A Chemical Probe for Dehydrobutyrine

Chambers Kaitlin A.; Abularrage Nile S.; Hill Caitlin J.; Khan Imran H.; Scheck Rebecca A.

摘要

Abstract >Bacterial phosphothreonine lyases, or phospholyases, catalyze a unique post‐translational modification that introduces dehydrobutyrine (Dhb) or dehydroalanine (Dha) in place of phosphothreonine or phosphoserine residues, respectively. We report the use of a phospha‐Michael reaction to label proteins and peptides modified with Dha or Dhb. We demonstrate that a nucleophilic phosphine probe is able to modify Dhb‐containing proteins and peptides that were recalcitrant to reaction with thiol or amine nucleophiles under mild aqueous conditions. Furthermore, we used this reaction to detect multiple Dhb‐modified proteins in mammalian cell lysates, including histone H3, a previously unknown target of phospholyases. This method should prove useful for identifying new phospholyase targets, profiling the biomarkers of bacterial infection, and developing enzyme‐mediated strategies for bioorthogonal labeling in living cells. </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> >细菌磷酸氨基酶，或磷解光酶，催化分别将脱氢丁酪丁胺（DHB）或脱氢胺（DHA）引入磷酸胆碱或磷源残留物的独特翻译后修饰。我们举报使用磷酰麦克尔反应对用DHA或DHB改性的标记蛋白和肽。我们证明亲核探针能够改变含DHB的蛋白质和肽，其在温和含水条件下与硫醇或胺亲核试剂反应。此外，我们使用该反应来检测哺乳动物细胞裂解物中的多个DHB改性蛋白质，包括组蛋白H3，先前未知的磷解物靶标。该方法应该证明可用于鉴定新的磷解化酶靶标，分析细菌感染的生物标志物，以及在活细胞中发育生物正交标记的酶介导的策略。</ 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19期</span><b style="margin: 0 2px;">|</b><span>共6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=Chambers Kaitlin A.&option=202" target="_blank" rel="nofollow">Chambers Kaitlin A.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Abularrage Nile S.&option=202" target="_blank" rel="nofollow">Abularrage Nile S.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Hill Caitlin J.&option=202" target="_blank" rel="nofollow">Hill Caitlin J.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Khan Imran H.&option=202" target="_blank" rel="nofollow">Khan Imran H.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Scheck Rebecca A.&option=202" target="_blank" rel="nofollow">Scheck Rebecca A.;</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 ChemistryTufts University62 Talbot Avenue Medford MA 02155 USA;</p> <p>Department of ChemistryMassachusetts Institute of TechnologyCambridge MA 02139 USA;</p> <p>Department of ChemistryTufts University62 Talbot Avenue Medford MA 02155 USA;</p> <p>Department of ChemistryTufts University62 Talbot Avenue Medford MA 02155 USA;</p> <p>Department of ChemistryTufts University62 Talbot Avenue Medford MA 02155 USA;</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/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=bioconjugation&option=203" rel="nofollow">bioconjugation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=bioorthogonal chemistry&option=203" rel="nofollow">bioorthogonal chemistry;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=lyases&option=203" rel="nofollow">lyases;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Michael addition&option=203" rel="nofollow">Michael addition;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=protein modification&option=203" rel="nofollow">protein modification;</a> </p> <div class="translation"> 机译：生物谐波;生物正交化;裂解酶;迈克尔加法;蛋白质改性; </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/0704028162393.html">A Chemical Probe for Dehydrobutyrine</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chambers Kaitlin A.&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Chambers Kaitlin A.,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Abularrage Nile S.&option=202" target="_blank" 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endocrine disrupting property of chemical substance using them</a> <b>[P]</b> . <span> 外国专利：  US2004002087A1 </span> <span> . 2004-01-01</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：用于检测化学物质的内分泌破坏特性的核酸，核酸检测探针和包含该核酸的核酸检测引物，固定有该核酸检测探针的探针固定芯片，源自该核酸的肽和识别该肽的抗体，探针包含抗体的固定化芯片，以及使用它们检测化学物质内分泌干扰特性的方法 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130445358600.html">NUCLEIC ACID FOR DETECTING HORMONE-DISRUPTIVE PROPERTY OF CHEMICAL SUBSTANCE, NUCLEIC ACID-DETECTING PROBE AND NUCLEIC ACID-DETECTING PRIMER CONTAINING THE SAME NUCLEIC ACID, PROBE-IMMOBILIZED CHIP EQUIPPED WITH THE SAME PROBE, PEPTIDE DERIVED FROM THE SAME NUCLEIC ACID, ANTIBODY RECOGNIZING THE SAME PEPTIDE, AND METHOD FOR DETECTING HORMONE-DISRUPTIVE PROPERTY OF CHEMICAL SUBSTANCE BY USING THEM</a> <b>[P]</b> . <span> 外国专利：  JP2003310282A </span> <span> . 2003-11-05</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：用于检测化学物质的荷尔蒙破坏性的核酸，用于检测核酸的探针和包含相同核酸的检测核酸的底漆，其探针由含相同探针的肽（相同的肽）混合而成相同的肽，以及通过使用它们检测化学物质的荷尔蒙破坏性的方法 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130419407796.html">ELECTROCHEMICAL AND RAMAN SPECTROSCOPIC MONITORING, SCANNING AND FEEDBACK STIMULATING PROBE CAPABLE OF SIMULTANEOUSLY OBTAINING ELECTROCHEMICAL INFORMATION AND SPECTROSCOPIC INFORMATION BY IMPROVING A SYSTEM HAVING SCANNING ELECTROCHEMICAL MICROSCOPY (SECM) METHODOLOGY AND PROBE</a> <b>[P]</b> . <span> 外国专利：  KR20130105708A </span> <span> . 2013-09-25</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：通过改进具有扫描电化学显微镜（SECM）方法和探针的系统，可同时获得电化学信息和光谱信息的电化学和拉曼光谱监测，扫描和反馈激励探针 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