Article
Biochemistry & Molecular Biology
Marc Caballe, Magda Faijes, Antoni Planas
Summary: Glycolipids, a type of complex molecule involved in important cellular processes, have attracted attention in biomedicine due to the immunostimulatory capabilities of a glycosphingolipid called alpha-galactosylceramide. Researchers have identified an enzyme, called ceramide glycosyltransferase, capable of synthesizing this glycolipid under specific conditions. Further protein engineering may enhance the stability and activity of this enzyme for the enzymatic synthesis of alpha-GalCer in biomedical applications.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Organic
Ishani Lakshika Hettiarachchi, Fenglang Wu, Maria Stoica, Xiaohua Li, Jianglong Zhu
Summary: Stereoselective construction of a variety of 8-glycosides can be realized using K2CO3-mediated stereoselective anomeric O-alkylation of sugar lactols with primary electrophiles. In addition, successful synthesis of various azido-modified glycosphingolipids has been achieved with good yields and excellent anomeric selectivity using sphingosine-derived primary triflate.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Jaggaiah N. Gorantla, Maniganda Santhi, Yanling Hua, James R. Ketudat Cairns
Summary: This study discovered an acyl migration-dependent method for synthesis by using appropriate blocking groups, which turns acyl migration into a tool for synthesis rather than an impediment.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Prathyush Pothukuchi, Ilenia Agliarulo, Marinella Pirozzi, Riccardo Rizzo, Domenico Russo, Gabriele Turacchio, Julian Nuechel, Jia-Shu Yang, Charlotte Gehin, Laura Capolupo, Maria Jose Hernandez-Corbacho, Ansuman Biswas, Giovanna Vanacore, Nina Dathan, Takahiro Nitta, Petra Henklein, Mukund Thattai, Jin-Ichi Inokuchi, Victor W. Hsu, Markus Plomann, Lina M. Obeid, Yusuf A. Hannun, Alberto Luini, Giovanni D'Angelo, Seetharaman Parashuraman
Summary: The Golgi matrix protein GRASP55 plays a crucial role in regulating the compartmentalized localization of key enzymes involved in glycosphingolipid biosynthesis. Lack of GRASP55 or expression of mutant enzymes without GRASP55 binding sites can affect the synthesis of glycosphingolipids by altering metabolic flux.
Article
Chemistry, Multidisciplinary
Xian-Yang Zhou, Ling-Xin Li, Zhen Zhang, Shi-Chao Duan, Ying-Wen Huang, Yi-Yang Luo, Xiao-Dong Mu, Zhi-Wei Chen, Yong Qin, Jing Hu, Jian Yin, Jin-Song Yang
Summary: Acinetobacter baumannii poses a serious threat to global health, and its lipopolysaccharide (LPS) has been found to have antigenic properties. Research has identified a potential antigenic epitope in one of the branches of the LPS, which is attractive for the development of carbohydrate vaccines against A. baumannii.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Biochemistry & Molecular Biology
Safoura Reza, Maciej Ugorski, Jaroslaw Suchanski
Summary: GlcCer and GalCer are involved in various physiological and pathological processes, playing important roles in maintaining myelin stability and differentiation of oligodendrocytes. Enzyme studies indirectly reveal the biological significance of these monohexosylcermides.
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, Multidisciplinary
Chun-Wei Chang, Mei-Huei Lin, Chieh-Kai Chan, Kuan-Yu Su, Chia-Hui Wu, Wei-Chih Lo, Sarah Lam, Yu-Ting Cheng, Pin-Hsuan Liao, Chi-Huey Wong, Cheng-Chung Wang
Summary: The acceptor nucleophilic constants (Aka) database quantifies the nucleophilicity of hydroxyl groups in glycosylation reactions, accurately predicting stereoselectivity and yield.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Yuexin Liu, Yang Jiao, Huajun Luo, Nianyu Huang, Mengnan Lai, Kun Zou, Hui Yao
Summary: An effective regiodivergent synthesis of 1- and 3-thiosugars was achieved using palladium and cobalt catalysis, respectively. The difference in the interaction of thiol moieties with Pd and Co catalysis conditions led to the selective formation of beta-1-thiosugars and (3S)-3-thiosugars. Experimental and theoretical calculations supported the proposed mechanism and provided insights into the regioselectivity based on the bond lengths of key intermediates.
Article
Chemistry, Multidisciplinary
Lea Spitzer, Sebastien Lecommandoux, Henri Cramail, Francois Jerome
Summary: An efficient method has been developed to synthesize end-functionalized oligosaccharides from unprotected monosaccharides, using a one-pot/two-step approach. The monosaccharides were first functionalized with an alkyne group at the anomeric position, then oligomerized to reach a DPn of up to 8. The obtained oligosaccharides showed complete propargylation and could be coupled to oleic acid to produce bio-based surfactants.
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.
Review
Chemistry, Organic
Cecilia Romano, Mads H. Clausen
Summary: Invariant natural killer T (iNKT) cells are a subpopulation of T lymphocytes stimulated by synthetic glycolipid alpha-galactosylceramide (alpha-GalCer) in complex with the CD1d receptor. Through cytokine production and co-stimulation of other lymphocytes, iNKT cells play a central role in directing immune responses in various physiological processes. Synthetic chemistry has advanced the field of iNKT cell stimulation, leading to the development of more efficient approaches and analogs for therapeutic applications.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
David Teze, Joan Coines, Folmer Fredslund, Kshatresh D. Dubey, Gonzalo N. Bidart, Paul D. Adams, John E. Dueber, Birte Svensson, Carme Rovira, Ditte H. Welner
Summary: The study found that UGT1 from Polygonum tinctorium can catalyze N-, O-, or S-glycosylation with similar rates, and elucidated the molecular basis of N-, O-, and S-specificities using experimental mutagenesis and simulations. It also showed that the active site can be engineered to increase or favor one of the three glycosylation activities over another, leading to the design of more active and specific enzyme variants for glycoside production.
Review
Microbiology
Chunmiao Jiang, Jinxin Ge, Bin He, Bin Zeng
Summary: Filamentous fungi are economically important fungi used in various productions such as fermented foods and industrial enzymes. Glycosphingolipids (GSLs) play crucial roles in growth, differentiation, and stress response in filamentous fungi. GSLs found in filamentous fungi can be classified into neutral GSLs and acidic GSLs, with glycosylceramides playing important roles in skin-barrier function and potential dietary benefits.
FRONTIERS IN MICROBIOLOGY
(2021)
Article
Chemistry, Organic
Wei-Yi Ding, Hao-Wen Zhao, Jun Kee Cheng, Zhiqiang Lu, Shao-Hua Xiang, Bin Tan
Summary: This report describes a highly efficient beta-selective C-glycosylation reaction using bicyclic galactals and 2-oxindoles as substrates. The reaction proceeds through a palladium-catalyzed decarboxylative pathway under mild reaction conditions, resulting in high yields. The decarboxylation intermediate of galactal acts as an efficient base to deprotonate the enol tautomer of 2-oxindole, enhancing its nucleophilicity. The beta-selective nucleophilic addition at the anomeric center is due to steric hindrance imposed by the palladium and bulky ligand.
Article
Chemistry, Organic
Daniela Imperio, Laura Morelli, Federica Compostella, Luigi Panza
Summary: A concise and stereoselective synthesis of alpha-GalCer was achieved by utilizing carefully designed protecting groups on both the donor and the acceptor to control the stereochemistry of the glycosylation reaction. This synthetic strategy proved to be efficient, giving good yields of alpha-GalCer in a small number of steps.
Article
Chemistry, Applied
Daniela Imperio, Laura Morelli, Luigi Panza
Summary: The study presents a synthesis method for a series of hydroxylated oleic acids without the use of protecting groups, which can serve as reference compounds for tracking the oxidation reaction of oleic acid. The final products are obtained through partial lactone reduction to hydroxyaldehyde, Grignard addition, selective oxidation of the primary hydroxyl group, and Wittig reaction.
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY
(2021)
Article
Multidisciplinary Sciences
Tobias Hartwig Bunning, Luigi Panza, Abdel Kareem Azab, Barbara Muz, Silvia Fallarini, Daniela Imperio
Summary: Boron Neutron Capture Therapy (BNCT) shows promise in treating non-curable cancers, with a new boron compound being discovered to selectively accumulate in tumor tissue. Hypoxia poses a challenge in cancer treatment, but a new compound exhibits toxicity in multiple myeloma cells and consistent intracellular boron accumulation.
Article
Chemistry, Applied
Daniela Imperio, Matteo Bordiga, Claudia P. Passos, Soraia P. Silva, Manuel A. Coimbra, Fabiano Travaglia, Marco Arlorio, Jean Daniel Coisson, Luigi Panza
Summary: In this study, low molecular weight oligosaccharides were purified and identified from grape seed extracts using chromotagraphy methods. The compounds were found to mainly consist of sucrose, glucose, and trisaccharides, with potential uses in the recovery and utilization of grape seeds.
Correction
Biochemistry & Molecular Biology
Laura Morelli, Laura Polito, Barbara Richichi, Federica Compostella
GLYCOCONJUGATE JOURNAL
(2021)
Review
Biochemistry & Molecular Biology
Laura Morelli, Laura Polito, Barbara Richichi, Federica Compostella
Summary: The escalating issue of antibiotic resistance poses a global health concern, with the need for new drugs or alternative containment strategies becoming urgent. Vaccination, improved sanitation, and infection control measures are effective ways to combat infections. Nanosystems are emerging as potential tools to enhance vaccine efficacy and immunogenicity.
GLYCOCONJUGATE JOURNAL
(2021)
Review
Biology
Wolfgang A. G. Sauerwein, Lucie Sancey, Evamarie Hey-Hawkins, Martin Kellert, Luigi Panza, Daniela Imperio, Marcin Balcerzyk, Giovanna Rizzo, Elisa Scalco, Ken Herrmann, PierLuigi Mauri, Antonella De Palma, Andrea Wittig
Summary: Boron neutron capture therapy (BNCT) has the potential to destroy tumor cells specifically without harming surrounding tissues. The current inability to non-invasively measure the B-10 concentration in specific tissues relies on the imprecise assumption of fixed uptake of B-10 from blood into tissues.
Article
Biochemistry & Molecular Biology
Laura Morelli, Luigi Lay, Darielys Santana-Mederos, Yury Valdes-Balbin, Vicente Verez Bencomo, Angela van Diepen, Cornelis H. Hokke, Fabrizio Chiodo, Federica Compostella
Summary: Vaccination is the most effective way to prevent invasive pneumococcal diseases, but current vaccines have limited coverage and new candidates are needed to control emerging serotypes. Research suggests that designing new saccharide fragments with shared structures among different serotypes could simplify vaccine composition and provide common antigen targets for protection.
ACS CHEMICAL BIOLOGY
(2021)
Article
Multidisciplinary Sciences
Daniela Imperio, Luigi Panza
Summary: Boron neutron capture therapy (BNCT) is a promising radiotherapy for cancer treatment. This review discusses the recent achievements in the synthesis and biological evaluation of boronated sugar derivatives, which can target tumor cells through specific transport proteins.
Article
Biochemistry & Molecular Biology
Barbara Muz, Abdel Kareem Azab, Laura Confalonieri, Erika Del Grosso, Silvia Fallarini, Daniela Imperio, Luigi Panza
Summary: This paper describes the synthesis of a D-glucoheptose derivative containing a boronic moiety. The derivative can mimic carbohydrate behavior and selectively accumulate in tumor tissues.
BIOORGANIC & MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Daniela Imperio, Ambra A. Grolla, Marianna Moro, Valeria Bortolotto, Erika Del Grosso, Armando A. Genazzani, Luigi Panza
Summary: This study reports a multivalent drug delivery and targeting system based on beta-cyclodextrin functionalized with PSMA-like ligand, which shows good selectivity and efficacy on prostate cancer cells.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Biochemistry & Molecular Biology
Laura Morelli, Federica Compostella, Luigi Panza, Daniela Imperio
Summary: This review discusses the essential role of glycosylation in producing and modifying carbohydrates, as well as the recent advances in studying new promoters and leaving groups in glycosylation reactions.
CARBOHYDRATE RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Laura Confalonieri, Alvaro Erhard, Silvia Fallarini, Federica Compostella, Erika del Grosso, Luigi Panza, Daniela Imperio, Marcin Balcerzy
Summary: This study describes the synthesis of a new class of sugar derivatives conjugated to a trifluoroborate moiety as potential theranostic agents. The compounds showed good stability and traceability, and preliminary in vivo experiments demonstrated promising results.
Article
Biochemistry & Molecular Biology
Rosaria Bassi, Michele Dei Cas, Cristina Tringali, Federica Compostella, Rita Paroni, Paola Giussani
Summary: Glioblastoma multiforme (GBM) is the most common and lethal brain tumor. Sphingolipids play important roles in the regulation of GBM cell growth and chemotherapy response. This study demonstrates that overexpression of EGFRvIII in U87MG glioma cells confers resistance to the alkylating agent temozolomide (TMZ), potentially through altered ceramide (Cer) metabolism.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
