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Affinity-based covalent sialyltransferase probes enabled by ligand-directed chemistry.
Chem Sci
January 2025
Chemical Biology and Drug Discovery, Bijvoet Center for Biomolecular Research and Utrecht Institute for Pharmaceutical Sciences, Utrecht University Universiteitsweg 99 3584 CG Utrecht The Netherlands
Sialyltransferases (ST) are key enzymes found in, among others, mammals and bacteria that are responsible for producing sialylated glycans, which play critical roles in human health and disease. However, chemical tools to study sialyltransferases have been limited to non-covalent inhibitors and probes that do not allow isolation and profiling of these important enzymes. Here we report a new class of covalent affinity-based probes (AfBP) for ST by using ligand-directed chemistry (LDchem).
View Article and Find Full Text PDFProcessing of N-glycans in the ER and Golgi influences the production of surface sialylated glycoRNA.
Glycoconj J
December 2024
Institute for Glyco-core Research (iGCORE), Gifu University, Gifu, 501-1193, Japan.
Glycoconjugates, including glycans on proteins and lipids, have obtained significant attention due to their critical roles in both intracellular and intercellular biological functions and processes. Notably, recent discoveries have revealed the presence of glycosylated RNAs (glycoRNAs) on cell surfaces. Despite the well-characterized roles of RNA modifications, RNA glycosylation remains relatively unexplored.
View Article and Find Full Text PDFDetection Strategies for Sialic Acid and Sialoglycoconjugates.
Chembiochem
December 2024
Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada.
Glycoconjugates are a vast class of biomolecules implicated in biological processes important for human health and disease. The structural complexity of glycoconjugates remains a challenge to deciphering their precise biological roles and for their development as biomarkers and therapeutics. Human glycoconjugates on the outside of the cell are modified with sialic (neuraminic) acid residues at their termini.
View Article and Find Full Text PDFA Kinetic Trapping Approach for Facile Access to 3FNeu5Ac and a Photo-Cross-Linkable Sialyltransferase Probe.
J Am Chem Soc
October 2024
Department of Chemistry, University of Alberta, Edmonton T6G 2G2, Canada.
Article Synopsis
- Sialic acid (Neu5Ac) is added to glycoconjugates by sialyltransferases (STs) using a specific donor molecule, CMP-β-d-Neu5Ac, while the only existing ST inhibitors are based on a modified form of sialic acid known as 3FNeu5Ac.
- Researchers aimed to create a controlled process for generating 3FNeu5Ac using the enzyme sialic acid aldolase, but faced challenges with properly positioning the fluorine atom in the molecule.
- They discovered a method using CMP-sialic acid synthetase that successfully produced CMP-3FNeu5Ac, leading to a novel compound (3FNeu5Ac-2
-Glycan profile of the cell membrane as a probe for lipopolysaccharide-induced microglial neuroinflammation uncovers the effects of common fatty acid supplementation.
Food Funct
August 2024
Department of Chemistry, University of California, Davis, 95616, USA.
Altered -glycosylation of proteins on the cell membrane is associated with several neurodegenerative diseases. Microglia are an ideal model for studying glycosylation and neuroinflammation, but whether aberrant -glycosylation in microglia can be restored by diet remains unknown. Herein, we profiled the -glycome, proteome, and glycoproteome of the human microglia following lipopolysaccharide (LPS) induction to probe the impact of dietary and gut microbe-derived fatty acids-oleic acid, lauric acid, palmitic acid, valeric acid, butyric acid, isobutyric acid, and propionic acid-on neuroinflammation using liquid chromatography-tandem mass spectrometry.
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