0201229370122.html">1H NMR确证6-氟-5(或7)-氯-3-苯基-4-(1H)-喹啉酮衍生物的结构</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=王晓莉&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 王晓莉</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=徐鸣夏&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,徐鸣夏</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=苏甫&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,苏甫</a> <span> <a href="/journal-cn-26656/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 波谱学杂志 </a> </span> <span> . 1998</span><span> ,第006期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-5916_thesis/020221498853.html">基于1H NMR代谢组学绿豆皮和绿豆仁的化学差异性比较</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=李爱平&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 李爱平</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=李震宇&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,李震宇</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=韩晓静&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,韩晓静</a> <span> <a href="/conference-cn-5916/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 2013年代谢组学与中医药现代研究学术论坛 </a> <span> <span> . 2013</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020315863194.html">1H NMR光谱法测定全血代谢组学在甲状腺乳头状癌诊断中的应用</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=孙志刚&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 孙志刚</a> <span> . 2020</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120113426429.html">一种基于1H qNMR的参麦注射液中人参总皂苷的定量法</a> <b>[P]</b> . <span> 中国专利： CN113466281A </span> <span> . 2021-10-01</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120103822805.html">一种地龙1H NMR指纹图谱的构建方法与应用</a> <b>[P]</b> . <span> 中国专利： CN111272894A </span> <span> . 2020-06-12</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130410037044.html">NOVEL CHIRAL METAL COMPLEX AND USE THEREOF FOR ANALYZING CHIRALITY OF CHARGED COMPOUND BY 1H NMR SPECTROSCOPY</a> <b>[P]</b> . <span> 外国专利：  US2017052131A1 </span> <span> . 2017-02-23</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：新型手性金属配合物及其在1H NMR光谱分析带电化合物手性中的应用 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130406913199.html">Chiral metal complex and use thereof for analyzing chirality of charged compound by <Sup>1</Sup>H NMR spectroscopy</a> <b>[P]</b> . <span> 外国专利：  US9851314B2 </span> <span> . 2017-12-26</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：手性金属配合物及其通过<Sup> 1 </ Sup> H NMR光谱分析带电化合物的手性 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130408625752.html">Novel chiral metal complexes and chiral analysis of charged molecules by spectroscopy using the same</a> <b>[P]</b> . <span> 外国专利：  KR101709124B1 </span> <span> . 2017-02-22</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：新型手性金属配合物和带电分子的光谱手性分析 </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('0704028163096','4',7,2,1,'',this,24)" class="delivery" prompt="010401" title="通过人工服务将文献原文发送至邮箱" >获取原文</div> <div class="journalsub-pop-up" style="display: none"> <div class="journal-sub"> 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