Article
Biochemistry & Molecular Biology
Maxim Musalov, Vladimir A. Potapov, Vladimir A. Yakimov, Maria Musalova, Arkady A. Maylyan, Sergey Zinchenko, Svetlana Amosova
Summary: The regioselective synthesis of novel functionalized condensed organochalcogen compounds was achieved through chalcogenocyclofunctionalization reactions based on chalcogen halides and natural products thymol and carvacrol. Various selenides, sulfides, telluranes, and ditellurides were successfully synthesized with high yields, highlighting the distinct reactivity of sulfur, selenium, and tellurium halides in the reactions.
Review
Biotechnology & Applied Microbiology
Jie Ren, Caleb Don Barton, Jixun Zhan
Summary: Polyphenolic compounds can be biosynthesized into glycosides with improved hydrophilicity through glycosylation, which decreases toxicity, increases bioavailability and stability, and changes bioactivity. Engineered biosynthesis provides an environmentally friendly and cost-effective approach to generate polyphenolic glycosides using glycosyltransferases and sugar biosynthetic enzymes.
BIOTECHNOLOGY ADVANCES
(2023)
Article
Biochemical Research Methods
Zhiqiang Xiao, Yongtong Wang, Juan Liu, Siqi Zhang, Xinjia Tan, Yifei Zhao, Jiwei Mao, Ning Jiang, Jingwen Zhou, Yang Shan
Summary: In this study, a biosynthetic pathway for flavonoid-7-O-disaccharide was constructed in Saccharomyces cerevisiae using metabolic engineering and promoter strategies. The optimized strain produced high yields of various flavonoid-7-O-disaccharides, making it the first report on the biosynthesis of flavonoid-7-O-disaccharide.
ACS SYNTHETIC BIOLOGY
(2023)
Article
Chemistry, Organic
Xiaopei Wu, Zhichao Zheng, Liming Wang, Yunxia Xue, Jinxi Liao, Hui Liu, Deyong Liu, Jian-Song Sun, Qingju Zhang
Summary: In this study, an efficient method for the synthesis of 2-nitroglycals using (Bu4NNO3)-Bu-n/Tf2O/DTBMP was reported. Additionally, a novel method for constructing challenging 1,2-cis-2,3-diamino-2,3-dideoxyglycosidic linkages was established by utilizing a 4-pyrrolidinopyridine (PPY) mediated relay glycosylation reaction. This method features mild reaction conditions, excellent selectivity, high yields, and a wide substrate scope.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
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
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
Swapan Kumar Jana, Pradip Shit, Anup Kumar Misra
Summary: In this study, the pentasaccharide repeating unit rich in 2-acetamidosugars corresponding to the O-antigenic polysaccharide from entero-pathogenic E. coli was successfully synthesized as the p-me-thoxyphenyl glycoside using a sequential glycosylation strategy. The key components of the synthetic strategy included regioselective glycosylation, use of a single monosaccharide intermediate in multiple glycosylations, and the use of thioglycosides as glycosyl donors in the presence of a combination of N-iodosuccinimide and perchloric acid supported over silica.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Helle H. Trinderup, Line Juul-Madsen, Laura Press, Michael Madsen, Henrik H. Jensen
Summary: A systematic study was conducted on the effect of various 6-O-acyl groups on anomeric selectivity in glucosylations with thioglycoside donors. It was found that all eight different esters induced moderate-to-high alpha-selectivity in glucosylation with L-menthol, with 6-O-p-nitrobenzoyl being the most effective. This effect appears to be general across various glucosyl acceptors, glucosyl donor types, and modes of activation, and there was no evidence supporting distal participation.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Mikhailo Slivka, Maksym Fizer, Ruslan Mariychuk, Marek Ostafin, Olexander Moyzesh, Galyna Koval, Oksana Holovko-Kamoshenkova, Ivan Rusyn, Vasyl Lendel
Summary: This study evaluated the antimicrobial potential of new derivatives of thiazole-triazoles. Effective, easy-to-implement and low-cost routes for their synthesis were reported. The microbiological evaluation showed that two compounds exhibited high bactericidal activity and one compound showed high fungicidal activity. These products or their derivatives may have practical benefits as bactericidal and fungicidal agents.
LETTERS IN DRUG DESIGN & DISCOVERY
(2022)
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.
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, 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
Chemistry, Organic
Ramu Sridhar Perali, Umamaheswara Rao Boddu, Drisya Chittadi Sankar
Summary: The study presents a simple and efficient strategy for the regio- and stereoselective synthesis of carbon-branched sugar derivatives. By implementing Wittig rearrangement on substrates derived from various glycals and 3-O-alkenyl glycals through Ferrier rearrangement, a highly selective [1,2]- or [2,3]-Wittig rearrangement is revealed, providing a novel class of stereodefined 3-C-branched glycals and C-glycosides that are otherwise difficult to obtain.
Article
Chemistry, Analytical
Luyao Liu, He Zhu, Lei Liu, Xin You, Jiawei Mao, Yan Wang, Xiaoyan Liu, Hongqiang Qin, Mingming Dong, Mingliang Ye
Summary: Mucin-type O-glycosylation plays a vital role in regulating protein functions and biological processes, but its analysis is challenging due to the diverse and dense O-glycans. In this study, an O-glycopeptide truncation strategy using proteases or O-glycopeptidases was developed to simplify and enhance the analysis of O-GalNAc glycoproteomics.
ANALYTICAL CHEMISTRY
(2023)
