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Expeditious synthesis of fluorogenic enzyme substrates for mucopolysaccharidosis types I and II. ⅰ型和ⅱ型粘多糖病荧光酶底物的快速合成。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-07 DOI: 10.1039/d6ob01496h
Yuchen Pan, Guoqing Zhang, Norbert Wimmer, Adeline A Lau, Kim M Hemsley, Marco Maccarana, Jin-Ping Li, Vito Ferro
{"title":"Expeditious synthesis of fluorogenic enzyme substrates for mucopolysaccharidosis types I and II.","authors":"Yuchen Pan, Guoqing Zhang, Norbert Wimmer, Adeline A Lau, Kim M Hemsley, Marco Maccarana, Jin-Ping Li, Vito Ferro","doi":"10.1039/d6ob01496h","DOIUrl":"https://doi.org/10.1039/d6ob01496h","url":null,"abstract":"<p><p>New, rapid and inexpensive syntheses of 4-methylumbelliferyl fluorogenic substrates for α-L-iduronidase and iduronate-2-sulfatase, have been developed from a common β-D-glucuronosyl fluoride intermediate. The syntheses feature an efficient purple light-promoted, CCl<sub>4</sub>-free, one-pot Ferrier photobromination/radical debromination sequence for the key C-5 epimerization. The substrates are useful chemical tools for studying mucopolysaccharidosis type I (MPS I) and type II (MPS II).</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149101307","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 hydrogen bonding topology modulates fluorescence in C4N4 fluorophores. 分子内氢键拓扑结构调节C4N4荧光团的荧光。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-07 DOI: 10.1039/d6ob01207h
Miki Kohei, Mao Niimura, Ryosuke Tsutsumi, Naoya Kumagai
{"title":"Intramolecular hydrogen bonding topology modulates fluorescence in C4N4 fluorophores.","authors":"Miki Kohei, Mao Niimura, Ryosuke Tsutsumi, Naoya Kumagai","doi":"10.1039/d6ob01207h","DOIUrl":"10.1039/d6ob01207h","url":null,"abstract":"<p><p>Systematic comparison of hydroxy-, amino-, amide-, sulfonamide-, and phosphinamide-substituted C4N4 fluorophores revealed that fluorescence is modulated not simply by hydrogen-bond donor strength, but by positional, geometrical, and conformational accessibility of intramolecular hydrogen bonding to the pyrimidine core. This insight was translated into an acetylation-responsive turn-on probe, providing a design basis for responsive C4N4 fluorophores.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"7886-7891"},"PeriodicalIF":2.8,"publicationDate":"2026-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148862632","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
Visible-light-driven alkynylation: a sustainable approach to rigid molecular architectures. 可见光驱动的炔基化：刚性分子结构的可持续方法。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-07 DOI: 10.1039/d6ob01050d
Archana Vijayakumar, Angel Maria, Deependu T R, M Manod, Chithra Mohan
{"title":"Visible-light-driven alkynylation: a sustainable approach to rigid molecular architectures.","authors":"Archana Vijayakumar, Angel Maria, Deependu T R, M Manod, Chithra Mohan","doi":"10.1039/d6ob01050d","DOIUrl":"10.1039/d6ob01050d","url":null,"abstract":"<p><p>Alkynes are indispensable molecular motifs in organic, materials, medicinal, and pharmaceutical chemistry, owing to their linear geometry, structural rigidity, distinctive reactivity, and widespread occurrence in bioactive molecules and bioorthogonal platforms. Conventional alkyne synthesis, such as Sonogashira and Glaser couplings, and metal acetylide-based methods, often require harsh conditions such as toxic metal catalysts, strong bases/oxidants, and elevated temperatures, while classical radical approaches typically rely on high-energy UV irradiation, leading to poor selectivity and limited functional group tolerance. In this context, visible-light-mediated photoredox catalysis has emerged as a mild, sustainable, and highly tunable platform for alkynylation reactions. This review elucidates the dynamic landscape in visible-light-mediated alkynylation from 2021 to 2025, critically analysing alkynyl precursor reactivity, radical intermediates, and the mechanistic intricacies of the single-electron-transfer processes that govern these transformations. Thus, it establishes a cohesive conceptual framework that rationalizes catalyst selection, highlights key reaction design principles, and underscores the interplay between radical reactivity and single-electron-transfer processes for the rational development of next-generation, site-selective alkynylation strategies. A comprehensive analysis of emerging strategies, existing limitations, and opportunities for future development is presented in this review.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"7846-7864"},"PeriodicalIF":2.8,"publicationDate":"2026-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148987245","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
Computational study on the substrate-controlled selectivity of Ru-catalyzed ring-closing metathesis. 钌催化合环复分解的底物控制选择性的计算研究。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-07 DOI: 10.1039/d6ob00927a
Fengyue Zhao, Wenchi Ren, Lingli Han, Tao Liu
{"title":"Computational study on the substrate-controlled selectivity of Ru-catalyzed ring-closing metathesis.","authors":"Fengyue Zhao, Wenchi Ren, Lingli Han, Tao Liu","doi":"10.1039/d6ob00927a","DOIUrl":"10.1039/d6ob00927a","url":null,"abstract":"<p><p>Dienes are classic substrates for ring-closing metathesis and hold significant synthetic value in the construction of cyclic compound skeletons. In this study, density functional theory (DFT) is employed to calculate the reaction mechanisms of Ru-catalyzed ring-closing metathesis for aza-diene or oxa-diene substrates. The origin of the reaction selectivity is systematically elucidated through structural analysis, electronic effects, and EDA analysis. The computational results suggest that the rate-determining transition state ts4-N along the reaction pathway of aza-diene substrates exhibits a more favorable planar conformation and stronger electrostatic interactions than ts4-O for the oxa-diene substrates, which further promotes the generation of ring-closing products.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"7987-7993"},"PeriodicalIF":2.8,"publicationDate":"2026-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149023286","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
Threefold annulation to diindolo[1,2-a:2',1'-c]quinoxaline via C-F bond functionalization. 二吲哚[1,2-a:2',1'-c]喹啉的三环化。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-07 DOI: 10.1039/d6ob01220e
Guanxing Zhu, Hanwen Zhao, Zhihai Zhang, Yuhe Song, Jilei Liang, Meiru Ding, Guanxiong Liu, Qingming He, Hailong Chen
{"title":"Threefold annulation to diindolo[1,2-<i>a</i>:2',1'-<i>c</i>]quinoxaline <i>via</i> C-F bond functionalization.","authors":"Guanxing Zhu, Hanwen Zhao, Zhihai Zhang, Yuhe Song, Jilei Liang, Meiru Ding, Guanxiong Liu, Qingming He, Hailong Chen","doi":"10.1039/d6ob01220e","DOIUrl":"https://doi.org/10.1039/d6ob01220e","url":null,"abstract":"<p><p>A transition-metal-free, one-pot threefold annulation of <i>ortho</i>-difluorobenzenes with 1,3-diynyl dianilines is reported for the synthesis of diindoloquinoxalines in up to 72% yield. This cascade integrates two C-F aminations and two alkyne-amine cyclizations in a single reaction system, with the final ring closed by an intramolecular SNAr. The process is promoted by conformational locking of the substrate scaffold and enhanced effective molarity. The second SNAr is synergistically driven by preorganization of the reacting centers, the leaving ability of fluoride, and electronic effects. The substrate scope primarily concerns variation of the fluoroarene component and tolerates selected electron-rich, electron-withdrawing, and sterically demanding substituents, including heteroarenes. A sustainable platform for functional aza-polycyclic aromatics is thus provided.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149126150","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
Co(III)-catalyzed conjugate addition of indole C2-H bonds to 1-azadienes. Co（III）催化吲哚C2-H键与1-偶氮二烯的共轭加成。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-06 DOI: 10.1039/d6ob01270a
Wei-Tao Hu, Zhong-Xia Wang
{"title":"Co(III)-catalyzed conjugate addition of indole C2-H bonds to 1-azadienes.","authors":"Wei-Tao Hu, Zhong-Xia Wang","doi":"10.1039/d6ob01270a","DOIUrl":"https://doi.org/10.1039/d6ob01270a","url":null,"abstract":"<p><p>In the presence of AgSbF<sub>6</sub>, the Cp*Co(CO)I<sub>2</sub>-catalyzed reaction of 3-methyl-1-(pyrimidin-2-yl)-1<i>H</i>-indoles with benzofuran-derived azadienes, 2-arylidene-<i>N</i>-mesylbenzofuran-3(2<i>H</i>)-imines, affords 2-(benzofuran-2-yl)(aryl)methyl-substituted indoles. The reaction between 1-(pyrimidin-2-yl)-1<i>H</i>-indoles and α,β-unsaturated imines, <i>N</i>-tosyl-1,3-diarylprop-2-en-1-imines, under the same conditions yields 2-aminoallylated indoles.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149101156","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
Photochemical C-C bond cleavage in α-haloketones via a pyridinium ylide radical: direct access to esters and amides. α-卤酮的光化学C-C键通过吡啶基裂解：直接进入酯类和酰胺类。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-06 DOI: 10.1039/d6ob01022a
Anup Barman, Krishnandu Dey, Sovan Dey, Suman Patra, Ram Naresh Yadav, Amit Kumar Paul, Md Firoj Hossain
{"title":"Photochemical C-C bond cleavage in α-haloketones <i>via</i> a pyridinium ylide radical: direct access to esters and amides.","authors":"Anup Barman, Krishnandu Dey, Sovan Dey, Suman Patra, Ram Naresh Yadav, Amit Kumar Paul, Md Firoj Hossain","doi":"10.1039/d6ob01022a","DOIUrl":"https://doi.org/10.1039/d6ob01022a","url":null,"abstract":"<p><p>We herein report a sustainable, metal-, photocatalyst-, and oxidant-free photooxidative approach for the C-C bond cleavage of phenacyl halides, enabling the direct synthesis of esters and amides from a broad range of alcohols and amines. In-depth mechanistic and DFT studies support the <i>in situ</i> generation of a pyridinium ylide diradical.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149101216","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
DDQ-catalyzed direct N-alkylation of azoles. ddq催化的唑类直接n -烷基化反应。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-05 DOI: 10.1039/d6ob01021k
Xuanzhen Han, Lang Tai, Renpeng Zhou, Zhixin Wang, Hanxiao Xu, Jin Zhu
{"title":"DDQ-catalyzed direct <i>N</i>-alkylation of azoles.","authors":"Xuanzhen Han, Lang Tai, Renpeng Zhou, Zhixin Wang, Hanxiao Xu, Jin Zhu","doi":"10.1039/d6ob01021k","DOIUrl":"https://doi.org/10.1039/d6ob01021k","url":null,"abstract":"<p><p>Herein, we have developed a new and efficient catalytic system for the C-H/N-H cross-coupling <i>N</i>-alkylation of azoles under metal-free, base-free, and room temperature conditions. In this transformation, DDQ serves as a catalyst to promote the coupling process <i>via</i> single electron transfer and hydrogen atom transfer, and BPO acts as an oxidant to regenerate DDQ. This method offers an economical and practical protocol with a broad substrate scope.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149101247","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
Correction: 8-Arylxanthines as clickable fluorescent tags. 更正：8-芳基黄嘌呤作为可点击的荧光标记。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-05 DOI: 10.1039/d6ob90125e
Mervenur Gökçe, Dilek Öztürk, Zehra Öztürk, Yaren Bal, Ferda Arı, Ömer Koz, Gamze Koz
{"title":"Correction: 8-Arylxanthines as clickable fluorescent tags.","authors":"Mervenur Gökçe, Dilek Öztürk, Zehra Öztürk, Yaren Bal, Ferda Arı, Ömer Koz, Gamze Koz","doi":"10.1039/d6ob90125e","DOIUrl":"https://doi.org/10.1039/d6ob90125e","url":null,"abstract":"<p><p>Correction for '8-Arylxanthines as clickable fluorescent tags' by Mervenur Gökçe <i>et al.</i>, <i>Org. Biomol. Chem.</i>, 2026, https://doi.org/10.1039/d6ob01013j.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149101153","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
N-Acetylation of aromatic amines using copper acetate as an acetyl source. 以乙酸铜为乙酰基源的芳香胺的n -乙酰化。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-02 DOI: 10.1039/d6ob01245k
Yash Dhaduk, Maulik Pethani, Shreeya Dave, Deepshankar Purkayastha, Hussain Bhukya, Togati Naveen
{"title":"<i>N</i>-Acetylation of aromatic amines using copper acetate as an acetyl source.","authors":"Yash Dhaduk, Maulik Pethani, Shreeya Dave, Deepshankar Purkayastha, Hussain Bhukya, Togati Naveen","doi":"10.1039/d6ob01245k","DOIUrl":"https://doi.org/10.1039/d6ob01245k","url":null,"abstract":"<p><p>Amide bond formation is fundamental to organic synthesis because amides are prevalent in pharmaceuticals, bioactive molecules, and industrial materials. Herein, we report a simple and efficient method for amine acetylation using copper acetate as the acetylating reagent and AIBN as the radical initiator. The reaction proceeds without additional catalysts or an inert atmosphere, offering an economical, environmentally friendly, and practical approach to synthesizing aromatic amides for research applications. To the best of our knowledge, this is the first report describing the <i>N</i>-acetylation of aromatic amines using copper acetate as the acetylating reagent.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149101195","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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