1,3,4,6-Tetra-O-acetyl-2-[(azidoacetyl)amino]-2-deoxy-β-D-galactopyranose FAQ
1,3,4,6-Tetra-O-acetyl-2-[(azidoacetyl)amino]-2-deoxy-β-D-galactopyranose FAQ
1,3,4,6-Tetra-O-acetyl-2-[(azidoacetyl)amino]-2-deoxy-β-D-galactopyranos is a peracetylated azido-modified galactosamine derivative widely used as a cell-permeable metabolic precursor for bioorthogonal labeling of O-GalNAc-type glycoproteins and glycolipids via copper-free or CuAAC click chemistry.
- Chemical Name
- 1,3,4,6-Tetra-O-acetyl-2-[(azidoacetyl)amino]-2-deoxy-β-D-galactopyranose
- Common Abbreviation
- Ac4GalNAz
- SKU
- T304292
- Primary Application
- Metabolic glycan labeling via bioorthogonal/click chemistry
- Key Functional Group
- Azide (–N₃) on C2 acetamido group
- Recommended Storage
- Store at –20 °C, protected from moisture and light
What Is 1,3,4,6-Tetra-O-acetyl-2-[(azidoacetyl)amino]-2-deoxy-β-D-galactopyranose?
1,3,4,6-Tetra-O-acetyl-2-[(azidoacetyl)amino]-2-deoxy-β-D-galactopyranose, commonly abbreviated Ac4GalNAz, is a synthetic, peracetylated analogue of N-acetylgalactosamine (GalNAc) in which the N-acetyl methyl group is replaced by an azidoacetyl (–CH₂N₃) moiety. The four O-acetyl groups render the molecule cell-permeable by masking its hydroxyl groups; once inside the cell, cytoplasmic esterases remove these acetate groups to release the free azido sugar, which is then metabolically incorporated into nascent glycoproteins and glycolipids through the hexosamine biosynthetic pathway.
The resulting cell-surface or intracellular azide handles are chemically inert to endogenous biomolecules, making them ideal bioorthogonal tags that can be selectively detected or conjugated using strained-alkyne reagents (e.g., DBCO, BCN) via strain-promoted azide–alkyne cycloaddition (SPAAC) or using terminal alkynes via copper-catalyzed azide–alkyne cycloaddition (CuAAC).
Key Applications and Use Cases
Ac4GalNAz (T304292) is primarily employed in the following research contexts:
- Metabolic glycan labeling: Cells or organisms are treated with Ac4GalNAz, which is taken up and processed by the hexosamine pathway to label O-GalNAc glycans, mucin-type O-glycoproteins, and GPI-anchored glycolipids with azide groups.
- Glycoprotein detection and imaging: After metabolic incorporation, azide-bearing glycoconjugates are visualized using fluorescent DBCO or BCN probes in live-cell or fixed-cell fluorescence microscopy.
- Proteomics and glycoproteomics: Azide-tagged glycoproteins can be selectively enriched from complex mixtures using alkyne-functionalized beads or resins, enabling mass-spectrometry-based identification of O-GalNAc-modified proteins.
- Drug delivery and bioconjugation: Azide handles introduced via metabolic labeling serve as attachment points for cytotoxic payloads, imaging agents, or nanoparticles in antibody–drug conjugate (ADC) and targeted-delivery research.
- Studying O-GalNAc glycosylation dynamics: Pulse–chase experiments with Ac4GalNAz allow researchers to track the biosynthesis, trafficking, and turnover of O-glycosylated proteins in real time.
Handling, Storage, and Safety Guidance
Storage: Ac4GalNAz should be stored at –20 °C in a tightly sealed container, protected from moisture and light. Under these conditions, the compound is expected to be stable for at least 12 months. Avoid repeated freeze–thaw cycles; aliquoting the stock upon first use is recommended.
Solubility and stock preparation: The compound is soluble in DMSO and other polar aprotic solvents. A common approach is to prepare a concentrated stock solution (e.g., 100 mM) in DMSO, then dilute into aqueous cell-culture medium immediately before use. Final DMSO concentrations in cell assays should be kept at ≤0.1–0.5% to avoid cytotoxicity.
Safety: As with all azide-containing compounds, standard laboratory precautions apply. Avoid contact with strong reducing agents or metal catalysts that could trigger rapid azide decomposition. Work in a well-ventilated area and consult the product Safety Data Sheet (SDS) before use. This compound is intended for research use only and is not approved for use in humans or animals.
Ordering and Product Information
1,3,4,6-Tetra-O-acetyl-2-[(azidoacetyl)amino]-2-deoxy-β-D-galactopyranose is available from Aladdin Scientific under SKU T304292. When placing an order, please verify the exact CAS number, purity specification, and pack size on the product detail page to ensure the material meets your experimental requirements.
For bulk quantities, custom packaging, or certificate of analysis (CoA) requests, contact Aladdin Scientific's technical sales team. A CoA confirming purity (typically assessed by HPLC and/or NMR) is available upon request for each lot number.
Lead times and availability may vary; registered account holders can view real-time stock status and apply reward coupons or institutional discount codes at checkout. For questions about compatibility with specific downstream click-chemistry kits or detection reagents, contact our technical support team before ordering.
Frequently asked questions
What is Ac4GalNAz and how does it work in cells?
Ac4GalNAz is a cell-permeable, peracetylated azido-galactosamine analogue. Once taken up by cells, cytoplasmic esterases cleave the four acetate groups, releasing the free azido sugar, which enters the hexosamine biosynthetic pathway and is incorporated into O-GalNAc glycans on glycoproteins and glycolipids. The resulting azide groups on the cell surface or in intracellular compartments can then be selectively reacted with alkyne-bearing probes via click chemistry for detection, imaging, or enrichment.
Which click chemistry reactions are compatible with Ac4GalNAz-labeled cells?
Ac4GalNAz-labeled cells display azide groups that are compatible with both copper-free strain-promoted azide–alkyne cycloaddition (SPAAC) using reagents such as DBCO- or BCN-functionalized fluorophores, and copper-catalyzed azide–alkyne cycloaddition (CuAAC) using terminal alkyne probes with a copper(I) catalyst. For live-cell applications, copper-free SPAAC is preferred because it avoids the cytotoxicity associated with copper ions.
What concentration of Ac4GalNAz is typically used in cell-based metabolic labeling experiments?
Typical working concentrations for metabolic glycan labeling with Ac4GalNAz range from approximately 25 µM to 200 µM in cell culture medium, with incubation times of 24–72 hours depending on the cell type and labeling efficiency desired. Researchers should perform a dose-response experiment to determine the optimal concentration that maximizes labeling without impairing cell viability.
How should I prepare a working solution of Ac4GalNAz for cell culture?
Dissolve Ac4GalNAz in DMSO to prepare a concentrated stock solution (e.g., 50–100 mM), then dilute the stock directly into pre-warmed cell culture medium to reach the desired working concentration. Ensure that the final DMSO concentration does not exceed 0.1–0.5% to minimize solvent-related cytotoxicity. Prepare the working solution fresh or store aliquots of the DMSO stock at –20 °C.
Can Ac4GalNAz be used in animal models for in vivo glycan labeling?
Peracetylated azido sugars including Ac4GalNAz have been reported in the scientific literature to label glycans in vivo when administered to model organisms such as mice. However, Aladdin Scientific's product T304292 is supplied for research use only; in vivo experimental designs, dosing, and safety assessments remain the responsibility of the investigator and must comply with institutional animal care and ethics requirements.
References
- Hang, H. C. et al. (2003). A metabolic labeling approach toward proteomic analysis of mucin-type O-linked glycosylation. Proceedings of the National Academy of Sciences, 100(25), 14846–14851.
- Prescher, J. A. & Bertozzi, C. R. (2005). Chemistry in living systems. Nature Chemical Biology, 1(1), 13–21.
- Saxon, E. & Bertozzi, C. R. (2000). Cell surface engineering by a modified Staudinger reaction. Science, 287(5460), 2007–2010.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
危险品化学品经营许可证（带存储）