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Mechanistic characterisation of a fungal fusicoccane-type diterpene synthase involved in the biosynthesis of talaro-7,13-diene 参与塔拉罗-7,13-二烯生物合成的真菌镰刀菌烷型二萜合成酶的机理特征
IF 3.2 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-10 DOI: 10.1039/d4ob01348d
Fu-Long Lin, Kizerbo A. Taizoumbe, Yi-Xuan Wang, Jia-Hua Huang, Gao-Qian Wang, Guo-Dong Chen, Jian-Ming Lv, Dan Hu, Hao Gao, Jeroen S. Dickschat
{"title":"Mechanistic characterisation of a fungal fusicoccane-type diterpene synthase involved in the biosynthesis of talaro-7,13-diene","authors":"Fu-Long Lin, Kizerbo A. Taizoumbe, Yi-Xuan Wang, Jia-Hua Huang, Gao-Qian Wang, Guo-Dong Chen, Jian-Ming Lv, Dan Hu, Hao Gao, Jeroen S. Dickschat","doi":"10.1039/d4ob01348d","DOIUrl":"https://doi.org/10.1039/d4ob01348d","url":null,"abstract":"The cyclisation mechanism of the fungal fusicoccane (FC)-type diterpene synthase (DTS) TadA was investigated by extensive isotopic labelling experiments, and the pH-dependency of the product selectivity of this enzyme was explored. These studies provide new insights into the cyclisation mechanisms of FC-type DTSs.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-09-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142202343","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Acid/base responsive pseudo[3]rotaxanes from amine naphthotubes and bis-pyridinium/isoquinolinium guests. 从胺萘管和双吡啶鎓/异喹啉鎓客体制备酸/碱响应性假[3]罗他烷。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-09 DOI: 10.1039/d4ob01268b
Li-Shuo Zheng, Hao Nian, Song-Meng Wang, Yan-Fang Wang, Wei Jiang, Li-Li Wang, Liu-Pan Yang
{"title":"Acid/base responsive pseudo[3]rotaxanes from amine naphthotubes and bis-pyridinium/isoquinolinium guests.","authors":"Li-Shuo Zheng, Hao Nian, Song-Meng Wang, Yan-Fang Wang, Wei Jiang, Li-Li Wang, Liu-Pan Yang","doi":"10.1039/d4ob01268b","DOIUrl":"https://doi.org/10.1039/d4ob01268b","url":null,"abstract":"<p><p>A novel cooperative pseudo[3]rotaxane system was successfully constructed by the inclusion complexation of two identical amine naphthotubes with a bis-pyridinium/isoquinolinium guest. Single crystal structure analysis revealed that weak C<sub>sp<sup>3</sup></sub>-H⋯O hydrogen bonds between the two hosts are responsible for the positive cooperativity during the formation of pseudo[3]rotaxanes. Moreover, intermolecular charge-transfer interactions between the electron-rich host and the electron-poor guests were observed. The pseudo[3]rotaxanes showed pH-controllable association/dissociation processes with naked-eye color changes in solution.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142152574","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of the bicyclic butenolide core of pallamolide A: a biomimetic approach 帕拉莫内酯 A 的双环丁烯内酯核心的合成：一种生物模拟方法
IF 3.2 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-09 DOI: 10.1039/d4ob01380h
Grace J. Drummond, Phillip S. Grant, Alisha M. Geurts, Daniel P. Furkert, Margaret A. Brimble
{"title":"Synthesis of the bicyclic butenolide core of pallamolide A: a biomimetic approach","authors":"Grace J. Drummond, Phillip S. Grant, Alisha M. Geurts, Daniel P. Furkert, Margaret A. Brimble","doi":"10.1039/d4ob01380h","DOIUrl":"https://doi.org/10.1039/d4ob01380h","url":null,"abstract":"Pallamolide A is a 7,8-<em>seco</em>-labdane terpenoid possessing a unique bicyclo[2.2.2]octane core and a spiro-butenolide moiety. A biomimetic synthesis of the bicyclic butenolide core over 10 steps is reported, featuring an unexpected autoxidation ring opening, and a vinylogous Mukaiyama aldol reaction which was spontaneously followed by an unusual intramolecular vinylogous aldol reaction to assemble the spiro-butenolide moiety and bicyclic core of pallamolide A.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142202346","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Intramolecular through-space NMR spectroscopic effect of steric compression on 1H NMR spectroscopy. 立体压缩对 1H NMR 光谱的分子内通空 NMR 光谱效应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-09 DOI: 10.1039/d4ob01108b
Ziyu Zeng, Ashraf M A Qasem, Ian S Blagbrough, Timothy J Woodman
{"title":"Intramolecular through-space NMR spectroscopic effect of steric compression on <sup>1</sup>H NMR spectroscopy.","authors":"Ziyu Zeng, Ashraf M A Qasem, Ian S Blagbrough, Timothy J Woodman","doi":"10.1039/d4ob01108b","DOIUrl":"https://doi.org/10.1039/d4ob01108b","url":null,"abstract":"<p><p>The intramolecular through-space NMR spectroscopic effect of steric compression is related to intramolecular through-space van der Waals repulsion. The electron cloud of a proton can be pushed away by the electron cloud of a nearby proton or functional group. As the electron population of the sterically compressed proton is decreased (therefore deshielded), the chemical shift sharply moves downfield, which may result in ambiguity for the proton signal assignment. Also, the conformation of the local area of the sterically compressed proton can be altered by the steric repulsion, therefore, the coupling constant/coupling pattern of a sterically compressed proton could be influenced. This review summarizes and presents the impacts on the chemical shift and coupling constant by the <sup>1</sup>H NMR spectroscopic effect of steric compression extracted from the reported examples from the 1950s to 2021.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142152575","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Zinc tetrafluoroborate catalyzed α-stereoselective synthesis of pseudoglycals: efficient synthesis of digitoxin α-L-amicetose 四氟硼酸锌催化α-严格选择性合成假甘氨酸：高效合成地高辛α-L-氨基乙糖
IF 3.2 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-09 DOI: 10.1039/d4ob01153h
Mrinmoy Manash Bharali, Abhishek Santra
{"title":"Zinc tetrafluoroborate catalyzed α-stereoselective synthesis of pseudoglycals: efficient synthesis of digitoxin α-L-amicetose","authors":"Mrinmoy Manash Bharali, Abhishek Santra","doi":"10.1039/d4ob01153h","DOIUrl":"https://doi.org/10.1039/d4ob01153h","url":null,"abstract":"We report here an efficient, fast, and cost-effective strategy for synthesizing pseudoglycals by the reaction of glycals with alcohols or nucleophiles using zinc tetrafluoroborate. This mild, transition metal-free approach allowed the α-selective synthesis of pseudoglycals using a wide range of acceptors containing various protecting groups/functionalities. This method is exemplified by the synthesis of digitoxin α-<small>L</small>-amicetose, a known potential cardiac glycoside anticancer agent. The improved 3-step synthesis from <small>L</small>-rhamnal afforded an overall yield of 54%, thus representing a significant improvement over the previous method.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142249941","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Investigating chemical diversity: o-propargylphenols as key compounds in the divergent synthesis of 2-substituted benzofurans and chromenes. 调查化学多样性：邻丙炔基苯酚是 2-取代苯并呋喃和苯并二氢吡喃分歧合成中的关键化合物。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-09 DOI: 10.1039/d4ob01272k
Alessandra Gritti, Elisa Brambilla, Ilaria Nania, Federico Turba, Valentina Pirovano, Giorgio Abbiati
{"title":"Investigating chemical diversity: <i>o</i>-propargylphenols as key compounds in the divergent synthesis of 2-substituted benzofurans and chromenes.","authors":"Alessandra Gritti, Elisa Brambilla, Ilaria Nania, Federico Turba, Valentina Pirovano, Giorgio Abbiati","doi":"10.1039/d4ob01272k","DOIUrl":"https://doi.org/10.1039/d4ob01272k","url":null,"abstract":"<p><p>In this study, we explored and optimized a MW-enhanced divergent approach for the synthesis of 2-substituted benzofurans and chromenes, starting from seventeen substituted <i>o</i>-propargylphenols characterized by a monoaryl substitution on the propargylic sp<sup>3</sup> carbon. Firstly, we developed a robust platform for the preparation of a library of <i>o</i>-propargylphenols. Under basic conditions, <i>o</i>-propargylphenols reacted regioselectively to yield benzofurans in yields ranging from 43% to 100%. Conversely, under cationic gold catalysis, we were able to obtain the corresponding 4<i>H</i>-chromenes, albeit in more variable yields (from 25% to 93%) and slightly lower regioselectively. We also proposed plausible mechanisms to explain the divergent outcomes observed. Our findings underscore the potential of diversity-oriented synthesis in the investigation of molecular complexity. Our neglected <i>o</i>-propargylphenols have proven to be versatile and strategic starting materials for accessing oxygen-containing heterocyclic scaffolds through intramolecular cyclization reactions.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142152576","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent progress in chemoenzymatic synthesis of human glycans. 人类聚糖化学合成的最新进展。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-09 DOI: 10.1039/d4ob01006j
Shengzhou Ma, Jinhua Gao, Yinping Tian, Liuqing Wen
{"title":"Recent progress in chemoenzymatic synthesis of human glycans.","authors":"Shengzhou Ma, Jinhua Gao, Yinping Tian, Liuqing Wen","doi":"10.1039/d4ob01006j","DOIUrl":"https://doi.org/10.1039/d4ob01006j","url":null,"abstract":"<p><p>Glycan is an essential cell component that usually exists in either a free form or a glycoconjugated form. Glycosylation affects the regulatory function of glycoconjugates in health and disease development, indicating the key role of glycan in organisms. Because of the complexity and diversity of glycan structures, it is challenging to prepare structurally well-defined glycans, which hinders the investigation of biological functions at the molecular level. Chemoenzymatic synthesis is an attractive approach for preparing complex glycans, because it avoids tedious protecting group manipulations in chemical synthesis and ensures high regio- and stereo-selectivity of glucosides during glycan assembly. Herein, enzymes, such as glycosyltransferases (GTs) and glycosidases (GHs), and sugar donors involved in the chemoenzymatic synthesis of human glycans are initially discussed. Many state-of-the-art chemoenzymatic methodologies are subsequently displayed and summarized to illustrate the development of synthetic human glycans, for example, <i>N</i>- and <i>O</i>-linked glycans, human milk oligosaccharides, and glycosaminoglycans. Thus, we provide an overview of recent chemoenzymatic synthetic designs and applications for synthesizing complex human glycans, along with insights into the limitations and perspectives of the current methods.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142152577","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthetic studies towards volvalerenol A: access to a fully functionalized cycloheptane framework in an asymmetric fashion through the exploitation of C2-symmetry 伏瓦来烯醇 A 的合成研究：通过利用 C2 对称性，以不对称方式获得全功能环庚烷框架
IF 3.2 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-09 DOI: 10.1039/d4ob01110d
Rajkumar Sahoo, Saubhik Ghosh, Suman Bhatta, Santu Bisui, Samik Nanda
{"title":"Synthetic studies towards volvalerenol A: access to a fully functionalized cycloheptane framework in an asymmetric fashion through the exploitation of C2-symmetry","authors":"Rajkumar Sahoo, Saubhik Ghosh, Suman Bhatta, Santu Bisui, Samik Nanda","doi":"10.1039/d4ob01110d","DOIUrl":"https://doi.org/10.1039/d4ob01110d","url":null,"abstract":"The enantioselective synthesis of a fully functionalized cycloheptane core of the naturally occurring triterpenoid volvalerenol A, exhibiting pseudo-<em>C</em><small><sub>2</sub></small> symmetry, was achieved. Enantioselective enzymatic desymmetrization (EED), asymmetric methallylation, and reductive ring opening of an cyclopropane overbred intermediate were the key reactions to access the cycloheptanone core. Further synthetic manipulations, <em>via</em> a unique “MPV” (Meerwein–Ponndorf–Verley) type reductive ring-opening of an epoxide and other synthetic transformations, afforded two fully functionalized cycloheptane frameworks of the target molecule.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142249942","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A rhodium-catalyzed C-H activation/cyclization approach toward the total syntheses of cassiarin C and 8-O-methylcassiarin A from a common intermediate. 一种铑催化的 C-H 活化/环化方法，用于从一种共同的中间体全合成决明素 C 和 8-O-甲基决明素 A。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-09 DOI: 10.1039/d4ob01122h
Didier F Vargas, Santiago Fonzo, Sebastian O Simonetti, Teodoro S Kaufman, Enrique L Larghi
{"title":"A rhodium-catalyzed C-H activation/cyclization approach toward the total syntheses of cassiarin C and 8-<i>O</i>-methylcassiarin A from a common intermediate.","authors":"Didier F Vargas, Santiago Fonzo, Sebastian O Simonetti, Teodoro S Kaufman, Enrique L Larghi","doi":"10.1039/d4ob01122h","DOIUrl":"https://doi.org/10.1039/d4ob01122h","url":null,"abstract":"<p><p>Three short and efficient total syntheses of cassiarin C are reported, from a chromanone common key intermediate. A C-H activation strategy, under rhodium catalysis on its pivaloyl oxime, enabled the installation of the pyridine ring. Dehydrogenation of 8-<i>O</i>-methylcassiarin C afforded 8-<i>O</i>-methylcassiarin A. A kinetic experiment and DFT calculations of the intermediates helped to gain insight into the unusual site- and stereo-specific H/D exchange of cassiarin C in CD<sub>3</sub>OD.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142152573","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A benzimidazole-based Cu(II) complex catalyzed site-selective C-H sulfenylation of imidazo-[1,2-a]pyridines using CS2 as a sulfur source. 一种苯并咪唑基 Cu(II) 复合物以 CS2 为硫源催化咪唑并[1,2-a]吡啶的位点选择性 C-H 亚磺酰化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-06 DOI: 10.1039/d4ob00868e
Kingkar Ghosh, Narendra Nath Ghosh, Prasun Choudhury, Subham Bhattacharjee, Rajat Saha, Mayukh Deb, Kinkar Biswas
{"title":"A benzimidazole-based Cu(II) complex catalyzed site-selective C-H sulfenylation of imidazo-[1,2-<i>a</i>]pyridines using CS<sub>2</sub> as a sulfur source.","authors":"Kingkar Ghosh, Narendra Nath Ghosh, Prasun Choudhury, Subham Bhattacharjee, Rajat Saha, Mayukh Deb, Kinkar Biswas","doi":"10.1039/d4ob00868e","DOIUrl":"https://doi.org/10.1039/d4ob00868e","url":null,"abstract":"<p><p>A new benzimidazole-based Cu(II) complex catalyzed site-selective sulfenylation of imidazo[1,2-<i>a</i>]pyridines with benzyl/alkyl/allyl bromides and CS<sub>2</sub> at 100 °C in DMF : H<sub>2</sub>O is reported. The present methodology has been developed for the synthesis of 3-sulfenyl imidazo[1,2-<i>a</i>]pyridines in good yields with a broad substrate scope. In this protocol, CS<sub>2</sub>, commonly known as a non-polar small molecule bioregulator (SMB), is converted to valuable sulfenylated imidazo[1,2-<i>a</i>]pyridine derivatives. In addition, theoretical investigations along with experimental evidence unfold the insights into the probable mechanistic pathway of site-selective sulfenylation from <i>S</i>,<i>S</i>-dibenzyltrithiocarbonate, which is particularly formed as an intermediate during the reaction.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142138675","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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