Article
Chemistry, Organic
Ananya Mukherji, Mahendra K. V. Rotta, Bikash K. Sarmah, Pavan K. Kancharla
Summary: This study investigates the influence of different silyl protecting groups (TBDMS, TIPS, and TBDPS) on 2-deoxyrhamnosylation. It is found that the TIPDS protecting group exhibits complete alpha-selectivity in C-glycosylation reactions. In contrast, the TBDPS protecting group shows superior protection for alpha-stereoselective O-glycosylation reactions with various acceptors.
JOURNAL OF ORGANIC CHEMISTRY
(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
Chemistry, Organic
Jie Wan, Leilei Wang, Guozhi Xiao
Summary: A total synthesis of nonasaccharide repeating units and shorter sequences from Phellinus ribis glycans with strong immunostimulating activities was achieved using an orthogonal one-pot glycosylation strategy. This strategy eliminates the issues inherent to thioglycosides-based orthogonal one-pot glycosylations, streamlining the chemical synthesis of glycans.
Article
Chemistry, Multidisciplinary
Sabrina M. Piazza, Michael R. Reynolds, Jonathan Chiaramonte, PeiHan Xu, Fabiola A. Chapa-Villarreal, John F. Trant
Summary: This paper presents a rapid method for the synthesis of Thomsen-Nouveau (Tn) glycoconjugate, which is the shortest reported synthesis from galactose for preparing a key component for large-scale solid phase peptide synthesis.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Dushen Chen, Akhilesh. K. K. Srivastava, Justyna Dubrochowska, Lin Liu, Tiehai Li, Joseph. P. P. Hoffmann, Jay. K. K. Kolls, Geert-Jan Boons
Summary: There is a pressing need for new treatment options for carbapenem-resistant Klebsiella pneumoniae (K. pneumoniae), a common cause of life-threatening infections. In this study, a synthetic glycoconjugate vaccine was developed using oligosaccharides derived from the lipopolysaccharide of K. pneumoniae. Mice immunized with this vaccine showed a strong antibody response against K. pneumoniae.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
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, Multidisciplinary
Samira Escopy, Yashapal Singh, Keith J. Stine, Alexei V. Demchenko
Summary: As the 21st century unfolds with rapid changes, new challenges have arisen in research and development. This article introduces a solution phase batch synthesis method based on the HPLC platform, which enables sequential synthesis of multiple oligosaccharides and automates the process.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Zhenguang Zhao, Reem Mousa, Norman Metanis
Summary: SELENOF is an endoplasmic reticulum selenoprotein that may be responsible for reducing non-native disulfide bonds in misfolded glycoproteins.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Mariya Novakova, Anupama Das, Catherine Alex, Alexei V. V. Demchenko
Summary: This study presents a streamlined synthesis of a rare sugar D-altrosamine and investigates the glycosylation of different glycosyl acceptors using differentially protected altrosamine donors. High facial stereoselectivity is achieved through the H-bond-mediated aglycone delivery (HAD) pathway with 3-O-picoloyl donors and reactive glycosyl acceptors. In contrast, glycosidations with altrosamine donors equipped with the 3-O-benzoyl group show poor stereoselectivity.
FRONTIERS IN CHEMISTRY
(2022)
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
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.
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, Organic
Bhawna Barpuzary, Mijin Kim, Young Ho Rhee
Summary: A novel metal-catalyzed method for stereoselective glycosidic bond formation in saccharomicin was reported, featuring high diastereoselectivity. This approach allowed for efficient synthesis of saccharosamine-rhamnose and rhamnose-fucose fragments through a combination of various reactions.
Review
Chemistry, Medicinal
Giulia Vessella, Serena Traboni, Antonio Laezza, Alfonso Iadonisi, Emiliano Bedini
Article
Chemistry, Physical
Serena Traboni, Emiliano Bedini, Alfredo Landolfi, Giulia Vessella, Alfonso Iadonisi
Summary: A solvent-free method has been developed for regioselective functionalization of carbohydrate polyols with tosyl group, using cheap reagents and simple experimental procedures, resulting in selective functionalization of a specific saccharide site in a short period of time.
Correction
Biochemistry & Molecular Biology
Giulia Vessella, Roberta Marchetti, Angela Del Prete, Serena Traboni, Alfonso Iadonisi, Chiara Schiraldi, Alba Silipo, Emiliano Bedini
Article
Biochemistry & Molecular Biology
Giulia Vessella, Roberta Marchetti, Angela Del Prete, Serena Traboni, Alfonso Iadonisi, Chiara Schiraldi, Alba Silipo, Emiliano Bedini
Summary: Recent research efforts have focused on obtaining fucosy-lated chondroitin sulfate (fCS) oligosaccharides and low molecular weight (LMW) polysaccharides with well-defined structures to address the potential issues with using native fCS from sea cucumbers as a drug. While total synthesis and controlled depolymerization of natural fCS polysaccharides are the main approaches, limitations exist which could be overcome through a semisynthesis strategy involving regioselective fucosylation and sulfation of a microbial sourced polysaccharide lacking fucose and sulfate decorations. By preparing structurally homogeneous fCS isomers through a multistep process and conducting detailed structural characterization and conformational behavior studies, researchers have made significant progress in this field.
Article
Chemistry, Applied
Giulia Vessella, Fabiana Esposito, Serena Traboni, Celeste Di Meo, Alfonso Iadonisi, Chiara Schiraldi, Emiliano Bedini
Summary: The study developed a semi-synthetic method for the preparation of new low molecular weight Curdlan polysaccharide derivatives with unprecedented sulfation patterns. The method involves protection-sulfation-deprotection steps and detailed structural characterization was conducted to analyze the obtained polysaccharides.
CARBOHYDRATE POLYMERS
(2021)
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
Biochemistry & Molecular Biology
Emiliano Bedini, Alfonso Iadonisi, Chiara Schiraldi, Laura Colombo, Diego Albani, Paola Petrini, Carmen Giordano, Marta Tunesi
Summary: Chondroitin sulfates (CS) are sulfated glycosaminoglycans with protective effects against neurodegenerative diseases like Alzheimer's. Research shows that the sulfation pattern of CS not only affects neuroprotection, but also drug release.
Article
Chemistry, Applied
Fabiana Esposito, Giulia Vessella, Corinne Sinquin, Serena Traboni, Alfonso Iadonisi, Sylvia Colliec-Jouault, Agata Zykwinska, Emiliano Bedini
Summary: Sulfated glycosaminoglycan (GAG) analogues derived from plant, algae or microbial sourced polysaccharides are a promising alternative to animal sources. A study investigated the structural modifications of an exopolysaccharide (EPS) from a bacterium found in deep-sea hydrothermal vents, resulting in multiple sulfated polysaccharides with varying degrees of sulfation. The binding strength between these polysaccharides and growth factors was found to depend on the sulfation degree.
CARBOHYDRATE POLYMERS
(2022)
Article
Biochemistry & Molecular Biology
Sonia Di Gaetano, Luciano Pirone, Ioannis Galdadas, Serena Traboni, Alfonso Iadonisi, Emilia Pedone, Michele Saviano, Francesco Luigi Gervasio, Domenica Capasso
Summary: Galectins are soluble proteins involved in cancer progression and disease outcome, making them important targets for therapeutic intervention. Developing small inhibitors to selectively block galectin activity is a promising strategy for cancer therapy. This study designed a novel compound with high binding affinity to galectins and demonstrated its potential anticancer properties, paving the way for further development as an anticancer agent.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Biochemistry & Molecular Biology
Luciano Pirone, Ferran Nieto-Fabregat, Sonia Di Gaetano, Domenica Capasso, Rita Russo, Serena Traboni, Antonio Molinaro, Alfonso Iadonisi, Michele Saviano, Roberta Marchetti, Alba Silipo, Emilia Pedone
Summary: This study focuses on the interaction between galectins and new inhibitors, and utilizes a combination of experimental and computational methods to depict the structure of the 3D complexes and discuss the hotspots for designing better galectin inhibitors.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Organic
Serena Traboni, Fabiana Esposito, Marcello Ziaco, Emiliano Bedini, Alfonso Iadonisi
Summary: In this study, a solvent-free approach for the condensation of carboxylic acids with alcohols and amines mediated by carbodiimides is reported. The procedure enabled fast and high-yielding reactions at room temperature or under conventional heating with a catalytic loading of DMAP as the additive, even at significantly lower amounts. It was found to be widely applicable in the synthesis of ester/amide linkages from non-trivial carbohydrate and amino acid precursors.
Article
Chemistry, Organic
Alfonso Iadonisi, Serena Traboni, Domenica Capasso, Emiliano Bedini, Sabrina Cuomo, Sonia Di Gaetano, Giulia Vessella
Summary: Symmetrical diglycosyl-selenides or diselenides can be prepared with high chemoselectivity by using elementary selenium and glycosyl iodides as reactants. The presence of triethyl phosphite and the stoichiometric ratio of sodium borohydride to selenium are critical factors in determining the selectivity of the synthesis. The strategy has been extended to the synthesis of unsymmetrical diglycosyl selenides, and preliminary biological experiments have shown potential antiproliferative effects of galactosyl diselenide.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Serena Traboni, Giulia Vessella, Emiliano Bedini, Alfonso Iadonisi
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Polymer Science
Giovanni Dal Poggetto, Salvatore Simone Troise, Claudia Conte, Roberta Marchetti, Francesca Moret, Alfonso Iadonisi, Alba Silipo, Rosa Lanzetta, Mario Malinconico, Fabiana Quaglia, Paola Laurienzo
Article
Chemistry, Organic
Giulia Vessella, Angela Casillo, Antonio Fabozzi, Serena Traboni, Alfonso Iadonisi, Maria Michela Corsaro, Emiliano Bedini
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
