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
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)
Article
Biochemistry & Molecular Biology
Soo-Hwan Lim, Jong-In Baek, Byeong-Min Jeon, Jung-Woo Seo, Min-Sung Kim, Ji-Young Byun, Soo-Hoon Park, Su-Jin Kim, Ju-Young Lee, Jun-Hyoung Lee, Sun-Chang Kim
Summary: In this study, a customized metabolic flux system based on CRISPRi technology was reported to increase the production of PPD in Saccharomyces cerevisiae.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Plant Sciences
Dahae Lee, Sungyoul Choi, Ki Sung Kang
Summary: This study evaluated the effect of ginsenosides on palmitic acid-induced pancreatic beta-cell death and impairment of glucose-stimulated insulin secretion (GSIS). Protopanaxadiol (PPD) was identified as a potential therapeutic agent, which protected against apoptosis and lipid accumulation. PPD also prevented palmitic acid-induced impairment of insulin secretion.
JOURNAL OF GINSENG RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Hui Liu, Zhi-Fen Liang, Han-Jian Liu, Jin-Xi Liao, Li-Jun Zhong, Yuan-Hong Tu, Qing-Ju Zhang, Bin Xiong, Jian-Song Sun
Summary: With easily accessible and operator-friendly reagents, shelf-stable ortho-methoxycarbonylethynylphenyl thioglycosides were efficiently prepared. A novel glycosylation protocol utilizing Au(I) or Cu(II) complexes was established, allowing for expanded substrate scope and versatility in glycoside synthesis. The mechanism and side product formation of C-glycosylation were also investigated.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Jianpeng Chen, Yu Tang, Biao Yu
Summary: A gold(I)-catalyzed rearrangement of glycosyl ortho-allenylbenzoates leading to the formation of C-glycosides has been discovered. The reaction proceeds through the fragmentation of the glycosyl ortho-allylbenzoate into intermediates of glycosyl cation and 3-[phosphine gold(I)methyl]-1H-isochrmen-1-one, followed by their recombination. The allyl gold(I) intermediate has been successfully trapped and characterized.
Review
Food Science & Technology
Priyanka Chopra, Himanshu Chhillar, Yu-Jin Kim, Ick Hyun Jo, Sun Tae Kim, Ravi Gupta
Summary: This review summarizes the distribution, structural diversity, biotransformation, and functional attributes of ginsenosides in both plants and animals. It also discusses the biosynthesis of ginsenosides and their metabolism in the human body, along with the major regulators and stimulators. Moreover, it consolidates the biotechnological interventions to enhance ginsenoside biosynthesis and advancements in synthetic biosystems for efficient ginsenoside production.
CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION
(2023)
Article
Agriculture, Multidisciplinary
Se-A Kim, Eun-Bi Jeong, Deok-Kun Oh
Summary: The extracellular enzymes from Aspergillus tubingensis have shown the ability to completely convert PPD-type ginsenosides in ginseng extract to compound K under optimized conditions, with the highest concentration and productivity reported so far. This is the first GRAS enzyme known to achieve complete conversion of all PPD-type ginsenosides to compound K.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Ye-Wei Huang, Meng Zhang, Li-Tian Wang, Yan Nie, Jin-Bo Yang, Wen-Luer Meng, Xuan-jun Wang, Jun Sheng
Summary: The study demonstrated that PPD can bind to LDLR and inhibit the role of PCSK9, leading to increased LDLR levels and reduced aortic plaques and hepatic steatosis in HFD-fed mice.
Article
Food Science & Technology
Yuan Liang, Tiehua Zhang, Yantong Sun, Mengxue Diao, Jie Zhang, Li Ren
Summary: The study demonstrated the cytotoxicity of 20(S, R)-protopanaxadiol and 20(S, R)-protopanaxatriol on HCT-116 cell lines, with 20(S, R)-PPD-BSA showing higher antioxidant activity than 20(S, R)-PPD alone. Ginsenosides were found to interfere with the microenvironment of SA and form complexes, indicating the stronger bioactivities of 20(S)-ginsenosides binding to HSA compared to 20(R)-ginsenosides.
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, Organic
Yan Chen, Zunxian Wu, Xiaona Li, Yi Hu, You Yang
Summary: A promoter-assisted glycosidation approach was reported for the stereoselective synthesis of 6-deoxy-beta-D-manno-heptopyranose oligosaccharides, with SphosAuNTf(2) promoting the glycosidation reactions to yield 6-deoxy-D-manno-heptosides with good to excellent beta-selectivities. The counterion and ligand of SPhosAuNTf(2) were found to have a significant effect on the formation of 1,2-cis-beta-linked 6-deoxy-D-manno-heptosides. This method was effectively applied to the stereocontrolled synthesis of 6-deoxy-beta-D-manno-heptopyranose oligosaccharides relevant to Burkholderia pseudomallei and Burkholderia mallei.
Article
Agricultural Engineering
Elena S. Glagoleva, Svetlana Konstantinova, Dmitry Kochkin, Vladimir Ossipov, Maria Titova, Elena Popova, Alexander M. Nosov, Kee-Yoeup Paek
Summary: Cell culture of Panax spp. is a strong and sustainable source of biologically active triterpene glycosides. The study showed that a 20-year-old cell culture of P. japonicus retained the ability for intensive growth and accumulation of a wide spectrum of ginsenosides.
INDUSTRIAL CROPS AND PRODUCTS
(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.
Review
Pharmacology & Pharmacy
Xin Cao, Xiaojing Du, Heng Jiao, Quanlin An, Ruoxue Chen, Pengfei Fang, Jing Wang, Biao Yu
Summary: Carbohydrates are essential molecules with diverse roles in life, and their derivatives have been extensively studied as therapeutic agents for various diseases. This review provides a comprehensive overview of the chemical structures, activities, and clinical trial results of carbohydrate-based drugs, categorized by their indications.
ACTA PHARMACEUTICA SINICA B
(2022)
Article
Chemistry, Multidisciplinary
Xianglai Liu, Yetong Lin, Wenyi Peng, Zhaolun Zhang, Longwei Gao, Yueer Zhou, Zhe Song, Yingjie Wang, Peng Xu, Biao Yu, Haopeng Sun, Weijia Xie, Wei Li
Summary: This study reports the use of 2-(diphenylphosphinoyl)acetyl as a remote stereodirecting group in the direct synthesis of challenging beta-glycosides. The method showed high effectiveness in the synthesis of a deoxy-trisaccharide mimic of landomycin E's sugar chain and in the assembly of Citrobacter freundii O-antigens.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Biochemistry & Molecular Biology
Shengyang Wang, You Yang, Qian Zhu, Guo-Qiang Lin, Biao Yu
Summary: In this article, we summarize the chemical syntheses of glycans containing over 20 monosaccharide units. The recent syntheses of ultra-long glycans, such as a 92mer arabinogalactan, a 100mer and a 151mer mannan, and a 128mer rhamnomannan, are highlighted. The assembly strategies, glycosylation methods, and protecting group manipulations, which are crucial for successful synthesis, are discussed to provide guidance for the future synthesis of various polysaccharides.
CURRENT OPINION IN CHEMICAL BIOLOGY
(2022)
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
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, Multidisciplinary
Fuzhu Yang, Wu Hou, Dapeng Zhu, Yu Tang, Biao Yu
Summary: A robust glycosylation protocol for the synthesis of 1,2-trans-beta-D- or alpha-L-glycosidic linkages without resorting to neighboring participation groups has been developed, demonstrating high yielding and exclusive 1,2-trans selectivity with a broad substrate scope.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
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)
