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
Biochemistry & Molecular Biology
Nathan Noel, Simon Duchateau, Gatien Messire, Fabien Massicot, Jean-Luc Vasse, Sandra Villaume, Aziz Aziz, Stephan Dorey, Jerome Crouzet, Jean-Bernard Behr
Summary: A straightforward method for synthesizing carbohydrate templated isoxazolidines using microwave activation is described. The reaction involves the interaction of unprotected glycosylhydroxylamines with methyl acrylate, resulting in the formation of rhamno- and erythro-isoxazolidines. These compounds are recognized by plant cells, triggering a strong immune response and exhibiting high antifungal activity against Botrytis cinerea.
BIOORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Yong-Ju Kwon, Won-Suk Kim
Summary: This study investigated the regioselective functionalization of protected compounds to synthesize unsymmetrical molecules. Different protecting groups were used to achieve selective functionalization at specific positions, leading to the synthesis of biologically active compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Lucas Kambanis, Timothy S. Chisholm, Sameer S. Kulkarni, Richard J. Payne
Summary: This study introduces an iterative one-pot peptide ligation strategy that combines the rapid diselenide-selenoester ligation reaction with photodeselenisation chemistry, enabling the efficient synthesis of protein fragments in a short period of time. The use of a novel photolabile protecting group for selenocysteine side chains allows for mild, reagent-free deprotection using visible light, facilitating subsequent ligation reactions without the need for purification.
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.
Review
Chemistry, Organic
Aslihan Ayvaz, Sinem Gorkem Demirbas, Ahmet Demirbas, Neslihan Demirbas
Summary: Due to the increasing environmental pollution and its detrimental impact on the ecosystem, scientists have developed new chemical strategies using eco-friendly chemicals, solvents, catalysts, and alternative energy sources. Deep eutectic solvents (DESs) are low-melting mixtures primarily consisting of quaternary ammonium salt and hydrogen-bond acceptors. DESs have advantages such as low toxicity, easy preparation, low cost, biodegradability, low vapor pressure, and recyclability.
CURRENT ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jyun-Siao Chen, Po-Hsun Huang, Ya-Chi Hsieh, Jen-Wei Liu, Hsiao-Lin Hsu, Kai-Min Zhang, Ren-Tsung Wu, Ting-Shuo Chang, Yu-Hao Liu, Hsin-Ru Wu, Shun-Yuan Luo
Summary: Trimethylsilyl esters, such as AcOTMS, BzOTMS, TCAOTMS, are inexpensive and chemically stable reagents that pose a negligible environmental hazard. These compounds are proven to be efficient dual-purpose reagents for acylation and trimethylsilylation of alcohols under acidic or basic conditions. Furthermore, a detailed study on protection of various substrates and new methodological investigations is described.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Physical
Giovanna Bosica, Riccardo De Nittis, Ryan Borg
Summary: An efficient and environmentally benign one-pot condensation reaction was achieved using 1,4-diazabicyclo[2-2-2]octane supported on Amberlyst-15 as a novel catalyst. The reaction involved cyclic diketones, aldehydes, and naphthols, resulting in the synthesis of various benzoxanthenones with good to excellent yields. The advantages of this reaction include the use of a heterogeneous catalyst, solventless conditions, atom-economical methodology, and low E-factor values. Seventeen xanthene derivatives, including two novel molecules, were synthesized and characterized. Aromatic aldehydes with electron-withdrawing groups showed excellent yields, and aliphatic aldehydes also gave appreciable results. The catalyst exhibited full recyclability and could be reused up to six times.
Article
Polymer Science
Ankita Mandal, Indradip Mandal, Andreas F. M. Kilbinger
Summary: Single chain transfer agents are used to synthesize narrowly distributed heterotelechelic ROMP polymers in one pot, exploiting a new mechanistic and synthetic approach. The strategy allows for excellent control over molecular weight and dispersity of the resulting polymers, showcasing a straightforward and efficient method for synthesizing heterotelechelic ROMP polymers.
Article
Chemistry, Multidisciplinary
Vipin K. Pandey, Chandra Shekhar Tiwari, Arnab Rit
Summary: A silver salt-catalyzed aminophosphonylation and Strecker reaction were developed, and mechanistic studies revealed a radical pathway. This reaction system can effectively operate at room temperature without the need for solvents, ligands, or bases, and it can produce diverse products.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Organic
Zhiyu Hu, Guofang Jiang, Zhiqiang Zhu, Bozhen Gong, Zongbo Xie, Zhanggao Le
Summary: A green multicomponent reaction using a deep eutectic solvent (DES) has been developed, resulting in high yields of desired products without the need for additional catalysts. The DES, composed of zinc chloride and choline chloride, is cost-effective and recyclable, reducing the synthesis cost.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Thi Minh Nguyet Trinh, Franck Schillinger, Sebastiano Guerra, Eric Meichsner, Iwona Nierengarten, Uwe Hahn, Michel Holler, Jean-Francois Nierengarten
Summary: A series of macrocyclic bis-malonates with different spacer units were used for regioselective functionalization of fullerene. By systematically modifying the spacers, fullerene bis-adducts with varied addition patterns were obtained. Finally, the bridging silylene groups were cleaved to yield acyclic fullerene bis-adducts with four alcohol functions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Tyler G. Chong, Alex Helbling, Remi D. Graff, C. Wade Downey
Summary: The combination of TMSOTf and i-Pr2NEt promotes the N-alkylation of primary and secondary amides with propargyl propionates. The amide substrates are converted to nucleophilic silyl imidates, which undergo N-propargylation through propargyl cation formation. This one-pot process can efficiently react a range of amides and propargyl propionates with yields ranging from 19% to 99%.
TETRAHEDRON LETTERS
(2023)
Article
Biochemistry & Molecular Biology
Giovanna Bosica, Fiona Cachia, Riccardo De Nittis, Nicole Mariotti
Summary: Multicomponent reactions offer economic and environmental advantages, with the Biginelli reaction being a significant method for synthesizing 3,4-dihydropyrimidin-2(1H)-ones (DHPMs). In this study, silicotungstic acid supported on Ambelyst-15 was used as a catalyst for the Biginelli reaction under solventless conditions, resulting in improved reaction yields.
Article
Chemistry, Applied
Siyu Zhang, Joseph R. Hyatt, Casimir C. Akoh
Summary: In this study, a multi-functional galloylated structured lipid DOGG was successfully synthesized using immobilized food grade Candida antarctica lipase B. The reaction conditions were optimized and the structure of the product was confirmed. The enzyme showed good reusability and DOGG has potential applications as an antioxidant and nutraceutical.
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)