Methyl β-D-ribopyranoside

Methyl β-D-ribopyranoside is a chemically synthesized methyl glycoside derivative of D-ribose in which the anomeric hydroxyl group is replaced by a methyl group maintaining the β-configuration of the ribopyranose ring. It is a white crystalline solid widely used as a stable, non-reducing sugar analog in carbohydrate chemistry, glycobiology, and pharmaceutical research. The methylation stabilizes the ring structure, preventing mutarotation and allowing its use as a reliable substrate analog and intermediate for oligosaccharide synthesis, glycomimetics, and enzymatic studies. The molecular formula is C6H12O5 with a molecular weight of approximately 164.16 g/mol. Synthesized through acid-catalyzed glycosylation of D-ribose with methanol, it achieves high purity (≥98%) and is devoid of microbial contamination thanks to strict synthetic protocols. Proper storage involves sealed containers at refrigerated temperatures (2–8 °C) with protection from moisture and light, which extends the shelf life up to two years. Its versatile applications include enzymology, drug design, molecular probes, and carbohydrate-based bioconjugates.

IUPAC Name

• Methyl β-D-ribopyranoside

Appearance

• White crystalline powder

Source

• Acid-catalyzed glycosylation of D-ribose with methanol under controlled laboratory synthesis
• Purification by chromatographic methods to ensure chemical and analytical purity

Molecular Weight and Structure

• Molecular Formula: C6H12O5
• Molecular Weight: 164.16 g/mol
• Structure: β-D-ribopyranose ring with methyl substitution at the anomeric carbon and hydroxyl groups at the remaining positions
• SMILES: COC1C(C(C(C(O1)O)O)O)O

Sugar Specificity

• Specific for the β-D-ribopyranoside form
• Recognized by ribose-binding proteins and enzymes involved in nucleoside metabolism

Biological Activity

• Functions as a stable sugar analog and substrate mimic
• Facilitates studies in enzymology, glycomimetics, and nucleoside analog synthesis
• No direct pharmacological activity but used in medicinal chemistry research

Purity and Microbial Contamination

• Typically greater than 98% purity as verified by NMR and chromatography
• Manufactured through sterile chemical processes minimizing microbial presence

Identity and Quality Control

• Confirmed by 1H and 13C NMR, mass spectrometry, and HPLC
• Certificates of Analysis and Safety Data Sheets issued
• Melting point and optical rotation data are batch-specific QC parameters

Shelf Life and Storage

• Store at 2–8 °C in airtight, moisture-free containers
• Protect from light and humidity
• Shelf life of 1–2 years when stored properly

Application

• Intermediate for synthesis of oligosaccharides, nucleosides, and glycoconjugates
• Used in enzymatic assays and molecular probe design
• Supports drug development and biochemical studies relating to carbohydrate metabolism

Key Characteristics

• Methylated β-D-ribopyranoside, glycoside sugar analog
• CAS number 1143-01-1
• Molecular weight 164.16 g/mol
• White crystalline solid with high purity
• Supports stereoselective and biochemical synthesis
• Full analytic and quality assurance documentation available
• Stable under recommended refrigerated storage

Citations

• AnaxLab chemical profile
• Glentham reagent catalog
• Sigma-Aldrich glycoside references
• PubChem database
• MedChemExpress substrates
• PMC glycoscience literature
• Synthose synthetic intermediates
• Patent literature
• Benchchem catalogue
• ScienceDirect reviews on glycochemistry