Organic Chemistry Frontiers最新文献_第2页

Discovery, total synthesis, and biosynthesis of lipopeptides with an L-threoninol unit from Aquimarina muelleri 发现，全合成和生物合成的脂肽与l -苏氨酸醇单位从水墨鱼

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-11-06 DOI: 10.1039/d6qo01405d

Jonghwan Kim,Min Kyung Ham,Seung Hwan Lee,Yumin Lee,Yujeong Jeong,Eun Jin Park,Su Jung Hwang,Jun-Pil Jang,Hyo-Jong Lee,Kyo Bin Kang,Yongseok Kwon,Chung Sub Kim

{"title":"Discovery, total synthesis, and biosynthesis of lipopeptides with an L-threoninol unit from Aquimarina muelleri","authors":"Jonghwan Kim,Min Kyung Ham,Seung Hwan Lee,Yumin Lee,Yujeong Jeong,Eun Jin Park,Su Jung Hwang,Jun-Pil Jang,Hyo-Jong Lee,Kyo Bin Kang,Yongseok Kwon,Chung Sub Kim","doi":"10.1039/d6qo01405d","DOIUrl":"https://doi.org/10.1039/d6qo01405d","url":null,"abstract":"Chemical investigation of Aquimarina muelleri KCTC 12285 T led to the identification of ten L-threoninol-containing lipopeptides, aquimarinols B-K (1-10), including seven new congeners (3 and 5-10). Detailed spectroscopic analysis and enantioselective total synthesis established the structure and absolute configuration of aquimarinol B (1) and C (4), which were found to undergo spontaneous acyl migration interconversion. The structures of the eight minor congeners were tentatively assigned through comparative LC-MS/MS analysis and chromatographic behavior. Their biosynthetic origins were elucidated by stable-isotope feeding experiments combined with ultrahigh-resolution FT-ICR MS analysis, which established L-threonine as the precursor of both the unusual L-threoninol moiety and the terminal formamide unit-the latter likely via metabolic conversion to glycine. Additionally, branched-chain amino acids (L-leucine and L-valine) and propionyl-CoA, derived from L-isoleucine catabolism, were identified as precursors of the diverse acyl chains. Together, these findings provide a comprehensive biosynthetic framework for this unusual family of L-threoninol-containing lipopeptides and significantly expand its known chemical diversity.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"34 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149360292","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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Encoding stability and dynamics in hydrogen-bonded octameric capsules through amino acid α-position design 氨基酸α-位置设计编码氢键八聚体胶囊的稳定性和动力学

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-11-06 DOI: 10.1039/d6qo01259k

Filip Perlitius,Grzegorz Markiewicz,Mateusz Gołdyn,Gokay Avci,Kim E. Jelfs,Artur R. Stefankiewicz

{"title":"Encoding stability and dynamics in hydrogen-bonded octameric capsules through amino acid α-position design","authors":"Filip Perlitius,Grzegorz Markiewicz,Mateusz Gołdyn,Gokay Avci,Kim E. Jelfs,Artur R. Stefankiewicz","doi":"10.1039/d6qo01259k","DOIUrl":"https://doi.org/10.1039/d6qo01259k","url":null,"abstract":"How local molecular determinants encode stability and dynamics in supramolecular assemblies remains a central challenge in adapting biological design principles for synthetic systems. Here, we systematically investigate eleven amino acid-functionalized benzene-1,3,5-tricarboxamides to elucidate how chirality, α-substitution, and side-chain architecture control the formation, stability and function of noncovalent octameric capsules. Achiral derivatives lacking an α-hydrogen exhibit poor solubility in noncompetitive solvents and preferentially form extended polymeric aggregates, highlighting the role of the α-H motif in mediating solvation and preorganization of hydrogen-bonding networks. In contrast, chiral analogues retaining the α-H group readily self-assemble into discrete, D2-symmetric octameric capsules. Substitution of the α-hydrogen with a methyl group disrupts solubility and capsular stability; however, introduction of long aliphatic side chains partially restores capsule formation, albeit with increased dynamics. Moreover, α-methylation profoundly affects capsule function, leading to a complete loss of fullerene encapsulation ability compared to the corresponding α-H-containing capsules. Overall, these results reveal how subtle variations at the α-position translate into emergent differences in stability, dynamics, function and architecture of hydrogen-bonded supramolecular capsules.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"12 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149360291","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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C–H functionalization of methyl groups of azaarenes and acetamides with DMF: one-pot synthesis of terminal and TMS-capped alkynes 用DMF催化氮扎芳烃和乙酰胺甲基的C-H功能化：端炔和tms端炔的一锅合成

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-11-05 DOI: 10.1039/d6qo01216g

Yufei Zhang,Yu Wu,Yan-En Wang,Shengmin Mou,Yaqi Yuan,Zifan Wang,Kerui Jian,Dan Xiong,Patrick J. Walsh,Jianyou Mao

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Synergistic Palladium/Copper-Catalyzed Regioselective Synthesis of Polysubstituted Pyridines from Cyclic Carbonates and Glycine Ester 钯/铜协同催化环碳酸酯和甘氨酸酯的区域选择性合成多取代吡啶

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-11-05 DOI: 10.1039/d6qo01336h

Jiayi Zong,Jiahao Wang,Binqi Fu,Keyun Zi,Wanghao Wu,Boxuan Zhang,Guohui Zheng,Miaolin Ke,Fener Chen

{"title":"Synergistic Palladium/Copper-Catalyzed Regioselective Synthesis of Polysubstituted Pyridines from Cyclic Carbonates and Glycine Ester","authors":"Jiayi Zong,Jiahao Wang,Binqi Fu,Keyun Zi,Wanghao Wu,Boxuan Zhang,Guohui Zheng,Miaolin Ke,Fener Chen","doi":"10.1039/d6qo01336h","DOIUrl":"https://doi.org/10.1039/d6qo01336h","url":null,"abstract":"Polysubstituted pyridines are privileged structural motifs widely found in pharmaceuticals, bioactive natural products, ligands, and functional materials. Despite their significance, the development of efficient and sustainable synthetic methods that employ readily available starting materials under mild conditions remains a considerable challenge. Herein, we report a Pd/Cu synergistic catalytic strategy for the construction of polysubstituted pyridines from readily available glycine esters and cyclic carbonates. Our approach copper leverages to activate the α C-H bond of amino protected glycine esters, while palladium facilitates the subsequent decarboxylative annulation with cyclic carbonates, enabling a streamlined one pot cascade process that involves C-allylic alkylation, amine ketone condensation and aromatization. This synergistic catalytic sys-tem operates under mild conditions, and exhibits broad substrate scope with excellent regioselectivity and functional group tolerance. This work not only provides a practical and sustainable route to polysubstituted pyridines but also highlights the potential of Pd/Cu cooperative catalysis in enabling complex heterocycle construction from simple building blocks, offering a valuable tool for medicinal chemistry and materials science.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"29 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149360152","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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Palladium-Bisphosphine-Catalyzed Enantioselective Allylic Amination for Construction of Non-Biheteroaryl N-N Atropisomers 钯-二膦催化烯丙基胺化反应构建非生物杂芳基N-N - Atropisomers

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-11-05 DOI: 10.1039/d6qo01330a

Huang-Jie Zhou,Chuan Wang,Jing Chen,Hao Chen,Jia-Rui Li,Xingwang Wang

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Access to Perfluoroalkenyl Pyrazolo[5,1-a]isoquinolines by Merging [3+2] Annulation with Successive Vicinal C(sp3)-F Bond Cleavage 全氟烯基吡唑啉[5,1-a]异喹啉类化合物[3+2]环化与相邻C(sp3)-F键连续裂解

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-11-05 DOI: 10.1039/d6qo01461e

Jiawei He,Qian Wang,Zheng Zhong,Yaling Zhu,Wenyu Liang,Xiang Liu,Hua Cao

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Metal-free regiospecific synthesis of 1,5-disubstituted 1,2,3-triazoles from aryldiazonium tetrafluoroborates and propargylamines 由四氟硼酸芳基重氮和丙胺合成1,5-二取代1,2,3-三唑的无金属区域特异性

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-11-05 DOI: 10.1039/d6qo01511e

Shiv Chand,Abhinay Shukla,Saurabh Kumar,Mayank Murthy,Krishna Nand Singh

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N-Methylacridone Salt as a PCET-Driven Photocatalyst in the Synthesis of γ-Lactones from Unsaturated Compounds and Cyclic Diacyl Peroxides n -甲基吖啶酮盐作为pcet驱动光催化剂在不饱和化合物和环二酰基过氧化物合成γ-内酯中的应用

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-11-05 DOI: 10.1039/d6qo01092j

Diana V. Shuingalieva,Alexander O. Ustyuzhanin,Alexander Olegovich Terent'ev,Vera A. Vil'

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Construction of 2H-Chromene and Quinoline Skeleton via Metal-Free CN Bond Cleavage of Unstrained Pyrrolidine 通过非应变吡咯烷的无金属CN键裂解构建2h -铬-喹啉骨架

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-11-05 DOI: 10.1039/d6qo01442a

Yi Zhang,Renchao Ma,Weiwei Fang,Lei Wang,Yongmin Ma,Bihong Zhu

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Assessing the Viability of 1,4‑Nickel/Hydrogen migration in Ni‑Catalyzed Reductive Cross‑Coupling: A Computational Perspective 评估镍催化还原交叉耦合中1,4 -镍/氢迁移的可行性：计算视角

IF 5.4 1区化学

Organic Chemistry Frontiers Pub Date : 2026-11-04 DOI: 10.1039/d6qo01423b

Song Liu,Wei Chen,Peng Yan,Liangqi Zhu,Xinyu Long,Dianmin Zhang,Mingyin Liao

{"title":"Assessing the Viability of 1,4‑Nickel/Hydrogen migration in Ni‑Catalyzed Reductive Cross‑Coupling: A Computational Perspective","authors":"Song Liu,Wei Chen,Peng Yan,Liangqi Zhu,Xinyu Long,Dianmin Zhang,Mingyin Liao","doi":"10.1039/d6qo01423b","DOIUrl":"https://doi.org/10.1039/d6qo01423b","url":null,"abstract":"Transition metal-catalyzed migratory cross-coupling has emerged as a powerful strategy for the selective functionalization of remote inert C–H bonds. In particular, 1,n-Ni/H (n = 2 or 4) migration offers a mild and efficient platform for late-stage functionalization of complex molecules. In this work, density functional theory calculations were performed to elucidate the mechanism of a Ni-catalyzed reductive cross-coupling reaction originally proposed to proceed via 1,4-Ni/H migration. Our computational results, however, rule out this pathway due to a prohibitively high kinetic barrier. Instead, an alternative metal non-migration mechanism is identified, involving sequential radical addition, concerted C–Ni bond homolytic cleavage coupled oxidative addition, and hydrogen atom transfer. The calculated regioselectivity is governed by the relative energies of competing radical addition and oxidative addition transition states, while stereoselectivity arises primarily from steric repulsion within the 1,5‑hydrogen atom transfer step. These findings provide a revised mechanistic framework for Ni-catalyzed reductive cross-coupling and offer valuable insights for the rational design of related transformations.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"21 1","pages":""},"PeriodicalIF":5.4,"publicationDate":"2026-11-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149359404","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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