5-Azido-5-deoxy-D-fructose (CAS 94801-02-2)

5-Azido-5-deoxy-D-fructose is a chemically engineered sugar derivative extensively utilized in the realm of synthetic chemistry for the development of novel carbohydrate-based materials and the study of biochemical pathways. This compound features an azido group replacing a hydroxyl group, which fundamentally alters its chemical reactivity and makes it an excellent candidate for bioorthogonal ligation reactions such as the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), commonly referred to as click chemistry. This reaction facilitates the covalent bonding of this azido-sugar to various alkyne-tagged molecules or surfaces under benign conditions, enabling the construction of complex molecular architectures without affecting native biochemical functions. The deoxy modification in 5-Azido-5-deoxy-D-fructose, where an oxygen atom is removed, further enhances its metabolic stability, making it an invaluable tool in studying carbohydrate metabolism and transport mechanisms in cells without involving pharmacological aspects. This sugar analogue is instrumental in creating glycoconjugates for research in glycomics, providing insights into the roles of sugars in biological systems through the creation of labeled molecules, affinity materials, and biomimetic structures.