A patchwork pathway for oxygenase‐independent degradation of side chain containing steroids

Warnke Markus; Jacoby Christian; Jung Tobias; Agne Michael; Mergelsberg Mario; Starke Robert; Jehmlich Nico; von Bergen Martin; Richnow Hans‐Hermann; Brüls Thomas; Boll Matthias

摘要

Summary > The denitrifying betaproteobacterium Sterolibacterium denitrificans serves as model organism for studying the oxygen‐independent degradation of cholesterol. Here, we demonstrate its capability of degrading various globally abundant side chain containing zoo‐, phyto‐ and mycosterols. We provide the complete genome that empowered an integrated genomics/proteomics/metabolomics approach, accompanied by the characterization of a characteristic enzyme of steroid side chain degradation. The results indicate that individual molybdopterin‐containing steroid dehydrogenases are involved in C25‐hydroxylations of steroids with different isoprenoid side chains, followed by the unusual conversion to C26‐oic acids. Side chain degradation to androsta‐1,4‐diene‐3,17‐dione (ADD) via aldolytic C–C bond cleavages involves acyl‐CoA synthetases/dehydrogenases specific for the respective 26‐, 24‐ and 22‐oic acids/‐oyl‐CoAs and promiscuous MaoC‐like enoyl‐CoA hydratases, aldolases and aldehyde dehydrogenases. Degradation of rings A and B depends on gene products uniquely found in anaerobic steroid degraders, which after hydrolytic cleavage of ring A, again involves CoA‐ester intermediates. The degradation of the remaining CD rings via hydrolytic cleavage appears to be highly similar in aerobic and anaerobic bacteria. Anaerobic cholesterol degradation employs a composite repertoire of more than 40 genes partially known from aerobic degradation in gammaproteobacteria/actinobacteria, supplemented by unique genes that are required to circumvent oxygenase‐dependent reactions. </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>None </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>2017年第11期</span><b style="margin: 0 2px;">|</b><span>共16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=Warnke Markus&option=202" target="_blank" rel="nofollow">Warnke Markus;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Jacoby Christian&option=202" target="_blank" rel="nofollow">Jacoby Christian;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Jung Tobias&option=202" target="_blank" rel="nofollow">Jung Tobias;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Agne Michael&option=202" target="_blank" rel="nofollow">Agne Michael;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Mergelsberg Mario&option=202" target="_blank" rel="nofollow">Mergelsberg Mario;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Starke Robert&option=202" target="_blank" rel="nofollow">Starke Robert;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Jehmlich Nico&option=202" target="_blank" rel="nofollow">Jehmlich Nico;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=von Bergen Martin&option=202" target="_blank" rel="nofollow">von Bergen Martin;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Richnow Hans‐Hermann&option=202" target="_blank" rel="nofollow">Richnow Hans‐Hermann;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Brüls Thomas&option=202" target="_blank" rel="nofollow">Brüls Thomas;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Boll Matthias&option=202" target="_blank" rel="nofollow">Boll Matthias;</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>Institute of Biology II MicrobiologyAlbert‐Ludwigs‐University FreiburgFreiburg Germany;</p> <p>Institute of Biology II MicrobiologyAlbert‐Ludwigs‐University FreiburgFreiburg Germany;</p> <p>Institute of Biology II MicrobiologyAlbert‐Ludwigs‐University FreiburgFreiburg Germany;</p> <p>Institute of Biology II MicrobiologyAlbert‐Ludwigs‐University FreiburgFreiburg Germany;</p> <p>Institute of Biology II MicrobiologyAlbert‐Ludwigs‐University FreiburgFreiburg Germany;</p> <p>Department of Molecular Systems BiologyHelmholtz Centre of Environmental SciencesLeipzig Germany;</p> <p>Department of Molecular Systems BiologyHelmholtz Centre of Environmental SciencesLeipzig Germany;</p> <p>Department of Molecular Systems BiologyHelmholtz Centre of Environmental SciencesLeipzig Germany;</p> <p>Department of Isotope BiogeochemistryHelmholtz Centre of Environmental SciencesLeipzig Germany;</p> <p>CEA DRF IG Genoscope EvryFrance;</p> <p>Institute of Biology II MicrobiologyAlbert‐Ludwigs‐University FreiburgFreiburg Germany;</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"> <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" 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Cole&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Richard B. Cole </a> <a href="/conference-foreign-257539/" target="_blank" rel="nofollow" class="tuijian_authcolor">American Society for Mass Spectrometry Conference on Mass Spectrometry and Allied Topics .</a> <span>2010</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：包括通过电喷雾阴离子附着形成的类固醇的内皮固体加合物的植物附着和分解的新型碎片途径</span> </p> </li> <li> <div> <b>9. </b><a class="enjiyixqcontent" href="/academic-degree-foreign_mphd_thesis/02061732346.html">NOVEL OXYGENASES AND METABOLIC PATHWAYS OF MICROBIAL AROMATIC CATABOLISM (SALICYLATE HYDROXYLASE, HYDROXYQUINOL 1,2-DIOXYGENASE, VMA BIODEGRADATION, CRESOL DEGRADATION, WHOLE-CELL NMR)</a> <b>[D] </b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=SZE, ISAAC SHUN-YAN&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">SZE, ISAAC SHUN-YAN </a> <span>1985</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：微生物芳香代谢的新加氧酶和代谢途径（水杨酸羟化酶，羟基喹啉1,2-二氧合酶，VMA生物分解，甲酚降解，全细胞核磁共振）</span> </p> </li> <li> <div> <b>10. </b><a class="enjiyixqcontent" href="/academic-journal-foreign-pmc_detail_thesis/040007256131.html">Further Studies on the 3-Ketosteroid 9α-Hydroxylase of Rhodococcus ruber Chol-4 a Rieske Oxygenase of the Steroid Degradation Pathway</a> <b>[O] </b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Sara Baldanta&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Sara Baldanta,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Juana María Navarro Llorens&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Juana María Navarro Llorens,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Govinda Guevara&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Govinda Guevara </a> <span>2021</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：进一步研究rhodococccus ruber Chol-4的3-酮类固醇9α-羟化酶类固醇降解途径的RIESKE氧气</span> </p> </li> <li> <div> <b>11. </b><a class="enjiyixqcontent" href="/open-access_resources_thesis/0100038111351.html ">Patchwork Assembly of nag-Like Nitroarene Dioxygenase Genes and the 3-Chlorocatechol Degradation Cluster for Evolution of the 2-Chloronitrobenzene Catabolism Pathway in Pseudomonas stutzeri ZWLR2-1▿</a> <b>[O] </b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Liu, Hong&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Liu, Hong,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wang, Shu-Jun&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Wang, Shu-Jun,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhang, Jun-Jie&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Zhang, Jun-Jie,</a> <span>2011</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：nat样亚硝基芳烃双加氧酶基因和3-氯邻苯二酚降解簇的拼布组装，用于斯氏假单胞菌ZWLR2-1▿中2-氯硝基苯分解代谢途径的进化</span> </p> </li> <li> <div> <b>12. </b><a class="enjiyixqcontent" href="/ntis-science-report_de_thesis/02071625700.html">Influence of water solubility, side chain degradability and side chain configuration on the degradation of phthalic acid esters under methanogenic conditions</a> <b>[R] </b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Alnervik, M.&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Alnervik, M. </a> <span>1996</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：水溶性，侧链降解性和侧链构型对产甲烷条件下邻苯二甲酸酯降解的影响</span> </p> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/academic-journal-cn_world-journal-gastroenterology-english_thesis/0201295298753.html">Anti-inflammatory pathways and alcoholic liver disease: Role of an adiponectin/interleukin-10/heme oxygenase-1 pathway</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Palash Mandal&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . Palash Mandal</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Michele T Pritchard&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,Michele T Pritchard</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Laura E Nagy&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,Laura E Nagy</a> <span> <a href="/journal-cn-52914/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 世界胃肠病学杂志：英文版 </a> </span> <span> . 2010</span><span>,第11期</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06130471507142.html">Prepn. of steroid hormone intermediates - by microbial degradation of c17 steroid side-chains</a> <b>[P]</b> . <span> 外国专利：  ES8607341A3 </span> <span> . 1986-06-01</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：准备甾体激素中间体的合成-通过微生物降解c17类固醇侧链 </span> </p> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06130471507141.html">Prepn. of steroid hormone intermediates - by microbial degradation of c17 steroid side-chains</a> <b>[P]</b> . <span> 外国专利：  ES8607341A3 </span> <span> . 1986-11-01</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：准备甾体激素中间体的合成-通过微生物降解c17类固醇侧链 </span> </p> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130482845003.html">A method for the production of 17 - ketostatines steroids the androstane series from the corresponding steroids with a side chain in 17 - position by microbiological degradation</a> <b>[P]</b> . <span> 外国专利：  DE1618582B2 </span> <span> . 1976-01-15</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：一种通过微生物降解由侧链在17位的相应类固醇生产雄甾酮系列17-酮丁酮类固醇的方法。 </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('0704028680663','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 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