2-Azido-2-deoxy-D-galactose 

2-Azido-2-deoxy-D-galactose is a chemically synthesized sugar derivative of D-galactose in which the hydroxyl group at the 2-position is replaced by an azido group (-N3). This molecular modification confers unique chemical reactivity to the sugar, particularly useful in bioorthogonal chemistry and click chemistry applications for biochemical labeling and conjugation purposes. It serves as a critical intermediate for the synthesis of azido-functionalized glycoconjugates, glycomimetics, and other carbohydrate-based therapeutics. The azido group allows for selective and efficient post-synthetic modifications without interfering with biological systems. 2-Azido-2-deoxy-D-galactose appears as a white to off-white solid and is commonly used to investigate carbohydrate-protein interactions, glycosylation, and enzyme specificity. It plays a key role in drug discovery and biomedical research due to its ability to serve as a bioorthogonal chemical handle for precise molecular engineering.

IUPAC Name

• 2-Azido-2-deoxy-D-galactose

Appearance

• White to off-white crystalline solid

Source

• Synthesized chemically via azide substitution on D-galactose or acetylated derivates thereof

Molecular Weight and Structure

• Molecular Formula: C6H11N3O5
• Molecular Weight: 205.17 g/mol
• Structure: D-Galactopyranose ring with azido group replacing the hydroxyl at C2
• SMILES: C([C@H]1C@@H[N3])O

Sugar Specificity

• Modified D-galactose analogue with azido substitution at position 2
• Serves as a substrate or probe in synthesis and enzymatic studies related to galactose metabolism

Biological Activity

• Utilized for labeling glycans and glycoconjugates through click chemistry in biological systems without interfering with natural biochemistry
• Enables studies on glycan structure-function relationships and enzymatic glycosylation
• Potential in drug design for targeted delivery and diagnostic development

Purity and Microbial Contamination

• Purity: ≥95-98% (HPLC, NMR verified)
• Supplied chemically pure and microbiologically clean from contamination by synthesis protocols

Identity and Quality Control

• Verified by NMR, mass spectrometry, and chromatographic analysis
• Stability and identity confirmed with Certificates of Analysis provided
• Melting point around 110-115 °C

Shelf Life and Storage

• Store at low temperatures, typically 0 to -20 °C
• Protect from moisture and light to maintain stability
• Shelf life extends 1-2 years under proper storage

Application

• Key intermediate in glycoscience for click chemistry and bioorthogonal labeling
• Used in the synthesis of azido-modified glycans for therapeutic research
• Facilitates selective conjugation of sugars to proteins, polymers, and drugs
• Important in studying carbohydrate-protein interactions and glycosylation pathways

Key Characteristics

• Azido-substituted 2-deoxy-D-galactose sugar derivative
• CAS number 19517-20-7
• Molecular weight 205.17 g/mol, white crystalline solid
• High purity with strong analytical characterization
• Stable with refrigeration and sealed storage
• Widely used in click chemistry and glycobiology research
• Enables targeted conjugation and development of glycomimetics
• Supplied with comprehensive COA and safety documentation

Citations

• PubChem 2-Azido-2-deoxy-D-galactose molecular data
• Synthose azido sugar derivatives product page
• ChemicalBook azido sugar compound
• Google Patents related synthesis methodologies
• TCI Chemicals azido sugar catalog
• Sigma-Aldrich acetylated sugar reagents
• Glentham product listing
• CymitQuimica azido sugar intermediates
• MedChemExpress azido sugar standards
• BOC Sciences related carbohydrate intermediates