25775-97-7

Basic information

• Product Name: 2',4'-dinitrophenylglucopyranoside
• Synonyms: 2',4'-dinitrophenylglucopyranoside;2,4-Dinitrophenyl beta-D-glucopyranoside;2,4-Dinitrophenyl D-glucopyranoside
• CAS NO: 25775-97-7
• Molecular Formula: C₁₂H₁₄N₂O₁₀
• Molecular Weight: 346.25
• Mol File: 25775-97-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 646.1°C at 760 mmHg
• Flash Point: 344.5°C
• Appearance: /
• Density: 1.729g/cm³
• Vapor Pressure: 1.42E-17mmHg at 25°C
• Refractive Index: 1.673
• CAS DataBase Reference: 2',4'-dinitrophenylglucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2',4'-dinitrophenylglucopyranoside(25775-97-7)
• EPA Substance Registry System: 2',4'-dinitrophenylglucopyranoside(25775-97-7)

Safety Data

• Hazardous Substances Data: 25775-97-7(Hazardous Substances Data)

Usage

General Description

2',4'-dinitrophenylglucopyranoside is a chemical compound commonly used in biochemical assays to detect the presence of glycosidase enzymes. It is a synthetic substrate that is hydrolyzed by glycosidases, releasing the 2',4'-dinitrophenyl (DNP) moiety. This reaction can be quantitatively measured by spectrophotometry, allowing for the determination of glycosidase activity in biological samples. The compound is also used in the study of carbohydrate metabolism and enzymology, as well as in the development of pharmaceuticals targeting glycosidase enzymes. Additionally, 2',4'-dinitrophenylglucopyranoside is a useful tool for the analysis and purification of glycosidases in research laboratories.

InChI:InChI=1/C12H14N2O10/c15-4-8-9(16)10(17)11(18)12(24-8)23-7-2-1-5(13(19)20)3-6(7)14(21)22/h1-3,8-12,15-18H,4H2/t8-,9-,10+,11-,12?/m1/s1

Upstream product

• 70-34-8 2,4-Dinitrofluorobenzene 
• 13100-46-4 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose 
• 604-69-3 β-D-glucose pentaacetate 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 17042-32-9 1-O-(2,4-dinitrophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 896-80-0 1-benzenesulfonyl-2,4-dinitro-benzene 

Downstream Products

• 5391-17-3 1-O-isopropyl-β-D-glucopyranoside 
• 492-61-5 β-D-glucose 
• 51-28-5 2,4-Dinitrophenol 
• 20379-59-3 D-glucopyranosyl azide 
• 50-99-7 D-glucose 
• 2280-44-6 D-Glucose 
• 565228-16-2 p-nitrophenyl 4-deoxy-4-thio-β-D-cellobioside 
• 2106-10-7 1-deoxy-1-fluoro-α-D-glucose 
• 17042-32-9 1-O-(2,4-dinitrophenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 29074-00-8 2,2,2-Trifluoroethyl β-D-glucopyranoside 
• 29074-00-8 2,2,2-Trifluoroethyl α-D-glucopyranoside 
• 3198-49-0 (2R,3R,4S,5S,6R)-2-Ethoxy-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 3198-49-0 ethyl α-D-glucopyranoside 

Relevant articles and documents

Solvent and α-secondary kinetic isotope effects on β-glucosidase

β-Glucosidase from sweet almond is a retaining, family 1, glycohydrolase. It is known that glycosylation of the enzyme by aryl glucosides occurs with little, if any, acid catalysis. For this reaction both the solvent and α-secondary kinetic isotope effects are 1.0. However, for the deglucosylation reaction (e.g., kcat for 2,4-dinitrophenyl-β-D-glucopyranoside) there is a small solvent deuterium isotope effect of 1.50 (± 0.06) and an α-secondary kinetic isotope effect of 1.12 (± 0.03). For aryl glucosides, kcat/KM is very sensitive to the pKa of the phenol leaving group [βlg - 1; Dale et al., Biochemistry 25 (1986) 2522-2529]. With alkyl glucosides the βlg is smaller (between - 0.2 and - 0.3) but still negative. This, coupled with the small solvent isotope effect on the pH-independent second-order rate constant for the glucosylation of the enzyme with 2,2,2-trifluoroethyl-β-glucoside [D2O(kcat/KM) = 1.23 (± 0.04)] suggests that there is more glycone-aglycone bond fission than aglycone oxygen protonation in the transition state for alkyl glycoside hydrolysis. The kinetics constants for the partitioning (between water and various alcohols) of the glucosyl-enzyme intermediate, coupled with the rate constants for the forward (hydrolysis) reaction provide an estimate of the stability of the glucosyl-enzyme intermediate. This is a relatively stable species with an energy about 2 to 4 kcal/mol higher than that of the ES complex. This article is part of a Special Issue entitled: Enzyme Transition States from Theory and Experiment.

Direct anomeric O-arylation and O-hetarylation of glucose electron deficient aromatic and hetaromatic compounds in aryl and hetaryl glycoside synthesis

Anomeric O-arylation and O-hctarylation of tetra-O-bcnzyl-, tetra-O-acctyl-, and O-unprotected glucose (1a-c) can be directly performed with electron dcficienl aromatic and hctcroaromatic systems having fluoro- (2A-2F) or phenylsulfonyl (3B, 3G-3K), respectively, as leaving groups. The reactions were carried out in DMF as solvent at room temperature with NaH as the base; they led in the products 4 to an exchange of the leaving group by the glucopyranosyloxy moicly; mainly β-products were obtained.