25775-99-9

Basic information

• Product Name: 2,4-Dinitrophenyl β-D-Galactoside Tetraacetate
• Synonyms: 2,4-Dinitrophenyl β-D-Galactoside Tetraacetate;2,4-Dinitrophenyl β-D-Galactoside 2,3,4,6-Tetraacetate
• CAS NO: 25775-99-9
• Molecular Formula: C₂₀H₂₂N₂O₁₄
• Molecular Weight: 514.39368
• Product Categories: Aromatics;Carbohydrates & Derivatives;Aromatics, Carbohydrates & Derivatives
• Mol File: 25775-99-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 610.0±55.0 °C(Predicted)
• Appearance: /
• Density: 1.47±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 2,4-Dinitrophenyl β-D-Galactoside Tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dinitrophenyl β-D-Galactoside Tetraacetate(25775-99-9)
• EPA Substance Registry System: 2,4-Dinitrophenyl β-D-Galactoside Tetraacetate(25775-99-9)

Safety Data

• Hazardous Substances Data: 25775-99-9(Hazardous Substances Data)

Usage

Description

2,4-Dinitrophenyl β-D-Galactoside Tetraacetate is a synthetic compound that is commonly utilized in the field of biochemistry and molecular biology. It is a derivative of β-D-galactoside, with a 2,4-dinitrophenyl group and four acetate groups attached to it. 2,4-Dinitrophenyl β-D-Galactoside Tetraacetate is particularly useful for studying enzyme activity and mechanisms, as it can serve as a substrate for various glycosidases.

Uses

Used in Biochemical Research:
2,4-Dinitrophenyl β-D-Galactoside Tetraacetate is used as a substrate for studying the mechanism of spontaneous β-glycoside hydrolysis. The compound is particularly useful in investigating the activity of glycosidases, which are enzymes that catalyze the hydrolysis of glycosidic bonds in carbohydrates. By using this compound, researchers can gain insights into the catalytic mechanisms of these enzymes and their role in various biological processes.
Used in Enzyme Assays:
In the field of enzyme kinetics, 2,4-Dinitrophenyl β-D-Galactoside Tetraacetate is employed as a colorimetric substrate for the quantitative measurement of glycosidase activity. The release of the 2,4-dinitrophenol group upon enzymatic hydrolysis results in a colorimetric change, allowing for the determination of enzyme activity and the study of enzyme kinetics.
Used in Drug Development:
2,4-Dinitrophenyl β-D-Galactoside Tetraacetate can also be used in the development of new drugs targeting glycosidase enzymes. By understanding the interactions between this compound and the enzymes, researchers can design inhibitors or activators that modulate enzyme activity, potentially leading to the development of therapeutic agents for various diseases.
Used in Analytical Chemistry:
In analytical chemistry, 2,4-Dinitrophenyl β-D-Galactoside Tetraacetate can be employed as a reference compound for the calibration of instruments used in the analysis of carbohydrates and related compounds. Its well-defined structure and properties make it a suitable standard for validating analytical methods and ensuring accurate measurements.
Used in Material Science:
Although not directly mentioned in the provided materials, 2,4-Dinitrophenyl β-D-Galactoside Tetraacetate could potentially be used in the development of novel materials with specific properties, such as those with enhanced stability or selectivity in chemical reactions. Its unique structure and functional groups may allow for the creation of new materials with applications in various industries, including pharmaceuticals, agriculture, and environmental science.

Upstream product

• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 51-28-5 2,4-Dinitrophenol 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 25878-60-8 D-galactose pentaacetate 
• 4163-60-4 β-D-galactose peracetate 

Downstream Products

• 25775-96-6 1-(2,4-dinitrophenyl)-β-D-galactopyranoside 

Relevant articles and documents

The role of sugar substituents in glycoside hydrolysis

A series of monosubstituted deoxy and deoxyfluoro 2,4-dinitrophenyl (DNP) β-D-glycopyranosides was synthesized and used to probe the mechanism of spontaneous β-glycoside hydrolysis. Their relative rates of hydrolysis followed the order 2-deoxy > 4-deoxy > 3-deoxy ? 6-deoxy > parent > 6-deoxy- 6-fluoro > 3-deoxy-3-fluoro > 4-deoxy-4-fluoro > 2-deoxy-2-fluoro. Hammett correlations of the pH-independent hydrolysis rates of each of the 6-, 4-, 3- , and 2-position substituted glycosides with the σ1 value for the sugar ring substituent were linear (r = 0.95 to 0.999, π(I) = -2.2 to -10.7), consistent with hydrolysis rates being largely dictated by field effects on an electron-deficient transition state. The relative rates of hydrolysis of the DNP glucosides can be rationalized on the basis of the stabilities of the oxocarbenium ion-like transition states, as predicted by the Kirkwood- Westheimer model. The primary determinant of the rate of hydrolysis within a series appears to be the field effect of the ring substituent on O5, the principal center of charge development at the transition state. Differences in the rates of hydrolysis between different series of hexopyranosides may not arise solely from field effects and likely also reflect differences in steric factors or solvation.

PHASE-TRANSFER-CATALYZED SYNTHESIS OF 2,3,4,6-TETRA-O-ACETYL-β-D-GALACTOPYRANOSIDE

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The effect of methanol and dioxan on the rates of the beta-galactosidase-catalysed hydrolyses of some beta-D-galactrophyranosides: rate-limiting degalactosylation. The ph-dependence of galactosylation and degalactosylation.

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