Article
Chemistry, Multidisciplinary
Carla Obradors, Benjamin Mitschke, Miles H. Aukland, Markus Leutzsch, Oleg Grossmann, Sebastian Brunen, Sebastian A. Schwengers, Benjamin List
Summary: Since early 2020, scientists have been striving to find effective solutions to combat SARS-CoV-2, focusing on developing reliable vaccines and repurposing drugs. However, the current synthetic routes for Remdesivir, the most widely used therapeutic during the early stages of infection, face challenges in cost-effective supply to patients. In this study, researchers have developed a straightforward method for adding (hetero)arenes to unprotected sugars, significantly expediting the synthesis of Remdesivir precursor GS-441524.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Saptashwa Chakraborty, Bijoyananda Mishra, Pratim Kumar Das, Sandip Pasari, Srinivas Hotha
Summary: The silver-assisted gold-catalyzed activation of alkynyl glycosyl carbonate donors is a versatile approach for the synthesis of various types of N-glycosides, including purine and pyrimidine nucleosides, asparagine glycosides, and quinolin-2-one N-glycosides. This method enables the synthesis of nucleosides that are difficult to obtain through other means. Additionally, it can be used to easily synthesize 2'-modified nucleosides and dipeptide disaccharide units of chloroviruses.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(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, Physical
Liwen Xia, Wenjing Fan, Xiang-Ai Yuan, Shouyun Yu
Summary: The synthesis of C-nucleoside analogues through photoredox-catalyzed radical coupling allows for good functional group tolerance and site- and stereoselectivities, making it applicable for coupling various monosaccharides, disaccharides, and polysaccharides with nonfunctionalized heteroarenes. Biologically important molecules can be glycosylated directly through a C-C bond using this method, and the site- and stereoselectivities can be rationalized and predicted by density functional theory (DFT) calculations.
Article
Chemistry, Physical
Alex J. Plajer, Charlotte K. Williams
Summary: Heteronuclear complexes exhibit high catalytic activity in ring opening copolymerizations. By studying a series of trinuclear complexes, it was found that certain catalysts show high activity for specific reactions, such as CHO/CO2 ROCOP and CHO/ PA copolymerization, allowing for controlled polyether block formation. These findings can guide future catalyst design and inspire other CO2 utilization processes.
Article
Food Science & Technology
Zhengcao Xiao, Liangliang He, Xiaohui Hou, Jianping Wei, Xiaoyu Ma, Zihan Gao, Yahong Yuan, Jianbo Xiao, Pengmin Li, Tianli Yue
Summary: Glycosylation decreased the antioxidant capacity and activity of flavonols, with 3-glycosylation having a more significant impact than 7-glycosylation. While glycosylation hindered antioxidant activity, it also inhibited dimer formation, contributing to the retention of free radical scavenging abilities by flavonol derivatives.
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, Organic
Khoi B. Luu, K. A. Woerpel
Summary: The stereochemical outcomes of O-glycosylation reactions of septanose intermediates are controlled by the alkoxy substituents at C4 and C2 positions. The presence of a bicyclic acetal byproduct in some substitution reactions suggests that the C4 benzyloxy substituent stabilizes intermediates by forming an oxonium ion intermediate through long-range participation. Inductive destabilization of the carbocationic intermediate provided by the C2 substituent is crucial for the participation of the remote alkoxy group.
Article
Biochemistry & Molecular Biology
Ana Pozo-Rodriguez, Juan A. Mendez-Liter, Laura I. de Eugenio, Manuel Nieto-Dominguez, Eva Calvino, Francisco Javier Canada, Andres G. Santana, Jaime Diez, Juan L. Asensio, Jorge Barriuso, Alicia Prieto, Maria Jesus Martinez
Summary: The study explores the use of endoxylanases and their glycosynthase variants in the valorization of hemicellulosic residues and the synthesis of glycosides with improved properties. The results demonstrate the high catalytic efficiency and substrate versatility of these enzymes, particularly in the degradation of beechwood xylan and wheat arabinoxylan. The glycosynthase variant shows enhanced capacity in the synthesis of xylooligosaccharides and glycosylation of phenolic compounds with antioxidant properties.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Multidisciplinary
Ignacio Sanz-Martinez, Ana Garcia-Garcia, Tomas Tejero, Ramon Hurtado-Guerrero, Pedro Merino
Summary: Protein O-fucosyltransferase 2 (PoFUT2) is an important glycosyltransferase that recognizes a diverse range of TSRs through water-mediated interactions. Water molecules not only play a role in ligand recognition but also in the catalytic mechanism of PoFUT2.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Plant Sciences
Qinggang Yin, Yiding Wei, Xiaoyan Han, Jingwang Chen, Han Gao, Wei Sun
Summary: Chinese horse chestnut flowers and leaves contain abundant flavonoids, with significantly higher content of seven flavonol glycosides in flowers than in leaves. The crude proteins of flowers can catalyze the formation of flavonol glucosides. These studies provide theoretical and experimental basis for the utilization of Chinese horse chestnut flowers and leaves as additives and dietary supplements.
FRONTIERS IN PLANT SCIENCE
(2022)
Article
Chemistry, Organic
Yousra Hamdane, Pradeep S. Chauhan, Suresh Vutla, Mukandila Mulumba, Huy Ong, William D. Lubell
Summary: Fifteen N-aminoimidazolone (Nai) dipeptides with different 5-position side-chain groups were synthesized through regioselective proline-catalyzed reactions and acid-mediated dehydration. Introducing 5-aryl-Nai dipeptides into CD36 receptor peptide ligands provided insights into the conformation responsible for binding affinity and anti-inflammatory activity.
Article
Chemistry, Multidisciplinary
Youxi Chen, Guozhi Xiao, Dapeng Zhu, Biao Yu
Summary: Sepositoside A is a prototypical cyclic steroid glycoside with a hybrid 16-membered ring composed of the steroid skeleton and a 1,2-trans-linked trisaccharide. We report a convenient method to construct the strained 16-membered ring via Au(I)-catalyzed intramolecular addition of alcohol to epoxide, leading to two simplified analogues. Although a similar macroetherification in relevant steroid trisaccharides has been extensively studied, it has failed to provide the macrocyclic skeleton of Sepositoside A.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Physical
Wei Huang, Yue He, Renwang Jiang, Zixin Deng, Feng Long
Summary: Cardiotonic steroids (CTSs) are important drugs for treating heart failure. Glycosylation of CTSs plays a significant role in their pharmacological applications. Plant steroid 3-O-glycosyltransferase (S3GT) is a tool to achieve CTS glycosylation, but a S3GT with both substrate and sugar donor promiscuity is still unidentified. This study identified and characterized a plant S3GT, UGT74AN2, and revealed the molecular basis for CTS glycosylation. Additionally, an engineered variant of UGT74AN2 with enhanced sugar donor promiscuity was constructed.
Article
Chemistry, Multidisciplinary
Ke Xiao, Yongxin Hu, Yongyong Wan, XinXin Li, Qin Nie, Hao Yan, Liming Wang, Jinxi Liao, Deyong Liu, Yuanhong Tu, Jiansong Sun, Jeroen D. C. Codee, Qingju Zhang
Summary: The new glycosylation system utilizes a charged thiourea hydrogen-bond-donor catalyst and PTFAI donors, showing broad substrate scope, stereoselectivity, and good yields. The mild catalysis conditions make it suitable for synthesizing challenging phenolic glycosides and a chemoselective glycosylation procedure.
Article
Chemistry, Medicinal
Vasco Cachatra, Maria Conceicao Oliveira, Oscar Lopez, Jose G. Fernandez-Bolanos, Amelia Pilar Rauter
Summary: We disclosed a new family of purine nucleoside cholinesterase inhibitors by tuning the structural and stereochemical features of nucleosides with perbenzylated glycosyl moieties. The design, synthesis, and biological evaluation of new purine nucleosides were conducted to investigate the required glycon protecting group pattern for anticholinesterase activity and selectivity. Regioselective chemistry and N-glycosylation were used to obtain the target nucleosides, which showed cholinesterase inhibition and selectivity for butyrylcholinesterase.
MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Andrea Mascherpa, Nozomii Ishii, Ayelen Tayagui, Jiang Liu, Matthieu Sollogoub, Antony J. J. Fairbanks
Summary: Beta-cyclodextrin and its derivatives have been approved for therapeutic use in over 30 clinical settings. They show promise as therapeutics for lysosomal storage disorders and other diseases involving metabolite accumulation in the lysosome. In this study, a synthetic glycan terminated with mannose-6-phosphate residues was attached to beta-cyclodextrin and its effect on cellular internalization and transport to the lysosome was investigated.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Editorial Material
Chemistry, Organic
Matthieu Sollogoub, Emmanuelle Schulz
Summary: The Division de Chimie Organique (DCO) of the Societe Chimique de France (SCF) and the European Journal of Organic Chemistry are collaborating for the second year in a row to honor the recipients of the 2021 DCO Awards.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Medicinal
Rita Goncalves-Pereira, Jose A. Figueiredo, Susana D. Lucas, Maria I. Garcia-Moreno, Carmen O. Mellet, Amelia P. Rauter, Maria I. Ismael
Summary: Alzheimer's disease is a multifactorial syndrome that causes memory loss, dementia, and eventually death. Acetylcholinesterase inhibitors are the main drugs used for symptomatic treatment of the disease. This study reports a new synthetic route for producing sugar amides that act as acetylcholinesterase inhibitors.
MEDICINAL CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Hugo Madec, Francisca Figueiredo, Kevin Cariou, Sylvain Roland, Matthieu Sollogoub, Gilles Gasser
Summary: The development of organometallic catalysis has expanded the toolbox of synthetic chemists and paved the way for bio-compatible reactions in water. Performing metal-catalysed reactions within living cells or organisms poses additional constraints, requiring metal complexes with good efficiency, low concentration, cell specificity, cellular uptake, and low toxicity.
Article
Chemistry, Multidisciplinary
Enxu Liu, Sawsen Cherraben, Laora Boulo, Claire Troufflard, Bernold Hasenknopf, Guillaume Vives, Matthieu Sollogoub
Summary: Researchers have developed a novel molecular information ratchet that is sensitive to both the position and orientation of a moving macrocycle. The use of a cone-shaped chiral macrocycle allows for kinetic biases, and the possibility of selective functionalization offers new opportunities in the design of molecular motors.
Article
Chemistry, Medicinal
Ignazio Schino, Mariangela Cantore, Modesto de Candia, Cosimo D. Altomare, Catarina Maria, Joao Barros, Vasco Cachatra, Patricia Calado, Karina Shimizu, Adilson A. Freitas, Maria C. Oliveira, Maria J. Ferreira, Jose N. C. Lopes, Nicola A. Colabufo, Amelia P. Rauter
Summary: Alzheimer's Disease (AD) is characterized by an imbalance in cholinergic neurotransmission, and the inhibition of acetylcholinesterase (AChE) and increase of butyrylcholinesterase (BChE) activity. Novel 6-benzamide purine nucleosides that selectively target BChE and possess chelating properties were synthesized. These compounds show potential as dual target compounds for the treatment of AD.
Article
Nanoscience & Nanotechnology
Anna Blasi-Romero, Molly Angstrom, Antonio Franconetti, Taj Muhammad, Jesus Jimenez-Barbero, Ulf Goransson, Carlos Palo-Nieto, Natalia Ferraz
Summary: This study combines the wound-healing properties of KR-12 peptide with wood-derived cellulose nanofibrils (CNFs) to create bioactive materials for treating chronic wounds. Different coupling chemistries were used to covalently attach KR-12 derivatives onto CNFs, and the bioactivity of KR12-CNF conjugates was evaluated in terms of antibacterial activities and anti-inflammatory effects. The results showed that thiol-ene chemistry produced the most bioactive conjugates, attributed to favorable peptide conformation and accessibility. This study advances the development of CNF-based materials for chronic wound care and provides insights into the effect of conjugation chemistry on the bioactivity of host defense peptides.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Article
Chemistry, Multidisciplinary
Dmitri Colesnic, Pedro J. Hernando, Lise-Marie Chamoreau, Laurent Bouteiller, Mickael Menand, Matthieu Sollogoub
Summary: Regioselective di-functionalization of a cyclodextrin enables controlled orientation of hydrophobic domains, leading to a unique hierarchical assembly in the solid state. This assembly involves synergistic host-guest inclusions, directed hydrophobic effect, and hydrogen bonding, which together create a porous organic architecture.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Forestry
Luciana Silva, Sofia Oriskova, Diogo Goncalves, Ivo Paulo, Jose Condeco, Miguel Monteiro, Nuno M. Xavier, Amelia P. Rauter, Joao M. Bordado, Rui Galhano dos Santos
Summary: Eucalyptus globulus sawdust, a residue from the pulp and paper industry, can be recycled through thermochemical liquefaction to produce bio-oil. The aqueous extract of the bio-oil contains carbohydrates, particularly fructose and glucose, which can be used in the industry to produce sustainable materials. The sugar composition of the aqueous extract was identified and quantified using analytical techniques such as HPLC, HSQC-NMR, FTIR-ATR, and elemental analysis.
Review
Chemistry, Multidisciplinary
Elisabete Lima, Amelia P. Rauter, Jorge Medeiros
Summary: The development of multitarget-directed ligands (MTDLs) is urgently needed to combat the multifactorial Alzheimer's disease (AD). Flavonoids from natural sources have shown activity on mechanisms associated with AD and have potential as anti-AD agents. The most active flavonoids against several clinical indications (CIs) of AD are flavanols and flavonols, which have specific structural features.
APPLIED SCIENCES-BASEL
(2023)
Article
Biochemistry & Molecular Biology
Catarina Maria, Amelia P. Rauter
Summary: Nucleosides have attracted attention since the discovery of DNA structure. Nucleoside analogues can be synthesized through multiple pathways, with N-glycosylation of a nucleobase being the most common method. This review focuses on the synthesis and therapeutic applications of FDA approved nucleoside analogues as antiviral and anticancer agents, as well as their potential as antibacterial and anti-Alzheimer's disease agents.
CARBOHYDRATE RESEARCH
(2023)
Review
Chemistry, Multidisciplinary
Jon I. Quintana, Unai Atxabal, Luca Unione, Ana Arda, Jesus Jimenez-Barbero
Summary: Nuclear Magnetic Resonance (NMR) is widely used to study glycan-protein molecular recognition events, providing qualitative and quantitative information at different levels of resolution and complexity. However, the weak affinity of lectin-sugar interactions is overcome by multivalency in biological processes. The application of NMR methods to monitor multivalent lectin-glycan interactions is challenging due to the disappearance of NMR signals when large macromolecular complexes are formed.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Chemistry, Multidisciplinary
Cecilie Hogfeldt Jessen, Jesper Bendix, Theis Brock Nannestad, Heloisa N. N. Bordallo, Martin Jaeger Pedersen, Christian Marcus Pedersen, Mikael Bols
Summary: α-cyclodextrin dissolved in water forms a 1:1 complex with methane, yielding crystals with a maximum yield of 57%. The binding constant is K-a=21 (±1.0) M-1. 3(A),6(A),3(D),6(D)-dianhydro-α-cyclodextrin, which has a smaller cavity than α-cyclodextrin, binds methane three times better with a binding constant of K-a=75 (±25) M-1.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Carlo Pifferi, Leire Aguinagalde, Ane Ruiz-de-Angulo, Nagore Sacristan, Priscila Tonon Baschirotto, Ana Poveda, Jesus Jimenez-Barbero, Juan Anguita, Alberto Fernandez-Tejada
Summary: The overexpression of aberrantly glycosylated tumor-associated mucin-1 (TA-MUC1) in human cancers makes it a major target for the development of anticancer vaccines derived from synthetic MUC1-(glyco)peptide antigens. However, glycopeptide-based subunit vaccines are weakly immunogenic, requiring adjuvants and/or additional immunopotentiating approaches to generate optimal immune responses.
