Methyl β-D-thiogalactopyranoside

Methyl β-D-thiogalactopyranoside is a chemically synthesized thioglycoside derivative of β-D-galactopyranose, in which the anomeric oxygen is replaced by sulfur bonded to a methyl group. This structural modification confers enhanced stability against enzymatic and chemical hydrolysis compared to traditional O-glycosides, making it a valuable glycosyl donor and intermediate in synthetic carbohydrate chemistry. The compound usually appears as a white crystalline solid with high purity. It has the molecular formula C7H14OS and a molecular weight of approximately 154.25 g/mol. Methyl β-D-thiogalactopyranoside is prepared via thiolysis of protected β-D-galactopyranosyl precursors with methyl mercaptan or equivalent methods, followed by chromatographic purification. Analytical confirmation includes NMR spectroscopy, mass spectrometry, and chromatographic assays, ensuring purity typically exceeding 95%, and it is free from microbial contamination due to controlled synthesis. The compound is stored sealed under refrigerated conditions (2–8 °C), away from moisture and light, with a recommended shelf life of 1–2 years. It is extensively applied in glycosylation reactions, medicinal chemistry, enzyme substrate research, and molecular probe design in glycobiology, supporting advances in carbohydrate-based therapeutics and diagnostics.

IUPAC Name

• Methyl 1-thio-β-D-galactopyranoside

Appearance

• White crystalline powder

Source

• Synthesized by chemical thiolysis of protected β-D-galactopyranosyl compounds with methyl mercaptan
• Purification via chromatography under strictly anhydrous and controlled conditions

Molecular Weight and Structure

• Molecular Formula: C7H14OS
• Molecular Weight: 154.25 g/mol
• Structure: β-D-galactopyranose ring with sulfur at C1 bonded to a methyl group
• Thioglycosidic linkage confers resistance to enzymatic hydrolysis

Sugar Specificity

• Retains β-anomer configuration of D-galactopyranoside
• Functions as a stable glycosyl donor with predictable stereochemistry

Biological Activity

• No inherent bioactivity
• Used as a synthetic intermediate and substrate analog in biochemical and medicinal chemistry studies

Purity and Microbial Contamination

• Purity generally above 95%, confirmed with NMR and chromatographic analyses
• Negligible microbial contamination due to synthetic origin and handling procedures

Identity and Quality Control

• Confirmed by 1H NMR, 13C NMR, MS, and HPLC purity profiles
• Supplied with Certificates of Analysis and Safety Data Sheets
• Includes batch-specific melting point and optical rotation data

Shelf Life and Storage

• Store at 2–8 °C, tightly sealed
• Protect from moisture, heat, and light exposure
• Shelf life typically 1–2 years when stored under recommended conditions

Application

• Used as glycosyl donor in stereoselective synthesis of glycoconjugates and oligosaccharides
• Supports drug discovery and glycomimetic design
• Applied in enzymatic and biochemical studies of glycosyltransferases and glycosidases
• Enables synthesis of molecular probes for carbohydrate recognition

Key Characteristics

• Methyl β-D-thioglucopyranoside, thioglycosidic β-D-galactoside
• CAS Number: 5339-18-2
• Molecular Weight: 154.25 g/mol
• White crystalline solid, chemically stable and hydrolytically resistant
• Robust glycosyl donor with well-defined stereoselectivity
• Comprehensive analytical characterization ensures quality and batch consistency
• Stable under refrigerated, anhydrous storage for extended periods

Citations

• Cymit Química product data
• PubChem molecular profile
• Sigma-Aldrich catalog listing
• MedChemExpress chemical reagents
• PMC enzymology articles
• ChemSpider chemical database
• Synthose synthetic intermediates
• Patent literature on thioglycosides
• Thermo Fisher Scientific reagents
• ScienceDirect glycochemistry reviews