Enantiopurity and absolute configuration determination of arene        <i >ciscis        ‐dihydrodiol metabolites and derivatives using chiral boronic acids

Boyd Derek R.; Sharma Narain D.; Goodrich Peter A.; Malone John F.; McConville Gareth; Harrison John S.; Stevenson Paul J.; Allen Christopher C.R.

摘要

Abstract > The relative merits of the methods employed to determine enantiomeric excess ( <fi>ee</fi> ) values and absolute configurations of chiral arene and alkene <fi>cis</fi> ‐1,2‐diol metabolites, including boronate formation, using racemic or enantiopure (+) and (?)‐2‐(1‐methoxyethyl)phenylboronic acid (MEPBA), are discussed. Further applications of: 1) MEPBA derived boronates of chiral mono‐ and poly‐cyclic arene <fi>cis</fi> ‐dihydrodiol, cyclohex‐2‐en‐1‐one <fi>cis</fi> ‐diol, heteroarene <fi>cis</fi> / <fi>trans</fi> ‐2,3‐diol, and catechol metabolites in estimating their <fi>ee</fi> values, and 2) new chiral phenylboronic acids, 2‐[1‐methoxy‐2,2‐dimethylpropyl]phenyl boronic acid (MDPBA) and 2‐[1‐methoxy‐1‐phenylmethyl]phenyl boronic acid (MPPBA) and their advantages over MEPBA, as reagents for stereochemical analysis of arene and alkene <fi>cis</fi> ‐diol metabolites, are presented. </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”> <标题类型=“main”>抽象</ title> >用于确定对映异构过量的方法的相对优点（<fi> ee </ fi>）值和绝对配置手性芳烃和烯烃<fi> cis </ fi> -1,2-二醇代谢物，包括硼酸盐形成，使用外消旋或对映（+）和（α） - 2-（1-甲氧基乙基）苯基硼酸（mepba）是讨论。进一步应用：1）手性单环和聚环芳烃的MEPBA衍生硼酸盐<FI> CIS </ FI> -DIHYDRODOO，环己-2-ZH-1-one <FI> CIS </ FI> - 二醇，杂种芳烃<fi> cis </ fi> / <fi>反式</ fi> -2,3-二醇，以及儿茶酚代谢物估算它们的<fi> ee </ fi>值，2）新的手性苯硼酸，2- [1-甲氧基-2,2-二甲基丙基]苯基硼酸（MDPBA）和2- [1-甲氧基-1-苯基甲基]苯基硼酸（MPPBA）及其优于MEPBA的优点，作为芳烃和烯烃的立体化学分析的试剂<fi> cis </ fi> -diol代谢物，呈现。 </ p> </ abstract> </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-16290/'>《Chirality: The pharmacological, biological, and chemical consequences of molecular asymmetry》</a> <b style="margin: 0 2px;">|</b><span>2018年第1期</span><b style="margin: 0 2px;">|</b><span>共14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=Boyd Derek R.&option=202" target="_blank" rel="nofollow">Boyd Derek R.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Sharma Narain D.&option=202" target="_blank" rel="nofollow">Sharma Narain D.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Goodrich Peter A.&option=202" target="_blank" rel="nofollow">Goodrich Peter A.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Malone John F.&option=202" target="_blank" rel="nofollow">Malone John F.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=McConville Gareth&option=202" target="_blank" rel="nofollow">McConville Gareth;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Harrison John S.&option=202" target="_blank" rel="nofollow">Harrison John S.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Stevenson Paul J.&option=202" target="_blank" rel="nofollow">Stevenson Paul J.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Allen Christopher C.R.&option=202" target="_blank" rel="nofollow">Allen Christopher C.R.;</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>School of Chemistry and Chemical EngineeringQueen's UniversityBelfast UK;</p> <p>School of Chemistry and Chemical EngineeringQueen's UniversityBelfast UK;</p> <p>School of Chemistry and Chemical EngineeringQueen's UniversityBelfast UK;</p> <p>School of Chemistry and Chemical EngineeringQueen's UniversityBelfast UK;</p> <p>School of Chemistry and Chemical EngineeringQueen's UniversityBelfast UK;</p> <p>School of Chemistry and Chemical EngineeringQueen's UniversityBelfast UK;</p> <p>School of Chemistry and Chemical EngineeringQueen's UniversityBelfast UK;</p> <p>School of Biological Sciences and Institute for Global and Food SecurityQueen's UniversityBelfast UK;</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/4812.html" title="结构化学">结构化学;</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=asymmetric synthesis&option=203" rel="nofollow">asymmetric synthesis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=bacterial metabolism&option=203" rel="nofollow">bacterial metabolism;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=boronate diastereomers&option=203" rel="nofollow">boronate diastereomers;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=boronic acid enantiomers&option=203" rel="nofollow">boronic acid enantiomers;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=cis ‐1&option=203" rel="nofollow">cis ‐1;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=2‐diol bioproducts&option=203" rel="nofollow">2‐diol bioproducts;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=enantiomeric excess values&option=203" rel="nofollow">enantiomeric excess values;</a> </p> <div class="translation"> 机译：不对称合成;细菌代谢;硼酸盐非对映异构体;硼酸对映体;CIS -1;2-二醇生物pro;对映体过量值; </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/0704022113381.html">Enantiopurity and absolute configuration determination of arene <i >ciscis ‐dihydrodiol metabolites and derivatives using chiral boronic acids</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Boyd Derek R.&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Boyd Derek R.,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Sharma Narain D.&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Sharma Narain D.,</a> <a 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Enantiopurity and absolute configuration determination of arene ciscis ‐dihydrodiol metabolites and derivatives using chiral boronic acids

摘要