Article
Chemistry, Multidisciplinary
Chaoyu Hu, Shengjie Wu, Fei He, Deqin Cai, Zhuojia Xu, Wenjing Ma, Yating Liu, Bangguo Wei, Tiehai Li, Kan Ding
Summary: Bioactive polysaccharides are potential target molecules for drug development, but the synthesis of branched complex polysaccharides with well-defined structures is challenging. In this study, a highly branched heptadecasaccharide moiety of a native bioactive polysaccharide from Carthamus tinctorius L. was efficiently synthesized, and its biological activity in targeting galectin-3 and inhibiting pancreatic cancer cell growth was demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Xiaona Li, You Yang
Summary: Automated chemical solid-phase synthesis is a reliable and efficient automation platform for synthesizing glycans. Automated Glycan Assembly (AGA), as a key breakthrough in the field, has evolved from a proof-of-concept to a robust technology for streamlined production of various glycans. In addition, HPLC-assisted automated synthesis shows promising potential in accessing glycans.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Bingxin Liang, Rong Li, Linji Li, Ming Tang, Xiang Li, Chunli Su, Hongli Liao
Summary: Cyclization and glycosylation are effective methods for enhancing the drug properties of peptides. Atypical arginine N-glycosylation has gained attention due to its role in cellular processes and signaling pathways. This study describes the synthesis of an arginine glycosylated cyclopeptide analog using solid-phase glycosylation and solution-phase cyclization, resulting in enhanced water solubility compared to the non-glycosylated peptide. This method provides a universal strategy for synthesizing arginine N-glycosylated cyclopeptides.
FRONTIERS IN CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Elena Calatrava-Perez, Luke A. Marchetti, Gavin J. McManus, Dylan M. Lynch, Robert B. P. Elmes, D. Clive Williams, Thorfinnur Gunnlaugsson, Eoin M. Scanlan
Summary: Real-time tracking of prodrug uptake, delivery and activation using novel glycosylated theranostics of the cancer pharmacophore Amonafide demonstrates highly-selective, enzymatic triggered release, preserving the potent cytotoxicity of Amonafide through targeted approach.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Xian-Yang Zhou, Ling-Xin Li, Zhen Zhang, Shi-Chao Duan, Ying-Wen Huang, Yi-Yang Luo, Xiao-Dong Mu, Zhi-Wei Chen, Yong Qin, Jing Hu, Jian Yin, Jin-Song Yang
Summary: Acinetobacter baumannii poses a serious threat to global health, and its lipopolysaccharide (LPS) has been found to have antigenic properties. Research has identified a potential antigenic epitope in one of the branches of the LPS, which is attractive for the development of carbohydrate vaccines against A. baumannii.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yasmeen Bakhatan, Israel Alshanski, Chieh-Kai Chan, Wei-Chih Lo, Po-Wei Lu, Pin-Hsuan Liao, Cheng-Chung Wang, Mattan Hurevich
Summary: Solid-phase synthesis is the main method for preparing biological oligomers. Accelerated solid-phase synthesis is crucial for chemical biology but is not easy for oligosaccharide synthesis. High shear stirring is a new approach to accelerate solid-phase synthesis by improving mixing efficiency. In this study, we used high shear mixing to perform diffusion-dependent glycosylation and completed full glycosylation cycles in minutes.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Lifeng Sun, Pradeep Chopra, Geert-Jan Boons
Summary: A new method for the synthesis of heparan sulfate oligosaccharides composed of unsulfonated fragments of different lengths was reported. Competition binding studies showed that the length of the unsulfonated fragment modulates the binding of chemokines.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Xuanjun Wu, Hunter McFall-Boegeman, Zahra Rashidijahanabad, Kunli Liu, Christian Pett, Jin Yu, Manuel Schorlemer, Sherif Ramadan, Sandra Behren, Ulrika Westerlind, Xuefei Huang
Summary: A synthetic MUC1-beta-Tf with enhanced stability was developed by altering the stereochemistry of the glycan/peptide linkage, leading to high levels of IgG antibodies in clinically relevant human MUC1 transgenic mice and recognizing MUC1 expressing tumor cells. This suggests a potential strategy for anti-cancer vaccine epitope design for glycopeptides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Hugo Minnee, Johannes G. M. Rack, Gijsbert A. van der Marel, Herman S. Overkleeft, Jeroen D. C. Codee, Ivan Ahel, Dmitri V. Filippov
Summary: ADP-ribosylation is a process that transfers an ADP ribose moiety to a nucleophilic side chain by consuming nicotinamide adenine dinucleotide, allowing for the regulation of key processes such as apoptosis and DNA repair. Recent studies have identified histidine as an acceptor site for ADP-ribose, leading to the development of a synthetic strategy for ADP-ribosylated histidine peptides. The stability and resistance of these peptides against chemical conditions and degradation by ADP-ribosylhydrolases have been investigated, showing promising results for their application in further research.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Yuexin Liu, Yang Jiao, Huajun Luo, Nianyu Huang, Mengnan Lai, Kun Zou, Hui Yao
Summary: An effective regiodivergent synthesis of 1- and 3-thiosugars was achieved using palladium and cobalt catalysis, respectively. The difference in the interaction of thiol moieties with Pd and Co catalysis conditions led to the selective formation of beta-1-thiosugars and (3S)-3-thiosugars. Experimental and theoretical calculations supported the proposed mechanism and provided insights into the regioselectivity based on the bond lengths of key intermediates.
Article
Chemistry, Multidisciplinary
Yuanyuan Bai, Xiaohong Yang, Hai Yu, Xi Chen
Summary: Innovation in process development is crucial for the industrial and laboratory production of organic compounds, such as HMOs, through biocatalysis. A substrate and process engineering strategy called MSOPME design allows for efficient synthesis of HMOs, including long-chain oligosaccharides, without the need for isolation of intermediate products. The method can be scaled up for large-scale synthesis and automation.
Article
Chemistry, Organic
Siyu Li, Yujuan Wang, Lei Zhong, Siyu Wang, Zhengli Liu, Yuanwei Dai, Yun He, Zhang Feng
Summary: In this study, we disclosed an efficient method for the stereospecific synthesis of 1-thioglycosides via a boron-promoted reductive deoxygenation coupling reaction from readily accessible sulfonyl chlorides and glycosyl bromides. Our protocol features mild conditions, excellent functional group tolerance, and stereoselectivity. The translational potential of this metal-free approach is demonstrated by the late-stage glycodiversification of natural products and drug molecules.
Article
Chemistry, Multidisciplinary
Sandra Behren, Jin Yu, Christian Pett, Manuel Schorlemer, Viktoria Heine, Thomas Fischoeder, Lothar Elling, Ulrika Westerlind
Summary: Mucin glycoproteins play a crucial role in protecting the host from pathogens by forming the mucosal barrier. Bacteria have evolved strategies to bypass this barrier through interactions with mucin O-glycans, causing virulent infections. A chemoenzymatic synthesis strategy was used to create a library of fucosylated mucin core glycopeptides, allowing for the study of bacterial lectin interactions. These glycopeptides, with biologically important Lewis and H-antigens, were tested in microarray binding studies with P. aeruginosa lectin LecB and C. difficile toxin A.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Ameer B. Taresh, Craig A. Hutton
Summary: This study presents a site-specific method for preparing N-glycosylated peptides through the incorporation of a peptide backbone thioamide linkage adjacent to an Asp residue, which facilitates site-specific conversion to N-glycosylated Asn residues in peptides promoted by Ag-I.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Xiaona Li, Cristina Di Carluccio, He Miao, Lvfeng Zhang, Jintao Shang, Antonio Molinaro, Peng Xu, Alba Silipo, Biao Yu, You Yang
Summary: We report a promoter-controlled cycloglycosylation approach for the synthesis of cyclic α-(1→6)-linked mannosides up to a length of 32 units. The method relies on the role of a gold(I) complex in the proper preorganization of the ultra-large cyclic transition state. NMR experiments and a computational study revealed that the cyclic 2-mer, 4-mer, 8-mer, 16-mer, and 32-mer mannosides adopted different conformational states and shapes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Nanoscience & Nanotechnology
Yu Shao, Zhan-Yi Sun, Yijie Wang, Bo-Dou Zhang, Dongsheng Liu, Yan-Mei Li
ACS APPLIED MATERIALS & INTERFACES
(2018)
Article
Biochemistry & Molecular Biology
Si-Qi Huang, Bei-Bei Han, Yan-Mei Li, Yong-Xiang Chen
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS
(2018)
Article
Chemistry, Multidisciplinary
Jun Hu, Pengcheng Zhu, Yanmei Li, Yongxiang Chen
CHINESE CHEMICAL LETTERS
(2018)
Article
Chemistry, Organic
Huai Chen, Yuan Zhang, Qian-Qian Li, Yu-Fen Zhao, Yong-Xiang Chen, Yan-Mei Li
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Jun-Jun Wu, Wen-Hao Li, Pu-Guang Chen, Bo-Dou Zhang, Hong-Guo Hu, Qian-Qian Li, Lang Zhao, Yong-Xiang Chen, Yu-Fen Zhao, Yan-Mei Li
CHEMICAL COMMUNICATIONS
(2018)
Article
Biochemistry & Molecular Biology
Na Gao, Yun-Peng Huang, Ting-Ting Chu, Qian-Qian Li, Bing Zhou, Yong-Xiang Chen, Yu-Fen Zhao, Yan-Mei Li
BIOORGANIC CHEMISTRY
(2019)
Article
Nanoscience & Nanotechnology
Chengcheng Liu, Wanlin Zhang, Yang Zhao, Changxu Lin, Kang Zhou, Yanmei Li, Guangtao Li
ACS APPLIED MATERIALS & INTERFACES
(2019)
Article
Biochemistry & Molecular Biology
Hong-Guo Hu, Pu-Guang Chen, Guanyu Wang, Jun-Jun Wu, Bo-Dou Zhang, Wen-Hao Li, Rebecca L. Davis, Yan-Mei Li
Review
Chemistry, Medicinal
Jun-Jun Wu, Lang Zhao, Hong-Guo Hu, Wen-Hao Li, Yan-Mei Li
MEDICINAL RESEARCH REVIEWS
(2020)
Article
Medicine, Research & Experimental
Pu-Guang Chen, Hong-Guo Hu, Zhan-Yi Sun, Qian-Qian Li, Bo-Dou Zhang, Jun-Jun Wu, Wen-Hao Li, Yu-Fen Zhao, Yong-Xiang Chen, Yan-Mei Li
MOLECULAR PHARMACEUTICS
(2020)
Article
Chemistry, Multidisciplinary
Bei-Bei Han, Yu-Chen Pan, Yan-Mei Li, Dong-Sheng Guo, Yong-Xiang Chen
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Qian-Qian Li, Yu-Qing Liu, Yun-Yi Luo, Ting-Ting Chu, Na Gao, Pu-Guang Chen, Yong-Xiang Chen, Yan-Mei Li
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Ashim Paul, Wen-Hao Li, Guru KrishnaKumar Viswanathan, Elad Arad, Satabdee Mohapatra, Gao Li, Raz Jelinek, Ehud Gazit, Yan-Mei Li, Daniel Segal
CHEMICAL COMMUNICATIONS
(2019)
Article
Biochemistry & Molecular Biology
Zhan-Yi Sun, Pu-Guang Chen, Yan-Fang Liu, Lei Shi, Bo-Dou Zhang, Jun-Jun Wu, Yu-Fen Zhao, Yong-Xiang Chen, Yan-Mei Li
Article
Biochemistry & Molecular Biology
Yan Liu, Yin-bo Li, Xiang Gao, Yong-fei Yu, Xiao-xia Liu, Zhi-liang Ji, Yuan Ma, Yan-mei Li, Yu-fen Zhao