α-D-Mannopyranoside, 2-(2-azidoethoxy)ethyl, 2,3,4,6-tetraacetate

α-D-Mannopyranoside, 2-(2-azidoethoxy)ethyl, 2,3,4,6-tetraacetate

α-D-Mannopyranoside, 2-(2-azidoethoxy)ethyl, 2,3,4,6-tetraacetate (CAS No. 206658-99-3) is a specialized glycosylated compound that plays a significant role in biochemical research and synthetic chemistry. This compound is notable for its potential applications in glycosylation studies and click chemistry, making it valuable for the development of glycosylated biomolecules.

Chemical Properties

• CAS Number: 206658-99-3
• MDL Number: Not available
• EINECS: Not available
• Molecular Formula: C18H27N3O11
• Molecular Weight: 461.42 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 α-D-Mannopyranoside, 2-(2-azidoethoxy)ethyl, 2,3,4,6-tetraacetate consists of a mannopyranoside backbone modified with an azido group and multiple acetyl groups. The key structural features include:

1. Azido Group: The presence of the azido functional group (-N₃) enables the compound to participate in click chemistry, allowing for efficient conjugation with other biomolecules.
2. Tetraacetate Modifications: The acetyl groups at positions 2, 3, 4, and 6 provide protection to the hydroxyl groups on the mannopyranoside, enhancing stability and solubility while facilitating selective reactions during synthesis.
3. Ethylene Glycol Linker: The ethylene glycol moiety enhances water solubility and can improve the bioavailability of the compound in biological systems.

Applications

α-D-Mannopyranoside derivatives are widely used in various applications:

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 α-D-Mannopyranoside 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, α-D-Mannopyranoside, 2-(2-azidoethoxy)ethyl, 2,3,4,6-tetraacetate (CAS No. 206658-99-3) is an essential 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://pmc.ncbi.nlm.nih.gov/articles/PMC2795031/
2. https://pubs.rsc.org/en/content/articlehtml/2016/ob/c6ob00083e
3. https://www.diva-portal.org/smash/get/diva2:850882/FULLTEXT02.pdf
4. http://www.diva-portal.org/smash/get/diva2:684322/fulltext01.pdf
5. https://www.beilstein-journals.org/bjoc/articles/6/58
6. https://pmc.ncbi.nlm.nih.gov/articles/PMC7181322/
7. https://pubs.acs.org/doi/10.1021/bc100421g