Article
Chemistry, Multidisciplinary
Qingpeng Zhao, Shihao Zhou, Yue Wang, Xiaoyu Yang, Youhui Meng, Yanxin Zhang, Jian Gao
Summary: A one-pot and convergent glycosylation strategy was used to efficiently synthesize a family of 3,6-branched Fuzi alpha-glucans, including the pentasaccharide repeating unit as well as its di- and trimers. The assembly of protected alpha-glucans up to 15-mer exhibited high yields and excellent alpha-stereoselectivity, which was achieved through the synergistic effects of the TolSCl/AgOTf promotion system and the steric beta facial shielding of bulky saccharide residues. The structurally well-defined synthetic alpha-glucans have potential applications in various biological studies.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Hirofumi Endo, Masaharu Ochi, Md Azadur Rahman, Tomoaki Hamada, Takahiro Kawano, Toshiki Nokami
Summary: Unnatural cyclic oligosaccharides composed of N-acetylglucosamine with alpha-1,4-glycosidic linkages have been successfully synthesized using electrochemical synthesis. The study also demonstrated that this method can be utilized for the isomerization of linear oligosaccharides and intramolecular glycosylation for cyclization.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Monika Bhardwaj, Debaraj Mukherjee
Summary: This study reports a new method for the rapid synthesis of 2-deoxy-3-thio pyranoses and their O-glycosides through the reaction of glycals with two different types of nucleophiles in the presence of SnCl4. The reaction involves thioaryl substitution at C-3 and alpha-selective O-glycosylation at C-1, combining two reactions with three interventions. The method offers operational simplicity at 0 degrees C in 10-20 minutes and is compatible with a wide range of primary and secondary alcohols, yielding products in good to excellent yields. Moreover, the strategy has the potential for the synthesis of various natural products and drug molecules, as supported by control experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xingchun Sun, Zhiyuan Chen, Rui Yang, Mei Wang, Xiufang Wang, Qi Zhang, Guozhi Xiao
Summary: This study achieved the first stereoselective one-pot synthesis of the icosasaccharide motif of EPS-1A glycan from Cordyceps sinensis. The synthetic approach showed high stereoselectivity and efficiently assembled the target icosasaccharide through different strategies.
Article
Biochemical Research Methods
Caihong Tang, Yue Zeng, Jianxin Zhang, Xing Zheng, Feng Tang, Xu Yao, Zhong-Xing Jiang, Wei Shi, Wei Huang
Summary: In this study, a facile and efficient method was developed to assemble dual-site-specific ADCs with defined DARs at both the N-glycosylation site and K248 site, either with the same payloads or with two types of payloads. The constructed dual-site ADCs showed acceptable homogeneity, excellent buffer stability, and enhanced in vitro and in vivo efficiency.
BIOCONJUGATE CHEMISTRY
(2023)
Article
Chemistry, Organic
Taeok Kim, Michael R. Bell, V. Narasimharao Thota, Todd L. Lowary
Summary: This study reports a one-pot strategy for functionalizing pyranoside 1,2-cis-diols with two different ester protecting groups. The approach selectively acylates through orthoester hydrolysis promoted by a carboxylic acid, and after removal of water and introduction of a coupling agent, the carboxylic acid is esterified with the liberated hydroxyl group. Although applied to 1,2-cis-diols on pyranoside scaffolds, this method can be applicable to similar motifs on any six-membered ring.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yafei Cao, Minmin Zhou, Run-Ze Mao, You Zou, Feng Xia, Da-Ke Liu, Jianhui Liu, Qin Li, De-Cai Xiong, Xin-Shan Ye
Summary: A new glycosylation method using visible light and 3,5-dimethoxyphenyl glycoside as the donor was developed, which delivers O-glycosides and N-glycosides in moderate to excellent yields with a wide range of O-nucleophiles and nucleobases as the glycosyl acceptors.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Zhiyuan Chen, Guozhi Xiao
Summary: The highly branched tetradecasaccharide repeating unit and shorter sequences of GLSWA-1 from Ganoderma lucidum, which possess immune-enhancing activities, were prepared using a one-pot glycan assembly strategy that features orthogonal one-pot glycosylation, one-pot assembly of oligosaccharides, and modular and convergent [4+5+5] assembly of the highly branched tetradecasaccharide.
Article
Biochemistry & Molecular Biology
Kanae Sano, Nozomi Ishii, Satoshi Takahashi, Yoichi Takeda, Ichiro Matsuo
Summary: A simple and efficient synthetic strategy for oligomannose-type glycans was demonstrated, achieving different branching patterns through sequential regioselective α-mannosylation and inversion of configuration.
CARBOHYDRATE RESEARCH
(2023)
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
Xuemei Zhong, Xiaoya Zhao, Jiaming Ao, Yan Huang, Yuhua Liu, Siai Zhou, Bizhi Li, Akihiro Ishiwata, Qianglin Fang, Chongguang Yang, Hui Cai, Feiqing Ding
Summary: This study presents a one-pot strategy for stereocontrolled glycosylation to generate both alpha- and beta-glycosides by altering reaction conditions. The selective formation of beta-glycosides was achieved by activating the perbenzylated trichloroacetimidate with a catalytic amount of SnCl4 at -40 degrees C. On the other hand, alpha-glycosides were obtained as the major products at room temperature by using 3.0 equivalents of SnCl4 and/or TiCl4. Control experiments and DFT calculations provided mechanistic insights into the glycosylation reaction, revealing a sequential occurrence of beta-glycosylation and anomerization.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Rui Yang, Haiqing He, Zixi Chen, Yingying Huang, Guozhi Xiao
Summary: The study presents a one-pot glycosylation strategy for synthesizing both glycans and nucleosides based on ortho-(1-phenylvinyl)benzyl glycosides. It offers several advantages such as no aglycon transfers, no interference of departing species, and no unpleasant odor, and allows for the construction of up to four different glycosidic linkages.
Review
Chemistry, Organic
Rekha Sangwan, Pintu Kumar Mandal
Summary: This review discusses the challenges in synthesizing complex saccharides in carbohydrate chemistry, emphasizes the importance of chemical synthesis, and highlights specific methodologies. The main goal is to rapidly synthesize biologically relevant glycans that can be utilized in carbohydrate-based vaccine development, diagnostics, and drug discovery.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Hua Min, Sun Yangxing, Zhang Xueqing, Yao Hui, Huang Nianyu
Summary: A method for the stereoselective synthesis of beta-D-thioglycosides using glucosyl-3-pyridinate donor and thiophenols/thiols catalyzed by Co(BF4)(2) was reported. The reaction has good compatibility with various mercaptans and thiophenols, as well as active sulfur nucleophiles, allowing for the efficient synthesis of thioglycopeptides and providing a new way for the rapid preparation of thioglycosides.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Laurent Cattiaux, Jean-Maurice Mallet
Summary: An alternative method for the synthesis of oligosaccharides based on polyol multi-glycosylation is proposed in this study. The method allows for simple separation based on an increase in molecular mass, without the need for aqueous workup or TLC/detector.
Article
Chemistry, Physical
Mengge Gong, Tiechuan Li, Lina Wu, Zhenxing Zhang, Lishi Ren, Xuexin Duan, Hongzhi Cao, Meishan Pei, Jian-Jun Li, Yuguang Du
Article
Chemistry, Multidisciplinary
Xuanjun Wu, Jinfeng Ye, Andrew T. DeLaitsch, Zahra Rashidijahanabad, Shuyao Lang, Tayeb Kakeshpour, Yuetao Zhao, Sherif Ramadan, Paulo Vilar Saavedra, Vilma Yuzbasiyan-Gurkan, Herbert Kavunja, Hongzhi Cao, Jeffrey C. Gildersleeve, Xuefei Huang
Summary: The new GD2 derivative 9NHAc-GD2 conjugated with a powerful carrier bacteriophage Q beta was able to induce strong and selective IgG antibodies in mice, while showing immunogenicity in canines with minimal adverse effects. This paves the way for potential clinical translation to humans in the future.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Tiantian Li, Jianjun Wang, Xinhao Zhu, Xin Zhou, Shaozi Sun, Peng Wang, Hongzhi Cao, Guangli Yu, Ming Li
Summary: Campylobacter jejuni, the leading cause of human diarrheal diseases, has been studied for potential antigens for innovative antibacterial glycoconjugation vaccines to address its high resistance. A novel method for synthesizing uncommon n-/L-6dHepp fluorides as glycosylating agents has been developed, allowing for the efficient construction of complex structures like the capsular polysaccharides of C. jejuni. This synthetic approach could serve as a rational starting point for developing synthetic vaccines combating Campylobacter infection.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Physical
Xiaoju Zheng, Lin Zhu, Tianlu Li, Wenjia Xu, Dongke Liu, Juzheng Sheng, Hongzhi Cao, Yikang Shi, Fengshan Wang
Summary: Glycosylation provides a solution for modifying peptide drugs, improving stability and receptor selectivity. The study introduces a enzymatic modular assembly strategy for the synthesis of active glycopeptides, which significantly increases the half-lives of the peptides in human serum.
Article
Chemistry, Medicinal
Enkang Zhang, Shixiong Wen, Jialiang Quan, Jiahuai Han, Hongzhi Cao, Shoufa Han
Summary: This study explored the introduction of high-affinity sialoside ligands in vivo, showing that the ligand of Siglec-1 has a moderate inhibitory effect on tumor growth while the ligand of Siglec-7 promotes tumor growth. These findings suggest a new perspective for tumor immunotherapy by displaying high-affinity ligands of Siglec-1 on the tumor surface.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Wenyuan Fang, Kan Zhong, Jiansong Cheng, Xian-Wei Liu, Chang-Cheng Liu, Zhongfu Wang, Hongzhi Cao
Summary: A convenient and efficient strategy was developed for the simplification of enzymatic synthesis and purification of oligosaccharides. The method involves extending glycosyl acceptors terminated with a thiol tag through enzymatic modular assembly in the aqueous phase, capturing the desired products during solid-phase workup using commercially available thiopropyl Sepharose 6B resin, and releasing the products in the presence of dithiothreitol (DTT) as a reducing agent. This strategy not only overcomes the uncertain influence of commonly used polymer- or ionic-supports in enzymatic glycosylation, but also shows perfect compatibility with all 10 enzyme modules for rapid assembly of complex oligosaccharides.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Microbiology
Xiaoyu Liu, Zhe Chen, Xuyao Jiao, Xukai Jiang, Jicheng Qiu, Fuping You, Hongan Long, Hongzhi Cao, Casey C. Fowler, Xiang Gao
Summary: This study reveals how the human-adapted bacterial pathogen Salmonella enterica serovar Typhi produces two distinct versions of typhoid toxin and explores the differences in structure and receptor specificity between these two toxins. The study also shows that the two toxins have different glycan-binding properties, resulting in distinct functional traits.
Article
Agriculture, Multidisciplinary
Xiaoqin Wang, Jing Liu, Cheng Li, Yifan Xu, Xinyi Wang, Yu Lu, Ting Zhang, Hongzhi Cao, Linjuan Huang, Zhongfu Wang
Summary: This study analyzed colostrum samples from mothers in Northwest China and found that the concentration of HMOs is affected by multiple factors. Mothers with gestational diabetes mellitus had lower levels of sialylated oligosaccharides, while those with pregnancy-induced hypertension had higher levels of fucosylated oligosaccharides. Mothers who underwent vaginal delivery had higher levels of HMOs compared to those who had C-sections.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Na Lu, Yun Li, Hui Xia, Kan Zhong, Chenning Jia, Jinfeng Ye, Xianwei Liu, Chang-Cheng Liu, Hongzhi Cao
Summary: This study presents a facile and general substrate engineering strategy for site-specific alpha 1,3-fucosylation of complex glycans containing multiple LacNAc units. The strategy utilizes galactose oxidase (GOase) to convert the LacNAc unit into an oxidized C6'-aldehyde LacNAc sequence, enabling site-specific alpha 1,3-fucosylation at intact LacNAc sites. The strategy demonstrates general applicability and robustness for synthesizing well-defined fucosides of linear and branched O- and N-linked glycans.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Biochemical Research Methods
Yingying Zhu, Hongzhi Cao, Hao Wang, Wanmeng Mu
Summary: Human milk oligosaccharides (HMOs) are the third largest solid component in human milk and have beneficial effects on infant health. However, the limited availability of HMOs hinders further research and large-scale application, necessitating the development of efficient synthetic approaches.
CURRENT OPINION IN BIOTECHNOLOGY
(2022)
Review
Agriculture, Multidisciplinary
Jiawei Meng, Yingying Zhu, Hao Wang, Hongzhi Cao, Wanmeng Mu
Summary: Human milk oligosaccharides (HMOs) are considered the new gold standard for premium infant formula due to their unique beneficial effects for infants. HMOs are a collection of unconjugated glycans, with over 200 distinct structures identified. The production of HMOs involves glycosylation using specific glycosyltransferases and nucleotide sugar donors.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Jun Yan, Jianghua Li, Zhifei Hu, Xiaoyao Ma, Yun Li, Xihuan Hu, Jinfeng Ye, Wei Wang, Renzhong Wan, Hongzhi Cao
Summary: An efficient enzymatic assembly strategy was developed for the synthesis of structurally well-defined sialylated chitooligosaccharides. Two enzyme modules were used to introduce N-acetyl lactosamine (LacNAc) units onto the chitooligosaccharides. The LacNAc grafted chitooligosaccharides were further modified with sialic acid to generate a total of 20 sialylated chitooligosaccharides.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Hui Xia, Jinfeng Ye, Hongzhi Cao, Xianwei Liu, Yan Zhang, Chang-Cheng Liu
Summary: The enzymatic synthesis of hybrid Lewis antigens was achieved using a modular assembly strategy, providing easy access to complex hybrid Lewis antigens at preparative scales. The regio-selective fucosylation was achieved by controlling the donor-acceptor ratio.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Kan Zhong, Jinfeng Ye, Xinhao Zhu, Hongzhi Cao, Chang-Cheng Liu
Article
Microbiology
Xiaoyu Liu, Zhe Chen, Xuyao Jiao, Xukai Jiang, Jicheng Qiu, Fuping You, Hongan Long, Hongzhi Cao, Casey C. Fowler, Xiang Gao
Summary: This study reveals that typhoid toxin has different versions, PltB and PltC are unable to form heteromeric delivery complexes and therefore form separate toxins, PltC exhibits stronger electrostatic interactions with PltA, enabling it to outcompete PltB in toxin assembly, and PltB and PltC exhibit significant differences in glycan binding specificity.
