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)
Review
Biophysics
Vanessa E. Abrantes-Coutinho, Andre O. Santos, Rafael B. Moura, Francisco N. Pereira-Junior, Lucia H. Mascaro, Simone Morais, Thiago M. B. F. Oliveira
Summary: Lectin-based biosensors have made significant progress in the field of electroanalysis, offering high sensitivity, specificity, precision, and stability for the detection of clinically relevant carbohydrates and glycoproteins. By combining different materials and functional groups, these sensors can further enhance detection performance and applicability.
COLLOIDS AND SURFACES B-BIOINTERFACES
(2021)
Review
Pharmacology & Pharmacy
Charlotte Sorieul, Francesco Papi, Filippo Carboni, Simone Pecetta, Sanjay Phogat, Roberto Adamo
Summary: Carbohydrates are widely expressed on the surface of cells and play important roles in immune responses and cancer progression. Vaccines and monoclonal antibodies targeting specific carbohydrates have been developed, but the immune tolerance associated with these glycans poses challenges. New strategies are being explored to enhance carbohydrate-based cancer therapies.
PHARMACOLOGY & THERAPEUTICS
(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
Annika J. E. Borg, Oriol Esquivias, Joan Coines, Carme Rovira, Bernd Nidetzky
Summary: UDP-glucuronic acid 4-epimerase is an example illustrating the challenge of balancing conformational flexibility and precise positioning in enzyme catalysis. The study reveals the rotational landscape of the 4-keto intermediate and demonstrates how distortion of the sugar ring induces torsional mobility in the enzyme's binding pocket. Epimerase variants that lack binding interactions with the carboxylate group in a specific rotational isomer of the substrate lead to decarboxylation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Pei-Yun Chiang, Avijit K. Adak, Wei-Lun Liang, Chen-Yen Tsai, Hsin-Kai Tseng, Jing-Yan Cheng, Jih Ru Hwu, Alice L. Yu, Jung-Tung Hung, Chun-Cheng Lin
Summary: In this paper, a viable chemoenzymatic method for the synthesis of globo-series GSLs is described. The method allows for the modification of lipid portions of the GSLs, leading to the discovery of lipid-modified Globo H-GSLs with different immunosuppressive activities. This strategy may be applicable to the rapid synthesis of other complex GSLs.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Organic
David Lim, Francesca Paradisi
Summary: Glycosylation can improve the pharmacokinetic properties of bioactive molecules, but their syntheses often require tedious protecting group manipulations. In this study, we developed a method for direct aqueous conversion of unprotected sugars into glycosides, and demonstrated its application with various biomolecules including resorcinol, resveratrol, and gimeracil. We also showed that the bioactive drug can be released from the sugar in an oxidatively-triggered manner, making them suitable for medicinal applications. This novel transformation provides access to various selenium-containing glycomimetics and glycoconjugates.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Eike Siebs, Elena Shanina, Sakonwan Kuhaudomlarp, Priscila da Silva Figueiredo Celestino Gomes, Cloe Fortin, Peter H. Seeberger, Didier Rognan, Christoph Rademacher, Anne Imberty, Alexander Titz
Summary: This study reports a new approach to inhibit the formation of Pseudomonas aeruginosa biofilms. By synthesizing galactosidic LecA inhibitors with aromatic moieties targeting the central pocket, the formation of biofilms was successfully reduced.
Review
Biochemistry & Molecular Biology
Christine M. Szymanski
Summary: Each microbe can produce a wide variety of sugar structures that are distinct from those in eukaryotes. Differences in carbohydrate building blocks and additional mechanisms for synthesis contribute to the structural heterogeneity of individual strains. Past research focused more on human pathogens, but recent advances in technology have highlighted the importance of studying microbial glycan diversity in commensals and environmental isolates.
FRONTIERS IN MOLECULAR BIOSCIENCES
(2022)
Editorial Material
Biochemistry & Molecular Biology
Roberto Adamo
Summary: Glycoconjugate vaccines, which involve carbohydrates bound to protein carriers, have been effective in combating diseases such as meningitidis, pneumonia, and typhoid fever. Despite advances in new technologies like RNA and adenovirus-based vaccines, targeting carbohydrates remains a challenge. This issue provides an overview of the evolving landscape in this field and aims to generate interest in this fundamental aspect of vaccinology.
GLYCOCONJUGATE JOURNAL
(2021)
Article
Chemistry, Organic
Debasish Pal, Aritra Chaudhury, Balaram Mukhopadhyay
Summary: This manuscript reports the chemical synthesis method of the trisaccharide repeating unit of the O-antigen from Pseudomonas putida BIM B-1100. The challenging residues were successfully incorporated through rational protecting group manipulations and a linear strategy, and the desired carboxylic acid moiety was introduced through TEMPO-mediated oxidation. The use of aminoethyl glycoside allows further glycoconjugate formation without affecting the anomeric stereochemistry.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Anjali Aghi, Akanksha Singh Baghel, Amit Kumar
Summary: We report a metal-free, diastereoselective method for synthesizing conformationally locked spiro bicyclic sugars with a quaternary center at the C5 position. The method involves the one-step construction of an oxazoline-containing spiro-bicyclic system from easily synthesizable C6-glycosylimidates under visible light conditions. Key features of this protocol include mild reaction conditions, green energy source, broad substrate scope, scalable synthesis, and high reaction yields.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Immunology
Armelle Phalipon, Laurence A. Mulard
Summary: This review discusses the molecular glycovaccine concept and its potential to develop a Shigella glycoconjugate vaccine. Using chemically synthesized oligosaccharides attached to a carrier, a fine-tuned Shigella glycovaccine prototype was developed and tested in clinical trials, showing good safety and bactericidal effects. Challenges in advancing this novel approach to a multivalent, cost-effective Shigella synthetic glycan conjugate vaccine are also discussed.
Article
Biochemistry & Molecular Biology
Roberto Adamo
Summary: These two papers extend the definition of glycoconjugates to new classes of carbohydrate containing molecules, highlighting the dynamic nature of the field of glycoscience.
GLYCOCONJUGATE JOURNAL
(2021)
Review
Chemistry, Multidisciplinary
Vinod K. Tiwari
Summary: The increasing demand for carbohydrate-containing molecules has led to thorough investigations into their chemical, biological, and pharmacological roles in important biological events, with clinical studies conducted globally for the treatment of various diseases. The perspective on carbohydrate-based molecular scaffolding and the author's experience in synthetic carbohydrate chemistry over the past 20 years, particularly in drug discovery & development, are briefly presented in the article.
Article
Plant Sciences
Tereza Prerovska, Svatopluk Henke, Roman Bleha, Vojtech Spiwok, Simona Gillarova, Jean-Claude Yvin, Vincent Ferrieres, Eric Nguema-Ona, Petra Lipovova
Summary: This study confirmed the presence of AGP-like glycoproteins in Ulva species for the first time and provided a simple extraction protocol, partial characterization, and comparison with Solanum lycopersicum AGPs. The unique glycosylation structure of Ulva lactuca AGP-like glycoproteins suggests a specialized adaptation to the marine environment, potentially shedding light on the evolution of plant cell walls.
JOURNAL OF PHYCOLOGY
(2021)
Article
Chemistry, Medicinal
El-Mahdi Ourhzif, Arnaud Paris, Isabelle Abrunhosa-Thomas, El Mostafa Ketatni, Pierre Chalard, Mostafa Khouili, Richard Daniellou, Yves Troin, Mohamed Akssira
Summary: A concise and versatile synthetic strategy was developed for the total synthesis of arylnaphthalene lignans and aza-analogs, demonstrating flexibility and potentiality. A series of novel compounds were synthesized and evaluated for their cytotoxic activities on cancer cell growth, with five compounds showing excellent activity against five tumor cell lines, with IC50 values ranging from 1 to 10 μM.
ARCHIV DER PHARMAZIE
(2021)
Article
Biochemistry & Molecular Biology
Damien Bretagne, Arnaud Paris, Rene de Vaumas, Pierre Lafite, Richard Daniellou
Summary: β-D-Xylosidase DtXyl from Dictyoglomus thermophilum is a potential thermostable biocatalyst for producing biologically active ginsenosides intermediates. The crystal structure of DtXyl reveals hydrophobic residues in the active site that play a crucial role in binding and hydrolyzing Notoginsenoside R1, showing distinct properties from other residues in the GH39 xylosidase family.
Article
Chemistry, Organic
Benedicte Favreau, Oznur Yeni, Simon Ollivier, Joel Boustie, Francoise Le Devehat, Jean-Paul Guegan, Mathieu Fanuel, Helene Rogniaux, Richard Bredy, Isabelle Compagnon, David Ropartz, Laurent Legentil, Vincent Ferrieres
Summary: This study explored the impact of hexoside ring size on the properties of glycoconjugates, aiming to identify specific signatures of different glycosyl entity connections using ion mobility and infrared multiple photon dissociation analysis techniques. The research found that different glycosyl entity connections resulted in specific features in mass spectrometry.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Bouchra Dahmoune, Fouzia Bachari-Houma, Mohamed Chibane, Philippe Jehan, Jean-Paul Guegan, Farid Dahmoune, Cherifa Aissou-Akrour, Lotfi Mouni, Vincent Ferrieres, Didier Hauchard
Summary: In this study, the inter-organ, sexual, and seasonal variability of saponins in the common Mediterranean starfish Echinaster sepositus was reported. The diversity of saponins in E. sepositus was found to be higher than previously reported, with 11 different saponins identified, including 9 new congeners. The levels of saponins varied qualitatively and quantitatively based on the organ, sex, and collecting season.
BIOCHEMICAL SYSTEMATICS AND ECOLOGY
(2021)
Article
Energy & Fuels
Bouchra Dahmoune, Fouzia Houma-Bachari, Mohamed Chibane, Cherifa Akrour-Aissou, Jean-Paul Guegan, Thomas Vives, Philippe Jehan, Farid Dahmoune, Lotfi Mouni, Vincent Ferrieres, Didier Hauchard
Summary: Microwave assisted extraction was applied to extract total saponins from starfish, with optimized conditions resulting in significantly higher extraction yield and activity compared to ultrasound assisted extraction and conventional solvent extraction. The microwave extraction method showed a 7.8 times higher saponins yield than CSE and 3.3 times more than UAE.
CHEMICAL ENGINEERING AND PROCESSING-PROCESS INTENSIFICATION
(2021)
Article
Chemistry, Organic
Cedric Peyrot, Blanka Didak, Laure Guillotin, Ludovic Landemarre, Pierre Lafite, Loic Lemiegre, Richard Daniellou
Summary: Arbutin, a natural glycoside, is known as a commercial tyrosinase inhibitor for preventing skin pigmentary disorders. Thioglycosidic analogs of arbutin have shown potential as tyrosinase inhibitors and inhibitors of melanin transfer.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jordan S. Ho, Amira Gharbi, Baptiste Schindler, Oznur Yeni, Richard Bredy, Laurent Legentil, Vincent Ferrieres, Laura L. Kiessling, Isabelle Compagnon
Summary: Sequencing glycans is challenging due to their structural diversity. In this study, researchers used infrared multiple photon dissociation spectroscopy with mass spectrometry to differentiate between pyranose- and furanose-linked galactose residues, offering a solution to distinguish between these isomers. By analyzing hexose ammonium adducts, the researchers determined diagnostic MS-IR signatures of galactose anomers in different forms, demonstrating the utility of MS-IR for analyzing unique substructures in bacterial glycans.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Plant Sciences
Tereza Prerovska, Barbora Jindrichova, Svatopluk Henke, Jean-Claude Yvin, Vincent Ferrieres, Lenka Burketova, Petra Lipovova, Eric Nguema-Ona
Summary: This study reveals the potential of AGP-like proteins isolated from Ulva lactuca in activating plant immune defense. Preventive application of Ulva extract enhances plant resistance against Leptosphaeria maculans in oilseed rape.
FRONTIERS IN PLANT SCIENCE
(2022)
Article
Biochemistry & Molecular Biology
Otmane Bourzikat, Abdelmoula El Abbouchi, Hamza Ghammaz, Nabil El Brahmi, Elmostfa El Fahime, Arnaud Paris, Richard Daniellou, Franck Suzenet, Gerald Guillaumet, Said El Kazzouli
Summary: In this study, new 2-phenyl-5,6,7,8-tetrahydroimidazo [1,2-b]pyridazines bearing sulfonamides were synthesized and evaluated for their anticancer activities. Compounds 4e and 4f showed excellent activities comparable to the reference drugs 5-fluorouracil and etoposide against MCF-7 and SK-MEL-28 cancer cell lines.
Review
Biochemistry & Molecular Biology
Karim Jarmoni, Khalid Misbahi, Vincent Ferrieres
Summary: This review firstly discusses the synthetic methods of imidazo[4,5-b]pyridine derivatives and then provides examples of their potential, with a focus on protein inhibition abilities, opening up possibilities for their application as anti-cancer or antimicrobial agents.
CURRENT MEDICINAL CHEMISTRY
(2023)
Article
Biochemical Research Methods
Simon Ollivier, Laurent Legentil, Oznur Yeni, Louis-Philippe David, Vincent Ferrieres, Isabelle Compagnon, Helene Rogniaux, David Ropartz
Summary: Carbohydrates are highly diverse and structurally heterogeneous biomolecules, making them a challenge for analytical chemists. The presence of isomerisms and tautomerism complicates their structural characterization by mass spectrometry. This study investigates the gas-phase behavior of Galf-containing oligosaccharides using high-resolution and multistage ion mobility. The findings reveal the contributions of additional gas-phase conformers in the IMS profile, shedding light on previously unknown features of these biomolecules.
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
(2023)
Article
Chemistry, Multidisciplinary
Oznur Yeni, Simon Ollivier, Baptiste Moge, David Ropartz, Helene Rogniaux, Laurent Legentil, Vincent Ferrieres, Isabelle Compagnon
Summary: The analysis of glycans is difficult due to their isomeric complexity. This study utilized tandem mass spectrometry and infrared ion spectroscopy (MS/MS-IR) to investigate compounds containing galactofuranose and galactopyranose. The study found that the ring size of galactose can be preserved under collision-induced dissociation (CID) conditions. These findings have two potential applications: the analysis of labeled oligosaccharide patterns by MS/MS-IR to obtain full sequence information, including the ring size of galactose unit, and the rapid identification of the presence of a galactofuranose unit in unlabeled oligosaccharides using MS/MS-IR.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Physical
Oznur Yeni, Abdul-Rahman Allouche, Laurent Legentil, Vincent Ferrieres, Isabelle Compagnon
Summary: A computational study was conducted to understand the conformational preferences of galactofuranose through molecular dynamics, density functional theory, and spectroscopy. The study revealed that methyl α-d-galactofuranose adopts E-2/E-1 conformations, while methyl β-d-galactofuranose adopts T-1(2)/E-1 conformations.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2023)
Article
Biochemistry & Molecular Biology
Yari Cabezas-Perusse, Franck Daligault, Vincent Ferrieres, Olivier Tasseau, Sylvain Tranchimand
Summary: The study successfully increased the transglycosylation yield of beta-d-galactofuranosyl by mutating and screening the catalyst, followed by molecular modeling. The mutations led to significant differences in regioisomer kinetic profiles compared to the wild-type enzyme.
