Article
Chemistry, Multidisciplinary
Zhen Wang, Ana Gimeno, Marta G. Lete, Herman S. Overkleeft, Gijsbert A. van der Marel, Fabrizio Chiodo, Jesus Jimenez-Barbero, Jeroen D. C. Codee
Summary: We report the first total synthesis of the Streptococcus pneumoniae serotype 1 (Sp1) oligosaccharide, which is a zwitterionic capsular polysaccharide carrying unstable O-acetyl esters. The synthesis was achieved by assembling trisaccharide building blocks in a highly stereoselective manner, up to the 9-mer level. The structure investigation revealed that the oligomers adopt a right-handed helical structure, with the acetyl esters exposed on the periphery and in close proximity of the neighboring AAT residues.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Wouter A. Remmerswaal, Kas J. Houthuijs, Roel van de Ven, Hidde Elferink, Thomas Hansen, Giel Berden, Herman S. Overkleeft, Gijsbert A. van der Marel, Floris P. J. T. Rutjes, Dmitri V. Filippov, Thomas J. Boltje, Jonathan Martens, Jos Oomens, Jeroen D. C. Codee
Summary: The stereoselective introduction of glycosidic bonds is crucial for oligosaccharide synthesis, and the participation of neighboring or distal acyl groups is commonly used for stereoselectivity control. A recent study found that the 2,2-dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) protection group exhibited enhanced stereoselective steering compared to other acyl groups. Through glycosylation reactions and infrared ion spectroscopy (IRIS) combined with isotopic labeling and population analysis, it was determined that the enhanced stereoselectivity of the DMNPA group is not a result of the direct participation of the nitro moiety, but rather due to the stabilization of a dioxolenium ion formed by the nitro group.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Guang-Jing Feng, Tao Luo, Yang-Fan Guo, Chun-Yang Liu, Hai Dong
Summary: A green method using sodium alkanethiolates instead of alkyl mercaptans and trifluoromethanesulfonic acid in nonpolar solvents is developed for synthesizing 1-thioalkyl glycosides and 1,2-cis-alpha-thioglycosides under mild conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Anna Niedzwiecka, Quyen Pham, Chang-Chun Ling
Summary: Pseudaminic acid and its biosynthetic altropyranoside precursors have potential as novel antibacterial strategies. The synthetic challenge lies in the different N-acylation patterns of the flagellar carbohydrates. A new one-pot methodology allows for the synthesis of diverse N2/N4-differentiated analogs.
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
Agriculture, Multidisciplinary
Xue-Ning Wang, Li-Li Hong, Jian-Qiang Kong
Summary: A stable acetyl-CoA-synthesizing biocatalyst was identified using maltose O-acetyltransferase (MAT) with diacerein as an acetyl donor, providing a promising and cost-effective alternative method for acetylation modifications. The mutant MAT-E125F showed the highest yield of acetyl-CoA production and could also synthesize glycosyl esters through acetylation or transesterification reactions. The multifunctional MAT displayed a potent capacity in synthesizing acetyl-CoA and glycosyl esters using diacerein as an acetyl donor.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yuge Chun, Wouter A. Remmerswaal, Jeroen D. C. Codee, K. A. Woerpel
Summary: A single acyloxy group at C-2 can control the outcome of nucleophilic substitution reactions of pyran-derived acetals, but the extent of the neighboring-group participation depends on a number of factors. We show that neighboring-group participation does not necessarily control the stereochemical outcome of acetal substitution reactions with weak nucleophiles. The 1,2-trans selectivity increases with the reactivity of the incoming nucleophile and the decreased electron-donating ability of the neighboring group.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Pharmacology & Pharmacy
Li-Wei Wang, Jiang-Feng He, Hai-Yan Xu, Peng-Fei Zhao, Jie Zhao, Cong-Cong Zhuang, Jian-Nan Ma, Chao-Mei Ma, Yong-Bin Liu
Summary: In this study, it was found that HGG from Safflower protects endothelial cells from oxygen-glucose deprivation and reoxygenation-induced injury, reduces cell apoptosis, and improves cellular function by regulating the expression of related proteins. Moreover, HGG exhibits anti-inflammatory and anti-thrombotic effects.
FRONTIERS IN PHARMACOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Kapil Upadhyaya, Yagya P. Subedi, David Crich
Summary: The study shows that the involvement of distal esters in glycosylation reactions is unfavorable due to the ground state conformation of the ester, which is stereoelectronically impossible. Methylation of the secondary ester to a more labile tertiary ester removes this barrier and makes participation more favorable. However, minor changes in selectivity suggest that distal group participation is not a major stereodirecting factor, even in the tertiary system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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, Multidisciplinary
Liangshen Duan, Qin Nie, Yongxin Hu, Liming Wang, Kaiyan Guo, Zhuoyi Zhou, Xu Song, Yuanhong Tu, Hui Liu, Thomas Hansen, Jian-song Sun, Qingju Zhang
Summary: In this study, we successfully synthesized the pentasaccharide and decasaccharide of A. baumannii ATCC 17961 O-antigen for the development of a synthetic carbohydrate-based vaccine against A. baumannii infection. We employed an organocatalytic glycosylation method to efficiently synthesize the rare sugar 2,3-diacetamido-glucuronate. We also discovered the improved beta-selectivity in glycosylations by the long-range levulinoyl group participation via a hydrogen bond, which solved the stereoselectivity problem of highly branched galactose acceptors. The proposed mechanism was supported by control experiments and DFT computations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Alexey P. Krinochkin, Mallikarjuna R. Guda, Aluru Rammohan, Dmitry S. Kopchuk, Igor L. Nikonov, Evgeny D. Ladin, Sougata Santra, Ilya N. Egorov, Grigory V. Zyryanov, Oleg N. Chupakhin
Summary: This article reports the reaction between 5-cyano-3,6-di(het)aryl-1,2,4-triazines and arylhydrazines, which forms hardly available 2-amino-3,6-di(het)aryl-pyridines through aza-Diels-Alder autoclave reaction. The reaction yields up to 67% after two steps and 75% in one-pot synthesis, making the obtained compounds promising for medicinal chemistry.
MENDELEEV COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Xiang Liu, Wen Li, Wenxuan Jiang, Hao Lu, Jiali Liu, Yijun Lin, Hua Cao
Summary: A Cu(II)-catalyzed C-H amidation/cyclization reaction using dioxazolones as acyl nitrene transfer reagents is reported. This reaction allows for the synthesis of a variety of 1,2,4-triazolo[1,5-a]pyridine derivatives with moderate to good yields and excellent functional group tolerance. Scale-up reactions and photoluminescence properties are also discussed.
Article
Biochemistry & Molecular Biology
Anirban Adak, Sakshi Balasaria, Balaram Mukhopadhyay
Summary: The synthesis of the tetrasaccharide repeating unit of E. coli O131 O-antigen was achieved using a linear strategy involving rationally protected monosaccharide units derived from commercially available sugars. The challenging alpha-glycosylation of N-acetyl neuraminic acid was successfully accomplished through the activation of thioglycoside using NIS-mediated glycosylation strategy. The resulting tetrasaccharide in 3-aminopropyl glycoside form can be utilized for further glycoconjugate formation without affecting the anomeric stereochemistry.
CARBOHYDRATE RESEARCH
(2022)
Review
Chemistry, Multidisciplinary
Shuang Yue, Xiaotong Wang, Wei Ge, Jiajia Li, Chuanlai Yang, Zeyang Zhou, Peng Zhang, Xiaodong Yang, Wenjin Xiao, Shuang Yang
Summary: Mucin-type O-glycosylation is a crucial protein post-translational modification expressed abundantly on cell surface proteins. It plays various roles in cellular functions, such as protein structure, signal transduction, and immune response. Dysregulation of mucin O-glycosylation can impair mucosal protection against infection or immune evasion. Truncated O-glycosylation, known as Tn antigen or O-GalNAcylation, is upregulated in diseases including cancer, autoimmune disorders, neurodegenerative diseases, and IgA nephropathy. Analyzing and understanding O-GalNAcylation have important clinical implications, although it remains challenging due to the lack of reliable assays compared to N-glycosylation.
Article
Chemistry, Multidisciplinary
Xiaofei Shao, Chang Zheng, Peng Xu, Taro Shiraishi, Tomohisa Kuzuyama, Antonio Molinaro, Alba Silipo, Biao Yu
Summary: A collective total synthesis of eight diastereoisomers associated with NMR analysis leads to a full stereochemistry assignment of the structurally unique nucleoside antibiotic A-94964, which features an octuronic acid uridine core decorated with an alpha-D-mannopyranosyl residue and an alpha-D-N-acylglucosaminopyranosyl residue via a phosphodiester bridge.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Jie Zhao, Jiazhi Liu, Xinnan Liu, Qi Cao, Hongbo Zhao, Lizhen Liu, Farong Ye, Can Wang, Hong Shao, Dongxiang Xue, Houchao Tao, Bin Li, Biao Yu, Ping Wang
Summary: This article reports a highly efficient method for preparing homogeneous glycosylated IL-2 and reveals that the activity of IL-2 in activating T cell subsets is dependent on glycans, highlighting the possibility of improving current clinical medicine.
CHINESE JOURNAL OF CHEMISTRY
(2022)
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
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
Wu Hou, Xin Cao, Peng Xu, Biao Yu
Summary: In this study, the synthesis of two tetranorditerpenoid dilactones, Wentilactones A and B, with promising antitumor activities is reported for the first time. The synthesis involves the use of a common precursor, 3 beta-hydroxydilactone 6, derived from (S)-Wieland-Miescher ketone, and allows for easy modification on the A-ring, resulting in compounds such as CJ-1445, asperolide B, and an unnamed natural congener 4.
CHEMICAL COMMUNICATIONS
(2022)
Review
Chemistry, Multidisciplinary
Peng Xu, Biao Yu
Summary: Glycans, the most abundant organic polymers in nature, hold great significance in studying condensed matter chemistry and their synthesis.
PROGRESS IN CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
