Thermodynamic enantioseparation behavior of phenylthiohydantoin‐amino acid derivatives in supercritical fluid chromatography on polysaccharide chiral stationary phases

Khater Syame; Canault Baptiste; Azzimani Taoufik; Bonnet Pascal; West Caroline

摘要

Abstract >Thirteen pairs of enantiomers belonging to the same structural family (phenylthiohydantoin‐amino acids) were analyzed on two polysaccharide chiral stationary phases, namely, tris‐(3,5‐dimethylphenylcarbamate) of amylose (Chiralpak AD‐H) or cellulose (Chiralcel OD‐H) in supercritical fluid chromatography with a carbon dioxide/methanol mobile phase (90:10 v/v). Five different temperatures (5, 10, 20, 30, 40°C) were applied to evaluate the thermodynamic behavior of these enantioseparations. On the cellulose stationary phase, the retention, and separation trends were most similar among the set of probe analytes, suggesting that the chiral cavities in this stationary phase have little diversity, or that all analytes accessed the same cavities. Conversely, the retention and separation trends on the amylose phase were much more diverse, and could be related to structural differences among the set of probe analytes (carbon chain length in the amino acid residue, secondary amine in proline, existence of covalent rings, or formation of pseudo‐rings via intramolecular hydrogen bonds). The large variability of behaviors on the amylose phase suggests that the chiral‐binding sites in this chiral stationary phase have more variety than on the cellulose phase, and that the analytes did access different cavities. </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”>摘要</标题> >属于相同结构家族的十三对对映体（苯基硫代丁酰氨基酸）进行了分析两种多糖手性固定相，即淀粉糖（Chiralpak Ad-H）或纤维素（Chiralcel OD-H）中的三 - （3,5-二甲基苯甲酸甲酯），其超临界流体色谱法与二氧化碳/甲醇流动相（90:10 V. / v）。应用五种不同的温度（5,10,20,30,40℃）以评估这些对映的热力学行为。在纤维素固定相的情况下，该组探针分析物中的保留和分离趋势最相似，这表明这种固定相中的手性腔几乎没有多样性，或者所有分析物都进入相同的腔。相反，直链淀粉相的保留和分离趋势更多样化，并且可能与探针分析物（氨基酸残基中的碳链长，脯氨酸中的仲胺，共价环的仲胺，或共价环中的结构差有关通过分子内氢键形成伪环）。直链淀粉阶段的行为的大变异表明，这种手性固定相中的手性结合位点具有比纤维素相的多样性，并且分析物确实进入不同的腔。</ 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-35800/'>《Journal of separation science. 》</a> <b style="margin: 0 2px;">|</b><span>2018年第6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=Khater Syame&option=202" target="_blank" rel="nofollow">Khater Syame;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Canault Baptiste&option=202" target="_blank" rel="nofollow">Canault Baptiste;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Azzimani Taoufik&option=202" target="_blank" rel="nofollow">Azzimani Taoufik;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Bonnet Pascal&option=202" target="_blank" rel="nofollow">Bonnet Pascal;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=West Caroline&option=202" target="_blank" rel="nofollow">West Caroline;</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>ICOAUniversity of OrléansOrléans France;</p> <p>ICOAUniversity of OrléansOrléans France;</p> <p>ICOAUniversity of OrléansOrléans France;</p> <p>ICOAUniversity of OrléansOrléans France;</p> <p>ICOAUniversity of OrléansOrléans France;</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/159.html" title="化学">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=amino acids&option=203" rel="nofollow">amino acids;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=chiral separation&option=203" rel="nofollow">chiral separation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=polysaccharide stationary phases&option=203" rel="nofollow">polysaccharide stationary phases;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=supercritical fluid chromatography&option=203" rel="nofollow">supercritical fluid chromatography;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=temperature influence&option=203" rel="nofollow">temperature influence;</a> </p> <div class="translation"> 机译：氨基酸;手性分离;多糖固定相;超临界流体色谱;温度影响; </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/0704025847008.html">Thermodynamic enantioseparation behavior of phenylthiohydantoin‐amino acid derivatives in supercritical fluid chromatography on polysaccharide chiral stationary phases</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Khater Syame&option=202" target="_blank" rel="nofollow" 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href="/academic-journal-cn_journal-heihe-university_thesis/0201290031094.html">氨基酸及其衍生物的分离提纯在手性合成中的应用</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=蔡昌武&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 蔡昌武</a> <span> <a href="/journal-cn-3967/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 黑河学院学报 </a> </span> <span> . 2021</span><span> ,第005期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-27452_thesis/020221830427.html">新型铑-二茂铁衍生物催化剂在手性氨基酸、手性胺不对称合成中的应用</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=贾娴&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 贾娴</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=黎星术&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,黎星术</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=陈新滋&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,陈新滋</a> <span> <a href="/conference-cn-27452/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 第七届全国青年药学工作者最新科研成果交流会 </a> <span> <span> . 2004</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020315566096.html">手性路易斯酸及小分子膦催化环状亚胺的Mannich反应：高效构建苯并磺酰胺类季碳氨基酸衍生物</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=苏秦&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 苏秦</a> <span> . 2019</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120107686130.html">使用由具有轴手性的N-(2-酰基芳基)-2-5,7-二氢-6H-二苯并c,e氮杂*-6-基乙酰胺化合物和氨基酸形成的手性金属络合物的光学活性α-氨基酸的合成方法</a> <b>[P]</b> . <span> 中国专利： CN105189524A </span> <span> . 2015-12-23</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/061203079284.html">具有轴手性的N-(2-酰基芳基)-2-5,7-二氢-6H-二苯并c,e氮杂*-6-基乙酰胺化合物及使用该化合物的α-氨基酸的手性转换方法</a> <b>[P]</b> . <span> 中国专利： CN104995175B </span> <span> . 2018.11.02</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130420944810.html">SUB-2 MICRON CHIRAL STATIONARY PHASE SEPARATION AGENTS FOR USE WITH SUPERCRITICAL FLUID CHROMATOGRAPHY</a> <b>[P]</b> . <span> 外国专利：  US2013277304A1 </span> <span> . 2013-10-24</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：用于超临界流体色谱的SUB-2微米级手性固定相分离剂 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130437881448.html">Chiral stationary phases based on derivatives of 4-amino-3,5-dinitrobenzoic acid</a> <b>[P]</b> . <span> 外国专利：  US7018537B2 </span> <span> . 2006-03-28</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4-氨基-3,5-二硝基苯甲酸衍生物的手性固定相 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130442887574.html">Chiral stationary phases based on derivatives of 4-amino-3,5-dinitrobenzoic acid</a> <b>[P]</b> . <span> 外国专利：  US2004144708A1 </span> <span> . 2004-07-29</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4-氨基-3,5-二硝基苯甲酸衍生物的手性固定相 </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;" 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