Article
Chemistry, Organic
Yujiro Hayashi
Summary: This article highlights the importance of time economy in chemical synthesis and the general considerations for the rapid production of desired molecules. Through modern strategies and technologies, important drugs such as Tamiflu and ibuprofen can now be synthesized in a short period of time.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Cell Biology
Intan M. W. Dewi, Cristina Cunha, Martin Jaeger, Mark S. Gresnigt, Marina E. Gkountzinopoulou, Fadel M. Garishah, Claudio Duarte-Oliveira, Claudia F. Campos, Lore Vanderbeke, Agustin Resendiz Sharpe, Roger J. Bruggemann, Paul E. Verweij, Katrien Lagrou, Greetje Vande Velde, Quirijn de Mast, Leo A. B. Joosten, Mihai G. Netea, Andre J. A. M. van der Ven, Joost Wauters, Agostinho Carvalho, Frank L. van de Veerdonk
Summary: Research suggests that blocking host NA may alter the immune response against Aspergillus fumigatus, potentially increasing susceptibility to pulmonary aspergillosis. Additionally, upregulation of the sialic acid-binding receptor SIGLEC15 in PBMCs stimulated with A. fumigatus is linked to decreased killing capacity of the fungus.
CELL REPORTS MEDICINE
(2021)
Article
Chemistry, Applied
Armando Carlone, Luca Bernardi, Peter McCormack, Tony Warr, Srinivas Oruganti, Christopher J. Cobley
Summary: The scale up development of an innovative synthetic process to pregabalin relies on continuous chemistry and asymmetric organocatalysis, with successful optimization of reaction conditions and organocatalyst recycle.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Multidisciplinary
Daniel J. Tindall, Steffen Mader, Alois Kindler, Frank Rominger, A. Stephen K. Hashmi, Thomas Schaub
Summary: Sugar alcohols are important for the food industry and can be produced in large quantities with increased yield and stereoselectivity through a homogeneous system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Applied
Dominik Dylong, Peter J. C. Hausoul, Regina Palkovits, Matthias Eisenacher
Summary: This review provides an overview of the most important synthetic menthol production processes, focusing on the last 20 years. The review includes the use of various starting materials and the application of asymmetric syntheses for high purity menthol production.
FLAVOUR AND FRAGRANCE JOURNAL
(2022)
Article
Chemistry, Medicinal
Saad Alqarni, Laura Cooper, Jazmin Galvan Achi, Ryan Bott, Veeresh Kumar Sali, Andrew Brown, Bernard D. Santarsiero, Aleksej Krunic, Balaji Manicassamy, Norton P. Peet, Pin Zhang, Gregory R. J. Thatcher, Irina N. Gaisina, Lijun Rong, Terry W. Moore
Summary: This study identifies a novel imidazo[1,2-a]dpyrimidine scaffold for targeting group 2 IAV entry. By exploring different regions of the lead compound, researchers have developed a series of small molecules with nanomolar activity against oseltamivir-sensitive and -resistant forms of group 2 IAVs. These small molecules target HA, blocking viral entry.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Saad Alqarni, Laura Cooper, Jazmin Galvan Achi, Ryan Bott, Veeresh Kumar Sali, Andrew Brown, Bernard D. Santarsiero, Aleksej Krunic, Balaji Manicassamy, Norton P. Peet, Pin Zhang, Gregory R. J. Thatcher, Irina N. Gaisina, Lijun Rong, Terry W. Moore
Summary: The study presents a novel drug scaffold and a series of small molecules that have nanomolar activity against both oseltamivir-sensitive and -resistant forms of group 2 IAVs, targeting hemagglutinin (HA) involved in viral entry.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xing-Liang Zhu, Yong-Qiang Luo, Lei Wang, Yong-Kang Huang, Yun-Gang He, Wen-Jing Xie, Shi-Ling Liu, Xiao-Xin Shi
Summary: The novel highly stereoselective syntheses of (+)-streptol and (-)-1-epi-streptol were achieved starting from naturally abundant (-)-shikimic acid. The key intermediate was obtained from (-)-shikimic acid in 11 steps with a 40% yield, followed by conversion to (+)-streptol in three steps with a 72% yield and to (-)-1-epi-streptol in one step with a 90% yield. Overall, the compounds were synthesized in 14 and 12 steps with 29% and 36% overall yields, respectively.
Review
Chemistry, Multidisciplinary
Yujiro Hayashi
Summary: Chemists aim to synthesize organic molecules rapidly to study their physical or biological properties, with concepts like time economy, step economy, and redox economy being crucial. One-pot reactions are useful in shortening synthesis time, increasing yield, and reducing chemical waste. The successful synthesis of natural products and medicines highlights the importance of pot and time economy, with efficient strategies such as using organocatalysts in one-pot reactions.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Fu-Li Wang, Lin Liu, Chang-Jiang Yang, Cheng Luan, Jing Yang, Ji-Jun Chen, Qiang-Shuai Gu, Zhong-Liang Li, Xin-Yuan Liu
Summary: The copper-catalyzed enantioconvergent radical C(sp(3))-C(sp(2)) cross-coupling reaction of tertiary alpha-bromo-beta-lactams with organoboronate esters provides a synthetic route to valuable alpha-quaternary beta-lactams. The challenge lies in the formation of sterically congested quaternary stereocenters between tertiary alkyl radicals and chiral copper(II) species. Through the use of a copper/hemilabile N,N,N-ligand catalyst, we have succeeded in achieving this transformation and demonstrated its synthetic potential in the conversion of products into valuable building blocks. This catalytic cycle opens up new possibilities for enantioconvergent cross-coupling reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Zheng Tan, Long Chen, Lingyu Li, Yuzhen Li, Yao Luo, Fei Wang, Shunxi Dong, Xiaoming Feng
Summary: In this study, a practical and efficient synthesis of a-methylene-?-butyrolactones was developed using chiral N,N'-dioxide/Al-III complex as the catalyst. The key success of this transformation was the kinetic resolution of allylboration intermediate via asymmetric lactonization. Taking advantage of this method, a catalytic asymmetric total synthesis of eupomatilones 2, 5, and 6 was accomplished.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Ricardo Molina Betancourt, Lucas Bacheley, Anzhela Karapetyan, Gerard Guillamot, Phannarath Phansavath, Virginie Ratovelomanana-Vidal
Summary: The Rh(III)-catalyzed asymmetric reduction of alpha-trifluoromethyl ketones through transfer hydrogenation was developed under mild conditions. It enables a dynamic kinetic resolution process to access a series of enantioenriched cis-trifluoromethyl alcohols. The reaction was performed efficiently in the green solvent 2-MeTHF using HCO2H/Et3N (1 : 1) as the hydrogen source. High yields and excellent diastereo- and enantioselectivities were achieved for the synthesis of CF3-chromanol, CF3-indanol, and CF3-tetralol derivatives.
Review
Chemistry, Multidisciplinary
Xiaohong Huo, Guanlin Li, Xi Wang, Wanbin Zhang
Summary: Bimetallic catalysis is an efficient strategy for developing new chemical reactions and stereodivergent synthesis, allowing for the preparation of products with different stereoisomers from the same set of starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Tobias Wagener, Lukas Lueckemeier, Constantin G. Daniliuc, Frank Glorius
Summary: This study successfully demonstrates the synthesis of sought-after, enantioenriched delta-lactams through an interrupted hydrogenation mechanism using oxazolidinone-substituted pyridines and water.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Roman Ivanov, Elizaveta Ivanova, Vladislav Merkulov, Mikhail Zharkov, Ilya Kuchurov, Sergei Zlotin
Summary: For the first time, amines have been condensed with carbonyl compounds in supercritical carbon dioxide (sc-CO2). The reactions with aldehydes or active ketones proceed at moderate temperatures without external catalysts. The process is autocatalytic, accelerated by the carbonic acid generated in situ. The imine products obtained in high yields in a crystalline form can be used in one-pot transfer hydrogenation and [4+2] cycloaddition reactions for green synthesis of more complex and valuable compounds.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Kenzo Yamatsugu, Shigehiro A. Kawashima, Kenzo Yamatsugu, Motomu Kanai
Summary: This study presents a one-step synthesis of phosphodiesters from alcohols using phosphoenolpyruvate phosphodiesters as phosphoryl donors. The method allows for the use of various functionalized alcohols as substrates and holds potential applications in diverse fields including biology and medicine.
Article
Chemistry, Organic
Mina Yamane, Yamato Kanzaki, Harunobu Mitsunuma, Motomu Kanai
Summary: The study utilizes a chlorine radical catalyzed strategy with titanium(IV) chloride to achieve C(sp(3))-H photoalkylation, allowing for hydrogen-atom transfer of unactivated alkanes. This reaction not only couples various alkanes with radical acceptors, but also enables direct photoalkylation of aromatic ketones.
Review
Chemistry, Organic
Yuri Katayama, Harunobu Mitsunuma, Motomu Kanai
Summary: Organochromium(III) species are versatile nucleophiles used in complex molecule synthesis due to their high tolerance of functional groups and chemoselectivity for aldehydes. Traditional methods of carbonyl addition reactions using organochromium(III) species require stoichiometric chromium(II) salts or catalytic chromium salts and stoichiometric reductants. Recent alternative methods involve organoradical formation from readily available starting materials and trapping the radical with stoichiometric or catalytic chromium(II) salts. These methods have the potential to develop sustainable chemical processes.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Xue Peng, Yuki Hirao, Shunsuke Yabu, Hirofumi Sato, Masahiro Higashi, Takuya Akai, Shigeyuki Masaoka, Harunobu Mitsunuma, Motomu Kanai
Summary: A ternary hybrid catalyst system composed of an acridinium photoredox catalyst, a thiophosphoric imide (TPI) catalyst, and a titanium complex catalyst has been identified to promote an intermolecular addition reaction between organic molecules and ketones through sp(3) C-H bond activation. This reaction provides an efficient and straightforward route to a broad range of tertiary alcohols.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Hiromu Fuse, Yu Irie, Masaaki Fuki, Yasuhiro Kobori, Kosaku Kato, Akira Yamakata, Masahiro Higashi, Harunobu Mitsunuma, Motomu Kanai
Summary: In this study, we developed an organocatalyst system that can promote the cleavage of stable C-H bonds through a hydrogen atom transfer process without the use of exogenous photosensitizers. The electronically tuned thiophosphoric acid, 7,7'-OMe-TPA, was assembled with substrate or co-catalyst N-heteroaromatics to form electron donor-acceptor complexes. Photoirradiation of these complexes induced stepwise single-electron transfer processes to generate a HAT-active thiyl radical. Spectroscopic studies and theoretical calculations characterized the stepwise SET process mediated by short-lived intermediates. This organocatalytic HAT system showed high functional group tolerance in four different C-H functionalization reactions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Kentaro Sakai, Kounosuke Oisaki, Motomu Kanai
Summary: Selective C(sp(3))-H functionalization using photoredox catalysis and hydrogen atom transfer catalysis has attracted increasing attention. We report the use of a Ph2GeCl2 cocatalyst that greatly improves the yield of alpha-C(sp(3))-H alkylation of primary amines catalyzed by a PC-HAT hybrid system. The alpha-position of the amino group selectively reacts, even when weaker C-H bonds exist in the substrates. This finding may aid in the design of novel site-selective hybrid catalysis.
Article
Chemistry, Applied
Yu Irie, Hongyu Chen, Hiromu Fuse, Harunobu Mitsunuma, Motomu Kanai
Summary: In this study, a linear-selective allylation reaction of aldehydes using simple alkenes as starting materials was developed by employing a quadruple hybrid catalyst system. The reaction proceeded under mild conditions, such as room temperature under visible light irradiation, and was applicable to asymmetric reactions. The addition of Ni(BF4)(2)center dot 6H(2)O catalyst to the previously reported ternary catalyst system accelerated the allylic transfer process from branch products to thermodynamically stable linear products by increasing the Bronsted acidity of thiophosphoric imide (TPI) catalyst.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Rahul A. Jagtap, Motomu Kanai
Summary: Catalytic acceptorless dehydrogenation of organic molecules plays a crucial role in fine-chemical synthesis as well as in energy storage and transport. Our research group aims to develop mild catalytic acceptorless dehydrogenation protocols, mainly using photoredox approaches. In this account, we discuss the advances made by our group on the dehydrogenation of saturated N-heterocycles, aliphatic alcohols, and challenging hydrocarbons.
Article
Chemistry, Organic
Motomu Kanai, Yuma Takeuchi
Summary: We are investigating catalytic approaches in the chemical networks of living organisms, which can activate stable molecules under physiological conditions and form the basis of catalysis medicine. Our research contributes to progress in both physical and life sciences. In this Perspective, we provide an overview of catalysis medicine and share examples of our recent achievements in synthetic epigenetics and amyloid degradation. This Perspective highlights the potential of catalysis research in solving interdisciplinary problems.
Article
Biochemical Research Methods
Katarzyna Joanna Malawska, Shinjiro Takano, Kounosuke Oisaki, Haruaki Yanagisawa, Masahide Kikkawa, Tatsuya Tsukuda, Motomu Kanai
Summary: We developed a method for bioconjugation of Au25 nanoclusters to monoclonal antibodies. This method allows for the attachment of the nanoclusters to rarely exposed tryptophan residues, making them suitable for high-resolution imaging techniques such as cryo-EM and cryo-ET. The use of hydroxylamine reagents instead of N-oxyl radicals improved the selectivity of the bioconjugation process, enabling the labeling of acid-sensitive proteins.
BIOCONJUGATE CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Kenzo Yamatsugu, Motomu Kanai
Summary: Carbohydrates, as fundamental units in biological processes, play pivotal roles. Developing methods for synthesizing, functionalizing, and manipulating carbohydrates is essential for understanding their functions and creating sugar-based functional materials. New approaches to site-selective transformations of carbohydrates are of great significance for revolutionizing sugar chemistry and accessing sugars of interest.
Article
Biology
Haruka Oda, Yuko Sato, Shigehiro A. Kawashima, Yusuke Fujiwara, Mate Palfy, Edlyn Wu, Nadine L. Vastenhouw, Motomu Kanai, Hiroshi Kimura
Summary: Filamentous actin (F-actin) in the cytoplasm plays a crucial role in cell regulation, and recent studies have discovered its association with various functions in the nucleus. By live imaging of zebrafish embryos, it was shown that F-actin accumulates in nuclei during the interphase and reaches a peak during the prophase. Even after the breakdown of the nuclear envelope, patches of F-actin remain near the condensing chromosomes. This accumulation of F-actin in the nucleus may contribute to proper mitotic progression in zebrafish embryos.
Article
Biochemistry & Molecular Biology
Hiroki Umeda, Taka Sawazaki, Masahiro Furuta, Takanobu Suzuki, Shigehiro A. Kawashima, Harunobu Mitsunuma, Yukiko Hori, Taisuke Tomita, Youhei Sohma, Motomu Kanai
Summary: Catalytic photo-oxygenation is a potential therapeutic approach for tauopathies, but its effects on tau from human patients have not been clarified. In this study, two assay systems were developed to evaluate the catalytic activity on human patient tau. Using these assays, a promising catalyst for oxygenation of human tau was identified. The results also suggest differences between aggregated tau induced by heparin and tau from actual AD patients in developing effective catalysts.
ACS CHEMICAL NEUROSCIENCE
(2023)
Review
Chemistry, Multidisciplinary
Ryota Matsukawa, Mina Yamane, Motomu Kanai
Summary: This review provides a thorough overview of the chemistry, resulting products, mechanisms, and analytical techniques involved in histidine photooxygenation. It explores the practical implications of this transformation in fields such as materials science, biomedical research, and drug development. By bridging the existing gap in literature, it serves as a resource for understanding the intricacies of histidine photooxygenation and its diverse ramifications.
Article
Chemistry, Multidisciplinary
Toshifumi Tatsumi, Koki Sasamoto, Takuya Matsumoto, Ryo Hirano, Kazuki Oikawa, Masato Nakano, Masaru Yoshida, Kounosuke Oisaki, Motomu Kanai
Summary: In recent years, the number of accessible drug modalities has increased. Peptides have become important in pharmaceuticals and biomaterials. Traditional peptide synthesis produces large amounts of chemical waste and burdens the environment. This study presents a new peptide elongation strategy that eliminates the need for complex reagents and protecting groups.
COMMUNICATIONS CHEMISTRY
(2023)