Article
Chemistry, Multidisciplinary
Quanquan Wang, Wanjun Zhu, Qikai Sun, Gang He, Gong Chen
Summary: A novel Pd-catalyzed ortho-directed C-H glycosylation reaction using N-linked bidentate auxiliaries has been developed for efficient synthesis of C-aryl glycosides with high yield and selectivity. This method allows for installation of a wide range of pyranose and furanose moieties on various substrates and facile installation and removal of the auxiliaries under mild conditions.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Plant Sciences
Qinggang Yin, Yiding Wei, Xiaoyan Han, Jingwang Chen, Han Gao, Wei Sun
Summary: Chinese horse chestnut flowers and leaves contain abundant flavonoids, with significantly higher content of seven flavonol glycosides in flowers than in leaves. The crude proteins of flowers can catalyze the formation of flavonol glucosides. These studies provide theoretical and experimental basis for the utilization of Chinese horse chestnut flowers and leaves as additives and dietary supplements.
FRONTIERS IN PLANT SCIENCE
(2022)
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, 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
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, Multidisciplinary
Yongliang Wei, Benjamin Ben-zvi, Tianning Diao
Summary: C-aryl glycosyl compounds offer improved in vivo stability compared to O- and N-glycoside analogues, making them attractive candidates for drug development and chemical biology studies. A new cross-coupling method has been developed for the preparation of C-aryl and heteroaryl glycosides, including nucleosides and 2-deoxysugars, from easily accessible glycosyl esters and bromoarenes, demonstrating the potential of this method in medicinal chemistry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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)
Review
Chemistry, Multidisciplinary
Weidong Shang, Rong Shi, Dawen Niu
Summary: C-glycosides are important natural products and potential medicinal candidates. Nickel-catalyzed C-glycosylation reactions provide a promising strategy for their synthesis. Achieving stereoselective synthesis of alpha- and beta-C-glycosides has been a challenge, but recent developments in nickel-mediated strategies have addressed this problem. This review summarizes the advancements in diastereoselective C-glycosylation reactions and discusses the mechanistic understandings of these methods.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Jianpeng Chen, Yu Tang, Biao Yu
Summary: A mild glycosylation method using glycosyl 1-methylimidazole-2-carboxylates has been developed, with the reaction being promoted by metal triflates and triflimides, especially Cu(OTf)(2). The reaction is initiated by coordination of the glycosyl ester donor with the metal cation assisted by the adjacent 1-methylimidazole chelating group.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yingle Feng, Jie Yang, Chenglin Cai, Taotao Sun, Qi Zhang, Yonghai Chai
Summary: An efficient and highly stereoselective catalytic protocol for the construction of beta-mannosides has been developed. The glycosylation reaction of 2,6-lactone-bridged mannopyranosyl ortho-hexynylbenzoate with various acceptors proceeded smoothly at room temperature in the presence of 5% Hg(II), resulting in high yield and exclusive beta-stereoselectivity of the desired beta-mannosides.
CHINESE CHEMICAL LETTERS
(2022)
Review
Chemistry, Multidisciplinary
Kenzo Yamatsugu, Motomu Kanai
Summary: Carbohydrates, as fundamental units in biological processes, play pivotal roles. Developing methods for synthesizing, functionalizing, and manipulating carbohydrates is essential for understanding their functions and creating sugar-based functional materials. New approaches to site-selective transformations of carbohydrates are of great significance for revolutionizing sugar chemistry and accessing sugars of interest.
Article
Biochemistry & Molecular Biology
Titli Ghosh, Toshiki Nokami
Summary: This review article summarizes selected literature from 2000 to 2022 on the synthetic development of C-glycosylation involving the generation of glycosyl radical as a crucial intermediate. The methods for controlling the generation of glycosyl radical are categorized based on the key source of the initiator, and the stereochemical outcome of the resultant C-glycosides is discussed. The synthesis of challenging C-linked building blocks via the generation of glycosyl radical provides a more facile approach for the development of drugs and inhibitors in the field of biological and medicinal chemistry.
CARBOHYDRATE RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Yue Liu, Songlin Bai, Yuanbo Du, Xiangbing Qi, Hongyin Gao
Summary: A metal- and oxidant-free method has been developed for the synthesis of versatile ortho-trifluoromethanesulfonylated anilines from arylhydroxylamines and trifluoromethanesulfinic chloride. The reaction proceeds smoothly with good yields and excellent ortho-selectivity, showcasing practical application potential in the synthesis of functional molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yuna Guo, Nan Wang, Yihong Zhong, Wei Li, Yiran Li, Guyu Wang, Yunyan Yao, Yue Shi, Liusheng Chen, Xiaojian Wang, Lin Ding, Huangxian Ju
Summary: Cell surface engineering allows for the customization of cell interfaces with desired properties and functions. Despite this, methods for cell-selective covalent labeling that can simultaneously install multiple molecules with different functions are limited. In this study, an aptamer-enabled proximity catalytic covalent labeling platform is presented for the multifunctional surface reconfiguration of target cells in mixed populations. By combining peroxidase with cell-selective aptamers, the resulting probes selectively bind to target cells and catalyze covalent labeling in situ. The platform can be universally applied to different phenol-modified functional molecules, enabling a variety of manipulations on target cells such as labeling, tracking, assembly regulation, and surface remodeling. Importantly, the platform allows for multiplexed covalent labeling, enabling the simultaneous installation of two mutually orthogonal click reactive molecules on the surface of target cells. This enables the programming and tracking of specific cell-cell interactions in complex multicellular systems. The functional molecules can also be extended to carbohydrates, enabling ultrafast neoglycosylation on living cells, which can be recognized and remodeled by a glycan-modifying enzyme, providing a method package for cell-selective engineering of the glycocalyx.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Yuna Guo, Nan Wang, Yihong Zhong, Wei Li, Yiran Li, Guyu Wang, Yunyan Yao, Yue Shi, Liusheng Chen, Xiaojian Wang, Huangxian Ju, Lin Ding
Summary: Cell surface engineering allows customization of cell interfaces with desirable properties and functions. However, methods for covalent labeling of cells that can simultaneously install multiple molecules with different functions are rare. In this study, a proximity catalytic covalent labeling platform enabled by aptamers was developed for multifunctional surface reconfiguration of target cells. The platform allows for selective binding and covalent labeling of target cells in mixed cell populations. It has the ability to perform a variety of manipulations on target cells, including labeling, tracking, assembly regulation, and surface remodeling. The platform also enables multiplexed covalent labeling, allowing the installation of two different reactive molecules simultaneously on the surface of target cells.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Xianglai Liu, Yetong Lin, Ao Liu, Qianhui Sun, Huiyong Sun, Peng Xu, Guolong Li, Yingying Song, Weijia Xie, Haopeng Sun, Biao Yu, Wei Li
Summary: The utilization of the DPPA group in glycosylation allowed for efficient synthesis of challenging carbohydrates with excellent beta-selectivities and broad substrate scope. Additionally, the chemoselective removal of the DPPA group under mild Ni(OTf)(2) catalysis facilitated rapid conversion to biologically important molecules.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Yu Tang, Biao Yu
Summary: A mild heteroatom methylation protocol has been developed using the combination of trimethyl phosphate (TMP) and calcium hydroxide (Ca(OH)2), which can be applied under flexible conditions for various O-, N-, and S-nucleophiles.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Dapeng Zhu, Mingyu Geng, Biao Yu
Summary: Starfish have developed a special type of secondary metabolite called starfish saponins to defend against predators and parasites. Among them, starfish cyclic steroid glycosides are structurally unique and pose a significant synthetic challenge.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(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
Chemistry, Organic
Qiuyu Zhu, Yu Tang, Biao Yu
Summary: A catalytic glycosyl fluoride activation system using the GeCl2·dioxane-AgBF4 combination was developed, involving reversible activation of C-F bond and reversible chloride ion transfer. This system is easy to operate, proceeds at room temperature, and has a broad scope of substrates.
Article
Oncology
Ahmed Elgehama, Yixuan Wang, Ying Yu, Lin Zhou, Zhixiu Chen, Liwei Wang, Lijun Sun, Jian Gao, Biao Yu, Yan Shen, Qiang Xu
Summary: This study unravels the action mechanism of PTP1B in stabilizing Bcr-Abl1 protein and indicates that the PTP1B-Bcr-Abl1 interaction might be one of druggable targets for TKI-resistant CML with point mutations.
Article
Biochemistry & Molecular Biology
J. Sebastian Temme, Jennifer A. Crainic, Laura M. Walker, Weizhun Yang, Zibin Tan, Xuefei Huang, Jeffrey C. Gildersleeve
Summary: This study has identified 26 anti-glycan antibodies, most of which bind microbial carbohydrates, and found that these antibodies predominantly originate from IgG+ memory B cells, rather than from naive, early emigrant, or immature B cells.
JOURNAL OF BIOLOGICAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Youxi Chen, Guozhi Xiao, Dapeng Zhu, Biao Yu
Summary: Sepositoside A is a prototypical cyclic steroid glycoside with a hybrid 16-membered ring composed of the steroid skeleton and a 1,2-trans-linked trisaccharide. We report a convenient method to construct the strained 16-membered ring via Au(I)-catalyzed intramolecular addition of alcohol to epoxide, leading to two simplified analogues. Although a similar macroetherification in relevant steroid trisaccharides has been extensively studied, it has failed to provide the macrocyclic skeleton of Sepositoside A.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Bingfeng Shi, Youxi Chen, Mingyu Geng, Dapeng Zhu, Biao Yu
Summary: Sepositoside A is a major cyclic steroid glycoside found in starfishes, featuring a strained 16-membered ring formed by a linear trisaccharide tethered to C3 and C6 of the steroid aglycone. Attempts to synthesize the desired steroid-pyranose etherate linkage and assemble the glycans stepwise have been unsuccessful. Alternative approaches to construct the steroid-pyranose etherate linkage will be explored in future articles.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Dapeng Zhu, Mingyu Geng, Dacheng Shen, Biao Yu
Summary: This article presents a formal total synthesis study of starfish cyclic steroid glycosides 1 and 2 isolated from the Pacific starfish Echinaster Luzonicus. The synthetic route is highly modular and versatile, involving Au(I)-catalyzed intramolecular glycosylation for constructing the 16-membered macrocycles, efficient installation of unsaturated sugar moieties using ortho-hexynylbenzoates, post-oxidation elaboration of the glucuronic acid unit, and de novo synthesis of the ether-linked pyranose unit.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Xiaojuan Zhang, Peng Xu, Zhengbing Zhou, Yazhou Zhang, Biao Yu, Yugen Zhu
Summary: Due to the complexity and diversity of carbohydrates, efficient methods for homogeneous oligosaccharides are limited. Chemical synthesis is a reliable approach for accessing homogeneous samples, relying on glycosylation reactions. This study presents a novel leaving group, 8-phenylethynyl-1-naphthoate, which enables efficient glycosylation reactions under mild gold(I)-catalysis. The unique base-stability of the anomeric naphthoate group allows compatibility with various chemical transformations, and the protocol allows for minimally protected glycosylation processes. Mechanistic studies explain the characteristics of 8-phenylethynyl-1-naphthoate.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Bei-Bei Zhan, Kai-Sheng Xie, Qian Zhu, Weiping Zhou, Dapeng Zhu, Biao Yu
Summary: A Cu-(OTf)(2)-catalyzed glycosylation protocol using glycosyl ortho-N-phthalimidoylpropynyl benzoates(NPPBs) as donors was developed, which exhibits an inexpensive catalyst, convenient conditions, high to excellent yields, and a broad substrate scope. Mechanistic studies showed the formation of an isochromen-4-ylcopper-(II) intermediate upon leaving group departure.
Article
Chemistry, Multidisciplinary
Wei Liu, Ziqiang Wang, Tayyab Gulzar, Xiaodong Zhang, Guoping Ding, Peng Xu, Biao Yu
Summary: We have revealed that EPP glycosides can be utilized as glycosylation donors through an unprecedented activation mechanism. We further report that EPP glycosides without the 3,5-dimethyl groups, previously installed to prevent side reactions, can also undergo effective glycosylation. By employing an EPP 2-azidoglucoside as a donor, we have successfully constructed the challenging alpha-GlcN-(1 -> 4)-GlcA linkage, leading to a heparin tri-saccharides precursor.
PURE AND APPLIED CHEMISTRY
(2023)
Article
Chemistry, Organic
Yan Xia, Yingjie Wang, Zhaolun Zhang, Tayyab Gulzar, Yuqi Lin, Jing Wang, Dapeng Zhu, Biao Yu
Summary: The synthesis of neopetrosins A and C, two 2-indolyl C-a-D- mannopyranosides, and their congeners has been achieved via a direct Ni/photoredox-catalyzed reductive coupling of 3-methoxycarbonyl-2-iodo-1H-indoles with pyranosyl bromides.
Article
Chemistry, Organic
Wei Liu, Zhifei Hu, Peng Xu, Biao Yu
Summary: Here, we presented a convenient procedure to prepare EPP glycosides and their application in the synthesis of the clinically approved anticoagulant fondaparinux. Additionally, we successfully achieved the synthesis of heparin-like tetrasaccharides using EPP glycosides in a one-pot orthogonal glycosylation reaction.
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)
