Modular Synthesis of Nona‐Decasaccharide Motif from Psidium guajava Polysaccharides: Orthogonal One‐Pot Glycosylation Strategy

Zhang Yunqin; Chen Zixi; Huang Yingying; He Shaojun; Yang Xingkuan; Wu Zhibing; Wang Xiufang; Xiao Guozhi

摘要

Abstract > The synthesis of long, branched, and complex carbohydrate sequences remains a challenging task in chemical synthesis. Reported here is an efficient and modular one‐pot synthesis of a nona‐decasaccharide and shorter sequences from Psidium guajava polysaccharides, which have the potent α‐glucosidase inhibitory activity. The synthetic strategy features: 1)?several one‐pot glycosylation reactions on the basis of N ‐phenyltrifluoroacetimidate (PTFAI) and Yu glycosylation to streamline the chemical synthesis of oligosaccharides, 2)?the successful and efficient assembly sequences (first O3′, second O5′, final O2′) toward the challenging 2,3,5‐branched Ara f motif, 3)?the stereoselective 1,2‐ cis ‐glucosylation by reagent control, and 4)?the convergent [6+6+7] one‐pot coupling reaction for the final assembly of the target nona‐decasaccharide. This orthogonal one‐pot glycosylation strategy can streamline the chemical synthesis of long, branched, and complicated carbohydrate chains. </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> > 长，支化和复合碳水化合物序列的合成仍然是化学合成中有挑战性的任务。这里报道的是一种有效且模块化的单糖合成非癸二糖和更短的序列 psidium guajava </ i> 具有有效的α-葡糖苷酶抑制活性的多糖。合成策略特点：1）？基于几种单壶糖基化反应 n </ i> - 苯三氟丙啶酰亚胺亚酸酯（PTFAI）和Yu糖基化，用寡糖的化学合成，2）αα成功和有效的组装序列（第一O3'，第二O5'，最终O2'）朝着挑战2,3,5分支的ARA f </ i> 图案，3）？立体选择性1,2- cis </ i> 用试剂对照和4）葡萄糖化，4）αα〜1罐偶联反应，用于靶非甲基糖的最终组装。这种正交的一盆糖基化策略可以简化长，支链和复杂的碳水化合物链的化学合成。 </ 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=Zhang Yunqin&option=202" target="_blank" rel="nofollow">Zhang Yunqin;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chen Zixi&option=202" target="_blank" rel="nofollow">Chen Zixi;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Huang Yingying&option=202" target="_blank" rel="nofollow">Huang Yingying;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=He Shaojun&option=202" target="_blank" rel="nofollow">He Shaojun;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yang Xingkuan&option=202" target="_blank" rel="nofollow">Yang Xingkuan;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wu Zhibing&option=202" target="_blank" rel="nofollow">Wu Zhibing;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wang Xiufang&option=202" target="_blank" rel="nofollow">Wang Xiufang;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Xiao Guozhi&option=202" target="_blank" rel="nofollow">Xiao Guozhi;</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>State Key Laboratory of Phytochemistry and Plant Resources in West ChinaChinese Academy of Sciences132 Lanhei Road Kunming 650201 China;</p> <p>State Key Laboratory of Phytochemistry and Plant Resources in West ChinaChinese Academy of Sciences132 Lanhei Road Kunming 650201 China;</p> <p>State Key Laboratory of Phytochemistry and Plant Resources in West ChinaChinese Academy of Sciences132 Lanhei Road Kunming 650201 China;</p> <p>State Key Laboratory of Phytochemistry and Plant Resources in West ChinaChinese Academy of Sciences132 Lanhei Road Kunming 650201 China;</p> <p>State Key Laboratory of Phytochemistry and Plant Resources in West ChinaChinese Academy of Sciences132 Lanhei Road Kunming 650201 China;</p> <p>State Key Laboratory of Phytochemistry and Plant Resources in West ChinaChinese Academy of Sciences132 Lanhei Road Kunming 650201 China;</p> <p>Department of ChemistryKunming University2 Puxing Road Kunming 650214 China;</p> <p>State Key Laboratory of Phytochemistry and Plant Resources in West ChinaChinese Academy of Sciences132 Lanhei Road Kunming 650201 China;</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=antidiabetic&option=203" rel="nofollow">antidiabetic;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=glycosylation&option=203" rel="nofollow">glycosylation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=saccharides&option=203" rel="nofollow">saccharides;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=structure elucidation&option=203" rel="nofollow">structure elucidation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=synthetic methods&option=203" rel="nofollow">synthetic methods;</a> </p> <div class="translation"> 机译：抗糖尿病;糖基化;糖类;结构阐明;合成方法; </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/0704028161752.html">Modular Synthesis of Nona‐Decasaccharide Motif from Psidium guajava Polysaccharides: Orthogonal One‐Pot Glycosylation Strategy</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhang Yunqin&option=202" target="_blank" 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