Article
Chemistry, Multidisciplinary
Peng Wen, Peijing Jia, Qiuhua Fan, Bethany J. McCarty, Weiping Tang
Summary: A streamlined iterative assembly of thio-oligosaccharides was developed by aqueous glycosylation, efficiently synthesizing 1,2-trans S-glycosides with high chemo- and stereoselectivity at room temperature. The method was successfully applied to the synthesis of a trimannoside moiety of N-linked glycans core region.
Article
Chemistry, Multidisciplinary
Samira Escopy, Yashapal Singh, Keith J. Stine, Alexei V. Demchenko
Summary: As the 21st century unfolds with rapid changes, new challenges have arisen in research and development. This article introduces a solution phase batch synthesis method based on the HPLC platform, which enables sequential synthesis of multiple oligosaccharides and automates the process.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Jianhong Zhang, Tetsuo Koyama, Takahiko Matsushita, Ken Hatano, Koji Matsuoka
Summary: Efficient synthesis of lauryl thioglycoside of Neu5Gc was achieved from a known thioglycoside of Neu5Ac. The reactivity of Neu5Gc thioglycoside in O-glycosidation was investigated, showing good activities with simple alcohols. The thioglycoside also demonstrated potential as a glycosyl donor in reactions with glucose and lactose derivatives.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Xiaona Li, You Yang
Summary: Automated chemical solid-phase synthesis is a reliable and efficient automation platform for synthesizing glycans. Automated Glycan Assembly (AGA), as a key breakthrough in the field, has evolved from a proof-of-concept to a robust technology for streamlined production of various glycans. In addition, HPLC-assisted automated synthesis shows promising potential in accessing glycans.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jose Danglad-Flores, Sabrina Leichnitz, Eric T. Sletten, A. Abragam Joseph, Klaus Bienert, Kim Le Mai Hoang, Peter H. Seeberger
Summary: The new AGA synthesizer offers better temperature control, more protecting group options, and shorter coupling cycles, enabling rapid and efficient synthesis of complex carbohydrates and expanding the range of glycans that can be prepared.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Shiyun He, Jinyu Hou, Meiling Ye, Jian Chen, Guanghui Lv, Tianle Huang, Zhongzhen Yang, Yong Wu
Summary: A visible-light-mediated glycosylation reaction has been reported, which efficiently produces S-aryl glycosides. The reaction proceeds through an EDA complex. This method shows potential applications in late-stage functionalisation of drug molecules and large-scale experiments.
CHEMICAL COMMUNICATIONS
(2023)
Article
Biotechnology & Applied Microbiology
Yunze Sun, Yiran Wu, Dachuan Ma, Jian-Jun Li, Xianming Liu, Yuanjiang You, Jun Lu, Zhen Liu, Xin Cheng, Yuguang Du
Summary: Glycans are important natural biopolymers with diverse functions. However, the tedious manual processes and high reagent consumption hinder the development of automatic glycan sequencing and synthesis. In this study, enzymatic degradation and synthesis of glycans were successfully conducted on a digital microfluidic device, enabling the development of automated glycan synthesizers and sequencers. The study also demonstrated the successful enzymatic degradation of tetra-N-acetyl chitotetraose and the two-step enzymatic synthesis of lacto-N-tetraose on the digital microfluidic platform. This work paves the way for the future development of automatic enzymatic glycan synthesizers and sequencers.
FRONTIERS IN BIOENGINEERING AND BIOTECHNOLOGY
(2023)
Article
Chemistry, Organic
Kumpei Yano, Norihiko Sasaki, Toshiyuki Itoh, Toshiki Nokami
Summary: The research utilizes automated electrochemical assembly to synthesize oligosaccharides, successfully producing oligosaccharides with different chain lengths and developing a method to convert linear oligosaccharides into cyclic ones through electrochemical glycosylation.
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
(2021)
Article
Chemistry, Multidisciplinary
Huiqing Hou, Xinhua Ma, Yingying Lin, Jin Lin, Weiming Sun, Lei Wang, Xiuzhi Xu, Fang Ke
Summary: The development of protocols for synthesizing quinazolinones using biocompatible catalysts in aqueous medium will help to resolve the difficulties of using green and sustainable chemistry for their synthesis. The use of I-2 in coordination with electrochemical synthesis successfully induced a C-H oxidation reaction in water as a solvent, leading to the efficient cyclization of amides to various quinazolinones.
Article
Chemistry, Multidisciplinary
Taeyeong Yun, Gang San Lee, Jungwoo Choi, Hyerim Kim, Geon Gug Yang, Ho Jin Lee, Jin Goo Kim, Hyuck Mo Lee, Chong Min Koo, Joonwon Lim, Sang Ouk Kim
Summary: Building macroscopic functional architectures with diverse structural dimensions in the field of 2D MXene research is a critical challenge. Electrochemical self-assembly of pure Ti3C2Tx MXenes can lead to highly performing supercapacitors and electromagnetic interference shielding films based on multidimensional assembly.
Article
Chemistry, Applied
Yuuki Hata, Sumiyo Hiruma, Yuta Sakurai, Kai Sugiura, Hiromi Miyazaki, Takeshi Serizawa, Shingo Nakamura
Summary: We report a method for bottom-up nanostructuring of conventional microfibrous cellulose materials using a molecular self-assembly strategy. By swelling the cellulose material with aqueous phosphoric acid, it undergoes partial dissolution and hydrolysis while maintaining its microfibrous structure. Upon the addition of water as a coagulant, dissolved cello-oligosaccharides start to self-assemble and form nanospike-like structures on the microfiber surfaces. The resulting nanospiked papers can serve as precursors for synthesizing silver nanoparticle-cellulose composites with bactericidal activities. This study promotes the development of cellulose-based functional materials with nanostructures designed via molecular self-assembly.
CARBOHYDRATE POLYMERS
(2023)
Article
Chemistry, Multidisciplinary
Yuntao Zhu, Martina Delbianco, Peter H. Seeberger
Summary: Polysaccharides are essential biomaterials in nature for plant cell wall construction and energy storage. Even minor structural differences can lead to entirely different functions. Recent research has developed a method to synthesize linear and branched α-glucan polymers with excellent stereoselectivity, providing new insights into the biosynthesis and structure of α-glucans.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Sujenth Kirupakaran, Glib Arago, Christoph Hirschhaeuser
Summary: A synthetic strategy for all aldohexoses with individually addressable protecting groups from dihalomethane C-1-units is reported. The underlying synthesis of C-6-sugar alcohols relies on three consecutive Matteson sequences, vinylation and bishydroxylation. Erythro and threo isomers have been realized for every glycol motif by strategic variation of the sequence.
Article
Chemistry, Multidisciplinary
Qiqiang Xie, Rui Zhang, Guangbin Dong
Summary: The detailed development of sequential insertion of nitrogen and carbon atoms into boronate C-B bonds has been reported, providing a modular and iterative approach to access functionalized tertiary amines. A new class of nitrenoid reagents allows for direct formation of aminoboranes from aryl or alkyl boronates via N-insertion. The resulting aminoalkyl boronate products can undergo further transformation, enabling the modular synthesis of bioactive compounds and the programmable construction of diamines and aminoethers. A plausible reaction mechanism is also proposed, supported by preliminary NMR and computational studies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Cangjie Yang, Yu Deng, Yang Wang, Chaoshuang Xia, Akul Y. Mehta, Kelly J. Baker, Anuj Samal, Putthipong Booneimsri, Chanthakarn Lertmaneedang, Seung Hwang, James P. Flynn, Muqing Cao, Chao Liu, Alec C. C. Zhu, Richard D. Cummings, Cheng Lin, Udayan Mohanty, Jia Niu
Summary: In this study, a new approach to HS glycomimetics was developed by iteratively assembling clickable disaccharide building blocks. The HS-mimetic oligomers with defined sulfation patterns were shown to bind protein FGF2 in a sulfation-dependent manner, indicating their potential application as alternatives to native HS in both fundamental research and disease models.
Article
Chemistry, Multidisciplinary
Heejin Kim, Yuya Yonekura, Jun-ichi Yoshida
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Ryutaro Hayashi, Akihiro Shimizu, Jonathan A. Davies, Yu Ishizaki, Chris Willis, Jun-ichi Yoshida
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Electrochemistry
Akihiro Shimizu
Article
Chemistry, Organic
Yu Miyamoto, Naoya Mitani, Rina Yanagi, Shigenori Kashimura, Seiji Suga, Jun-ichi Yoshida, Kouichi Matsumoto
Article
Chemistry, Multidisciplinary
Shinobu Arikawa, Akihiro Shimizu, Ryo Shintani
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Physical
Aiichiro Nagaki, Katsuyuki Hirose, Yuya Moriwaki, Masahiro Takumi, Yusuke Takahashi, Koji Mitamura, Kimihiro Matsukawa, Norio Ishizuka, Jun-ichi Yoshida
Article
Chemistry, Multidisciplinary
Lars J. Wesenberg, Erika Diehl, Till J. B. Zaehringer, Carolin Doerr, Dieter Schollmeyer, Akihiro Shimizu, Jun-Ichi Yoshida, Ute A. Hellmich, Siegfried R. Waldvogel
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Organic
Akihiro Shimizu, Yu Ishizaki, Shun Horiuchi, Takashi Hirose, Kenji Matsuda, Hiroyasu Sato, Jun-ichi Yoshida
Summary: The study focused on designing and synthesizing small pi-conjugated zwitterions with electron-donating anions and electron-accepting cations. By adjusting the energy difference and interplanar angle between the anion's HOMO and the cation's LUMO, the molecules exhibited small HOMO-LUMO energy gaps, showing amphoteric redox properties and near-infrared electronic absorption exceeding 1000 nm.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ayane Kayama, Akihiro Shimizu, Ryo Shintani
Summary: The study describes the design and synthesis of a novel anthracene-based zwitterion with amphoteric redox properties and low-energy-light absorption. DFT calculations indicate that replacing C-H with N+-Me and introducing O- is essential for significantly altering the electronic structure and properties of anthracene.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Shinobu Arikawa, Akihiro Shimizu, Daisuke Shiomi, Kazunobu Sato, Ryo Shintani
Summary: By introducing bulky substituents onto the reactive zigzag edges, a kinetically stabilized crystalline form of triangulene was successfully synthesized and isolated for the first time, opening up new possibilities for the synthesis and isolation of other hydrocarbons with higher spin multiplicity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Akihiro Shimizu, Tetsuya Morikoshi, Kenji Sugisaki, Daisuke Shiomi, Kazunobu Sato, Takeji Takui, Ryo Shintani
Summary: This study describes the design, synthesis, and isolation of a Kekule hydrocarbon with a triplet ground state. The triplet ground state was confirmed through ESR experiments, and the structure and fundamental physical properties were also revealed. The key aspect of the molecular design is the decrease in bonding interaction in the singlet state through aromatic stabilization of benzene rings and the increase of exchange interaction of unpaired electrons, which is favorable for the triplet state. These findings contribute to the development of hydrocarbon-based organic magnetic materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Shinobu Arikawa, Akihiro Shimizu, Daisuke Shiomi, Kazunobu Sato, Takeji Takui, Hikaru Sotome, Hiroshi Miyasaka, Masahito Murai, Shigehiro Yamaguchi, Ryo Shintani
Summary: A kinetically-stabilized nitrogen-doped triangulene cation derivative with a triplet ground state that exhibits near-infrared emission has been synthesized and isolated. The triplet ground state with a large singlet-triplet energy gap was experimentally confirmed by magnetic measurements. The nitrogen-doped triangulene cation derivative is highly stable even in solution under air and exhibits near-infrared absorption and emission due to the broken alternancy symmetry of triangulene.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Akihiro Shimizu, Shun Horiuchi, Ryutaro Hayashi, Kouichi Matsumoto, Yu Miyamoto, Yusuke Morisawa, Tomonari Wakabayashi, Jun-ichi Yoshida
Review
Chemistry, Multidisciplinary
Jun-ichi Yoshida, Akihiro Shimizu, Ryutaro Hayashi