Article
Chemistry, Organic
Manoj Kumar, Aakanksha Gurawa, Nitin Kumar, Sudhir Kashyap
Summary: A direct and highly stereoselective glycosylation reaction catalyzed by Bi(OTf)(3) has been reported. The chemoselectivity of deactivated glycal donors can be controlled by tuning the solvent, leading to improved substrate scope. The versatility of this method has been demonstrated in the synthesis of oligosaccharides, as well as the 2-deoxyglycosylation of high-value natural products and drugs.
Article
Chemistry, Organic
Yoshiyuki Manabe, Takuya Matsumoto, Yuka Ikinaga, Yuya Tsutsui, Shota Sasaya, Yuichiro Kadonaga, Akihito Konishi, Makoto Yasuda, Tomoya Uto, Changhao Dai, Kumpei Yano, Atsushi Shimoyama, Ayana Matsuda, Koichi Fukase
Summary: The study found that catalytic glycosylations using BF3·Et2O could efficiently proceed without the use of dehydrating agents, in contrast to traditional reactions requiring excess Lewis acid and additives. Mechanistic studies showed that chemical species formed by the reaction of in situ generated HF and glass vessels are involved in the catalytic cycle.
Review
Chemistry, Physical
Ram Naresh Yadav, Firoj Hossain, Aparna Das, Ashok Kumar Srivastava, Bimal Krishna Banik
Summary: Organocatalysis is a method of using low-molecular-weight organic molecules to accelerate stereoselective chemical transformations. It has recently gained attention in synthetic and medicinal chemistry for its potential in asymmetric synthesis of important compounds. Organocatalysts have advantages over metal-based catalysts, such as better tolerance to air and moisture, easy availability, easy handling, non-toxicity, and high enantiomeric purity. This perspective focuses on the application of asymmetric organocatalysis in the synthesis of biologically significant O-glycosides.
CATALYSIS REVIEWS-SCIENCE AND ENGINEERING
(2022)
Article
Chemistry, Multidisciplinary
Chao Wang, Rupeng Qi, Zhaoqing Xu
Summary: This article summarizes the important application of radical-based reactions in glycosylation modifications, focusing on the synthesis of unnatural amino acids and the late-stage modification of peptides and proteins. It also provides an outlook on the future development in this direction.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Zhi Qiao, Peng Wang, Jingxuan Ni, Dongwei Li, Yao Sun, Tiantian Li, Ming Li
Summary: This study presents a novel catalytic glycosylation reaction using disarmed glycosyl ortho-isopropenylphenylacetates (GIPPAs) and ortho-isopropenylbenzyl thioglycosides as glycosylating agents. Various O-, S-, and C-nucleophiles can be efficiently glycosylated under mild conditions. This work provides new glycosyl ester and thioglycoside donors for acid-catalyzed glycosylation.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Krista Gulbe, Jevgenija Luginina, Edijs Jansons, Artis Kinens, Maris Turks
Summary: Liquid SO2 can be used as a promoting solvent for glycosylation without external additives, showing good yields under various temperature regimes. The formation of fluorosulfite species during glycosylation in liquid SO2 is confirmed by F-19 NMR spectroscopy, and a proposed glycosylation mechanism involves solvent-separated ion pairs, with substrate-controlled alpha,beta-selectivity depending on the thermodynamic equilibrium.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Qing Long, Jingru Gao, Ningjie Yan, Peng Wang, Ming Li
Summary: This study presents an efficient catalytic system for the glycosylation of disarmed glycosyl fluorides, achieving good yields in a wide range of substrates. Preliminary mechanistic studies reveal the actual catalyst involved in the reaction, providing valuable insights for further research in this field.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Kazuki Kurahayashi, Kengo Hanaya, Takeshi Sugai, Go Hirai, Shuhei Higashibayashi
Summary: Metabolically stable C-glycosides play a crucial role in bioactive natural products, therapeutic agents, and biological probes. The development of synthetic methods for connecting glycosides and aglycons with strict stereocontrol is essential. In this study, a copper-catalyzed one-step borylation of glycosyl bromides to glycosyl boronates and a palladium-catalyzed cross-coupling of β-glycosyl borates with aryl bromides were successfully achieved, resulting in the synthesis of aryl β-C-glycosides.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Poulomi Nandi, Komal Goel, Chinnabattigalla Sreenivasulu, Gedu Satyanarayana
Summary: A simple Lewis acid-mediated route has been developed for the synthesis of alkenyl halides under microwave-assisted conditions. The reaction involves condensation between secondary alcohols and terminal acetylenes, and regioselective hydrohalogenation across the triple bond in the presence of zinc halides. The methodology shows versatility with three different halide sources and leads to a diverse range of alkenyl halide products.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Analytical
Diana Campos, Michael Girgis, Qiang Yang, Guanghui Zong, Radoslav Goldman, Lai-Xi Wang, Miloslav Sanda
Summary: Mass spectrometry can provide valuable insights into glycosylation analysis, but analyzing isobaric glycopeptide structures remains challenging. Modulating collision energy can improve structural elucidation, especially for qualitative purposes. Our research identified the potential for false-positive structure assignments and established a minimum intensity threshold to prevent misidentification of structure-specific fragments in glycoproteomics analysis.
ANALYTICAL CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Thomas Hansen, Tim P. Ofman, Joey G. C. Vlaming, Ivan A. Gagarinov, Jessey van Beek, Tessa A. Gote, Jacoba M. Tichem, Gijs Ruijgrok, Herman S. Overkleeft, Dmitri V. Filippov, Gijsbert A. van der Marel, Jeroen D. C. Codee
Summary: By systematically studying the reactivity-stereoselectivity relationships of caryophyllose donor and acceptor glycosides, using experimental and computational techniques, we were able to design carbohydrate building blocks with the necessary properties to assemble mycobacterial lipooligosaccharide fragments of M. marinum.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Pallavi Sarkar, Shubhajit Das, Swapan K. Pati
Summary: This article summarizes the progress in the study of non-boron Lewis acids since 2015, which are an important component of Frustrated Lewis pairs.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Nanxing Gao, Yanshun Li, Dawei Teng
Summary: The structure of primary alkylated arenes is crucial for the molecular action of drugs and natural products. This study presents a nickel-catalyzed reaction that efficiently synthesizes primary alkylated arenes by cross-electrophile coupling of aryl bromides and primary alkyl bromides, demonstrating excellent tolerance towards functional groups such as ester, aldehyde, ketone, ether, benzyl, and imide.
Article
Chemistry, Organic
Lei Zhao, Xiao Meng, Yifeng Zou, Junsong Zhao, Lili Wang, Lanlan Zhang, Chao Wang
Summary: This report describes an intermolecular syn-arylalkylation and alkenylalkylation of alkenyl amines with two different organohalides using a Ni(II) catalyst. By utilizing cleavable bidentate quinolinamide, the reaction enables olefin difunctionalization with high levels of regio-, chemo-, and diastereocontrol, providing rapid access to branched aliphatic amines with high diastereoselectivities.
Review
Plant Sciences
Richard Strasser, Georg Seifert, Monika S. Doblin, Kim L. Johnson, Colin Ruprecht, Fabian Pfrengle, Antony Bacic, Jose M. Estevez
Summary: Glycosylation is a crucial modification process that can alter the biological function of proteins and lipids, affecting the development and physiology of an organism. While challenges remain in understanding plant glycosylation, high throughput approaches may help to address these gaps, revolutionizing the identification and characterization of unknown plant glycosyltransferases and hydrolases.
FRONTIERS IN PLANT SCIENCE
(2021)
Article
Chemistry, Applied
Motonari Shibakami, Gen Tsubouchi, Mitsugu Sohma, Masahiro Hayashi
CARBOHYDRATE POLYMERS
(2015)
Article
Chemistry, Applied
Motonari Shibakami, Gen Tsubouchi, Mitsugu Sohma, Masahiro Hayashi
CARBOHYDRATE POLYMERS
(2015)
Article
Chemistry, Applied
Motonari Shibakami, Gen Tsubouchi, Mitsugu Sohma, Masahiro Hayashi
CARBOHYDRATE POLYMERS
(2016)
Article
Materials Science, Paper & Wood
Motonari Shibakami, Tadashi Nemoto, Mitsugu Sohma
Article
Chemistry, Applied
Motonari Shibakami, Mitsugu Sohma, Masahiro Hayashi
CARBOHYDRATE POLYMERS
(2012)
Article
Chemistry, Applied
Motonari Shibakami, Gen Tsubouchi, Makoto Nakamura, Masahiro Hayashi
CARBOHYDRATE POLYMERS
(2013)
Article
Chemistry, Applied
Motonari Shibakami, Gen Tsubouchi, Makoto Nakamura, Masahiro Hayashi
CARBOHYDRATE POLYMERS
(2013)
Article
Chemistry, Applied
Motonari Shibakami, Gen Tsubouchi, Masahiro Hayashi
CARBOHYDRATE POLYMERS
(2014)
Article
Chemistry, Applied
Motonari Shibakami, Mitsugu Sohma
CARBOHYDRATE POLYMERS
(2018)
Article
Materials Science, Composites
Yukari Sato, Kyoko Yoshioka, Teiichi Murakami, Mutsuo Tanaka, Osamu Niwa
COMPOSITE INTERFACES
(2014)
Article
Chemistry, Multidisciplinary
Yukari Sato, Kyoko Yoshioka, Teiichi Murakami, Soichiro Yoshimoto, Osamu Niwa
Article
Chemistry, Multidisciplinary
Teiichi Murakami, Yukari Sato, Kyoko Yoshioka, Mutsuo Tanaka
Article
Chemistry, Multidisciplinary
Motonari Shibakami, Kazuhiko Shibata, Akira Akashi, Nobuteru Onaka, Jun Takezaki, Gen Tsubouchi, Hiroaki Yoshikawa
PHARMACEUTICAL RESEARCH
(2019)
Article
Chemistry, Applied
Motonari Shibakami
CARBOHYDRATE POLYMERS
(2017)
Article
Chemistry, Applied
Motonari Shibakami, Mitsugu Sohma
CARBOHYDRATE POLYMERS
(2017)
