Enfumafungin synthase represents a novel lineage of fungal triterpene cyclases

Kuhnert Eric; Li Yan; Lan Nan; Yue Qun; Chen Li; Cox Russell J.; An Zhiqiang; Yokoyama Kenichi; Bills Gerald F.

摘要

Summary > Enfumafungin is a glycosylated fernene‐type triterpenoid produced by the fungus Hormonema carpetanum . Its potent antifungal activity, mediated by its interaction with β ‐1,3‐glucan synthase and the fungal cell wall, has led to its development into the semi‐synthetic clinical candidate, ibrexafungerp (=SCY‐078). We report on the preliminary identification of the enfumafungin biosynthetic gene cluster (BGC) based on genome sequencing, phylogenetic reconstruction, gene disruption, and cDNA sequencing studies. Enfumafungin synthase (e fuA ) consists of a terpene cyclase domain (TC) fused to a glycosyltransferase (GT) domain and thus represents a novel multifunctional enzyme. Moreover, the TC domain bears a phylogenetic relationship to bacterial squalene–hopene cyclases (SHC) and includes a typical DXDD motif within the active centre suggesting that efuA evolved from SHCs. Phylogenetic reconstruction of the GT domain indicated that this portion of the fusion gene originated from fungal sterol GTs. Eleven genes flanking efuA are putatively involved in the biosynthesis, regulation, transport and self‐resistance of enfumafungin and include an acetyltransferase, three P450 monooxygenases, a dehydrogenase, a desaturase and a reductase. A hypothetical scheme for enfumafungin assembly is proposed in which the E‐ring is oxidatively cleaved to yield the four‐ring system of enfumafungin. EfuA represents the first member of a widespread lineage of fungal SHCs. </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”>摘要</ title> > enfumafungin是由真菌 Hormonema Carpetanum </ i>产生的糖基化的苯丙胺型三萜。其有效的抗真菌活性，通过其与<iβ/ i> -1,3-葡聚糖合成酶和真菌细胞壁的相互作用介导的，导致其发展成为半合成临床候选者，Ibrexafungerp（= SCY-078 ）。我们基于基因组测序，系统发育重建，基因破坏和cDNA测序研究报告了enfumungin生物合成基因簇（BGC）的初步鉴定。 Enfumafungin合成酶（E FUA </ I>）由稠合到糖基转移酶（GT）结构域（GT）结构域的萜烯环酶结构域（TC）组成，因此代表一种新型多功能酶。此外，TC结构域与细菌角鲨烯环酶（SHC）进行系统发育关系，并且在活性中心内包括典型的DXDD基序，表明EFUA从SHCS演变。 GT结构域的系统发育重建表明该部分融合基因源自真菌甾醇GTS。 Flanking Efua </ i>的11个基因涉及Enfumafungin的生物合成，调节，运输和自体阻力，包括乙酰转移酶，三个P450单氧基酶，脱氢酶，去饱和酶和还原酶。提出了一种假设的Enfumafungin组件方案，其中E形环氧化地切割，得到Enfumafungin的四环体系。 EFUA代表了血清SHC的广泛血统谱系的第一个成员。 </ 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-22868/'>《Environmental microbiology》</a> <b style="margin: 0 2px;">|</b><span>2018年第9期</span><b style="margin: 0 2px;">|</b><span>共18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=Kuhnert Eric&option=202" target="_blank" rel="nofollow">Kuhnert Eric;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Li Yan&option=202" target="_blank" rel="nofollow">Li Yan;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lan Nan&option=202" target="_blank" rel="nofollow">Lan Nan;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yue Qun&option=202" target="_blank" rel="nofollow">Yue Qun;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chen Li&option=202" target="_blank" rel="nofollow">Chen Li;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Cox Russell J.&option=202" target="_blank" rel="nofollow">Cox Russell J.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=An Zhiqiang&option=202" target="_blank" rel="nofollow">An Zhiqiang;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yokoyama Kenichi&option=202" target="_blank" rel="nofollow">Yokoyama Kenichi;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Bills Gerald F.&option=202" target="_blank" rel="nofollow">Bills Gerald F.;</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>Texas Therapeutics Institute the Brown Foundation Institute of Molecular MedicineUniversity of Texas Health Science Center at HoustonHouston TX USA;</p> <p>Texas Therapeutics Institute the Brown Foundation Institute of Molecular MedicineUniversity of Texas Health Science Center at HoustonHouston TX USA;</p> <p>Texas Therapeutics Institute the Brown Foundation Institute of Molecular MedicineUniversity of Texas Health Science Center at HoustonHouston TX USA;</p> <p>Texas Therapeutics Institute the Brown Foundation Institute of Molecular MedicineUniversity of Texas Health Science Center at HoustonHouston TX USA;</p> <p>Texas Therapeutics Institute the Brown Foundation Institute of Molecular MedicineUniversity of Texas Health Science Center at HoustonHouston TX USA;</p> <p>Leibniz University HannoverInstitute for Organic Chemistry and BMWZHannover Germany;</p> <p>Texas Therapeutics Institute the Brown Foundation Institute of Molecular MedicineUniversity of Texas Health Science Center at HoustonHouston TX USA;</p> <p>Duke University School of MedicineDepartment of BiochemistryDurham NC USA;</p> <p>Texas Therapeutics Institute the Brown Foundation Institute of Molecular MedicineUniversity of Texas Health Science Center at HoustonHouston TX 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/183.html" title="微生物学">微生物学;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> </p> </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> <li >中文文献</li> <li >专利</li> </ul> </div> <div 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initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：Enfumafungin衍生物，包含它们的药物组合物及其在制备用于治疗真菌感染的药物中的用途 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130411927011.html">DERIVATIVES OF ENFUMAFUNGIN AS INHIBITORS OF(1,3)-BETA.-D-GLUCAN SYNTHASE</a> <b>[P]</b> . <span> 外国专利：  CA2731941C </span> <span> . 2016-09-27</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：作为（1,3）-β-D-葡糖合酶抑制剂的恩富玛菌素衍生物 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130427620247.html">DERIVATIVES OF ENFUMAFUNGIN AS INHIBITORS OF(1,3)-BETA.-D-GLUCAN SYNTHASE</a> <b>[P]</b> . <span> 外国专利：  CA2731941A1 </span> <span> . 2010-02-18</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：作为（1,3）-β-D-葡糖合酶抑制剂的恩富玛菌素衍生物 </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> <div id="thesis_get_original1" class="downloadBth" style="bottom: 19px;z-index: 999;" onclick="ywcd('0704023228885','4',7,2,1,'',this,24)" class="delivery" prompt="010401" title="通过人工服务将文献原文发送至邮箱" >获取原文</div> <div class="journalsub-pop-up" style="display: none"> <div class="journal-sub"> <h2>期刊订阅</h2> <img src="https://cdn.zhangqiaokeyan.com/img/loginclose.png" alt="关闭" onclick="$('.journalsub-pop-up').hide()"> <p class="pardon">抱歉，该期刊暂不可订阅，敬请期待！</p> <p class="current">目前支持订阅全部北京大学中文核心（2020）期刊目录。</p> <div style="display: flex;margin-top: 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