Methyl b-D-galactopyranoside

Methyl β-D-galactopyranoside is a chemically synthesized methyl glycoside form of D-galactose with the methyl group attached at the anomeric carbon in the β-configuration. This white crystalline solid is widely used in carbohydrate chemistry and glycobiology as a non-reducing sugar analog, offering increased stability and resistance to mutarotation. Its molecular formula is C7H14O6 with a molecular weight of approximately 194.18 g/mol. The compound is synthesized via acid-catalyzed glycosylation of D-galactose with methanol and purified to a high degree (≥98%). It serves as a substrate analog in enzyme assays and as a building block for glycomimetics, glycoconjugates, and molecular probes in medicinal chemistry and biochemical research. Produced under sterile synthetic conditions, it exhibits negligible microbial contamination. It requires storage in a sealed container at 2–8 °C, protected from moisture and light, maintaining its shelf life for 1–2 years.

IUPAC Name

• Methyl 2,3,4,6-tetra-OH-β-D-galactopyranoside

Appearance

• White crystalline powder

Source

• Produced by acid-catalyzed glycosylation of D-galactose with methanol in laboratory settings
• Chemical synthesis ensures controlled purity and reproducibility

Molecular Weight and Structure

• Molecular formula: C7H14O6
• Molecular weight: 194.18 g/mol
• Comprises a β-D-galactopyranose ring with a methyl group at the anomeric carbon and free hydroxyl groups at C2, C3, C4, and C6
• SMILES: CO[C@@H]1C@HC@@HC@HC@HO1

Sugar Specificity

• Stereospecific to the β-anomer of D-galactopyranose
• Recognized by β-galactosidase enzymes and carbohydrate-binding proteins

Biological Activity

• Non-reducing sugar analog; functions as a substrate mimic in enzymatic assays
• No direct pharmacological activity, but important in glycan recognition and enzyme specificity studies

Purity and Microbial Contamination

• Purity of ≥98%, confirmed through NMR and chromatographic analysis
• Synthetic production prevents microbial contamination, maintaining chemical grade quality

Identity and Quality Control

• Confirmed identity via 1H and 13C NMR, MS, and HPLC chromatograms
• Melting point and optical rotation data provided for batch validation
• Supplied with Certificate of Analysis (COA) and Safety Data Sheets (SDS)

Shelf Life and Storage

• Store in airtight containers at 2–8 °C
• Protect from moisture, light, and heat sources
• Shelf life is 1–2 years under optimal storage conditions

Application

• Widely applied in synthetic oligosaccharide and glycoconjugate synthesis
• Used as a substrate or control in enzymatic beta-galactosidase assays
• Supports glycomimetic development, drug discovery, and molecular probe design
• Facilitates research in carbohydrate metabolism and recognition

Citations

• ChemicalBook
• CalpacLab
• PubChem
• Sigma-Aldrich
• MedChemExpress
• PMC Articles
• Synthose
• Patent Literature
• Benchchem
• ScienceDirect