Deracemization and Stereoinversion of α‐Amino Acids by l‐Amino Acid Deaminase

Rosini Elena; Melis Roberta; Molla Gianluca; Tessaro Davide; Pollegioni Loredano

摘要

Abstract > Enantiomerically pure α‐amino acids are compounds of primary interest for the fine chemical, pharmaceutical, and agrochemical sectors. Amino acid oxidases are used for resolving <sc>d,l</sc> ‐amino acids in biocatalysis. We recently demonstrated that <sc>l</sc> ‐amino acid deaminase from Proteus myxofaciens (PmaLAAD) shows peculiar features for biotechnological applications, such as a high production level as soluble protein in Escherichia coli and a stable binding with the flavin cofactor. Since <sc>l</sc> ‐amino acid deaminases are membrane‐bound enzymes, previous applications were mainly based on the use of cell‐based methods. Now, taking advantage of the broad substrate specificity of PmaLAAD, a number of natural and synthetic <sc>l</sc> ‐amino acids were fully converted by the purified enzyme into the corresponding α‐keto acids: the fastest conversion was obtained for 4‐nitrophenylalanine. Analogously, starting from racemic solutions, the full resolution ( ee 99%) was also achieved. Notably, <sc>d,l</sc> ‐1‐naphthylalanine was resolved either into the <sc>d</sc> ‐ or the <sc>l</sc> ‐enantiomer by using PmaLAAD or the <sc>d</sc> ‐amino acid oxidase variant having a glycine at position 213, respectively, and was fully deracemized when the two enzymes were used jointly. Moreover, the complete stereoinversion of <sc>l</sc> ‐4‐nitrophenylalanine was achieved using PmaLAAD and a small molar excess of borane tert ‐butylamine complex. Taken together, recombinant PmaLAAD represents an <sc>l</sc> ‐specific amino acid deaminase suitable for producing the pure enantiomers of several natural and synthetic amino acids or the corresponding keto acids, compounds of biotechnological or pharmaceutical relevance. > <blockFixed type="graphic"> <mediaResourceGroup> <mediaResource alt="image" href="urn:x-wiley:16154150:media:adsc201700806:adsc201700806-toc-0001"/> </mediaResourceGroup> </blockFixed> </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 xmlns =“http://www.wiley.com/namespaces/wiley”type =“main”xml：lang =“en”> <title type =“main”>抽象</ title> >对抗纯粹α-氨基酸是精细化学，药物和农业化学型材的主要兴趣的化合物。氨基酸氧化酶用于解析生物分析中的<SC> D，L </ SC>氨基酸。我们最近证明<sc> l </ sc>-氨基酸脱氨酶从蛋白质myxofaciens（pmalaad）显示出生物技术应用的特殊特征，例如在大肠杆菌中的高生产水平作为可溶性蛋白质COLI </ i>与黄素辅因子的稳定结合。由于<sc> l </ sc> - 氨基酸脱氨酶是膜结合的酶，以前的应用主要基于使用基于细胞的方法。现在，利用PMALAAD的宽底物特异性，将许多天然和合成的<sc> -L </ sc> - 氨基酸完全由纯化的酶完全转化为相应的α-酮酸：获得最快的转化率4-硝基苯丙氨酸。类似地，从外消旋溶液开始，还实现了全分辨率（ e </ i>＆ 99％）。值得注意的是，通过使用pmalaad或<sc>将<sc> d，l </ sc> -1-萘丙氨酸分解为<sc> d </ sc> - 或<sc> l </ sc> - 甲基。 D </ sc> - 氨基酸氧化酶变体分别具有甘氨酸在213的位置，并且当共同使用两种酶时，完全被衰变。此外，使用PMALAAD和小摩尔过量的硼烷达到-4-硝基苯氨基的完全立体转化率 TERT </ I> - 丁胺络合物。共同携带，重组pMalaAC代表了一种<sc> l </ sc>特异性氨基酸脱氨基酶，其适用于产生几种天然和合成氨基酸的纯对映体或相应的酮酸，生物技术化合物或药物相关性。 </ p> > <blockfixed类型=“图形”> <mediaresourcegroup> <mediaresource alt =“图像”href =“URN：X-Wiley：16154150：介质：ADSC201700806：ADSC201700806-TOC-0001”/> </ mediaresourcegroup> </ blockfixed> </ 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-19407/'>《Advanced synthesis & catalysis》</a> <b style="margin: 0 2px;">|</b><span>2017年第21期</span><b style="margin: 0 2px;">|</b><span>共9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=Rosini Elena&option=202" target="_blank" rel="nofollow">Rosini Elena;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Melis Roberta&option=202" target="_blank" rel="nofollow">Melis Roberta;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Molla Gianluca&option=202" target="_blank" rel="nofollow">Molla Gianluca;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Tessaro Davide&option=202" target="_blank" rel="nofollow">Tessaro Davide;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Pollegioni Loredano&option=202" target="_blank" rel="nofollow">Pollegioni Loredano;</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 Biotechnology and Life SciencesUniversità degli Studi dell'Insubriavia J.H. Dunant 3 21100 Varese Italy;</p> <p>Department of Biotechnology and Life SciencesUniversità degli Studi dell'Insubriavia J.H. Dunant 3 21100 Varese Italy;</p> <p>Department of Biotechnology and Life SciencesUniversità degli Studi dell'Insubriavia J.H. Dunant 3 21100 Varese Italy;</p> <p>The Protein FactoryPolitecnico di Milano and Università degli Studi dell'Insubriavia Mancinelli 7 20131 Milano Italy;</p> <p>Department of Biotechnology and Life SciencesUniversità degli Studi dell'Insubriavia J.H. Dunant 3 21100 Varese Italy;</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/238.html" title="化学工业">化学工业;</a><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><a href="https://www.zhangqiaokeyan.com/clc/7777.html" title="化学反应过程">化学反应过程;</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=biocatalysis&option=203" rel="nofollow">biocatalysis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=biotransformation&option=203" rel="nofollow">biotransformation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=deracemization&option=203" rel="nofollow">deracemization;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=stereoinversion&option=203" rel="nofollow">stereoinversion;</a> </p> <div class="translation"> 机译：氨基酸;生物分析;生物转化;DracaCemization;立体化; </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" 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Baek J.O.</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=胡小丽&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,胡小丽</a> <span> <a href="/journal-cn-7153/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 中国畜牧兽医 </a> </span> <span> . 2012</span><span>,第2期</span> </span> </div> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/academic-journal-cn_acta-chimica-sinica_thesis/0201272163257.html">N-磷酰化氨基酸生成五配位磷中间体过程中氨基酸侧链立体化学效应的理论研究</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=赵丽娇&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 赵丽娇</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=钟儒刚&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,钟儒刚</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=甄岩&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,甄岩</a> <span> <a href="/journal-cn-53859/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 化学学报 </a> </span> <span> . 2006</span><span>,第009期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-373_thesis/02022673323.html">易错PCR法提高L-氨基酸脱氨酶全细胞转化L-异亮氨酸生产α-酮-β-甲基正戊酸效率</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Guo Mengmeng&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . Guo Mengmeng</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=郭濛檬&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,郭濛檬</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Liu Long&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,Liu Long</a> <span> <a href="/conference-cn-373/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 2016年工业生物过程优化与控制研讨会 </a> <span> <span> . 2016</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020314316821.html">L-α-氨基酸乙酯衍生物的合成、结构及生物活性测定：（Ⅰ）：L-N-（2-噻吩磺酰基）-α-氨基酸乙酯的合成与生物活性;（Ⅱ）：L-N-（取代酰氨基硫羰基）-α-氨基酸乙酯的合成与生物性;（Ⅲ）：生物活性化合物的单晶培养及晶体结构测定</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=申杰峰&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 申杰峰</a> <span> . 2007</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120113921122.html">具有增强的细胞色素C活性的L-氨基酸生产微生物及使用其的L-氨基酸生产方法</a> <b>[P]</b> . <span> 中国专利： CN114008206A </span> <span> . 2022-02-01</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/061204344103.html">能够产生L-氨基酸的微生物及使用其产生L-氨基酸的方法</a> <b>[P]</b> . <span> 中国专利： CN105695382B </span> <span> . 2021.04.13</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130423209362.html">Stereoinversion of amino acids in a single reactor</a> <b>[P]</b> . <span> 外国专利：  US8133717B2 </span> <span> . 2012-03-13</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：在单个反应器中对氨基酸进行立体转化 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130433158322.html">STEREOINVERSION OF AMINO ACIDS</a> <b>[P]</b> . <span> 外国专利：  US2008153137A1 </span> <span> . 2008-06-26</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：氨基酸的立体转化 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130432217653.html">STEREOINVERSION OF AMINO ACIDS</a> <b>[P]</b> . <span> 外国专利：  WO2008080138A1 </span> <span> . 2008-07-03</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：氨基酸的立体转化 </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> 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