3,4,6-Tri-O-acetyl-2-azido-2-deoxy-D-galactose

3,4,6-Tri-O-acetyl-2-azido-2-deoxy-D-galactose

3,4,6-Tri-O-acetyl-2-azido-2-deoxy-D-galactose (CAS No. 83025-10-9) is a specialized azido sugar derivative that plays an important role in carbohydrate chemistry and biochemical research. This compound is characterized by its unique structure, which includes multiple acetyl groups and an azido group, making it a valuable reagent for various synthetic applications, particularly in the field of glycosylation.

Chemical Properties

• CAS Number: 83025-10-9
• MDL Number: MFCD08703948
• EINECS: Not available
• Molecular Formula: C12H17N3O8
• Molecular Weight: 331.28 g/mol
• Boiling Point: 688.2 ± 55.0 °C (predicted)
• Melting Point: 165-166 °C
• Appearance: White to off-white crystalline solid

Structure and Composition

The structure of 3,4,6-Tri-O-acetyl-2-azido-2-deoxy-D-galactose features several key components:

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 at positions 3, 4, and 6 protect the hydroxyl groups, facilitating selective reactions during synthesis and enhancing the compound’s stability.
3. D-Galactose Backbone: The D-galactose structure provides a carbohydrate framework that is essential for biological recognition processes.

Applications

3,4,6-Tri-O-acetyl-2-azido-2-deoxy-D-galactose is utilized in several 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.

Chemical Synthesis

1. Intermediate in Synthesis: It can be used as an intermediate in the synthesis of more complex carbohydrate derivatives and glycoconjugates.

Safety and Handling

While specific safety data for this compound 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 2 to 8 °C to maintain stability.
4. Disposal Guidelines: Dispose of waste according to local regulations regarding hazardous materials.

Summary

In summary, 3,4,6-Tri-O-acetyl-2-azido-2-deoxy-D-galactose (CAS No. 83025-10-9) is an important reagent in carbohydrate chemistry 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://www.chemicalbook.com/ChemicalProductProperty_EN_CB31092597.htm
2. https://pubchem.ncbi.nlm.nih.gov/compound/3_4_6-Tri-O-acetyl-2-azido-2-deoxy-D-galactose
3. https://pubchem.ncbi.nlm.nih.gov/compound/10904812
4. https://www.sigmaaldrich.com/IN/en/product/aablocksinc/aabh9a954ebf
5. https://www.sigmaaldrich.com/SK/en/product/combiblocksinc/com448654700?context=bbe
6. https://www.biosynth.com/p/W-203885/83025-10-9-346-tri-o-acetyl-2-azido-2-deoxy-d-ga
7. https://www.chemicalbook.com/ChemicalProductProperty_US_CB31092597.aspx
8. https://cymitquimica.com/products/3D-W-203885/83025-10-9/346-tri-o-acetyl-2-azido-2-deoxy-d-galactose-non-animal-origin/