β-D-Glucopyranoside, 2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl 2-(acetylamino)-2-deoxy-, 3,4,6-triacetate

β-D-Glucopyranoside, 2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl 2-(acetylamino)-2-deoxy-, 3,4,6-triacetate

β-D-Glucopyranoside, 2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl 2-(acetylamino)-2-deoxy-, 3,4,6-triacetate (CAS No. 212896-45-2) is a specialized chemical compound primarily used in biochemical and pharmaceutical research. This compound is notable for its role in glycosylation reactions and as a substrate in various enzymatic assays.

Chemical Properties

• CAS Number: 212896-45-2
• MDL Number: Not available
• EINECS: Not available
• Molecular Formula: C22H36N4O12
• Molecular Weight: 548.54 g/mol
• Boiling Point: Not specified
• Melting Point: Not specified
• Solubility: Soluble in organic solvents such as DMSO and DMF

Structure and Composition

The structure of β-D-Glucopyranoside, 2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl 2-(acetylamino)-2-deoxy-, 3,4,6-triacetate consists of a glucopyranoside backbone modified with multiple ethylene glycol units and an azido group. The presence of acetyl groups at the 3, 4, and 6 positions enhances the solubility and stability of the molecule, making it suitable for various applications in chemical biology.

Structural Features

1. Azido Group: The azido functional group (-N3) is significant for click chemistry applications, allowing for further conjugation with other biomolecules.
2. Acetyl Groups: The triacetate modifications provide protection to the hydroxyl groups, facilitating selective reactions during synthesis.
3. Ethylene Glycol Linkers: These linkers enhance water solubility and can improve the bioavailability of the compound in biological systems.

Applications

β-D-Glucopyranoside derivatives are widely used in:

Biochemical Research

1. Glycosylation Studies: This compound serves as a substrate for glycosyltransferases, enabling researchers to study glycosylation pathways and enzyme kinetics.
2. Click Chemistry: The azido group allows for efficient labeling and conjugation with various biomolecules, including peptides and proteins.

Pharmaceutical Development

1. Drug Formulation: Its properties make it a candidate for developing drug delivery systems that require glycosylation or specific targeting mechanisms.

Enzymatic Assays

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

Safety and Handling

While specific safety data for β-D-Glucopyranoside 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 in a cool, dry place away from light to maintain stability.
4. Disposal Guidelines: Dispose of waste according to local regulations regarding hazardous materials.

Summary

In summary, β-D-Glucopyranoside, 2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl 2-(acetylamino)-2-deoxy-, 3,4,6-triacetate (CAS No. 212896-45-2) is a versatile compound used in biochemical research and pharmaceutical applications. Its unique structural features enable its use in glycosylation studies and click chemistry, making it an essential tool for researchers exploring carbohydrate chemistry and drug development.

Citations:

1. https://pubchem.ncbi.nlm.nih.gov/compound/ss-GalNAc-PEG4-Azide
2. https://www.sigmaaldrich.com/US/en/search/1-azido-2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethane?focus=products&page=1&perpage=30&sort=relevance&term=1-azido-2-%282-%282-%282-azidoethoxy%29ethoxy%29ethoxy%29ethane&type=product
3. https://pubchem.ncbi.nlm.nih.gov/compound/2-_2-_2-Azidoethoxy_ethoxy_ethanol
4. https://www.sigmaaldrich.com/NO/en/search/1-azido-2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethane?focus=products&page=1&perpage=30&sort=relevance&term=1-azido-2-%282-%282-%282-azidoethoxy%29ethoxy%29ethoxy%29ethane&type=product_name
5. https://www.lookchem.com/ProductWholeProperty_LCPL6004040.htm
6. https://glycomindsynth.com/product_detail/660/Sugar%20PEG
7. https://www.chemsrc.com/en/cas/212896-45-2_3298183.html
8. https://abcr.com/de_en/ab308777