Article
Biochemistry & Molecular Biology
Yogesh Yadav, Rajdeep Tyagi, Kanchan Yadav, Ghanshyam Tiwari, Ram Sagar
Summary: The Ferrier rearrangement using SnCl4 as catalyst allows for the synthesis of 2,3-unsaturated glycopyranosides with high stereoselectivity starting from the hydroxyl group at the C-3 position. This method has several advantages, including strong anomeric selectivity, high yields, and short reaction time.
CARBOHYDRATE RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Naresh Bhuma, Ludivine Lebedel, Hiroki Yamashita, Yutaka Shimizu, Zahra Abada, Ana Arda, Jerome Desire, Bastien Michelet, Agnes Martin-Mingot, Ali Abou-Hassan, Masahiro Takumi, Jerome Marrot, Jesus Jimenez-Barbero, Aiichiro Nagaki, Yves Bleriot, Sebastien Thibaudeau
Summary: Ferrier's research in 1962 on the transformation of glycals into unsaturated glycosyl derivatives involved an alpha,beta unsaturated glycosyl cation. Through NMR-based structural analysis and DFT calculations, this elusive ionic species was characterized, leading to the synthesis of unsaturated nitrogen-containing C-aryl glycosides and C-alkyl glycosides under different conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Anselme Geulin, Yann Bourne-Branchu, Kawther Ben Ayed, Thomas Lecourt, Antoine Joosten
Summary: 3-Amino-3-deoxyglycosides are important nitrogen-containing sugars, with many important ones having a 1,2-trans configuration. The synthesis of 3-amino-3-deoxyglycosyl donors that can form a 1,2-trans glycosidic linkage is a significant challenge due to their biological applications. This work presents a new sequence involving Ferrier rearrangement and subsequent aza-Wacker cyclization for the rapid synthesis of orthogonally protected 3-amino-3-deoxyglycals. Additionally, the epoxidation/glycosylation of a 3-amino-3-deoxygalactal derivative was successfully achieved with high yield and diastereoselectivity, demonstrating FAWEG as a new approach for accessing 1,2-trans 3-amino-3-deoxyglycosides.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
Nan Jiang, Yuling Mei, Yu Yang, Youxian Dong, Zekun Ding, Jianbo Zhang
Summary: A two-step methodology was developed for the synthesis of chiral pyrroles from 2-nitroglycals via Ferrier rearrangement and Barton-Zard reaction without transition metal catalysts. The highly stereoselective synthesis of diverse 2-nitro-2,3-unsaturated glycosides in excellent yields was achieved using N-heterocyclic carbene (NHC) catalyst and K2CO3. Successful demonstration of gram-scale synthesis of one chiral pyrrole was shown using a one-pot strategy.
Article
Biochemistry & Molecular Biology
Zhiqiang Lu, Yanzhi Li, Shaohua Xiang, Mengke Zuo, Yangxing Sun, Xingxing Jiang, Rongkai Jiao, Yinghong Wang, Yuqin Fu
Summary: The use of perfluorinated solvent in the stereoselective formation of O-/S-glycosidic linkages via a Ferrier rearrangement of acetylated glycals has been demonstrated for the first time. This method shows enhanced reactivity and stereocontrol through weak interactions with substrates, and it is environmentally friendly with low toxicity, easy recovery of the medium, and simple product isolation.
Article
Chemistry, Multidisciplinary
Yu Yang, Nan Jiang, Yuling Mei, Zekun Ding, Jianbo Zhang
Summary: A sustainable magnetic core-shell nanocatalyst Fe3O4@C@Fe(III) was successfully used for the synthesis of a series of 2-nitro-2,3-unsaturated O-glycosides with high yields and stereoselectivity. The catalyst exhibited wide substrate applicability, including different kinds of alcohols and structurally complex acceptors. In addition, the catalyst could be easily separated and reused multiple times without significant decrease in catalytic performance.
FRONTIERS IN CHEMISTRY
(2022)
Article
Chemistry, Organic
Agustin H. Rojas, Leticia Lafuente, Virginia Vetere, Agustin Ponzinibbio
Summary: This study presents the selective synthesis of new 2-iodo-2,3-unsaturated O- and S-glycosides, marking the first report on the Ferrier rearrangement of 2-halo-glycals with S-nucleophiles. The alpha-glycosides were obtained in good yields and with high anomeric selectivity. Additionally, the particular behavior of heteroaromatic thio sugar derivatives, including an alternative mechanism for C3 addition, was described, with a complete structure and conformation analysis provided by NMR.
TETRAHEDRON LETTERS
(2021)
Article
Biochemistry & Molecular Biology
Laura Morelli, Laura Legnani, Silvia Ronchi, Laura Confalonieri, Daniela Imperio, Lucio Toma, Federica Compostella
Summary: This study investigated the role of cyclic 2,3-N,O-carbamate protecting group in directing the selectivity of mannosylation reactions of diacetone-D-glucose. Computational and experimental methods were used to show the preference of the formation of beta-adduct with mannosyl donors equipped with or without the 4,6-O-benzylidene protection. The results confirmed the preference for beta-adducts with an alpha/beta selectivity of 4:6.
CARBOHYDRATE RESEARCH
(2021)
Article
Chemistry, Organic
Xiaoxiao Zhao, Zhentao Zhang, Jing Xu, Nengzhong Wang, Nianyu Huang, Hui Yao
Summary: In this study, a novel O-glycosylation method was developed using palladium and copper catalysts, which resulted in the formation of 2,3-unsaturated O-glycosides and 2-deoxy O-glycosides. This method showed tolerance towards a wide range of trialkyl/triaryl borates and various glycals, with high yields and exclusive stereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Keisuke Iwata, Yasunobu Egawa, Katsunori Yamanishi, Hayato Tsuji
Summary: The acid-induced intramolecular cyclization of 1,1-disubstituted 3-aryl-2,3-dibromoallylalcohols leads to the formation of 2,3-dibromo-1H-indene derivatives and tetrabromodihydro-s-indacenes. These multi-brominated compounds can serve as versatile building blocks for the synthesis of various indene and indacene derivatives. The synthesis of dialkylmethylene-bridged oligo(phenylenevinylene)s demonstrates the attractive photophysical properties of these compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jiagen Li, Xuefeng Jiang
Summary: C-aryl glycosides, important carbohydrate derivatives in drug discovery, can resist hydrolysis from enzymes. This study establishes a synthesis method for 2-sulfur C-aryl glycals and 1,2-dihydrobenzofuran-fused C-aryl glycosides via interrupted Pummerer process, involving a sulfonium-tethered [3,3]-sigmatropic rearrangement. The protocol can be applied to a wide range of glycosyl and phenol substrates, and analogs of Dapagliflozin, Empagliflozin, and Ipragliflozin were successfully obtained.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Eric M. Miller, Maciej A. Walczak
Summary: This study presents stereoselective C-arylation and etherification reactions of anomeric trifluoroborates derived from BMIDA esters, exhibiting high anomeric selectivities for 2-deoxysugars and showing a broad substrate scope, including disaccharides and trifluoroborates with free hydroxyl groups. This new class of carbohydrate reagents adds to the palette of anomeric nucleophile reagents suitable for efficient installation of C-C bonds.
Review
Biochemistry & Molecular Biology
Sasilada Sirirungruang, Collin R. Barnum, Sophia N. N. Tang, Patrick M. M. Shih
Summary: Glycosylation is an effective method to modify the pharmacological properties of small molecules and expand the chemical diversity of natural products for drug discovery. While traditional glycosylation is chemically-based, enzymatic glycosylation using glycosyltransferases provides an alternative approach to produce new glycosides. plant glycosyltransferases have a wide range of applications in generating bioactive glycosides and altering their pharmacological properties.
NATURAL PRODUCT REPORTS
(2023)
Article
Chemistry, Applied
Kameshwar Prasad, Ananay Sharma, Soumyaranjan Pati, Marc Taillefer, Florian Jaroschik, Srinivas Hotha
Summary: We report metal free conditions for the activation of alkynyl glycosyl carbonate donors using I-2/TMSOTf in stoichiometric quantities. The extrusion product was characterized as vinylidene iodide by single crystal X-ray analysis. The reaction conditions were suitable for the synthesis of various glycosides, purine/pyrimidine nucleosides, and a pentasaccharide repeating unit of Klebsiella pneumoniae (O-3 antigen).
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Carla Obradors, Benjamin Mitschke, Miles H. Aukland, Markus Leutzsch, Oleg Grossmann, Sebastian Brunen, Sebastian A. Schwengers, Benjamin List
Summary: Since early 2020, scientists have been striving to find effective solutions to combat SARS-CoV-2, focusing on developing reliable vaccines and repurposing drugs. However, the current synthetic routes for Remdesivir, the most widely used therapeutic during the early stages of infection, face challenges in cost-effective supply to patients. In this study, researchers have developed a straightforward method for adding (hetero)arenes to unprotected sugars, significantly expediting the synthesis of Remdesivir precursor GS-441524.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Biochemistry & Molecular Biology
Jimei Ma, Yupeng Li, Hangwei Chen, Zhen Zeng, Zi-Long Li, Hong Jiang
Article
Polymer Science
Zi-Long Li, Linhao Sun, Jimei Ma, Zhen Zeng, Hong Jiang
Article
Chemistry, Multidisciplinary
Bin Liu, Ji-Mei Ma, Hang-Wei Chen, Zi-Long Li, Lin-Hao Sun, Zhen Zeng, Hong Jiang
Article
Polymer Science
Fu-Rong Zeng, Ji-Mei Ma, Lin-Hao Sun, Zhen Zeng, Hong Jiang, Zi-Long Li
MACROMOLECULAR RAPID COMMUNICATIONS
(2018)
Article
Polymer Science
Zi-Long Li, Fu-Rong Zeng, Ji-Mei Ma, Lin-Hao Sun, Zhen Zeng, Hong Jiang
MACROMOLECULAR RAPID COMMUNICATIONS
(2017)
Article
Chemistry, Organic
Linhao Sun, Xing Zhang, Zilong Li, Jimei Ma, Zhen Zeng, Hong Jiang
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Review
Chemistry, Organic
Hongze Liao, Jimei Ma, Hui Yao, Xue-Wei Liu
ORGANIC & BIOMOLECULAR CHEMISTRY
(2018)
Article
Chemistry, Analytical
Xin Cheng, Yan Huang, Chao Yuan, Ke Dai, Hong Jiang, Jimei Ma
SENSORS AND ACTUATORS B-CHEMICAL
(2019)
Article
Materials Science, Multidisciplinary
Jimei Ma, Xin Cheng, Fangfang Peng, Na Zhang, Ruifeng Li, Linhao Sun, Zi-Long Li, Hong Jiang
JOURNAL OF MATERIALS SCIENCE
(2019)
Article
Chemistry, Analytical
Heng Zhang, Zhen Wang, Xiaoqing Yang, Zi-Long Li, Linhao Sun, Jimei Ma, Hong Jiang
ANALYTICA CHIMICA ACTA
(2019)
Article
Chemistry, Analytical
Xin Cheng, Yan Huang, Diying Li, Chao Yuan, Zi-Long Li, Linhao Sun, Hong Jiang, Jimei Ma
SENSORS AND ACTUATORS B-CHEMICAL
(2019)
Article
Chemistry, Analytical
Xin Cheng, Linhao Sun, Ruifeng Li, Yan Huang, Haiwei Xu, Zhen Wang, Zi-Long Li, Hong Jiang, Jimei Ma
Article
Chemistry, Analytical
Jimei Ma, Heng Zhang, Fangfang Peng, Xiaoqing Yang, Zi-Long Li, Linhao Sun, Hong Jiang
ANALYTICA CHIMICA ACTA
(2020)
Article
Chemistry, Multidisciplinary
Linhao Sun, Xing Zhang, Chenguang Wang, Huailong Teng, Jimei Ma, Zilong Li, Hao Chen, Hong Jiang
Article
Chemistry, Organic
Jimei Wang, Lingyun Xie, Longwen Wang, Hangwei Chen, Zhen Zeng, Hao Chen, Hong Jiang
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Medicinal
Shibin Zhao, Julian Maceren, Mia Chung, Samantha Stone, Raphael Geiben, Melissa L. Boby, Bradley S. Sherborne, Derek S. Tan
Summary: Antibiotic resistance is a major threat to public health, with Gram-negative bacteria presenting unique challenges due to their low permeability and efflux pumps. Limited understanding of the chemical rules for overcoming these barriers hinders antibacterial drug discovery. Efforts to address this issue, such as screening compound libraries and using cheminformatic analysis, have led to the design of sulfamidoadenosines with diverse substituents, showing potential utility in accumulation in Escherichia coli.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Jichun Li, Qing Li, Shuai Xia, Jiahuang Tu, Longbo Zheng, Qian Wang, Shibo Jiang, Chao Wang
Summary: This study successfully developed a short peptide mimetic as a MERS-CoV fusion inhibitor by reproducing the key recognition features of the HR2 helix. The resulting 23-mer lipopeptide showed comparable inhibitory effect to the 36-mer HR2 peptide HR2P-M2. This has important implications for developing short peptide-based antiviral agents to treat MERS-CoV infection.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Krista Jaunsleine, Linda Supe, Jana Spura, Sten van Beek, Anna Sandstrom, Jessica Olsen, Carina Halleskog, Tore Bengtsson, Ilga Mutule, Benjamin Pelcman
Summary: Beta(2)-adrenergic receptor agonists can stimulate glucose uptake by skeletal muscle cells and are therefore potential treatments for type 2 diabetes. The chirality of compounds has a significant impact on the activity of these agonists. This study found that certain synthesized compounds showed higher glucose uptake activity. These findings provide important information for the design of novel beta(2)AR agonists for T2D treatment.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Xin Xu, Jia Chen, Guan Wang, Xiaojuan Zhang, Qiang Li, Xiaobo Zhou, Fengying Guo, Min Li
Summary: The study focuses on EZH2, a promising therapeutic target for various types of cancers. Researchers designed and synthesized a series of novel derivatives aiming to enhance the EZH2 inhibition activity. Among them, compound 28 displayed potent EZH2 inhibition activity and showed high anti-proliferative effects in lymphoma cell lines and xenograft mouse models. The study suggests that compound 28 has potential as a therapeutic candidate for EZH2-associated cancers.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Wei Zhang, Wei Liu, Ya-Dong Zhao, Li-Zi Xing, Ji Xu, Rui-Jun Li, Yun-Xiao Zhang
Summary: This study developed a series of aromatic amide derivatives based on Rhein and investigated their inhibitory activity against alpha-Syn aggregation. Two of these compounds showed promising potential in treating Parkinson's disease by stabilizing alpha-Syn's conformation and disassembling alpha-Syn oligomers and fibrils.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
Article
Chemistry, Medicinal
Mani Sharma, S. S. S. S. Sudha Ambadipudi, Neeraj Kumar Chouhan, V. Lakshma Nayak, Srihari Pabbaraja, Sai Balaji Andugulapati, Ramakrishna Sistla
Summary: Therapeutically active lipids in drug delivery systems can enhance the safety and efficacy of treatment. The liposome formulation created using synthesized biologically active lipids showed additive anti-cancer effects and reduced tumorigenic potential.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2024)
