Organic & Biomolecular Chemistry最新文献_第6页

Recent advances in the enantioselective synthesis of chiral sulfones via asymmetric hydrogenation. 通过不对称加氢法对映体选择性合成手性砜的最新进展。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-28 DOI: 10.1039/d4ob01515k

Xiaoxue Wu, Guohua Hou

引用次数: 0

A mitochondria-targeted colorimetric and NIR ratiometric fluorescent probe for biothiols with large Stokes shift based on thiol-chromene click reaction. 一种基于硫醇-色素点击反应的线粒体靶向比色和近红外比色荧光探针，用于检测具有较大斯托克斯位移的生物硫醇。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-25 DOI: 10.1039/d4ob01324g

Dongjian Zhu, Aishan Ren, Lin Xue

{"title":"A mitochondria-targeted colorimetric and NIR ratiometric fluorescent probe for biothiols with large Stokes shift based on thiol-chromene click reaction.","authors":"Dongjian Zhu, Aishan Ren, Lin Xue","doi":"10.1039/d4ob01324g","DOIUrl":"https://doi.org/10.1039/d4ob01324g","url":null,"abstract":"In this study, a carbazole-based mitochondria-targeted colorimetric and NIR ratiometric fluorescent probe 1 for biothiols based on the thiol-chromene click reaction was subtly designed and synthesized. Upon interaction with biothiols (Cys, Hcy and GSH), the absorption of 1 shifted from 496 nm to 388 nm, while its fluorescence spectrum shifted from 650 nm to 530 nm. These transformations were accompanied by a visible color change from pink to colorless under visible light and from red to green when observed under a 365 nm UV lamp, which can be attributed to the click reaction of biothiols with the α,β-unsaturated ketone of the chromene moiety, subsequent pyran ring-opening and phenol formation as well as 1,6-elimination of a p-hydroxybenzyl moiety yielding 2. These advancements in 1 have allowed us to ratiometrically detect biothiols with high sensitivity (LODs of 97 nM, 94 nM and 93 nM for Cys, GSH and Hcy, respectively), a large Stokes shift (154 nm) and excellent selectivity. In addition, 1 can target mitochondria and image the fluctuation of intracellular biothiols through fluorescence ratiometry. Furthermore, the novel design strategy of modifying chromene to the N atom of quinoline was proposed for the first time.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142491283","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

Palladium-catalyzed cascade cyclization of α,β-unsaturated N-tosylhydrazones with iodoarenes: access to 2H-chromenes and 2H-quinolines. 钯催化的α、β-不饱和 N-对甲苯磺酰肼与碘醛的级联环化反应：获得 2H-苯并吡喃和 2H-喹啉。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-25 DOI: 10.1039/d4ob01300j

Yiyi Zheng, Xi-Wei Zhu, Yi-Yun Pan, Fei Sun, Long Yao, Xin-Xing Wu

引用次数: 0

Theoretical mechanistic insights on the thermal and acid-catalyzed rearrangements of N-methyl-N-nitroanilines. 关于 N-甲基-N-硝基苯胺热重排和酸催化重排的理论机理见解。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-25 DOI: 10.1039/d4ob01449a

Shi Cheng, Chongjie Su, Tian Chen, Jiaxi Xu

{"title":"Theoretical mechanistic insights on the thermal and acid-catalyzed rearrangements of N-methyl-N-nitroanilines.","authors":"Shi Cheng, Chongjie Su, Tian Chen, Jiaxi Xu","doi":"10.1039/d4ob01449a","DOIUrl":"https://doi.org/10.1039/d4ob01449a","url":null,"abstract":"The thermal and acid-catalyzed rearrangement mechanisms of N-methyl-N-nitroanilines were theoretically investigated via density functional theory (DFT) calculations for all possible proposed mechanisms. The results indicate that the thermal rearrangement of N-methyl-N-nitroanilines undergoes a radical pair complex mechanism through the homolysis of their N-N bond to generate a radical pair complex and the recombination of the radical pairs followed by aromatization. For the acid-catalyzed rearrangements, N-methyl-N-nitroanilines are first protonated on the nitrogen atom of their aniline moiety and then generate protonated N-methyl-O-nitroso-N-phenylhydroxylamines through a three-membered spirocyclic oxadiaziridine transition state. The N-protonated N-methyl-O-nitroso-N-phenylhydroxylamines favor homolytic dissociation to generate N-methylaniline cationic radical and nitrogen dioxide complexes, which further combine together and aromatize to afford protonated N-methyl-o-nitroanilines and N-methyl-p-nitroanilines, respectively. The radical pair complexes are more stable than the corresponding solvent-caged radical pairs. The thermal rearrangements require higher activation energy than the corresponding acid-catalyzed rearrangements.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142491290","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

Palladium-catalyzed C-H bond activation and decarboxylation for the assembly of indolo[1,2-f]phenanthridine. 钯催化 C-H 键活化和脱羧以组装吲哚并[1,2-f]菲啶。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-24 DOI: 10.1039/d4ob01383b

Xiaobing Liu, Yong-Liang Ban, Yanjie Liu, Mengdie Zhuang, Yao Zhou

引用次数: 0

Zn²⁺ ions improve the fidelity of metal-mediated primer extension while suppressing intrinsic and Mn²⁺-induced mutagenic effects by DNA polymerases. Zn2+ 离子提高了金属介导的引物延伸的保真度，同时抑制了 DNA 聚合酶的内在诱变效应和 Mn2+ 诱导的诱变效应。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-24 DOI: 10.1039/d4ob01433b

Tatsuya Funai, Natsumi Tanaka, Riyo Sugimachi, Shun-Ichi Wada, Hidehito Urata

{"title":"Zn2+ ions improve the fidelity of metal-mediated primer extension while suppressing intrinsic and Mn2+-induced mutagenic effects by DNA polymerases.","authors":"Tatsuya Funai, Natsumi Tanaka, Riyo Sugimachi, Shun-Ichi Wada, Hidehito Urata","doi":"10.1039/d4ob01433b","DOIUrl":"https://doi.org/10.1039/d4ob01433b","url":null,"abstract":"While Mn2+ ions are well-established for reducing the fidelity of DNA polymerases, leading to the misincorporation of nucleotides, our investigation of the effects of metal ions revealed a contrasting role of Zn2+. Here, we demonstrate that Zn2+ ions enhance the fidelity of DNA polymerases (the 3' → 5' exonuclease-deficient Klenow fragment and Taq DNA polymerase) by suppressing misincorporation during primer extension reactions. Remarkably, Zn2+ ions inhibit both intrinsic misincorporation and Mn2+-induced misincorporation of nucleotides. Furthermore, Zn2+ ions also effectively suppressed misincorporation during metal-mediated primer extension reactions, which involved forming Ag+ and Hg2+ ion-mediated base pairs. These findings suggest that Zn2+ ions inhibit both intrinsic and Mn2+-induced mismatched base pair formation. Consequently, the combined use of Mn2+ and Zn2+ ions may offer a strategy for precisely regulating the fidelity of DNA polymerases. Remarkably, Zn2+ ions even suppress misincorporation in primer extension reactions that rely on metal-mediated base pairs, and conversely, this suggests that DNA polymerases recognize metal-mediated base pairs such as T-Hg2+-T, C-Ag+-A, and C-Ag+-T as relatively stable base pairs. These results imply that Zn2+ ions may also enhance the fidelity of DNA polymerases when incorporating non-canonical nucleobases, potentially paving the way for the expansion of the genetic alphabet.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142491291","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 di/tri-substituted carbazoles involving Pd-mediated Sonogashira coupling of indolyltriflates with aryl acetylenes. 通过钯介导的吲哚基三氟酸盐与芳基乙炔的 Sonogashira 偶联合成二/三代咔唑。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-23 DOI: 10.1039/d4ob01536c

Rudrasenan Agneswaran, Arasambattu K Mohanakrishnan

引用次数: 0

Synthesis of 1,4-benzodioxepines via electrochemical oxyselenenylation of 2-O-tethered alkenyl phenylmethanol and diselenides. 通过电化学氧化 2-O 系烯基苯基甲醇和二硒化物合成 1,4-苯并二氧杂环庚烷。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-23 DOI: 10.1039/d4ob01483a

Junsheng Hou, Bingxin You, Ruiqi Lv, Xinxin Zhang, Jinyang Shen, Jiaojiao Li, Xi Zuo, Qiang Liu

引用次数: 0

Radical alkylation of acrylamides with peroxides to access mono/dialkylated fused N-heterocycles. 用过氧化物对丙烯酰胺进行自由基烷基化，以获得单/二烷基化的融合 N-杂环。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-23 DOI: 10.1039/d4ob01555j

Jie Fan, Qinqin Yan, Xueli Wang, Lijun Li, Zejiang Li

引用次数: 0

Synthesis of bis(indolyl)methanes using N-heterocyclic carbene salt as a C1 precursor. 使用 N-杂环碳烯盐作为 C1 前体合成双(吲哚基)甲烷。

IF 2.9 3区化学

Organic & Biomolecular Chemistry Pub Date : 2024-10-22 DOI: 10.1039/d4ob01568a

Bingwei Zhou, Zhao Gao, Yanhao Yang, Yuanyuan Hu

引用次数: 0