CID 91213358

CID 91213358, also known as 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl chloride, is a versatile carbohydrate compound widely utilized in the field of synthetic organic chemistry and glycobiology research. Characterized by its acetyl-protected glucose backbone and reactive chloride group, this compound serves as an essential glycosyl donor in a variety of glycosylation reactions. The acetyl groups on the sugar moiety enhance its stability and solubility in organic solvents, while the anomeric chloride provides a reactive handle for the formation of glycosidic bonds. Owing to these unique structural features, the compound has become a valuable intermediate for researchers seeking to construct complex oligosaccharides, glycoproteins, and other glycoconjugates. Its role in the assembly of carbohydrate-based molecules has positioned it at the forefront of efforts to explore structure-function relationships in biological systems and to develop novel biomaterials.

Glycosylation Reactions: As a premier glycosyl donor, 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl chloride is fundamental in the synthesis of glycosidic linkages, enabling the stepwise construction of diverse oligosaccharides. Through activation by suitable promoters or catalysts, the anomeric chloride facilitates the transfer of the protected glucose moiety onto various acceptor molecules, such as alcohols or other sugars. This approach allows chemists to precisely control the stereochemistry and regiochemistry of the resulting glycosidic bonds, which is critical for replicating the natural structures found in complex carbohydrates. The compound's reactivity and selectivity make it a preferred choice for assembling both linear and branched saccharide chains in laboratory settings.

Glycoconjugate Synthesis: The utility of this acetylated glucosyl chloride extends to the preparation of glycoconjugates, including glycopeptides, glycolipids, and glycosylated small molecules. By serving as a building block for the attachment of glucose units to biomolecular scaffolds, it enables the generation of conjugates that mimic naturally occurring glycosylated structures. Researchers employ it to investigate the role of glycosylation in modulating biological recognition events, such as cell-cell interactions and protein-carbohydrate binding. Its compatibility with a wide range of functional groups and its capacity for selective modification make it indispensable for the synthesis of structurally defined glycoconjugates used in fundamental studies and as molecular probes.

Carbohydrate-Based Material Development: In the realm of materials science, the compound's protected glucose structure is leveraged in the fabrication of carbohydrate-based polymers and hydrogels. By incorporating it into polymerization processes, scientists can engineer materials with tailored physical and chemical properties, such as enhanced biocompatibility or tunable degradation rates. These materials find application in diverse research areas, including drug delivery systems, tissue engineering scaffolds, and environmentally responsive coatings. The ease of chemical modification afforded by the acetyl and chloride functionalities allows for the precise tuning of material characteristics to suit specific experimental needs.

Enzyme Substrate Design: The acetylated glucopyranosyl chloride is also employed in the design and synthesis of enzyme substrates, particularly for glycosidases and glycosyltransferases. By incorporating it into substrate analogs with defined glycosidic linkages, researchers can probe enzyme specificity, catalytic mechanisms, and substrate recognition features. Such studies are instrumental in elucidating the molecular basis of carbohydrate-processing enzymes and in developing selective inhibitors or activity-based probes for biochemical research. The compound's stability and reactivity profile enable the preparation of substrates that closely mimic natural enzyme targets.

Analytical Method Development: Analytical chemists utilize this carbohydrate derivative in the development and validation of methods for carbohydrate analysis, such as chromatography and mass spectrometry techniques. By serving as a reference standard or derivatization agent, it aids in the quantification and structural characterization of complex carbohydrate mixtures. The compound's defined structure and predictable chemical behavior facilitate the establishment of reliable analytical protocols, supporting research in glycomics, food science, and quality control of carbohydrate-containing products.

In summary, 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl chloride serves as a cornerstone reagent across multiple research disciplines, including synthetic carbohydrate chemistry, glycobiology, materials science, enzymology, and analytical chemistry. Its unique combination of reactivity, selectivity, and structural versatility continues to drive innovation in the synthesis and analysis of carbohydrate-based molecules, enabling advances in both fundamental research and practical applications.

1. Implications of ligand-receptor binding kinetics on GLP-1R signalling

2. Myotropic activity and immunolocalization of selected neuropeptides of the burying beetle Nicrophorus vespilloides (Coleoptera: Silphidae)

3. C-peptide and its C-terminal fragments improve erythrocyte deformability in type 1 diabetes patients

4. An Isolated TCR αβ Restricted by HLA-A* 02: 01/CT37 Peptide Redirecting CD8+ T Cells to Kill and Secrete IFN-γ in Response to Lung Adenocarcinoma Cell Lines

5. Therapeutic potential of an intestinotrophic hormone, glucagon-like peptide 2, for treatment of type 2 short bowel syndrome rats with intestinal bacterial and fungal dysbiosis