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
Chen Zhang, Hao Zuo, Ga Young Lee, Yike Zou, Qiu-Di Dang, K. N. Houk, Dawen Niu
Summary: The chemistry of carbohydrates has a long history, and a simple, stereoselective and efficient glycosylation method is still needed for studying sugars. This study presents a strategy for 1,2-cis-glycosylation without using metals or strong acids. The method activates glycosyl donors through a radical cascade, resulting in the formation of 1,2-cis-glycosides with high stereoselectivity. The reaction shows remarkable tolerance to functional groups and is applicable to a broad range of donors.
Review
Chemistry, Multidisciplinary
Samira Escopy, Alexei Demchenko
Summary: This review highlights recent methods for thioglycoside activation that rely on transition metal catalysis. The requirement for toxic and/or large access of activators needed for common glycosylations with thioglycosides is a notable drawback, driving the goal of finding non-toxic reagents in synthetic studies.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Samira Escopy, Yashapal Singh, Keith J. Stine, Alexei V. Demchenko
Summary: This research describes a direct conversion of thioglycosides using a regenerative approach, bypassing the need for bromide intermediates and heavy-metal-based promoters. The reaction conditions are mild, with only 1 equiv. NIS and catalytic HOFox needed under neutral conditions.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
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, Organic
Helle H. Trinderup, Sofie M. Andersen, Mads Heuckendorff, Henrik H. Jensen
Summary: The study showed that increasing the concentration and amount of triflic acid catalyst can enhance beta-selectivity in the reaction, while lowering temperature has a significant effect on the glycosylation outcome. The alpha/beta-ratio in the reaction with L-menthol as glycosyl acceptor was not affected by the molecular sieve pore size or NIS activator amount.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jordi Mestre, Isabel Bascuas, Miguel Bernus, Sergio Castillon, Omar Boutureira
Summary: Fluorinated carbohydrate mimetics are important in Glycoscience, but the synthesis of complex C(sp(3))-CF3 congeners is underdeveloped. A new protocol for preparing 2-deoxy-2-trifluoromethyl-d-hexopyranosides from d-glycals is presented. The stereoselectivity of glycosylation is mainly controlled by electronic and steric factors, resulting in the formation of 1,2-trans glycosides due to the configuration of the CF3 moiety at C-2. This approach was successfully applied in the synthesis of 2-CF3-glycoconjugates of natural origin.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Alejandro E. Cristofalo, Maria Emilia Cano, Maria Laura Uhrig
Summary: This review discusses the research on introducing N-acetylhexosamine residues into thiodisaccharides, including classic substitution and addition reactions. Recent developments in addition reactions to vinyl azides, cross-coupling reactions, and novel chemoenzymatic methods are also highlighted.
Article
Chemistry, Physical
Zihao Rei Gao, Salvador R. G. Balestra, Luis Gomez-Hortiguela, Jian Li, Carlos Marquez-Alvarez, Miguel A. Camblor
Summary: The chiral zeolite STW has been successfully synthesized using a large dication with three aromatic rings. The presence and structure of the occluded organics in the zeolite are confirmed by various experimental techniques. Molecular simulations provide insights into the location and interactions of the aromatic rings in the cavities, and their blocking effect on certain pores. The study also discusses the implications of a structure-directing agent spanning three cavities.
CHEMISTRY OF MATERIALS
(2022)
Article
Chemistry, Organic
Kevin Muru, Maude Cloutier, Arianne Provost-Savard, Sabrina Di Cintio, Oceane Burton, Justin Cordeil, Marie-Christine Groleau, Jean Legault, Eric Deziel, Charles Gauthier
Summary: The study presents a total synthesis of a chimeric glycolipid incorporating both sponge-derived agminoside E and bacterial rhamnolipids. The synthesis of the branched pentaglucolipid skeleton involved a [3 + 2] disconnection approach, with key glycosidic bonds synthesized through stereoselective glycosylations. This work lays the foundation for the total synthesis of sponge-derived agminosides and the exploration of their biological functions in sponges.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yongyong Wan, Lei Deng, Liming Wang, Yuanhong Tu, Hui Liu, Jian-song Sun, Qingju Zhang
Summary: Researchers have developed an efficient method for the site-selective and stereoselective synthesis of potential bioactive 2-amino-2-deoxy-1,3-dithioidoglycosides using organocatalysis sequential C3-Ferrier rearrangement and Michael addition of 3-O-acetyl-2-nitrogalactals. This method offers advantages such as mild reaction conditions, high yields, broad substrate scopes, and environmental friendliness.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Koji Morimoto, Kana Yanase, Tetsuya Kajimoto, Yasuyuki Kita
Summary: A method using hypervalent iodine reagents for oxidative glycosylation was discovered, resulting in the synthesis of sugars of different sizes, providing new possibilities for further research.
Article
Chemistry, Inorganic & Nuclear
Jichen Zhao, Jiaxi Xu, Xikun Zhang, Yiwen Liu, Chiwei Xu, Junwei Zhang, Haoxiang Yu, Lei Yan, Jie Shu
Summary: In this study, a possible Ni2+ storage material for rechargeable aqueous batteries, K-ZnHCF, is reported. The material exhibits high reversible capacity, stable host structure, and favorable rate performance. The study investigates the reversible nickel ion storage mechanism and proves the suitability of K-ZnHCF for repeated nickel ion storage in rechargeable batteries.
INORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Bhavesh Deore, Joseph E. Ocando, Lan D. Pham, Carlos A. Sanhueza
Summary: A voltammetric study of alkyl and arylS-glucosides revealed their reactivity patterns. The oxidation potential of alkylS-glucosides is influenced by the steric properties of the aglycone, with bulky groups leading to higher oxidation potentials. In contrast, arylS-glucosides' oxidation potentials correlate with the substituents' parameters and radical stabilization energies, indicating the importance of inherent stability in controlling their electrochemical reactivity. The reactivity differences between alkyl and arylS-glucosides also extend to the protective group's effect on the oxidation potential.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Feng Zhang, Yang Si, Jianyong Yu, Bin Ding
Summary: This article introduces a new type of biomimetic sub-nanoporous engineered aerogel molecular sieves, which achieve efficient and reversible molecular separation through coupling size-thermodynamic gated functions, demonstrating potential widespread applications in chemical, energy, and environmental processes.
Article
Pharmacology & Pharmacy
Szu-Huei Wu, Chun-Hsu Yao, Chieh-Jui Hsieh, Yu-Wei Liu, Yu-Sheng Chao, Jen-Shin Song, Jinq-Chyi Lee
EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES
(2015)
Article
Biochemistry & Molecular Biology
Kuang-Feng Chu, Chun-Hsu Yao, Jen-Shin Song, Chiung-Tong Chen, Teng-Kuang Yeh, Tsung-Chih Hsieh, Chung-Yu Huang, Min-Hsien Wang, Szu-Huei Wu, Wei-En Chang, Yu-Sheng Chao, Jinq-Chyi Lee
BIOORGANIC & MEDICINAL CHEMISTRY
(2016)
Article
Biochemistry & Molecular Biology
Wan-Ting Tsai, Yin-Chiu Lo, Ming-Sian Wu, Chia-Yang Li, Yi-Ping Kuo, Yi-Hui Lai, Yu Tsai, Kai-Chieh Chen, Tsung-Hsien Chuang, Chun-Hsu Yao, Jinq-Chyi Lee, Li-Chung Hsu, John T. -A. Hsu, Guann-Yi Yu
JOURNAL OF BIOLOGICAL CHEMISTRY
(2016)
Article
Plant Sciences
Chun-Hsu Yao, Chi-Hui Tsai, Jinq-Chyi Lee
JOURNAL OF NATURAL PRODUCTS
(2016)
Article
Chemistry, Medicinal
Chia-Yi Cheng, Chun-Ping Chang, Tsai-Ling Yang Lauderdale, Guann-Yi Yu, Jinq-Chyi Lee, Yi-Wun Jhang, Chien-Huang Wu, Yi-Yu Ke, Amit A. Sadani, Ching-Fang Yeh, I-Wen Huang, Yi-Ping Kuo, De-Jiun Tsai, Teng-Kuang Yeh, Chen-Tso Tseng, Jen-Shin Song, Yu-Wei Liu, Lun K. Tsou, Kak-Shan Shia
ACS MEDICINAL CHEMISTRY LETTERS
(2016)
Article
Chemistry, Medicinal
Mao-Chia Yuan, Teng-Kuang Yeh, Chiung-Tong Chen, Jen-Shin Song, Yu-Chen Huang, Tsung-Chih Hsieh, Chung-Yu Huang, Yu-Ling Huang, Min-Hsien Wang, Szu-Huei Wu, Chun-Hsu Yao, Yu-Sheng Chao, Jinq-Chyi Lee
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2018)
Article
Chemistry, Medicinal
Chun-Hsu Yao, Jen-Shin Song, Chiung-Tong Chen, Teng-Kuang Yeh, Tsung-Chih Hsieh, Szu-Huei Wu, Chung-Yu Huang, Yu-Lin Huang, Min-Hsien Wang, Yu-Wei Liu, Chi-Hui Tsai, Chidambaram Ramesh Kumar, Jinq-Chyi Lee
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2012)
Article
Chemistry, Organic
Shang-Cheng Hung, Xin-An Lu, Jinq-Chyi Lee, Margaret Dah-Tsyr Chang, Shun-lung Fang, Tan-chi Fan, Medel Manuel L. Zulueta, Yong-Qing Zhong
ORGANIC & BIOMOLECULAR CHEMISTRY
(2012)
Article
Oncology
Yue-Zhi Lee, Cheng-Wei Yang, Hsin-Yu Chang, Hsing-Yu Hsu, Ih-Shen Chen, Hsun-Shuo Chang, Chih-Hao Lee, Jinq-Chyi Lee, Chidambaram Ramesh Kumar, Ya-Qi Qiu, Yu-Sheng Chao, Shiow-Ju Lee
Article
Biochemistry & Molecular Biology
Kuang-Feng Chu, Jen-Shin Song, Chiung-Tong Chen, Teng-Kuang Yeh, Tsung-Chih Hsieh, Chung-Yu Huang, Min-Hsien Wang, Szu-Huei Wu, Chun-Hsu Yao, Yu-Sheng Chao, Jinq-Chyi Lee
BIOORGANIC CHEMISTRY
(2019)
Article
Chemistry, Medicinal
Chun-Hsu Yao, Tsung-Chih Hsieh, Jen-Shin Song, Jinq-Chyi Lee
FUTURE MEDICINAL CHEMISTRY
(2020)
Article
Chemistry, Medicinal
Yi-Fan Chen, Chien-Huang Wu, Li-Hsien Chen, Hao-Wei Lee, Jinq-Chyi Lee, Teng-Kuang Yeh, Jang-Yang Chang, Ming-Chen Chou, Hui-Ling Wu, Yen-Po Lai, Jen-Shin Song, Kai-Chia Yeh, Chiung-Tong Chen, Chia-Jui Lee, Kak-Shan Shia, Meng-Ru Shen
Summary: Chemotherapy-induced neurotoxicity is a common adverse effect of cancer treatment, and there is currently no effective medication for prevention or treatment. However, the discovery of CN016 as a neuroprotective agent shows promise, as it can inhibit inflammatory responses and alleviate nerve damage caused by chemotherapy.
JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Chun-Hsu Yao, Mine-Hsine Wu, Po-Wei Chang, Szu-Huei Wu, Jen-Shin Song, Hsing-Hao Huang, Yu-Chun Chen, Jinq-Chyi Lee
Summary: A series of 1-benzo[1,3]dioxol-5-yl-indoles bearing 3-N-fused heteroaryl moieties were designed, synthesized, and evaluated for their anticancer activity against prostate, pancreatic, and acute lymphoblastic leukemia cancer cell lines. Two compounds, 3-N-benzo[1,2,5]oxadiazole 17 and 3-N-2-methylquinoline 20, showed promising activity against CCRF-CEM and MIA PaCa-2 cell lines. Mechanistic studies revealed that compound 20 induced cell cycle arrest and apoptosis in CCRF-CEM cells. These compounds may serve as a template for developing more potent indole anticancer molecules and understanding their structure-activity relationships.
MOLECULAR DIVERSITY
(2023)
Meeting Abstract
Chemistry, Multidisciplinary
Wen-Chieh Wang, Yung Chang Hsu, Hui-Yi Shiao, Hui-Chen Hung, Ching-Chuan Kuo, Jinq-Chyi Lee, Tsu-An Hsu, Hsing-Pang Hsieh
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
