Enzymatic Cleavage of Aryl Acetates

Bauch Marcel; B?ttcher Dominique; Bornscheuer Uwe T.; Linker Torsten

摘要

Abstract > Seven enzymes have been screened for the cleavage of aryl acetates. Phenyl and naphthyl acetates react with lipases and esterases, whereas the sterically demanding anthracene acetate gave a conversion only with porcine liver esterase and esterase?2 from Bacillus subtilis (BS2) . These two enzymes have been employed on a preparative (0.5?mmol) scale and afforded cleavage products in 91 and 94?% yields, even for anthracene acetate. Thus, this method is superior to chemical cleavage with catalytic amounts of sodium methoxide (Zemplén conditions), which gave only low conversions. Finally, regioselectivity has been achieved with an anthracene bisacetate, in which an ethyl group controls the cleavage of the first acetate. This indicates that steric interactions play a crucial role in the enzymatic cleavage of aryl acetates, which might be interesting for future applications or the development of enzyme inhibitors. </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> > 已经筛选出七种酶的芳基乙酸裂解。苯基和萘基乙酸乙酸酯与脂肪酶和酯酶反应，而本空心急需的炭酸盐仅通过猪肝酯酶和酯酶α2致掺杂枯草芽孢杆菌</ i> （BS2）。这些两种酶已经在制备型（0.5μmol）规模上，得到91和94℃的裂解产物，即使对于炭酮，也能得到91％的产率。因此，该方法优于具有催化量的甲醇钠（Zemplén条件）的化学切割，其仅产生低转化率。最后，通过蒽双乙酸酯实现了地区选择性，其中乙基控制了第一乙酸酯的切割。这表明空间相互作用在乙酸芳基酶的酶促切割中起至关重要的作用，这可能对未来的应用或酶抑制剂的发育可能是有趣的。 </ 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-16041/'>《ChemCatChem 》</a> <b style="margin: 0 2px;">|</b><span>2016年第17期</span><b style="margin: 0 2px;">|</b> <span>共5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=Bauch Marcel&option=202" target="_blank" rel="nofollow">Bauch Marcel;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=B?ttcher Dominique&option=202" target="_blank" rel="nofollow">B?ttcher Dominique;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Bornscheuer Uwe T.&option=202" target="_blank" rel="nofollow">Bornscheuer Uwe T.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Linker Torsten&option=202" target="_blank" rel="nofollow">Linker Torsten;</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>Department of ChemistryUniversity of PotsdamKarl-Liebknecht-Str. 24-25 14476 Potsdam Germany;</p> <p>Department of Biotechnology &</p> <p>Enzyme CatalysisUniversity of GreifswaldFelix-Hausdorff-Str. 4 17487 Greifswald Germany;</p> <p>Department of Biotechnology &</p> <p>Enzyme CatalysisUniversity of GreifswaldFelix-Hausdorff-Str. 4 17487 Greifswald Germany;</p> <p>Department of ChemistryUniversity of PotsdamKarl-Liebknecht-Str. 24-25 14476 Potsdam Germany;</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/1186.html" title="物理化学（理论化学）、化学物理学">物理化学（理论化学）、化学物理学 ;</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=arenes&option=203" rel="nofollow">arenes;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=enzyme catalysis&option=203" rel="nofollow">enzyme catalysis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=regioselectivity&option=203" rel="nofollow">regioselectivity;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=steric hindrance&option=203" rel="nofollow">steric hindrance;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=substituent effects&option=203" rel="nofollow">substituent effects;</a> </p> <div class="translation"> 机译：arenes;酶催化;区域选择性;空间障碍;取代效应; 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