Article
Chemistry, Organic
Taichi Saito, Yuka Shimizu, Yusuke Araki, Yoshino Ohgami, Yu Kitazawa, Yoshinori Nishii
Summary: The study successfully developed a highly enantioselective chirality exchange method for transforming enantioenriched D-A cyclopropylcarbinols into enantioenriched 1-aryl-1,2-dihydronaphthalenes and 1-arylnaphthalenes with high stereoinduction, providing a new pathway for synthesizing chiral compounds.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Chun-Lin Zhang, Yuan-Yuan Gao, Hai-Ying Wang, Bang-An Zhou, Song Ye
Summary: An NHC-catalyzed de novo synthesis method for axially chiral benzothiophene/benzofuran-fused biaryls has been reported, providing a convenient and efficient access to these compounds with high enantioselectivities. The method also works well for the synthesis of tetra-ortho-substituted biaryls, addressing an unsolved problem in the field.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Guillaume Dauvergne, Jean-Valere Naubron, Michel Giorgi, Xavier Bugaut, Jean Rodriguez, Yannick Carissan, Yoann Coquerel
Summary: The synthetic equivalents of enantiopure binaphthyl bis(aryne) atropisomers derived from BINOL have been generated in a solution for the first time. These atropisomers can be prepared enantiospecifically in high enantiomeric purity using various reactions, leading to potential applications in nanographene design.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Qianwen Guan, Tingting Zhu, Zeng-Kui Zhu, Huang Ye, Shihai You, Peng Xu, Jianbo Wu, Xinyi Niu, Chengshu Zhang, Xitao Liu, Junhua Luo
Summary: In this study, a pair of unprecedented three-dimensional chiral halide perovskitoids was successfully synthesized, demonstrating unique chiroptoelectronic performance. The new material exhibited natural chiroptical activity and the ability to distinguish circularly polarized light, as well as sensitive X-ray detection performance.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Inorganic & Nuclear
Dominik Baran, Sergei I. Ivlev, Eric Meggers
Summary: In this work, an auxiliary-mediated deracemization protocol was introduced for the synthesis of a non-C-2-symmetric chiral-at-ruthenium catalyst, which was then applied to an enantioselective ring-closing reaction.
Article
Chemistry, Multidisciplinary
Xiu-Lian Zhang, Jun Gu, Wen-Hao Cui, Zhiwen Ye, Wenbin Yi, Qiang Zhang, Ying He
Summary: This study reports a novel method for the efficient synthesis of configurationally stable axially chiral B,N-heterocycles. By using a stepwise asymmetric synthesis strategy, compounds with two different types of stereogenic axes were successfully constructed. The NH center and pi interactions were found to play an important role in achieving stereoisomerization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Guang-Jian Mei, Jonathan J. Wong, Wenrui Zheng, Anjanay A. Nangia, K. N. Houk, Yixin Lu
Summary: The first catalytic asymmetric synthesis of N-N axially chiral compounds has been achieved, adding a new dimension to axially chiral molecules and atropisomerism. DFT calculations have been used to understand enantioselectivity and guide the design of similar molecules. Research on N-N axial atropisomerism holds promise for new discoveries in medicinal chemistry and asymmetric catalysis.
Article
Chemistry, Organic
Sen Zhang, Zhang-Hong Luo, Wen-Tao Wang, Linghui Qian, Jia-Yu Liao
Summary: In this study, a novel strategy is reported for the simultaneous construction of a remote C-N stereogenic axis and three contiguous stereogenic carbon centers through silver-catalyzed desymmetrization [3 + 2] cycloaddition of prochiral N-aryl maleimides with activated isocyanides. This method is characterized by its operational simplicity, wide substrate scope, high efficiency, and good to excellent stereoselectivity. Importantly, it represents the first example of catalytic enantioselective synthesis of C-N atropisomers using activated isocyanides.
Article
Crystallography
Ksenia Kozlovskaya, Elena Ovchinnikova, Jun Kokubun, Andrei Rogalev, Fabrice Wilhelm, Francois Guillou, Francois de Bergevin, Alisa F. Konstantinova, Vladimir E. Dmitrienko
Summary: A new method for determining the absolute structure of chiral crystals based on chiral asymmetry of multiple scattering diffraction is proposed, which does not use X-ray anomalous dispersion. Experimental demonstration on quartz single crystals shows its applicability to various crystal structures, including opaque, organic, and monoatomic crystals. The Renninger plot of a single forbidden reflection is sufficient for determining the type of isomer.
Article
Chemistry, Multidisciplinary
Jing-Yi Wang, Meng Sun, Xian-Yang Yu, Yu-Chen Zhang, Wei Tan, Feng Shi
Summary: This work presents a catalytic enantioselective construction of axially chiral alkene-indole frameworks using alpha-amido sulfones as nucleophiles and chiral phosphoric acid as catalyst. The strategy resulted in high yields, excellent (E/Z)-selectivity, and good enantioselectivities, representing the first of its kind in the construction of axially chiral alkene-indole scaffolds.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Applied
Magesh Sampath, Sembian Ruso Jayaraman, Vishnuvardhan Reddy Eda, Rajendar Potham, Rajeev Rehani Budhdev, Saikat Sen, Rakeshwar Bandichhor, Srinivas Oruganti
Summary: An efficient and elegant enantioselective synthesis of the key chiral pyrrolidine fragment for Upadacitinib (ABT-494) was described using Oppolzer's chiral sultam-directed asymmetric 1,3 dipolar cycloaddition. The method provided the desired level of diastereoselectivity and enantioselectivity in the construction of the 3,4-syn substituted pyrrolidine moiety.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Organic
Francesca Mangiavacchi, Giuseppe Mazzeo, Maria Chiara Graziani, Francesca Marini, Jozef Drabowicz, Ewelina Wielgus, Luca Sancineto, Giovanna Longhi, Riccardo Vivani, Sergio Abbate, Claudio Santi
Summary: In this study, the base induced activation of beta-naphthol was utilized for the synthesis of a novel 1,1'-diselanediylbis(naphthalen-2-ol), which was fully characterized using NMR and X-Ray analysis. The reactivity of this compound was investigated, leading to the discovery of a novel synthesis method for chiral selenium containing heterocycles. Chiroptical methods, specifically VCD and ECD, were successfully employed to determine the absolute configuration of these compounds, representing the first example reported for organoselenium derivatives.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Lixiang Zhu, Heling Peng, Yan Guo, Jixing Che, Jia-Hong Wu, Zhishan Su, Tianli Wang
Summary: An effective and modular method for synthesizing axially chiral biaryl molecules bearing phosphorus groups has been developed. This method involves the cascade reaction between phosphorus-containing nitroolefins and alpha,alpha-dicyanoolefins catalyzed by a chiral phosphonium salt. The reaction pathway includes cycloaddition, oxidative hydroxylation, and aromatization, and features chirality transfer from the central to axial position.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Lukas Brieger, Tobias Schrimpf, Rebecca Scheel, Christian Unkelbach, Carsten Strohmann
Summary: This article investigates the metalation of N,N-dimethylaminomethylferrocene by superbase and the preparation of enantiomerically pure superbase. Quantum chemical calculations provide insights into the mechanism of substrate-reagent interaction, and a closer look at the reaction site is presented through experimental studies.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Xingxing Wu, Juraj Malincik, Alessandro Prescimone, Christof Sparr
Summary: The determination of absolute configuration of chiral molecular entities is crucial in stereochemistry. X-ray crystallography of quasi-racemates provides a useful approach for determining absolute configuration, especially in the development of stereoselective methods.
HELVETICA CHIMICA ACTA
(2022)
Article
Chemistry, Multidisciplinary
Raymond Malabed, Shinya Hanashima, Michio Murata, Kaori Sakurai
Article
Biophysics
Yo Yano, Shinya Hanashima, Hiroshi Tsuchikawa, Tomokazu Yasuda, J. Peter Slotte, Erwin London, Michio Murata
BIOPHYSICAL JOURNAL
(2020)
Article
Chemistry, Physical
Sangjae Seo, Michio Murata, Wataru Shinoda
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2020)
Article
Biochemistry & Molecular Biology
Shinya Hanashima, Nanami Fukuda, Raymond Malabed, Michio Murata, Msanao Kinoshita, Peter Greimel, Yoshio Hirabayashi
Summary: The study showed that glucosylation reduces the effect of cholesterol on the ordering of sphingomyelin chains, leading to decreased interactions between cholesterol and sphingomyelin, which in turn affects the stability of specific locations in biological membranes.
BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES
(2021)
Article
Chemistry, Medicinal
Joan Candice Ondevilla, Shinya Hanashima, Akane Mukogawa, Yuichi Umegawa, Michio Murata
Summary: DGN, a sterol found in plants of the Dioscorea family, has been found to have similar effects to cholesterol in lipid bilayer membranes, suggesting that both compounds have similar impacts on basic biomembrane properties.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Biochemistry & Molecular Biology
Mikito Nakano, Shinya Hanashima, Toshiaki Hara, Kazuya Kabayama, Yuya Asahina, Hironobu Hojo, Naoko Komura, Hiromune Ando, Thomas K. M. Nyholm, J. Peter Slotte, Michio Murata
Summary: GM3 in the plasma membranes suppresses cell growth by preventing the autophosphorylation of the epidermal growth factor receptor (EGFR). The lateral interaction between GM3 and the transmembrane segment of EGFR disturbs the formation of active EGFR dimers.
BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES
(2021)
Article
Biophysics
Shinya Hanashima, Ryuji Ikeda, Yuki Matsubara, Tomokazu Yasuda, Hiroshi Tsuchikawa, J. Peter Slotte, Michio Murata
Summary: In this study, the properties of LacCer domains formed in multicomponent membranes were investigated using deuterium solid-state NMR and fluorescence lifetimes. The results showed that Cho destabilized the LacCer gel phase and formed a liquid-ordered phase in binary membranes. In the absence of Cho, LacCer formed stable gel phases. Furthermore, the presence of Cho decreased the area and chain order of the LacCer gel phase, and facilitated the formation of small domains in the liquid crystalline domain of ternary membranes.
BIOPHYSICAL JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Hiroshi Tsuchikawa, Mami Monji, Yuichi Umegawa, Tomokazu Yasuda, J. Peter Slotte, Michio Murata
Summary: In this study, the depth-dependent melting of stearoyl-D-sphingomyelin (SSM) was investigated using solid-state deuterium NMR, revealing a characteristic melting pattern not observed in saturated lipid palmitoylstearoylphosphatidylcholine (PSPC). This depth-dependent melting is likely caused by intermolecular hydrogen bonding in sphingomyelin, and may play a role in the biological properties of SM-based lipid rafts.
Article
Multidisciplinary Sciences
Yuichi Umegawa, Tomoya Yamamoto, Mayank Dixit, Kosuke Funahashi, Sangjae Seo, Yasuo Nakagawa, Taiga Suzuki, Shigeru Matsuoka, Hiroshi Tsuchikawa, Shinya Hanashima, Tohru Oishi, Nobuaki Matsumori, Wataru Shinoda, Michio Murata
Summary: In this study, the three-dimensional structure of the molecular assemblies formed by Amphotericin B in membranes was experimentally elucidated using spectroscopy and simulations. The observed structure explains the drug's structure-activity relationships and will contribute to improving drug efficacy and reducing adverse effects.
Review
Biophysics
Michio Murata, Nobuaki Matsumori, Masanao Kinoshita, Erwin London
Summary: This review summarizes recent studies on the molecular basis of the liquid-ordered (Lo) phase, highlighting the significance of sphingomyelin nanodomains in the Lo phase.
BIOPHYSICAL REVIEWS
(2022)
Article
Chemistry, Multidisciplinary
Darcy Lacanilao Garza, Shinya Hanashima, Yuichi Umegawa, Michio Murata, Masanao Kinoshita, Nobuaki Matsumori, Peter Greimel
Summary: The interaction between ginsenoside Rh2 and biological membranes was investigated in this study. It was found that Rh2 showed no specific interaction with particular lipids, but its behavior in the membrane was influenced by the formation of the liquid-ordered (Lo) phase. Surface tension measurements and fluorescence experiments revealed that Rh2 preferentially bound to the liquid-disordered (Ld) phase and had a higher affinity for the relatively shallow interior of the Ld phase.
Article
Chemistry, Multidisciplinary
Shinya Hanashima, Mikito Nakano, Michio Murata
Summary: Glycosphingolipids (GSLs) play important roles in various biological events on cell membranes, but the details of their interactions and functions are still not fully understood. This study investigated the dynamic assembly of lactosylceramide (LacCer) in cholesterol-containing membranes, and found that LacCer-LacCer interaction reduced the incorporation of cholesterol in LacCer domains. Furthermore, increasing the amount of cholesterol induced the formation of nanometer-scale LacCer domains. The study also examined the interaction between ganglioside GM3 and the epidermal growth factor receptor (EGFR) transmembrane segment, and suggested that GM3 interacts with EGFR and inhibits its dimerization. Understanding the GSL-GSL and GSL-protein interactions in membrane environments can provide insights into the cellular functions of GSLs.
PURE AND APPLIED CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Hirofumi Watanabe, Shinya Hanashima, Yo Yano, Tomokazu Yasuda, Michio Murata
Summary: This study established a method to determine the distribution ratio of phospholipids between the outer and inner leaflets of asymmetric large unilamellar vesicles (aLUVs). The study found that in cholesterol-containing vesicles, phospholipids are mostly distributed in either the outer or inner leaflet, and the lipid translocation rate is affected by changes in membrane order.
Article
Chemistry, Organic
Shinya Hanashima, Kanako Mito, Yuichi Umegawa, Michio Murata, Hironobu Hojo
Summary: N-Myristoylation is a protein modification process that promotes protein-membrane interaction. The cooperation of two acyl chains increases the interaction with membranes containing anionic lipids. This lipid-driven mechanism may play a role in recruiting proteins to specific signaling domains on cell membranes.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Physics, Applied
Shigeru Sugiyama, Keisuke Kakinouchi, Hiroaki Adachi, Tsugio Nagasawa, Noriaki Kunimune, Michio Murata, Yusuke Mori
Summary: This study introduced a new method for protein crystallization in high-strength hydrogels to prevent protein damage at high temperatures and found that this method is applicable to various proteins due to its low-temperature operation.
JAPANESE JOURNAL OF APPLIED PHYSICS
(2021)
