1,3,4,6-Tetra-O-acetyl-N-azidoacetylmannosamine | CAS 361154-30-5

1,3,4,6-Tetra-O-acetyl-N-azidoacetylmannosamine is a cell-permeable, acetyl-protected azido-sugar designed for bioorthogonal labeling workflows that rely on azide click chemistry. As an azide-bearing monosaccharide derivative, it is commonly used to introduce an azide handle into glycoconjugates, enabling subsequent conjugation via copper-free or copper-catalyzed azide–alkyne cycloaddition. The tetra-O-acetyl protecting group pattern supports uptake and intracellular processing in glycoengineering studies, making the reagent widely relevant for mapping and manipulating cell-surface and intracellular glycan populations.

1. Glycan Metabolic Labeling

1,3,4,6-Tetra-O-acetyl-N-azidoacetylmannosamine is used in metabolic glycoengineering to install azide-functional groups into newly synthesized glycans. Researchers employ it to generate azide-tagged glycoproteins and glycolipids, which can then be visualized, enriched, or quantified using click-compatible probes such as fluorescent dyes, affinity tags, or biotinylated reporters. This application is especially common in cell biology and chemical biology laboratories focused on comparing glycosylation states across experimental conditions, including perturbations of glycan biosynthesis pathways.

2. Fluorescent Imaging Probes

1,3,4,6-Tetra-O-acetyl-N-azidoacetylmannosamine serves as a starting reagent for preparing azide-labeled biomolecules that are compatible with fluorescence-based detection. After incorporation into glycan structures, the azide handle enables labeling with cycloaddition-ready fluorophores to support microscopy workflows, flow cytometry readouts, and imaging of glycan distribution on membranes or within cellular compartments. This approach is frequently selected when researchers need spatially resolved information about glycosylation patterns using established click-reactive imaging reagents.

3. Glycoprotein Enrichment Workflows

1,3,4,6-Tetra-O-acetyl-N-azidoacetylmannosamine is applied to streamline enrichment of azide-containing glycoproteins from complex lysates using click chemistry affinity reagents. By converting the incorporated azide groups into biotin or other capture handles through cycloaddition, downstream streptavidin-based pull-downs and related affinity purification strategies become practical for isolating glycoforms of interest. Such workflows are widely used in proteomics-adjacent glycoscience research to improve sample specificity before mass spectrometry, immunoblotting, or targeted analytical characterization.

4. Surface Functionalization Materials

1,3,4,6-Tetra-O-acetyl-N-azidoacetylmannosamine is also used to generate azide-functional biomolecular surfaces that can be further conjugated to materials and interfaces. In biomaterials and molecular imaging development, azide-labeled glycoconjugates can be clicked onto alkyne-functional substrates to create glycan-patterned coatings, probe arrays, or cell-interactive surfaces for assay development. This application supports the construction of reproducible, chemically defined glycan-presenting materials where the azide handle provides a robust coupling point to downstream click-compatible linkers and reporters.