2-Azidoethyl β-D-lactoside

2-Azidoethyl β-D-lactoside

2-Azidoethyl β-D-lactoside (CAS No. 230286-11-0) is a specialized glycosylated compound that serves as a valuable reagent in biochemical research, particularly in the fields of click chemistry and carbohydrate chemistry. This compound is characterized by its azido group, which allows for efficient conjugation with various biomolecules, making it an essential tool for researchers exploring glycosylation processes and molecular interactions.

Chemical Properties

• CAS Number: 230286-11-0
• MDL Number: MFCD19981033
• EINECS: Not available
• Molecular Formula: C14H25N3O11
• Molecular Weight: 411.36 g/mol
• Appearance: White crystalline solid
• Melting Point: 149-152 °C
• Solubility: Soluble in DMSO, methanol, and water

Structure and Composition

The structure of 2-Azidoethyl β-D-lactoside consists of a β-D-lactoside backbone modified with an azidoethyl group. Key structural features include:

1. Azido Group: The azido functional group (-N₃) enables the compound to participate in click chemistry reactions, facilitating the formation of stable conjugates with other biomolecules such as proteins and nucleic acids.
2. Lactoside Backbone: The β-D-lactoside structure provides a carbohydrate framework that is essential for biological recognition processes, making it suitable for various applications in glycobiology.
3. Hydroxyl Groups: The presence of multiple hydroxyl groups enhances the solubility and reactivity of the compound, allowing for diverse chemical modifications.

Applications

2-Azidoethyl β-D-lactoside is widely used in several applications:

Biochemical Research

1. Click Chemistry: The azido group allows for efficient labeling and conjugation with biomolecules, enabling researchers to study interactions between carbohydrates and proteins or nucleic acids.
2. Glycosylation Studies: This compound can be utilized as a substrate for glycosyltransferases, providing insights into glycosylation pathways and enzyme kinetics.

Pharmaceutical Development

1. Drug Delivery Systems: Its properties make it a candidate for developing targeted drug delivery systems that require glycosylation or specific binding mechanisms.

Enzymatic Assays

1. Substrate for Enzymes: It can be employed in assays to measure the activity of specific enzymes involved in carbohydrate metabolism.

Safety and Handling

While specific safety data for 2-Azidoethyl β-D-lactoside 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 temperatures between 0 to -20 °C to maintain stability.
4. Disposal Guidelines: Dispose of waste according to local regulations regarding hazardous materials.

Summary

In summary, 2-Azidoethyl β-D-lactoside (CAS No. 230286-11-0) is an important reagent in biochemical research for studying glycosylation processes and facilitating click chemistry reactions. Its unique structural features enable its use in synthesizing glycosylated compounds with potential applications in drug development and enzymatic assays.

Citations:

1. https://synthose.com/products/AL230
2. https://www.sigmaaldrich.com/US/en/product/sigma/smb00406
3. https://file.medchemexpress.com/batch_PDF/HY-151793/2-Azidoethyl-%CE%B2-D-lactoside-DataSheet-MedChemExpress.pdf
4. https://www.glentham.com/en/products/product/GC9441/
5. https://www.medchemexpress.com/2-azidoethyl-%CE%B2-d-lactoside.html
6. https://www.invivochem.com/product/V92337
7. https://onlinelibrary.wiley.com/doi/abs/10.1002/pola.22070
8. https://synthose.com/products/AL926