Methyl α-L-rhamnopyranoside

Methyl α-L-rhamnopyranoside is a chemically synthesized methylated glycoside of L-rhamnose, characterized by the substitution of the anomeric hydroxyl group in L-rhamnopyranose with a methoxy group, resulting in a stable α-glycosidic bond. This compound appears as a white crystalline solid used extensively in carbohydrate chemistry and biochemical research to study rhamnose-containing glycans, enzyme interactions, and glycosylation mechanisms. Serving as a model compound for natural rhamnosides, it plays vital roles in the synthesis of glycomimetics, saponins, and other bioactive molecules. Methyl α-L-rhamnopyranoside enables exploration of sugar recognition by lectins and enzymes and is significant in medicinal chemistry for developing antimicrobial and cytotoxic agents. The compound is supplied with high purity and detailed quality control, making it ideal for biochemical assays, pharmaceutical research, and synthetic organic chemistry.

IUPAC Name

• (2R,3R,4R,5R,6S)-2-methoxy-6-methyloxane-3,4,5-triol

Appearance

• White to off-white crystalline powder

Source

• Produced synthetically by methylation of L-rhamnose
• Also available through carbohydrate derivative synthesis for biochemical use

Molecular Weight and Structure

• Molecular formula: C7H14O5
• Molecular weight: 178.18 g/mol
• Structure: Six-membered pyranose ring with methoxy substitution at the anomeric carbon; stereochemically L-configured sugar
• SMILES: CO[C@H]1OC@HC@HC@H[C@H]1O

Sugar Specificity

• A methyl glycoside derivative of 6-deoxy-L-mannose (L-rhamnose)
• Specific substrate for studies involving rhamnose-binding proteins and enzymes

Biological Activity

• Model substrate for glycosyltransferase and glycosidase enzyme studies
• Evaluated for antimicrobial and cytotoxic potential in derivative forms
• Used in assessing carbohydrate-protein recognition and lectin binding

Purity and Microbial Contamination

• Purity generally ≥98% by HPLC or NMR spectral analysis
• Low levels of microbial contamination, controlled by synthesis quality
• Supplied with Certificates of Analysis specifying data

Identity and Quality Control

• Confirmed by NMR, MS, HPLC chromatograms, and optical rotation
• Melting point around 106–108 °C
• Detailed spectral and analytical documentation supplied

Shelf Life and Storage

• Store sealed at 2–8 °C, away from moisture and light
• Stable for up to 3 years under proper conditions
• Keep in desiccated containers to prevent degradation

Application

• Important reagent in glycobiology and synthetic carbohydrate chemistry
• Used for synthesizing rhamnose-containing oligosaccharides, glycoconjugates, and bioactive molecules
• Serves as a standard compound in lectin-binding and enzyme kinetic studies
• Applied in developing antimicrobial and anticancer agents from sugar derivatives

Key Characteristics

• Methylated α-glycoside of L-rhamnose in pyranose form
• CAS number 15814-59-2
• White crystalline powder, molecular weight 178.18 g/mol
• High purity with rigorous quality controls
• Biological and synthetic chemistry relevance in glycosylation research
• Stable and reliable for long-term storage under refrigeration
• Verifiable by comprehensive spectral techniques
• Utilized in medicinal chemistry and biochemical investigations
• Supports development of glycomimetics and therapeutic compounds
• Recognized for glycosidic enzyme and lectin interaction studies

Citation 

• A2B Chem Methyl α-L-rhamnopyranoside data
• ChemicalBook datasheet
• PubChem chemical info
• Fisher Scientific product details
• TCI Chemicals catalog
• ScienceDirect structural analysis
• PMC NIH antimicrobial research
• API Publishers antimicrobial evaluation
• Sigma-Aldrich reagent information
• LookChem product and research data