Article
Chemistry, Organic
Mosidur Rahaman Molla, Rima Thakur
Summary: A new readily synthesized orthogonal protecting group, cyanomethyl (CNMe) ether, has been reported for efficient protection of saccharides with easy removal.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Cheng-Yu Long, Hao Chen, Cheng Ma, Bo-Wei Zhao, Shen-Huan Li, Yue Cui, Xinge Yang, Shao-Fei Ni, Xue-Qiang Wang
Summary: A Ni-catalyzed protecting-group-free C-C coupling protocol has been developed for the efficient synthesis of 2,2'-biphenol derivatives. This newly developed strategy demonstrates remarkable chemoselectivity control ability, wide substrate scope, and excellent functional group tolerance.
Correction
Chemistry, Multidisciplinary
Gao-Lan Zhang, Madhusudhan Reddy Gadi, Xikai Cui, Ding Liu, Jiabin Zhang, Varma Saikam, Christopher Gibbons, Peng G. Wang, Lei Li
Summary: The study presents a protection-group-free method for S-glycosylation, which can be applied in the synthesis of thioglycosides and thioglycopeptides in water.
Article
Chemistry, Multidisciplinary
Xiaoqian Li, Zhi Ma, Rongkun Liu, Mattan Hurevich, You Yang
Summary: A green and efficient photolabile protecting group (PPG)-mediated glycosidation approach for the synthesis of 2-deoxy-glycosides is reported. Multiple oNBC groups in the 2-deoxy-glycosides can be completely cleaved by irradiation at 365 nm, resulting in the desired 2-deoxy-glycosides in an efficient manner. Oligosaccharides with three to six oNBC groups are effectively achieved based on this PPG-mediated glycosidation approach.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Debashis Dhara, Laurence A. Mulard
Summary: The stereoselective synthesis of S. sonnei oligosaccharides comprising two, three and four repeating units is reported for the first time in this study. The use of multiple protecting groups and a specific building block design enabled the successful iterative glycosylation and deprotection steps.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Kim Greis, Carla Kirschbaum, Giulio Fittolani, Eike Mucha, Rayoon Chang, Gert von Helden, Gerard Meijer, Martina Delbianco, Peter H. Seeberger, Kevin Pagel
Summary: This study investigates the influence of fluorination on the structure of the glycosyl cation, an intermediate in glycosylation reactions. The results reveal that C3 and C6 fluorination of glucosyl building blocks can alter the structure of the glycosyl cation, with neighboring group participation being the dominant motif.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xianglai Liu, Yingying Song, Ao Liu, Yueer Zhou, Qian Zhu, Yetong Lin, Huiyong Sun, Kaidi Zhu, Wei Liu, Ning Ding, Weijia Xie, Haopeng Sun, Biao Yu, Peng Xu, Wei Li
Summary: The study demonstrates that PTFAI can serve as a stereodirecting group for 1,2-cis alpha-glycosylation, leading to improved selectivity in glycosylation reactions. The involvement of 6-PTFAI in remote participation was confirmed using low-temperature NMR, shedding light on the reaction mechanism. This strategy shows promise for the synthesis of complex carbohydrates and derivatives.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Biochemistry & Molecular Biology
Gefei Li, Masato Noguchi, Masaki Ishihara, Yuka Takagi, Marina Nagaki, Sachie Saito, Masashi Saito, Xin-shan Ye, Shin-ichiro Shoda
Summary: Chemical O-glycosylation is crucial for synthesizing sugar-containing molecules like glycolipids. However, traditional carbohydrate chemistry involves extensive use of protective groups, which is time-consuming and inefficient. In this study, a protecting-group-free glycosylation strategy using DBT-glycosides as glycosyl donors was developed. The method allows for direct synthesis of DBT-glycosyl donors from unprotected sugars in water. O-glycosylation of alcohols using DBT-glycosyl donors under mild hydrogenolytic conditions resulted in stereo-selective formation of alkyl glycosides with high yields.
CARBOHYDRATE RESEARCH
(2023)
Article
Chemistry, Organic
Polina I. Abronina, Nelly N. Malysheva, Alexander I. Zinin, Natalya G. Kolotyrkina, Leonid O. Kononov
Summary: Glycosylation using different glucosyl donors can lead to different selectivity, with the position of the benzoyl group playing a key role in the alpha selectivity.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Alexanndra Behm, Jessica Hafner, Natalie Goeckner, Matthew Lohman, Cristina De Meo
Summary: In this study, the reactivities of phenylthio alpha- and beta-sialyl donors protected at C-4 with tert-butyldimethyl silyl (TBDMS) and tri-isopropylsilyl (TIPS) groups in coupling reactions with different types of galactosyl acceptors were compared. The effect of solvent and donor's anomeric configuration on the reactions were investigated. The results demonstrate the significant influence of silicon groups at C-4 in sialylation reactions, with overall performance optimized using acetonitrile.
CARBOHYDRATE RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Jacob M. A. van Hengst, Rik J. C. Hellemons, Wouter A. Remmerswaal, Koen N. A. van de Vrande, Thomas Hansen, Stefan van der Vorm, Hermen S. Overkleeft, Gijsbert A. van der Marel, Jeroen D. C. Codee
Summary: By systematically surveying 67 acceptor alcohols in glycosylation reactions, this study reveals how the reactivity of a carbohydrate acceptor depends on its configuration and substitution pattern, which greatly influences the yield and stereoselectivity of the reaction. The study demonstrates the influence of functional groups flanking the acceptor alcohol on its reactivity, highlighting the importance of both the nature and relative orientation. The empirical acceptor reactivity guidelines obtained will assist in the rational optimization of glycosylation reactions and serve as an important tool in oligosaccharide assembly.
Article
Chemistry, Multidisciplinary
Xin Qiu, Anna L. Garden, Antony J. Fairbanks
Summary: In this study, a new method for synthesizing glycosides was discovered. Unprotected 2-acetamido sugars were directly converted into their oxazolines in aqueous solution using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and a suitable base. Freeze drying and acid-catalyzed reaction with an alcohol as solvent yielded 1,2-trans-glycosides in good yield. Alternatively, using an aprotic solvent system and acidic activation with an excess of unprotected glycoside as a glycosyl acceptor led to the stereoselective formation of 1,2-trans-linked disaccharides without any protecting group manipulations. Reactions using aryl glycosides as acceptors were completely regioselective, producing only (1->6)-linked disaccharides.
Article
Chemistry, Multidisciplinary
Kazuki Ohira, Chih-Hsin Yu, Keiichi Imato, Yousuke Ooyama
Summary: New cyano-substituted phenazine-2,3-diol-based dyes, YC-1 and YC-2, were developed as halogen-atom-free-heteroanthracene-based photosensitizers with the ability to generate singlet oxygen. YC-1 and YC-2 exhibited blue-shifted photoabsorption edges compared to nitro-substituted phenazine-2,3-diol-based dyes. TDDFT calculations showed that YC-2 had the smallest energy gap between the S-1 and Tn states, leading to efficient intersystem crossing. YC-1 had a significantly lower Phi(Delta) value due to the relatively large Delta E-ST value and the acceleration of internal conversion, resulting in inferior ISC.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Yoshiyasu Ichikawa, Daisuke Kaneno, Nobuyoshi Saeki, Takahiro Minami, Toshiya Masuda, Kumi Yoshida, Tadao Kondo, Rika Ochi
Summary: The first protecting group-free synthesis of N-glycosyl carbamates was achieved by reacting D-glucose with n-butyl carbamate in acidic aqueous media. The structures of the N-glucosyl carbamates were determined by comparison with authentic samples, and an anomeric pair of N-xylopyranosyl carbamates were prepared to assess the anomeric effect of nitrogen in the carbamate group.
CARBOHYDRATE RESEARCH
(2021)
Review
Biochemistry & Molecular Biology
Joseph J. Barchi Jr, Caitlin N. Strain
Summary: A wide range of glycan structures on cell surfaces have significant roles in various biological processes and immune functions. Immune responses to foreign carbohydrate antigens and tumour-associated carbohydrate antigens are important for microbial clearance and anti-tumour vaccines. The linkage point of antigenic glycans affects their presentation to the immune system as well as carbohydrate binding molecules. The understanding of these presentations provides insights into the design of vaccines and recognition mechanisms.
FRONTIERS IN MOLECULAR BIOSCIENCES
(2023)
Article
Chemistry, Multidisciplinary
Nobuya Nishi, Kazuhiro Sueoka, Kiyoko Iijima, Ryuichi Sawa, Daisuke Takahashi, Kazunobu Toshima
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Takashi Kitamura, Mai Okuyama, Daisuke Takahashi, Kazunobu Toshima
CHEMISTRY-AN ASIAN JOURNAL
(2019)
Article
Biochemistry & Molecular Biology
Daisuke Takahashi
TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY
(2019)
Article
Chemistry, Organic
Yuka Matsumoto, Hajime Kuriki, Takashi Kitamura, Daisuke Takahashi, Kazunobu Toshima
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Multidisciplinary Sciences
Masamichi Tanaka, Koji Sato, Ryoki Yoshida, Nobuya Nishi, Rikuto Oyamada, Kazuki Inaba, Daisuke Takahashi, Kazunobu Toshima
NATURE COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Takashi Kitamura, Saori Shiroshita, Daisuke Takahashi, Kazunobu Toshima
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Multidisciplinary
Kazuki Inaba, Masato Endo, Naoto Iibuchi, Daisuke Takahashi, Kazunobu Toshima
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Organic
Shunpei Tomita, Masamichi Tanaka, Michitaka Inoue, Kazuki Inaba, Daisuke Takahashi, Kazunobu Toshima
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Nobuya Nishi, Katsunori Seki, Daisuke Takahashi, Kazunobu Toshima
Summary: The study demonstrates the synthesis of a pentasaccharide repeating unit of APEC O1's LPS, showing its potential as an antigen for vaccine development.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Takanori Kondo, Chihiro Yasui, Taisuke Banno, Kouichi Asakura, Tokuma Fukuoka, Kazunori Ushimaru, Maito Koga, Hiroyuki Minamikawa, Azusa Saika, Tomotake Morita, Daisuke Takahashi, Kazunobu Toshima
Summary: This study investigated the self-assembling properties and structure-activity relationship of chemically synthesized MELs, as well as their recovery effects on damaged skin cells. It was found that the synthetic MELs formed droplets or giant vesicles and the length of the fatty acid chains significantly affected their recovery effects.
Article
Chemistry, Multidisciplinary
Takashi Kitamura, Hirotaka Nakata, Daisuke Takahashi, Kazunobu Toshima
Summary: A novel tumor-related biomarker, a H2O2-activatable photosensitizer 4 based on hypocrellin B (3), was synthesized. Photosensitizer 4 showed selective and effective photo-cytotoxicity against high H2O2-expressing cancer cells under 660 nm light irradiation, demonstrating potential for targeted cancer therapy.
CHEMICAL COMMUNICATIONS
(2021)
Article
Biochemistry & Molecular Biology
Tatsuki Koike, Aoi Sugimoto, Shuhei Kosono, Sumika Komaba, Yuko Kanno, Takashi Kitamura, Itsuki Anzai, Tokiko Watanabe, Daisuke Takahashi, Kazunobu Toshima
Summary: Study showed that Fucoidan derivative 10 exhibited the highest inhibitory activity against SARS-CoV-2 virus, surpassing existing anticoagulants. Furthermore, 10 also demonstrated inhibitory effects on the binding of various mutant virus proteins with heparin, without affecting factor Xa that could lead to adverse anticoagulant activity.
RSC MEDICINAL CHEMISTRY
(2021)
Review
Chemistry, Organic
Daisuke Takahashi
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
(2020)
Article
Chemistry, Organic
Naoto Iibuchi, Takahiro Eto, Manabu Aoyagi, Reiji Kurinami, Hayato Sakai, Taku Hasobe, Daisuke Takahashi, Kazunobu Toshima
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Meeting Abstract
Chemistry, Multidisciplinary
Daisuke Takahashi
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2019)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
