Article
Chemistry, Applied
Bohdan Biletskyi, Lingyu Kong, Alphonse Tenaglia, Herve Clavier
Summary: A novel cobalt-catalyzed hydroalkynylation reaction was discovered, enabling the synthesis of enynes from vinylaziridines. The study showed that the cobalt-catalyzed hydroalkynylation reaction is mainly applicable to phenylacetylene derivatives, with branched and linear enynes formed in equimolar proportions in most cases.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Organic
Tanumay Sarkar, Kangkan Talukdar, Bijay Ketan Das, Tariq A. Shah, Bijoy Debnath, Tharmalingam Punniyamurthy
Summary: In recent years, the transition-metal-aided stereoselective construction of sp(3)-carbon-rich heterocyclic scaffolds using strained-ring systems has received considerable attention. Catalytic ring-enlargement of vinylaziridines and vinyloxiranes plays a predominant role in synthesizing high sp(3)-content biorelevant heterocyclic compounds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Tao Zhang, Shichong Wang, Dandan Zuo, Jingjing Zhao, Wen Luo, Chaojie Wang, Pan Li
Summary: A palladium-catalyzed carbonylative [5+1] cycloaddition reaction of N-tosyl vinylaziridines with CO has been developed, providing a practical and efficient method for synthesizing different types of δ-lactams. The choice of solvent allows for control over the type of lactam produced. Additionally, this method exhibits excellent step- and atom-economy and shows higher regioselectivity towards [5+1] cycloaddition.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Weibin Xie, Masahiko Hayashi, Ryosuke Matsubara
Summary: In this study, we report a novel synthesis method for borylfuroxans through the reaction of sulfonylfuroxans with Lewis base-ligated boranes under radical conditions. Additionally, we demonstrate the transformation of borylfuroxans to a variety of 1,2-dioximes and their derivatives.
Review
Chemistry, Multidisciplinary
Lana K. Moree, Logan A. V. Faulkner, James D. Crowley
Summary: In this tutorial review, the general methods for synthesizing heterometallic metallosupramolecular architectures (MSAs), specifically heterometallic cages, are examined. The intrinsic properties and potential applications of these cages as host-guest systems and reaction catalysts are discussed.
CHEMICAL SOCIETY REVIEWS
(2024)
Article
Chemistry, Organic
Melanie A. Drew, Andrew J. Tague, Christopher Richardson, Stephen G. Pyne, Christopher J. T. Hyland
Summary: A two-step Pd-catalyzed (3 + 2) cycloaddition/HNO2 elimination reaction sequence has been developed to efficiently produce novel cyclic 1,3-dien-5-yne systems with high atom efficiency. The research allows for the selective isolation of a single diastereoisomer of the cycloadduct, demonstrating the potential for practical applications in organic synthesis.
Review
Chemistry, Multidisciplinary
Dylan G. Boucher, Emily Carroll, Zachary A. Nguyen, Rohit G. Jadhav, Olja Simoska, Kevin Beaver, Shelley D. Minteer
Summary: Bioelectrocatalytic synthesis involves the conversion of electrical energy into valuable products using biocatalysts, combining the specificity of biocatalysis with energy-related electrocatalysis. This review provides an introduction to key concepts in bioelectrosynthetic systems, including methods of biocatalyst utilization, setup of bioelectrosynthetic cells, and analytical methods for assessing bioelectrocatalysts. It outlines important applications in ammonia production and small-molecule synthesis for enzymatic and microbial systems, serving as a valuable resource for non-specialists interested in bioelectrosynthetic research.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Joshua L. Turnbull, Brittany R. Benlian, Ryan P. Golden, Evan W. Miller
Summary: Xanthene fluorophores, including 3-phosphonofluoresceins, exhibit enhanced water solubility and cellular permeability compared to their 3-carboxy counterparts, while also showing improved photo-stability and modulation of spirocyclization tendency through esterification. The esterified bis-acetoxymethyl form of 3-phosphonofluorescein can enter living cells, resulting in significantly increased cellular brightness. The development of phosphono-voltage sensitive fluorophores, such as Phosphono-VF2.1.Cl, demonstrates excellent membrane localization, cellular brightness, and voltage sensitivity for intracellular imaging and membrane potential sensing applications.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Polymer Science
Xabier Lopez de Pariza, Paula Fanlo, Lucas Polo Fonseca, Alaitz Ruiz de Luzuriaga, Haritz Sardon
Summary: This review article focuses on the potential of polythiourethanes as sustainable alternatives in the circular economy. The synthesis routes for polythiourethanes, particularly catalysis and non-isocyanate routes, are discussed. The properties and dynamic behavior of polythiourethane materials, as well as the opportunities in chemical recycling and reprocessing, are highlighted. Furthermore, the future challenges and opportunities in advanced applications and manufacturing processes are explored.
PROGRESS IN POLYMER SCIENCE
(2023)
Review
Chemistry, Multidisciplinary
Li Ding, Zi-Di Yu, Xiao-Ye Wang, Ze-Fan Yao, Yang Lu, Chi-Yuan Yang, Jie-Yu Wang, Jian Pei
Summary: Polymer semiconductors, composed of carbon-based pi conjugated backbone, have been studied for decades as active layers of various organic electronic devices. They combine the advantages of metal and semiconductor electrical conductivity with the mechanical behavior of plastics, making them a promising modulable electronic material. However, despite significant efforts, there is still no clear understanding of the relationship between intrinsic molecular structures, microstructures, and device performances. This review summarizes the development of polymer semiconductors, emphasizing the role of multilevel microstructures in determining device performance, and discusses the challenges and future opportunities in this field.
Review
Chemistry, Multidisciplinary
Zhenhui Ma, Jeotikanta Mohapatra, Kecheng Wei, J. Ping Liu, Shouheng Sun
Summary: The review discusses the effects of anisotropy on magnetic nanoparticles and their potential applications in various fields.
Review
Chemistry, Multidisciplinary
Dario Marchionni, Sumon Basak, Alireza Nazari Khodadadi, Assunta Marrocchi, Luigi Vaccaro
Summary: The past decade has witnessed a renewed interest in borazines and BN-doped polycyclic aromatic hydrocarbons due to their potential in various applications. This review critically examines the synthesis methods of (substituted) B3N3 motifs and focuses on the discussion of borazine-doped carbon structures developed for materials science applications.
ADVANCED FUNCTIONAL MATERIALS
(2023)
Review
Chemistry, Applied
Damiano Tanini, Antonella Capperucci
Summary: The synthesis and study of organoselenium compounds have received extensive attention, with selenium-containing organic molecules being widely used in organic synthesis, materials science, and medicinal chemistry. Selenols are a versatile class of molecules that easily undergo various transformations and play important roles in chemical sciences.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Multidisciplinary
Siowwoon Ng, Martin Pumera
Summary: Germanene, as a germanium analog of graphene, has shown great potential as a two-dimensional layered material with customizable properties and new functionalities. This review comprehensively covers the preparation, functionalization, and properties of germananes, as well as their applications in optoelectronics, catalysis, energy conversion and storage, sensors, and biomedical areas.
ADVANCED MATERIALS
(2023)
Article
Engineering, Chemical
Catia Algieri, Enrico Drioli
Summary: Membrane-based technology is attracting attention due to its low energy consumption, mild operating conditions, and high efficiency. Polymeric membranes are widely used for their low cost and reproducible preparation, but face issues like fouling and trade-off between permeability and selectivity. Inorganic membranes like zeolite membranes, with their hydrophilic nature, high stability, permeability, and selectivity, offer solutions to these problems. Their molecular-level pore size and adsorption property make them suitable for a variety of separation processes, although challenges like reproducibility, defects, and high manufacturing costs still hinder their industrial-scale application.
SEPARATION AND PURIFICATION TECHNOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Junpei Matsuoka, Shinsuke Inuki, Yuka Matsuda, Yoichi Miyamoto, Mayumi Otani, Masahiro Oka, Shinya Oishi, Hiroaki Ohno
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Biochemistry & Molecular Biology
Takuro Matsuoka, Chihiro Motozono, Akira Hattori, Hideaki Kakeya, Sho Yamasaki, Shinya Oishi, Hiroaki Ohno, Shinsuke Inuki
Summary: The study showed that the stereocenters at the 2'- and 3'- OH groups in the ribityl tail are crucial for MAIT cell activation, while the 4'- OH group does not significantly affect the regulation of MAIT cell activity. Furthermore, it was found that 5-OP-RU forms a covalent bond to MR1 in cells within 1 hour.
Correction
Chemistry, Organic
Ayuta Yamaguchi, Shinsuke Inuki, Yusuke Tokimizu, Shinya Oishi, Hiroaki Ohno
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Shinsuke Inuki, Hiroaki Ohno
Summary: This review discusses the total syntheses of sphingosine analogues, including myriocin, mycestericins, and sphingofungin E, focusing on the strategies used for constructing the unique α-amino acid motifs in these compounds with stereoselectivity. Various methods, such as C-C/C-N bond formation and desymmetrization strategies, have been developed to create efficient and divergent synthetic routes.
Article
Chemistry, Multidisciplinary
Luca C. Greiner, Junpei Matsuoka, Shinsuke Inuki, Hiroaki Ohno
Summary: The exploitation of nitrogen-functionalized reactive intermediates plays a crucial role in the synthesis of biologically relevant scaffolds, especially those based on gold carbenes. This personal account provides a detailed explanation of the contribution to this sector by developing efficient gold-catalyzed cascade processes based on diversely functionalized azido-alkynes, with challenging cyclizations and their subsequent applications in the synthesis of pharmaceutically relevant scaffolds and natural products being key features of the research.
Article
Chemistry, Multidisciplinary
Luca C. Greiner, Shinsuke Inuki, Norihito Arichi, Shinya Oishi, Rikito Suzuki, Tomohiro Iwai, Masaya Sawamura, A. Stephen K. Hashmi, Hiroaki Ohno
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Luca C. Greiner, Shinsuke Inuki, Norihito Arichi, Shinya Oishi, Rikito Suzuki, Tomohiro Iwai, Masaya Sawamura, A. Stephen K. Hashmi, Hiroaki Ohno
Summary: This study demonstrates the successful synthesis of benzannulated indole-fused medium-sized tetracycles through alpha-imino gold carbene chemistry, providing a new approach to explore bioactive compounds.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Hiroki Komatsu, Takaya Ikeuchi, Hitomi Tsuno, Norihito Arichi, Kosuke Yasui, Shinya Oishi, Shinsuke Inuki, Aiko Fukazawa, Hiroaki Ohno
Summary: A novel method based on gold-catalyzed cascade cyclization of aminoallenynes for the direct construction of tricyclic nitrogen heterocycles is described. Efficient synthesis of 1,2-dihydrobenzo[cd]indole derivatives was achieved by promoting the expected biscyclization reaction of hydroxyisobutyryl-protected aminoallenynes with a catalytic amount of BrettPhosAuNTf(2) in the presence of iPrOH. The resulting tricyclic products were further converted into nitrogen-containing polycyclic aromatic compounds (N-PACs) with highly conjugated pi-electron systems.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Medicinal
Takashi Kitamura, Rikito Suzuki, Shinsuke Inuki, Hiroaki Ohno, Kerry L. McPhail, Shinya Oishi
Summary: A coibamide A mimetic was designed with altered ester linkage and amino acid configurations in the macrocyclic structure, leading to the discovery of more potent derivatives. The structural-activity relationship study revealed a shared SAR with apratoxin A, suggesting a common binding site for the Tyr(Me) side chain at the luminal end of Sec61 alpha.
ACS MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Multidisciplinary Sciences
Hiroki Akiba, Tomoko Ise, Satoshi Nagata, Haruhiko Kamada, Hiroaki Ohno, Kouhei Tsumoto
Summary: In this study, a bispecific antibody (BsAb) linked by IMPTS without an extra Cys residue was successfully designed and used to bind to both TNFR2 and CD30. Cleaved side product formation was minimized under optimized conditions, making the fine-tuned design suitable for producing IgG-like BsAbs with high symmetry between antigen-binding fragments.
SCIENTIFIC REPORTS
(2021)
Article
Chemistry, Multidisciplinary
Luca C. C. Greiner, Norihito Arichi, Shinsuke Inuki, Hiroaki Ohno
Summary: In this study, phenyl azides substituted by an (alkylphenyl)ethynyl group were found to facilitate benzylic sp(3)(C-H) functionalization under the presence of a JohnPhosAu catalyst, resulting in the synthesis of indole-fused tetra- and pentacycles through divergent N- or C-cyclization. The chemoselectivity of the reaction was found to be influenced by the counter-anion, the electron density of the alpha-imino gold(I) carbene, and the alkyl groups stabilizing the benzylic carbocation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Medicinal
Atsuhito Tsuji, Takahiro Masuya, Norihito Arichi, Shinsuke Inuki, Masatoshi Murai, Hideto Miyoshi, Hiroaki Ohno
Summary: We identified a symmetric bis-sulfonamide compound, KPYC01112, as an inhibitor targeting NADH-quinone oxidoreductase. Structural modifications of KPYC01112 led to the discovery of more potent inhibitors 32 and 35. A photoaffinity labeling experiment with a newly synthesized photoreactive bis-sulfonamide revealed its binding to the subunits of complex I.
ACS MEDICINAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Medicinal
Shinsuke Inuki, Hitomi Tabuchi, Chiaki Matsuzaki, Yasunori Yonejima, Keiko Hisa, Ikuo Kimura, Kenji Yamamoto, Hiroaki Ohno
Summary: Exopolysaccharides (EPSs) are widely present in natural products made by bacteria, fungi, and algae, and some of them have interesting biological properties such as anticancer and immunomodulatory activities. Our recent study found that EPSs derived from Leuconostoc mesenteroides ssp. mesenteroides strain NTM048 enhanced the production of mucosal immunoglobulin A (IgA) in mice. In this study, we described the synthesis and evaluation of tetrasaccharide fragments of NTM048 EPS to gain insights into the molecular mechanism responsible for the induction of IgA.
CHEMICAL & PHARMACEUTICAL BULLETIN
(2022)
Article
Chemistry, Organic
Ayuta Yamaguchi, Shinsuke Inuki, Katsumi Ohta, Shinya Oishi, Akira Asai, Hiroaki Ohno
Summary: Indoleamine 2,3-dioxygenase 1 (IDO1) is a promising target for cancer immunotherapy due to its overexpression in various tumor cells and its role in immune escape. A novel IDO1 inhibitor was identified in this study, providing useful insights for the design of new inhibitors.
Review
Chemistry, Organic
Hiroaki Ohno, Shinsuke Inuki
Summary: This review discusses the nonbiomimetic total syntheses of indole alkaloids using alkyne chemistry, highlighting the importance of nonbiomimetic strategies in natural product synthesis and clarifying the differences between nonbiomimetic synthesis and biosynthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
