Stereospecific control of peptide gas‐phase ion chemistry with <i xmlns='http://www.wiley.com/namespaces/wiley'>ciscis and <i xmlns='http://www.wiley.com/namespaces/wiley'>transtrans cyclo ornithine residues

Marek Ale?; Nguyen Huong T.H.; Bro? B?etislav; Ture?ek Franti?ek

摘要

Abstract > We report non‐chiral amino acid residues <fi>cis</fi> ‐ and <fi>trans</fi> ‐1,4‐diaminocyclohexane‐1‐carboxylic acid (cyclo‐ornithine, cO) that exhibit unprecedented stereospecific control of backbone dissociations of singly charged peptide cations and hydrogen‐rich cation radicals produced by electron‐transfer dissociation. Upon collision‐induced dissociation (CID) in the slow heating regime, peptide cations containing <fi>trans</fi> ‐cO residues undergo facile backbone cleavages of amide bonds C‐terminal to <fi>trans</fi> ‐cO. By contrast, peptides with <fi>cis</fi> ‐cO residues undergo dissociations at several amide bonds along the peptide ion backbone. Diastereoisomeric cO‐containing peptides thus provide remarkably distinct tandem mass spectra. The stereospecific effect in CID of the <fi>trans</fi> ‐cO residue is explained by <fi>syn</fi> ‐facially directed proton transfer from the 4‐ammonium group at cO to the C‐terminal amide followed by neighboring group participation in the cleavage of the CO―NH bond, analogous to the aspartic acid and ornithine effects. Backbone dissociations of diastereoisomeric cO‐containing peptide ions generate distinct [b <sub>n</sub> ] + ‐type fragment ions that were characterized by CID‐MS 3 spectra. Stereospecific control is also reported for electron‐transfer dissociation of <fi>cis</fi> ‐ and <fi>trans</fi> ‐cO containing doubly charged peptide ions. The stereospecific effect upon electron transfer is related to the different conformations of doubly charged peptide ions that affect the electron attachment sites and ensuing N―C </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> >我们报告非手性氨基酸残基<fi> cis </ fi> -1,4-二氨基环己烷-1-羧酸（环核，CO），其表现出前所未有的骨干解剖控制通过电子转移解离产生的单电荷肽阳离子和富含氢阳离子的基团。在缓慢加热状态下碰撞诱导的解离（CID）时，含有<fi>反式的肽阳离子-CO残基的肽阳离子经受酰胺键C-末端C-末端的容纳骨干裂解至<fi>反式 - COR-FO -CO。相比之下，具有<fi> cis的肽</ fi> -co残基在沿肽离子骨架的几种酰胺键处经过分离。因此，非对映异构的共聚肽提供了显着明显不同的串联质谱。通过在C-在C-末端酰胺中的4-铵基团中，将<fi>反式-ce-co -co -co -co -co残基的直立效应解释邻近群体参与CO-NH键的切割，类似于天冬氨酸和鸟氨酸效应。基映异构体Co型肽离子的骨干解离子产生明显的[B <sub> n </ sub>] + </ sup> -Type片段离子，其特征在于CID-MS 3 </ sup>光谱。还报道了立体特异性对照的<FI> CIS </ FI> - 以及含有双电荷肽离子的</ FI> - 和<fi>反式</ fi> -Co。对电子传递的立体特异性效应与影响电子连接位点和随后的双电荷肽离子的不同构象有关。 </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-34906/'>《Journal of mass spectrometry: JMS》</a> <b style="margin: 0 2px;">|</b><span>2018年第2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=Marek Ale?&option=202" target="_blank" rel="nofollow">Marek Ale?;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Nguyen Huong T.H.&option=202" target="_blank" rel="nofollow">Nguyen Huong T.H.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Bro? B?etislav&option=202" target="_blank" rel="nofollow">Bro? B?etislav;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ture?ek Franti?ek&option=202" target="_blank" rel="nofollow">Ture?ek Franti?ek;</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 WashingtonBagley Hall Box 351700 Seattle WA 98195‐1700 USA;</p> <p>Department of ChemistryUniversity of WashingtonBagley Hall Box 351700 Seattle WA 98195‐1700 USA;</p> <p>Czech Academy of SciencesInstitute of Organic Chemistry and BiochemistryPrague Czech Republic;</p> <p>Department of ChemistryUniversity of WashingtonBagley Hall Box 351700 Seattle WA 98195‐1700 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/1187.html" title="分析化学">分析化学;</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=cis and trans isomers&option=203" rel="nofollow">cis and trans isomers;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=cyclo ornithine&option=203" rel="nofollow">cyclo ornithine;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=peptide dissociations&option=203" rel="nofollow">peptide dissociations;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=peptide ion structures&option=203" rel="nofollow">peptide ion structures;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=stereochemistry&option=203" rel="nofollow">stereochemistry;</a> </p> <div class="translation"> 机译：CIS和Trans异构体;Cyclo鸟氨酸;肽解离;肽离子结构;立体化学; </div> </li> </ul> </div> </div> <div class="literature cardcommon" id="literaturereference" style="display:none"> <div class="similarity "> <h3 class="all_title" id="enpatent111">引文网络</h3> <div class="referencetab clearfix"> <ul id="referencedaohang"> <li dataid="referenceul">参考文献</li> <li dataid="citationul">引证文献</li> <li dataid="commonreferenceul">共引文献</li> <li dataid="commoncitationul">同被引文献</li> <li dataid="tworeferenceul">二级参考文献</li> <li dataid="twocitationul">二级引证文献</li> </ul> </div> <div class="reference_details" id="referenceList"> <ul id="referenceul"></ul> <ul id="citationul"></ul> <ul id="commonreferenceul"></ul> <ul id="commoncitationul"></ul> <ul id="tworeferenceul"></ul> <ul id="twocitationul"></ul> </div> </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> </ul> </div> <div class="similarity_details"> <ul > <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704025633301.html">Stereospecific control of peptide gas‐phase ion chemistry with <i xmlns="http://www.wiley.com/namespaces/wiley">ciscis and <i xmlns="http://www.wiley.com/namespaces/wiley">transtrans cyclo ornithine residues</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Marek Ale?&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Marek Ale?,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Nguyen Huong T.H.&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Nguyen Huong T.H.,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Bro? 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Ryoji Nagoya (Nagoya University Japan). Wiley: New York (http://www.wiley.com/). 1994. Pages: 400 Pages Hardcover. Price: $94.95. ISBN: 0-471-57267-5</a> <b>[O] </b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> </a> <span>2001</span> </span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：有机合成中的不对称催化。名古屋良治（日本名古屋大学）。 Wiley：纽约（http://www.wiley.com/）。 1994.页数：400页精装。价格：$ 94.95书号：0-471-57267-5</span> </p> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/open-access_resources_thesis/01000130110912.html">On stability, <mml:math altimg="si1.gif" display="inline" overflow="scroll" xmlns:xocs="http://www.elsevier.com/xml/xocs/dtd" xmlns:xs="http://www.w3.org/2001/XMLSchema" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xmlns="http://www.elsevier.com/xml/ja/dtd" xmlns:ja="http://www.elsevier.com/xml/ja/dtd" xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:tb="http://www.elsevier.com/xml/common/table/dtd" xmlns:sb="http://www.elsevier.com/xml/common/struct-bib/dtd" xmlns:ce="http://www.elsevier.com/xml/common/dtd" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:cals="http://www.elsevier.com/xml/common/cals/dtd"><mml:msub><mml:mrow><mml:mi>L</mml:mi></mml:mrow><mml:mrow><mml:mn>2</mml:mn></mml:mrow></mml:msub></mml:math>-gain and <mml:math altimg="si2.gif" display="inline" overflow="scroll" xmlns:xocs="http://www.elsevier.com/xml/xocs/dtd" xmlns:xs="http://www.w3.org/2001/XMLSchema" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xmlns="http://www.elsevier.com/xml/ja/dtd" xmlns:ja="http://www.elsevier.com/xml/ja/dtd" xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:tb="http://www.elsevier.com/xml/common/table/dtd" xmlns:sb="http://www.elsevier.com/xml/common/struct-bib/dtd" xmlns:ce="http://www.elsevier.com/xml/common/dtd" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:cals="http://www.elsevier.com/xml/common/cals/dtd"><mml:msub><mml:mrow><mml:mi>H</mml:mi></mml:mrow><mml:mrow><mml:mi>∞</mml:mi></mml:mrow></mml:msub></mml:math> control for switched systems</a> <b>[O] </b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Jun Zhao&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Jun Zhao,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=David J. Hill&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">David J. Hill </a> <span>2008</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：在稳定性上，<MML：MATH ALTIMG =“SI1.GIF”显示=“内联”overflow =“滚动”XMLNS：XOCS =“http://www.elsevier.com/xml/xocs/dtd”xmlns：xs =“ http://www.w3.org/2001/xmlschema“xmlns：xsi =”http://www.w3.org/2001/xmlschema-instance“xmlns =”http://www.elsevier.com/xml/ JA / DTD“XMLNS：JA =”http://www.elsevier.com/xml/ja/dtd“xmlns：mml =”http://www.w3.org/1998/math/mathml“xmlns：tb = “http://www.elsevier.com/xml/common/table/dtd”xmlns：sb =“http://www.elsevier.com/xml/common/struct-bib/dtd”xmlns：ce =“http ：//www.elsevier.com/xml/common/dtd“xmlns：xlink =”http://www.w3.org/1999/xlink“xmlns：cals =”http://www.elsevier.com/xml / Common / Cals / DTD“> <MML：MSUB> <MML：MROW> <MML：MI> L </ MML：MI> </ MML：MROW> <MML：MROW> <MML：MN> 2 </ MML ：Mn> </ mml：mrow> </ mml：msub> </ mml：math> -gain和<mml：math altimg =“si2.gif”display 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Stereospecific control of peptide gas‐phase ion chemistry with ciscis and transtrans cyclo ornithine residues

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