Oxalyl‐CoA Decarboxylase Enables Nucleophilic One‐Carbon Extension of Aldehydes to Chiral α‐Hydroxy Acids

摘要

Abstract > The synthesis of complex molecules from simple, renewable carbon units is the goal of a sustainable economy. Here we explored the biocatalytic potential of the thiamine‐diphosphate‐dependent (ThDP) oxalyl‐CoA decarboxylase (OXC)/2‐hydroxyacyl‐CoA lyase (HACL) superfamily that naturally catalyzes the shortening of acyl‐CoA thioester substrates through the release of the C <sub>1</sub> ‐unit formyl‐CoA. We show that the OXC/HACL superfamily contains promiscuous members that can be reversed to perform nucleophilic C <sub>1</sub> ‐extensions of various aldehydes to yield the corresponding 2‐hydroxyacyl‐CoA thioesters. We improved the catalytic properties of Methylorubrum extorquens OXC by rational enzyme engineering and combined it with two newly described enzymes—a specific oxalyl‐CoA synthetase and a 2‐hydroxyacyl‐CoA thioesterase. This enzymatic cascade enabled continuous conversion of oxalate and aromatic aldehydes into valuable ( S )‐α‐hydroxy acids with enantiomeric excess up to 99?%. </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> > 来自简单，可再生碳单位的复杂分子的合成是可持续经济的目标。在这里，我们探讨了硫胺 - 二磷酸依赖性（THDP）的生物催化潜力，其氧氧基 - CoA脱羧酶（OXC）/ 2-羟基乙酰-COA裂解酶（HACL）超家族，其天然催化通过释放酰基-Coa硫酯基材的缩短C <sub> 1 </ sub> - 单甲醛-COA。我们表明OXC / HACL超家族含有可逆转的混杂构件以进行亲核C. <sub> 1 </ sub> - 各种醛的延伸，得到相应的2-羟基乙酰CoA硫代酯。通过Rational酶工程改善了甲基鲁姆克劳骨溶剂的催化性质，并将其与两个新描述的酶 - 特异性氧基辅酶合成酶和2-羟基乙基-COA硫酯酶组合。这种酶级联使将草酸盐和芳香醛的连续转化为有价值（ s </ i> ）-α-羟基酸，对映体超出至99℃。 </ 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>2020年第14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"> </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"> </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=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=C1 building blocks&option=203" rel="nofollow">C1 building blocks;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=C?C coupling&option=203" rel="nofollow">C?C coupling;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=oxalyl-CoA decarboxylase&option=203" rel="nofollow">oxalyl-CoA decarboxylase;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=thiamine diphosphate&option=203" rel="nofollow">thiamine diphosphate;</a> </p> <div class="translation"> 机译：生物催化;C1构建块;C？C偶联;ohahalyl-Coa脱羧酶;硫胺素二磷酸盐; </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/0704028161173.html">Cover Picture: Oxalyl‐CoA Decarboxylase Enables Nucleophilic One‐Carbon Extension of Aldehydes to Chiral α‐Hydroxy Acids (Angew. Chem. Int. Ed. 14/2020)</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> </a> <a href="/journal-foreign-19011/" target="_blank" rel="nofollow" class="tuijian_authcolor">Angewandte Chemie .</a> <span>2020</span><span>,第14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：封面图片：Oxalyl-CoA脱羧酶使醛的亲核单碳延伸能够对手性α-羟基酸（Chem.Chem.Int.SED。14/2020）</span> </p> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/academic-journal-foreign_detail_thesis/0204118501422.html">Oxalate-Degrading Activity in Bifidobacterium animalis subsp. lactis: Impact of Acidic Conditions on the Transcriptional Levels of the Oxalyl Coenzyme A (CoA) Decarboxylase and Formyl-CoA Transferase Genes</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Silvia Turroni&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Silvia Turroni,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Claudia Bendazzoli&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Claudia Bendazzoli,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Samuele C. 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class="tuijian_auth tuijian_authcolor"> . 叶楠</a> <span> <a href="/conference-cn-58797/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 2001中国药学会学术年会 </a> <span> <span> . 2001</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020312285145.html">2-甲基吲哚作不同亲为亲核核试性指剂的三示剂发组分展醛反应与两种</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=姜丹&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 姜丹</a> <span> . 2015</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/061204778959.html">一种手性醛催化剂及制备方法以及催化不对称亲核加成反应的方法</a> <b>[P]</b> . <span> 中国专利： CN109908954B </span> <span> . 2021.11.16</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120100714218.html">一种手性醛催化剂及制备方法以及催化不对称亲核加成反应的方法</a> <b>[P]</b> . <span> 中国专利： CN109908954A </span> <span> . 2019-06-21</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130442710466.html">Human oxalyl-CoA decarboxylase</a> <b>[P]</b> . <span> 外国专利：  US2003211561A1 </span> <span> . 2003-11-13</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：人草酰辅酶A脱羧酶 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130445799096.html">HUMANE OXALYL-CoA DECARBOXYLASE</a> <b>[P]</b> . <span> 外国专利：  DE69428054T2 </span> <span> . 2002-06-06</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：人草酰辅酶A脱羧酶 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130447197836.html">Human oxalyl-CoA Decarboxylase</a> <b>[P]</b> . <span> 外国专利：  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