4-Nitrophenyl 2-(acetylamino)-2-deoxy-beta-D-glucopyranoside
[CAS# 3459-18-5]

Identification

• Classification: Biochemical >> Carbohydrate >> Monosaccharide
• Name: 4-Nitrophenyl 2-(acetylamino)-2-deoxy-beta-D-glucopyranoside
• Synonyms: N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]acetamide
• Molecular Formula: C₁₄H₁₈N₂O₈
• Molecular Weight: 342.30
• CAS Registry Number: 3459-18-5
• EC Number: 222-398-7
• SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=CC=C(C=C2)[N+](=O)[O-])CO)O)O

Properties

• Solubility: Slightly soluble (7.9 g/L) (25 °C), Calc.^*
• Density: 1.51±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 214 °C (methanol )^**
• Boiling point: 694.7±55.0 °C 760 mmHg (Calc.)^*
• Flash point: 374.0±31.5 °C (Calc.)^*
• Index of refraction: 1.62 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

^** Westphal, Otto

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

4-Nitrophenyl 2-(acetylamino)-2-deoxy-beta-D-glucopyranoside is a synthetic glycoside derivative widely used as a chromogenic substrate in enzymology and biochemical research. It consists of a beta-D-glucopyranoside moiety linked to a 4-nitrophenyl group through a glycosidic bond, with an acetylated amino group at the C-2 position of the sugar. The acetylamino substitution mimics the natural structure of N-acetylglucosamine, an important component of bacterial cell walls and glycoproteins.

This compound was developed to provide a convenient and sensitive tool for detecting and measuring the activity of enzymes such as N-acetyl-beta-D-glucosaminidases. These enzymes catalyze the hydrolysis of the glycosidic bond, releasing 4-nitrophenol, which can be quantified spectrophotometrically due to its strong absorbance at 405 nm under alkaline conditions. The chromogenic property allows rapid and straightforward monitoring of enzymatic reactions in solution.

4-Nitrophenyl 2-(acetylamino)-2-deoxy-beta-D-glucopyranoside has become essential in studies of bacterial cell wall remodeling, lysosomal storage diseases, and the characterization of glycoside hydrolases. It serves as a model substrate in screening for enzyme inhibitors, enzyme kinetics, and enzyme purification protocols. The compound's stability and well-defined chemical structure contribute to its reproducibility and reliability in experimental assays.

Beyond enzymology, this glycoside derivative is used in analytical chemistry and pharmaceutical research to evaluate the specificity and efficacy of potential therapeutic agents targeting glycosidases. Its synthetic accessibility and cost-effectiveness further support its widespread application in both academic and industrial laboratories.

The compound’s design aligns with the structural requirements for recognition by enzymes that process N-acetylglucosamine residues, enabling detailed investigation into enzyme-substrate interactions and catalytic mechanisms. These insights have broad implications for understanding biological processes such as bacterial pathogenicity, cellular degradation pathways, and glycobiology.

In summary, 4-nitrophenyl 2-(acetylamino)-2-deoxy-beta-D-glucopyranoside is a vital biochemical reagent developed to facilitate the study of specific glycosidase enzymes. Its chromogenic nature enables convenient detection of enzymatic activity, supporting research in microbiology, medicine, and biochemistry with implications for diagnostics and drug discovery.

References

1997. Enzymatic syntheses of GlcNAc beta 1-2Man and Gal beta 1-4GlcNAc beta 1-2Man as components of complex type sugar chains. Glycoconjugate Journal, 14(1).
DOI: 10.1023/a:1018565032297

2009. Inactivation Kinetics of β-N-Acetyl-D-glucosaminidase from Green Crab (Scylla serrata) in Dioxane Solution. Journal of Biomolecular Structure and Dynamics, 26(4).
DOI: 10.1080/07391102.2009.10507266

2018. Twofold enhanced dispersin B activity by N-terminal fusion to silver-binding peptide for biofilm eradication. International Journal of Biological Macromolecules, 118(Pt A).
DOI: 10.1016/j.ijbiomac.2018.06.066