β-D-GalNAc-PEG4-azide

β-D-GalNAc-PEG4-azide

β-D-GalNAc-PEG4-azide (CAS No. 879004-92-9) is a specialized compound that serves as a functionalized ligand for the asialoglycoprotein receptor (ASGPR), making it significant in biochemical research, particularly in targeted drug delivery and lysosomal targeting chimera (LYTAC) development. This compound is characterized by its unique structure, which includes a β-D-galactosamine (GalNAc) moiety linked to a polyethylene glycol (PEG) chain and an azide group, facilitating its use in various chemical applications.

Chemical Properties

• CAS Number: 879004-92-9
• MDL Number: Not available
• EINECS: Not available
• Molecular Formula: C16H30N4O9
• Molecular Weight: 422.43 g/mol
• Boiling Point: Not specified
• Melting Point: Not specified
• Appearance: White waxy solid

Structure and Composition

The structure of β-D-GalNAc-PEG4-azide consists of several key components:

1. β-D-Galactosamine Moiety: The presence of the GalNAc sugar enhances binding to ASGPR, which is crucial for targeted delivery to hepatocytes.
2. PEG4 Linker: The PEG4 chain improves solubility and biocompatibility, facilitating the compound’s use in biological systems.
3. Azide Group: The azido functional group (-N₃) provides a reactive handle for click chemistry, allowing for conjugation with other biomolecules or cargoes such as RNA or Cas9 complexes.

Applications

Biochemical Research

1. ASGPR Targeting: β-D-GalNAc-PEG4-azide acts as a ligand for ASGPR, enabling efficient internalization of conjugated molecules via ASGPR-mediated endocytosis. This property is particularly useful for delivering therapeutic agents specifically to liver cells.
2. LYTAC Development: The compound can be employed in the design of lysosomal targeting chimeras (LYTACs), which utilize the ASGPR pathway for enhanced delivery of biologics.
3. Cargo Delivery: It can be used to effectively deliver various cargoes, including RNA molecules and CRISPR-Cas9 complexes, in a cell-specific manner to hepatocytes.

Chemical Synthesis

1. Building Block for Multivalent Compounds: β-D-GalNAc-PEG4-azide can serve as a building block for constructing multivalent compounds that enhance ASGPR binding and improve therapeutic efficacy.
2. Click Chemistry Applications: The azide group allows for straightforward conjugation with alkyne-containing molecules through copper-catalyzed azide-alkyne cycloaddition (CuAAC), facilitating the synthesis of complex bioconjugates.

Safety and Handling

While specific safety data for β-D-GalNAc-PEG4-azide are not extensively documented, standard laboratory safety practices should be followed:

1. Personal Protective Equipment (PPE): Use gloves, goggles, and lab coats when handling this compound to avoid skin or eye contact.
2. Ventilation: Work in a well-ventilated area or fume hood to minimize exposure to vapors or dust.
3. Storage Conditions: Store the compound at -20 °C to maintain stability and prevent degradation.
4. Disposal Guidelines: Dispose of waste according to local regulations regarding hazardous materials.

Summary

In summary, β-D-GalNAc-PEG4-azide (CAS No. 879004-92-9) is an important reagent in biochemical research for studying ASGPR-mediated targeting and developing LYTACs. Its unique structural features enable its use in synthesizing glycosylated compounds with potential applications in targeted drug delivery and therapeutic development.

Citations:

1. https://www.rndsystems.com/products/beta-galnac-peg4-azide_7780
2. https://www.tocris.com/products/b-galnac-peg4-azide_7780
3. https://www.baseclick.eu/product/tri-%CE%B2-galnac-peg3-azide/
4. https://synthose.com/products/GL712
5. https://www.medchemexpress.com/%CE%B2-galnac-peg4-azide.html
6. https://www.fishersci.co.uk/shop/products/beta-galnac-peg4-azide/18715676
7. https://www.sigmaaldrich.com/IN/en/product/sigma/smb00393
8. https://www.glentham.com/en/products/product/GC6873/