2-Deoxy-D-galactose

2-Deoxy-D-galactose is a synthetic deoxy sugar derived from D-galactose by replacing the hydroxyl group at the 2-position with a hydrogen, creating a hexose analog with unique biological properties. This modification imparts significant biochemical utility: the compound acts as an inhibitor of glycoprotein synthesis and interferes with cellular glycosylation pathways, including glycolysis and fucosylation. Researchers employ 2-Deoxy-D-galactose for studying galactose transport, metabolism, and the functional roles of glycosylation in mammalian cells and microbial systems. It is also notable for its antiviral and cytotoxic effects, including inhibiting tumor growth. High-purity grades are available for biochemical and molecular biology research, making it a valuable tracer and inhibitor in cell biology and biochemistry investigations.

IUPAC Name

• (3R,4R,5R)-3,4,5,6-tetrahydroxyhexanal
• Sometimes presented as 2-deoxy-D-lyxo-hexose

Appearance

• White to almost white crystalline powder or crystal

Source

• Chemically synthesized via selective deoxygenation of D-galactose or via enzymatic reactions in laboratory settings

Molecular Weight and Structure

• Molecular formula: C6H12O5
• Molecular weight: 164.16 g/mol
• Structure: Deoxy hexose with a missing hydroxyl at carbon 2, six-carbon backbone

Sugar Specificity

• Mimics D-galactose but is not metabolized in the same way, serving as a transporter system probe and competitive substrate in glycosylation experiments

Biological Activity

• Inhibits glycoprotein and glycolipid synthesis via interference with glycosylation
• Used to isolate galactose permease mutants
• Exhibits antiviral, cytotoxic, and hepatotoxic effects
• Blocks fucosylation and phosphate/nucleotide metabolism in cells

Purity and Microbial Contamination

• Purity: ≥98% by HPLC; some sources report ≥99%
• Microbial contamination: Not detected or specified in most suppliers’ analytical certificates due to its synthetic nature and chemical purity

Identity and Quality Control

• Verified by HPLC, NMR, and mass spectrometry
• Certificates of Analysis and specification sheets provided
• Specific optical rotation: +55 to +62° (20°C, water)
• Melting point: 107–110°C
• Structural ID via InChI, SMILES, and NMR

Shelf Life and Storage

• Stable for 2–5 years when stored at 0–4°C or -20°C, in a cool, dry, and dark place
• Hygroscopic; avoid humidity
• Should be stored under inert gas in some cases

Application

• Tool for studying galactose transport and metabolism in bacteria and mammalian cells
• Probe for glycosylation pathways in molecular biology and biochemistry
• Used in studies of glycoprotein function, glycan mimetics, and metabolic engineering
• Employed to investigate antiviral and cytotoxic effects for therapeutic research

Key Characteristics

• Chemically and biologically active deoxy hexose
• High purity (≥98–99%), available in crystalline powder form
• Selectively inhibits glycosylation
• Used as a metabolic probe and biochemical tool
• Stable under cool and dry storage conditions
• Not a substrate for growth in E. coli, but transported through galactose systems
• Valuable for cell biology, viral studies, and glycoprotein synthesis research

Citation Links

• Sigma-Aldrich product summary
• TCI Chemicals product specifications
• ZellX product data
• GoldBio description & use
• Thermo Fisher product identifiers
• ChemicalBook molecular data
• SRL Chemicals storage & shelf life
• RPI product details
• PubChem ID & synonyms
• PMC publication – galactose transport