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, 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
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
Gael M. Vos, Yunfei Wu, Roosmarijn van der Woude, Robert P. de Vries, Geert-Jan Boons
Summary: This paper introduces a chemo-enzymatic strategy for synthesizing poly-N-acetyl lactosamines (polyLacNAc) in a regioselective manner. The strategy involves enzymatic assembly of oligo-LacNAc chains and modification at specific positions using traceless blocking groups. The methodology allows for the synthesis of polyLacNAc chains with various topologies.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Peng Wen, Peijing Jia, Qiuhua Fan, Bethany J. McCarty, Weiping Tang
Summary: A streamlined iterative assembly of thio-oligosaccharides was developed by aqueous glycosylation, efficiently synthesizing 1,2-trans S-glycosides with high chemo- and stereoselectivity at room temperature. The method was successfully applied to the synthesis of a trimannoside moiety of N-linked glycans core region.
Article
Chemistry, Organic
Ganesh Shrestha, Matteo Panza, Yashapal Singh, Keith J. Stine, Alexei V. Demchenko
Summary: In this study, the activation process of N-alkylated SInR derivatives was investigated by NMR, leading to the discovery of different activation pathways for SIn and SInR derivatives. The orthogonality between SInR leaving groups and thioglycosides, as well as the selective activation of thioimidates over SInR glycosides, were also examined.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Kazuki Inaba, Yuna Naito, Mina Tachibana, Kazunobu Toshima, Daisuke Takahashi
Summary: A regioselective and beta-stereospecific d-/l-arabinofuranosylation method has been developed for efficient synthesis of biologically active natural glycosides. The method showed high regioselectivity and yield with complete beta-stereoselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Samim Sahaji, Pradip Shit, Anup Kumar Misra
Summary: A convergent [4+2] stereoselective block glycosylation strategy was developed for the synthesis of the hexasaccharide repeating unit of Klebsiella K19 strain's capsular polysaccharide with high yield. Temporary alkyl protecting group p-methoxybenzyl (PMB) was used and removed through glycosylation conditions. Thioglycoside served as a glycosyl acceptor in an orthogonal glycosylation reaction. TEMPO-mediated selective oxidation and thiophilic promoter N-iodosuccinimide (NIS) in combination with perchloric acid supported over silica (HClO4-SiO2) were used.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Serena Traboni, Emiliano Bedini, Alba Silipo, Giulia Vessella, Alfonso Iadonisi
Summary: The novel glycosylation method reported in this study, based on the direct activation of per-O-acylated donors using methanesulfonic acid as a catalyst in the absence of solvents, offers a sustainable and environmentally friendly approach for the synthesis of carbohydrates and their derivatives. The method not only avoids the use of toxic and polluting organic solvents, but also shows high stereoselectivity and efficiency in obtaining desired glycosides.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Swapan Kumar Jana, Pradip Shit, Anup Kumar Misra
Summary: In this study, the pentasaccharide repeating unit rich in 2-acetamidosugars corresponding to the O-antigenic polysaccharide from entero-pathogenic E. coli was successfully synthesized as the p-me-thoxyphenyl glycoside using a sequential glycosylation strategy. The key components of the synthetic strategy included regioselective glycosylation, use of a single monosaccharide intermediate in multiple glycosylations, and the use of thioglycosides as glycosyl donors in the presence of a combination of N-iodosuccinimide and perchloric acid supported over silica.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Yashapal Singh, Samira Escopy, Melanie Shadrick, Mithila D. Bandara, Keith J. Stine, Alexei V. Demchenko
Summary: Human milk oligosaccharides (HMO) are an active area of research in glycoscience and nutrition due to their involvement in infant development and potential disease prevention. This study reports the chemical synthesis of two core hexasaccharides found in human milk, pLNH and pLNnH, using a 3+3 convergent coupling strategy.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Mei-Huei Lin, Jakob B. Wolf, Eric T. Sletten, Dario Cambie, Jose Danglad-Flores, Peter H. Seeberger
Summary: This article discusses the complexity of synthesizing defined oligosaccharides and introduces several enabling technologies that have been introduced in the past two decades to facilitate their synthesis. The application of automated glycan assembly, flow chemistry, and data science are highlighted as examples, emphasizing how the synergies between these technologies can further advance the field of glycochemistry.
Article
Chemistry, Analytical
Juhi Samal, Tana V. Palomino, Judy Chen, David C. Muddiman, Tatiana Segura
Summary: N-linked glycosylation is a complex protein modification that plays a role in cellular signaling and metabolism. Aberrant protein glycosylation is a characteristic feature of many diseases. Spatial profiling of N-glycans through imaging on tissue sections can be used for disease diagnosis. Infrared matrix-assisted laser desorption electrospray ionization (IR-MALDESI) is a sensitive technique that can be used for mass spectrometry imaging.
ANALYTICAL CHEMISTRY
(2023)
Article
Chemistry, Analytical
Petra Jezkova, Jana Skrickova, Gejza Wimmer, Jana Zelinkova, Zbynek Zdrahal, Erika Lattova
Summary: In this study, the advantage of phenylhydrazine labeling for the detection and discrimination of sialic acid linkages was demonstrated. The results showed that phenylhydrazine-labeled sialylated oligosaccharides can be easily recognized and produce favorable fragmentation patterns during mass spectrometry experiments. A comparison of two esterification methods showed that methylation exhibited slightly higher linkage specificity. The simplicity and effectiveness of this methodology were confirmed using model compounds and serum samples.
ANALYTICAL CHEMISTRY
(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)
