2-Acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosyl Azide (CAS 168397-51-1)

2-Acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosyl azide is a versatile compound in glycoscience research. Its structural composition features an azide group that plays a key role in click chemistry applications, particularly in Cu(I)-catalyzed azide-alkyne cycloaddition reactions, enabling researchers to synthesize triazole-linked glycosyl derivatives for studying carbohydrate-protein interactions. The benzylidene protecting group offers selective stability, while the acetamido functional group structurally mimics naturally occurring glycosyl residues, providing a scaffold that allows for strategic modifications. Researchers leverage this compound to probe the enzymatic specificity of glycosyltransferases and glycosidases by modifying the protective groups and labeling the azide with fluorophores or other markers. This provides valuable data on enzyme-substrate interactions and the mechanisms of glycosylation. Additionally, this compound serves as a precursor in synthesizing more complex glycan structures and conjugates used in glycan array development. The arrays facilitate high-throughput screening of carbohydrate-binding proteins involved in cellular recognition, signaling, and immune responses. Furthermore, 2-Acetamido-4,6-O-benzylidene-2-deoxy-beta-D-glucopyranosyl azide is critical in the synthesis of glycomimetics to explain the structural principles underlying glycan-mediated molecular recognition and to aid in the discovery of new molecular probes in glycoscience research.