2-Nitrophenyl β-D-glucopyranoside

2-Nitrophenyl β-D-glucopyranoside is a chemically synthesized glycoside consisting of a β-D-glucopyranose sugar moiety linked to a 2-nitrophenyl aglycone. This compound is widely used as a chromogenic substrate for enzymatic assays, particularly for measuring β-glucosidase activity, because its cleavage releases the yellow-colored 2-nitrophenol chromophore that can be quantitatively detected spectrophotometrically. It appears as a white to off-white crystalline solid, known for its stability and high purity. The glucose unit confers sugar specificity, making it an effective mimic of natural β-D-glucosides in enzymatic processes. The compound is produced through controlled chemical synthesis ensuring reproducible quality, with purity levels typically exceeding 98% and negligible microbial contamination. It is stored under proper refrigerated conditions to preserve stability and has a shelf life of 1-2 years. Its principal applications span biochemistry, molecular biology, enzymology, and diagnostics where it serves as a substrate in enzyme kinetics studies, drug discovery, and glycosidase inhibitor screening.

IUPAC Name

• β-D-Glucopyranosyl 2-nitrophenyl ether

Appearance

• White to off-white crystalline powder

Source

• Synthesized chemically by glycosylation of 2-nitrophenol with protected β-D-glucopyranose derivatives under laboratory-controlled conditions

Molecular Weight and Structure

• Molecular Formula: C12H15NO8
• Molecular Weight: 301.25 g/mol
• Structure: β-D-glucopyranose ring linked via an oxygen glycosidic bond at C1 to 2-nitrophenyl group at ortho position
• SMILES: C1C@@HO

Sugar Specificity

• β-D-glucopyranoside, substrate mimic for β-glucosidase and related enzymes
• Highly specific for enzymatic recognition and cleavage assays

Biological Activity

• Serves mainly as a biochemical substrate; not directly pharmacologically active
• Enables quantitative measurement of β-glucosidase activity and inhibitor screening
• Facilitates mechanistic enzyme studies in glycobiology and drug discovery

Purity and Microbial Contamination

• Typically >98% purity confirmed by chromatographic and NMR analysis
• Produced via chemical synthesis minimizing risks of microbial contamination

Identity and Quality Control

• Verified by 1H, 13C NMR spectroscopy, mass spectrometry, and HPLC purity profiling
• Detailed Certificates of Analysis and Safety Data Sheets provided
• Melting point data and optical rotation for QC purposes

Shelf Life and Storage

• Store in sealed containers, refrigerated at 2–8 °C
• Protect from light and moisture to maintain stability
• Shelf life generally 1–2 years with proper storage

Application

• Widely used in enzymatic assays to measure β-glucosidase and related glycosidase activities
• Key tool in screening enzyme inhibitors and analyzing enzyme kinetics
• Applied in molecular biology for diagnosing enzyme deficiencies and metabolic disorders
• Supports research in glycobiology, drug development, and biochemical pathway analysis

Key Characteristics

• Nitrophenyl glycoside of β-D-glucopyranose
• CAS number: 3451-94-3
• Molecular weight: 301.25 g/mol
• White crystalline powder, highly pure and chemically stable
• Specific substrate for β-glucosidase with chromogenic detection capabilities
• Provided with comprehensive quality assurance and analytic data
• Supports broad biochemical and pharmaceutical research

Citations

• AnaxLab product details
• PubChem molecular and chemical info
• Sigma-Aldrich analytical data
• PMC studies on enzymatic assays
• MedChemExpress substrate reagents
• Scientific literature on glycosidase assays
• Chemistry Europe glycosylation reviews
• Glentham Life Sciences catalog
• Patent literature for enzyme substrate usage
• Synthose glycoside synthesis