3-Amino-3-deoxy-D-glucopyranose

3-Amino-3-deoxy-D-glucopyranose

3-Amino-3-deoxy-D-glucopyranose, also known as alpha-D-kanosamine, is an amino sugar with the molecular formula C₆H₁₃NO₅ and a molecular weight of 179.17 g/mol. This compound is characterized by the presence of an amino group at the third carbon position and the absence of a hydroxyl group at the same position, distinguishing it from glucose and other related sugars.

Chemical Properties:

• CAS Number: 19309-98-9
• MDL Number: Not specified
• EINECS: Not specified
• Molecular Formula: C₆H₁₃NO₅
• Molecular Weight: 179.17 g/mol

Biological Activity:

3-Amino-3-deoxy-D-glucopyranose is notable for its biological activities. It has demonstrated antifungal properties against pathogens such as Candida albicans and Aspergillus fumigatus. Its mechanism may involve interference with fungal cell wall synthesis or glucose transport within fungal cells. Additionally, it can inhibit glucose efflux in organisms like baker’s yeast (Saccharomyces cerevisiae), potentially influencing glucose homeostasis and enhancing the effectiveness of therapeutic agents by inhibiting efflux pumps.

Applications:

Due to its structural similarity to glucose, 3-amino-3-deoxy-D-glucopyranose serves as a valuable research tool for studying cellular glucose uptake and metabolism. It can be labeled with radioactive isotopes or fluorescent tags to track glucose transport pathways in cells, aiding in the understanding of metabolic regulation.

Synthesis:

There are several methods for synthesizing 3-amino-3-deoxy-D-glucopyranose, which involve enzymatic modifications of glucose. The unique properties of this compound allow it to interact with various biomolecules, influencing metabolic pathways and potentially modulating oxidative stress responses.

Citations:

1. https://www.smolecule.com/products/s531585
2. https://pubchem.ncbi.nlm.nih.gov/compound/4369044
3. https://www.ebi.ac.uk/chebi/chebiOntology.do?chebiId=CHEBI%3A72725
4. https://pubchem.ncbi.nlm.nih.gov/compound/71296194
5. https://ontosight.ai/glossary/term/introduction-to-3-trehalosamine-compound–67a074ec6c3593987a4c6ed5
6. https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI%3A4167