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Paired electrocatalysis enabled oxidative coupling of styrenes with alkyl radicals. 成对电催化使苯乙烯与烷基自由基发生氧化偶联。
IF 2.9 3区 化学 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-11-07 DOI: 10.1039/d4ob01605j
Dong Li, Ling Zhang, Daixi Li, Peng Yu, Tao Shen

A paired electrocatalysis strategy for intermolecular oxidative cross-dehydrocoupling between styrenes and ethers or p-methylphenol derivatives using ketone as a mild oxidant is described. This approach enables the generation of Csp3 carbon-centered radicals through anodic oxidation, followed by reductive coupling of ketones at the cathode, ultimately yielding valuable oxidative alkylation products.

本文介绍了一种配对电催化策略,该策略使用酮作为温和的氧化剂,实现苯乙烯与醚或对甲基苯酚衍生物之间的分子间氧化交叉脱氢偶联。这种方法通过阳极氧化生成 Csp3 碳中心自由基,然后在阴极进行酮的还原偶联,最终产生有价值的氧化烷基化产物。
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引用次数: 0
Interrogating the potential of helical aromatic foldamers for protein recognition. 探究螺旋芳香折叠器识别蛋白质的潜力。
IF 2.9 3区 化学 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-11-06 DOI: 10.1039/d4ob01436g
Sunbum Kwon, Vasily Morozov, Lingfei Wang, Pradeep K Mandal, Stéphane Chaignepain, Céline Douat, Ivan Huc

A biotinylated helical aromatic oligoamide foldamer equivalent in size to a 24mer peptide was designed without any prejudice other than to display various polar and hydrophobic side chains at its surface. It was synthesized on solid phase, its P- and M-helical conformers were separated by HPLC on a chiral stationary phase, and the solid state structure of a non-biotinylated analogue was elucidated by X-ray crystallography. Pull-down experiments from a yeast cell lysate using the foldamer as a bait followed by proteomic analysis revealed potential protein binding partners. Three of these proteins were recombinantly expressed. Biolayer interferometry showed submicromolar binding demonstrating the potential of a given foldamer to have affinity for certain proteins in the absence of design considerations. Yet, binding selectivity was low in all three cases since both P- and M-conformers bound to the proteins with similar affinities.

除了在其表面显示各种极性和疏水侧链外,我们还设计了一种生物素化的螺旋芳香族寡酰胺折叠聚合物,其大小相当于 24 聚肽。该产品在固相上合成,其 P-和 M-螺旋构象在手性固定相上通过高效液相色谱进行分离,并通过 X 射线晶体学阐明了非生物素化类似物的固态结构。以折叠酶为诱饵从酵母细胞裂解物中进行拉取实验,然后进行蛋白质组分析,发现了潜在的蛋白质结合伙伴。其中三种蛋白质被重组表达。生物层干涉测量法显示了亚摩尔级的结合力,这表明在没有设计考虑的情况下,特定的折叠聚合体对某些蛋白质具有亲和力。然而,这三种情况下的结合选择性都很低,因为 P 型和 M 型折叠体与蛋白质的结合亲和力相似。
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引用次数: 0
Synthesis of the 5/5-spiroindimicin alkaloids: development of a general synthetic approach and biological investigations. 5/5 螺吲哚生物碱的合成:通用合成方法的开发和生物学研究。
IF 2.9 3区 化学 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-11-06 DOI: 10.1039/d4ob01552e
Ankush Banerjee, Tiffany A Brisco, Sneha Ray, Arani Datta, Xiaoyu Zhang, Zhen Zhang, Alexander A Busse, Hanspeter Niederstrasser, Krissty Sumida, Bruce A Posner, Dawn M Wetzel, Margaret A Phillips, Myles W Smith

We describe the development of a unified synthetic strategy for the preparation of all known 5/5-spirocyclic spiroindimicin (SPM) alkaloids, namely spiroindimicins B-G. The present synthetic route relies on four fundamental transformations: Grignard-based fragment coupling between halogenated pyrrolemetal and isatin partners, Suzuki coupling to generate a triaryl scaffold encompassing all requisite skeletal atoms of the natural products, Lewis acid-mediated spirocyclization to construct the 5/5-spirocyclic core, and chemoselective lactam reduction. The developed syntheses are step-economic (6-7 steps from commercial materials), scalable, and amenable to analogue synthesis. Preliminary investigations into a catalytic asymmetric spirocyclization towards an enantioselective SPM synthesis are also described. Further studies of the antiparasitic properties of this class have revealed promising activity against T. brucei for certain congeners. Together with our prior approach to the 6/5-family members, our work constitutes a synthetic solution to all known spiroindimicin natural products.

我们介绍了一种用于制备所有已知 5/5-螺环螺环吲哚生物碱(SPM)(即螺环吲哚生物碱 B-G)的统一合成策略。本合成路线依赖于四种基本转化:卤化吡咯金属和异靛红伙伴之间基于格氏片段偶联,通过铃木偶联生成包含天然产物所有必要骨架原子的三芳基支架,通过路易斯酸介导的螺环化反应构建 5/5 螺环核心,以及化学选择性内酰胺还原。所开发的合成方法具有步骤经济性(使用商业材料只需 6-7 个步骤)、可扩展性和可进行类似物合成的特点。此外,还介绍了催化不对称螺环化实现对映体选择性 SPM 合成的初步研究。对该类化合物抗寄生虫特性的进一步研究表明,某些同系物对布鲁西绦虫具有良好的活性。结合我们之前对 6/5 家族成员的研究,我们的研究工作为所有已知的螺氨蛋白天然产物提供了一种合成解决方案。
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引用次数: 0
Electrochemical one-pot cascade synthesis of thio(seleno)cyanato-substituted thiazolidine-2-imines without external electrolyte. 无外加电解质电化学一锅级联合成硫(硒)氰基取代的噻唑烷-2-亚胺。
IF 2.9 3区 化学 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-11-05 DOI: 10.1039/d4ob01626b
Xiao Yu, Liqiang Hao, Xian Liu, Shengkui Jin, Yangchen Li, Yiping Liu, Yafei Ji

A novel synthetic method has been developed for generating thio(seleno)cyanato-substituted thiazolidine-2-imines via an electrochemical one-pot cascade reaction. This reaction employs isothiocyanates, N-2-en-1-amines, and KSCN (or KSeCN) under mild conditions, obviating the need for metals, chemical oxidants, and external electrolytes. The protocol is effective with unactivated alkenes and facilitates the synthesis of five- and six-membered thio(seleno)cyanato-substituted thiazolidine-2-imines. The versatility is demonstrated by its straightforward operation and scalability to gram-scale production, underscoring its potential for broader application.

我们开发了一种新的合成方法,通过电化学单锅级联反应生成硫(硒)氰基取代的噻唑烷-2-亚胺。该反应采用异硫氰酸酯、N-2-烯-1-胺和 KSCN(或 KSeCN),条件温和,无需金属、化学氧化剂和外部电解质。该方法对未活化的烯类有效,并有助于合成五元和六元硫(硒)氰基取代的噻唑烷-2-亚胺。该方法操作简便,可扩大到克级生产规模,突出了其广泛应用的潜力。
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引用次数: 0
Recent advances in photocatalytic and transition metal-catalyzed synthesis of disulfide compounds. 光催化和过渡金属催化合成二硫化物的最新进展。
IF 2.9 3区 化学 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-11-05 DOI: 10.1039/d4ob01362j
Jia-Lin Tu

Disulfide bonds are essential in protein folding, cellular redox balance, materials science, and drug development. Despite existing synthetic methods, the efficient and selective synthesis of unsymmetrical disulfides remains challenging. This review highlights innovative approaches in visible light photocatalysis, including decarboxylation, deoxydisulfidation of alcohols, and direct C-H disulfidation, showcasing broad substrate applicability and functional group tolerance under mild conditions. Additionally, it explores transition metal-catalyzed systems with copper, nickel, palladium, chromium, Iridium, Rhodium molybdenum, and scandium, offering effective strategies for unsymmetrical disulfide bond formation and late-stage functionalization of complex molecules through reductive coupling, selective oxidation, and novel insertion reactions.

二硫键在蛋白质折叠、细胞氧化还原平衡、材料科学和药物开发中至关重要。尽管已有合成方法,但高效、选择性地合成非对称二硫化物仍具有挑战性。本综述重点介绍了可见光光催化的创新方法,包括脱羧、醇的脱氧二硫化和直接 C-H 二硫化,展示了温和条件下广泛的底物适用性和官能团耐受性。此外,该书还探讨了铜、镍、钯、铬、铱、铑钼和钪等过渡金属催化系统,通过还原偶联、选择性氧化和新型插入反应,为非对称二硫键的形成和复杂分子的后期官能化提供了有效的策略。
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引用次数: 0
Novel electron donor-acceptor (EDA) complex promoted arylation of 2-oxo-2H-chromene-3-carbonitriles under visible light irradiation. 新型电子供体-受体(EDA)复合物在可见光照射下促进了 2-oxo-2H-chromene-3-carbonitriles 的芳基化反应。
IF 2.9 3区 化学 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-11-05 DOI: 10.1039/d4ob01493f
Tanmoy Sahoo, Dasari Vijaya Prasanna, B Sridhar, B V Subba Reddy

An efficient and operationally simple photochemical method has been demonstrated under transition metal-free, photocatalyst-free, and oxidant-free conditions. In recent times, diaryliodonium salts have become one of the most popular arylating sources under photoinduced conditions. Herein, we developed a visible light induced arylation of heterocycles using an EDA complex that is formed in situ from 2,6-lutidine and diaryliodonium triflate. Under light irradiation, the EDA complex generates the aryl radical that undergoes addition with 2-oxo-2H-chromene-3-carbonitriles via an SET process. This method serves as an effective tool to access biologically active and pharmaceutically relevant coumarin scaffolds.

在无过渡金属、无光催化剂和无氧化剂的条件下,一种高效且操作简单的光化学方法已经得到证实。近来,二芳基碘鎓盐已成为光诱导条件下最受欢迎的芳基化源之一。在此,我们开发了一种利用 2,6- 丁烷和三酸二亚碘鎓原位形成的 EDA 复合物进行可见光诱导的杂环芳基化反应。在光照射下,EDA 复合物生成芳基自由基,芳基自由基通过 SET 过程与 2-氧代-2H-铬-3-甲腈发生加成反应。这种方法是获得具有生物活性和医药相关性的香豆素支架的有效工具。
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引用次数: 0
[Au]/[Ag]-catalysed synthesis of non-hydrolysable C-glycosides. [金]/[银]催化的非水解 C-糖苷的合成。
IF 2.9 3区 化学 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-11-04 DOI: 10.1039/d4ob01339e
Saptashwa Chakraborty, Daksh Telang, Bijoyananda Mishra, Srinivas Hotha

Many C-glycosides are found in natural products, drugs and small molecular probes. Herein, we report the synthesis of C-glycosides by the [Au]/[Ag]-catalysed activation of ethynylcyclohexyl glycosyl carbonate donors. This mild, catalytic, fast and high yielding protocol enables the synthesis of a diverse array of C-glycosides that were otherwise challenging to synthesize.

在天然产物、药物和小分子探针中发现了许多 C-糖苷。在此,我们报告了通过[Au]/[Ag]催化活化乙炔基环己糖基碳酸酯供体合成 C-糖苷的过程。这种温和、催化、快速、高产的方法可以合成多种多样的 C-糖苷,而这些糖苷的合成在其他方法中是很难实现的。
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引用次数: 0
Silver-mediated radical cascade trifluoromethylthiolation/cyclization of benzimidazole derivatives with AgSCF3. 以 AgSCF3 为媒介的苯并咪唑衍生物的银介导自由基级联三氟甲基硫代化/环化反应。
IF 2.9 3区 化学 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-11-04 DOI: 10.1039/d4ob01582g
Pan Liu, Yang Geng, Dapeng Zou, Yangjie Wu, Yusheng Wu

A silver-mediated cascade trifluoromethylthiolation/cyclization of unactivated alkenes has been investigated. This strategy employs AgSCF3 as the trifluoromethylthiolating reagent to obtain a variety of useful trifluoromethylthiolated tricyclic imidazol derivatives in reasonable yields. Preliminary mechanistic studies indicate that the present reaction takes place via a radical process. This method is distinguished by its atom economy, wide functional group compatibility, operational simplicity and product diversity.

研究了银介导的未活化烯烃的级联三氟甲基硫代/环化反应。该策略采用 AgSCF3 作为三氟甲基硫代试剂,以合理的产率获得了多种有用的三氟甲基硫代三环咪唑衍生物。初步的机理研究表明,本反应是通过自由基过程进行的。该方法具有原子经济性、广泛的官能团兼容性、操作简便性和产品多样性等特点。
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引用次数: 0
Non-natural sialic acid derivatives with o-nitrobenzyl alcohol substituents for light-mediated protein conjugation and cell imaging. 具有邻硝基苄醇取代基的非天然硅酸衍生物,用于光介导的蛋白质连接和细胞成像。
IF 2.9 3区 化学 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-11-04 DOI: 10.1039/d4ob01563k
Guo-Biao Zhu, Chen Guo, Xue-Lian Ren, Ming-Zhe Li, Di-Ya Lu, Xi-Le Hu, He Huang, Tony D James, Xiao-Peng He

We have synthesized two sialic acid derivatives substituted with an ortho-nitrobenzyl alcohol (o-NBA) group that can undergo light-mediated conjugation with primary amines at their 5- or 9-carbon position. The o-NBA derivatives were shown to react with multiple lysine residues of human serum albumin (HSA) when exposed to 365 nm light irradiation within 10 min. The resulting sugar conjugates were characterized by mass spectroscopy and used for fluorescence-based cell imaging.

我们合成了两种被邻硝基苯甲醇(o-NBA)基团取代的硅酸衍生物,它们可以在 5 碳位或 9 碳位与伯胺发生光介导的共轭反应。在 365 纳米的光照射下,o-NBA 衍生物在 10 分钟内可与人血清白蛋白(HSA)的多个赖氨酸残基发生反应。所产生的糖共轭物通过质谱进行表征,并用于基于荧光的细胞成像。
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引用次数: 0
Base-promoted tandem ring-opening/ring-closing of N-alkynyl-2-oxazolidinones enables facile synthesis of 2-oxazolines. 在碱促进下,N-炔基-2-噁唑烷酮的串联开环/闭环可简化 2-噁唑啉的合成。
IF 2.9 3区 化学 Q1 CHEMISTRY, ORGANIC Pub Date : 2024-10-31 DOI: 10.1039/d4ob01561d
Xingyuan Ye, Peng Bao, Yan Pan, Han Xiao, Qiuwen Li, Guangke He

A K2CO3-promoted tandem ring-opening/ring-closing of N-alkynyl-2-oxazolidinones has been described, affording 2-oxazolines in 42-99% yields without column chromatography isolation. This operationally simple reaction proceeds under ambient conditions without a transition-metal catalyst and an external oxidant and can be applied for the late-stage functionalization of biologically active compounds.

该研究描述了一种由 K2CO3 促进的 N-alkynyl-2-oxazolidinones 串联开环/闭环反应,无需柱层析分离即可得到产率为 42-99% 的 2-恶唑啉类化合物。这种操作简单的反应在环境条件下进行,无需过渡金属催化剂和外部氧化剂,可用于生物活性化合物的后期官能化。
{"title":"Base-promoted tandem ring-opening/ring-closing of <i>N</i>-alkynyl-2-oxazolidinones enables facile synthesis of 2-oxazolines.","authors":"Xingyuan Ye, Peng Bao, Yan Pan, Han Xiao, Qiuwen Li, Guangke He","doi":"10.1039/d4ob01561d","DOIUrl":"10.1039/d4ob01561d","url":null,"abstract":"<p><p>A K<sub>2</sub>CO<sub>3</sub>-promoted tandem ring-opening/ring-closing of <i>N</i>-alkynyl-2-oxazolidinones has been described, affording 2-oxazolines in 42-99% yields without column chromatography isolation. This operationally simple reaction proceeds under ambient conditions without a transition-metal catalyst and an external oxidant and can be applied for the late-stage functionalization of biologically active compounds.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142556614","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
期刊
Organic & Biomolecular Chemistry
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