143716-62-5

Basic information

• Product Name: 2',4'-dinitrophenyl 2-deoxy-2-fluorogalactopyranoside
• Synonyms: 2',4'-dinitrophenyl 2-deoxy-2-fluorogalactopyranoside;2,4-Dinitrophenyl 2-Deoxy-2-fluoro-β-D-galactoside;2,4-Dinitrophenyl 2-Deoxy-2-fluoro-
• CAS NO: 143716-62-5
• Molecular Formula: C₁₂H₁₃FN₂O₉
• Molecular Weight: 348.2380232
• Product Categories: Aromatics;Carbohydrates & Derivatives;Aromatics, Carbohydrates & Derivatives
• Mol File: 143716-62-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 168-170°C
• Boiling Point: 615.7°Cat760mmHg
• Flash Point: 326.2°C
• Appearance: /
• Density: 1.69g/cm³
• Storage Temp.: Amber Vial, Refrigerator
• Solubility: Methanol (Slightly)
• CAS DataBase Reference: 2',4'-dinitrophenyl 2-deoxy-2-fluorogalactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2',4'-dinitrophenyl 2-deoxy-2-fluorogalactopyranoside(143716-62-5)
• EPA Substance Registry System: 2',4'-dinitrophenyl 2-deoxy-2-fluorogalactopyranoside(143716-62-5)

Safety Data

• Hazardous Substances Data: 143716-62-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Pale Yellow Solid

Uses

Different sources of media describe the Uses of 143716-62-5 differently. You can refer to the following data:
1. Fluorinated and deoxygenated glycosides as mechanistic probes of Escherichia coli (lacZ) β-galactosidase. By use of the slow substrate 2,4-dinitrophenyl-2-deoxy-2-fluoro-β-D-galactopyranoside, a glycosyl enzyme intermediate has been trapped on the enzyme. Glu-268 was identified as the catalytic nucleophile of human lysosomal β-galactosidase precursor.
2. 2',4'-Dinitrophenyl 2-deoxy-2-fluorogalactopyranoside is fluorinated and deoxygenated glycosides as mechanistic probes of Escherichia coli (lacZ) β-galactosidase. By use of the slow substrate 2,4-dinitrophenyl-2-deoxy-2-fluoro-β-D-galactopyranoside, a glycosyl enzyme intermediate has been trapped on the enzyme.

Upstream product

• 93253-40-8 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-galactopyranosyl bromide 
• 108794-37-2 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-D-galactopyranoside 
• 75414-44-7 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-β-D-galactopyranosyl fluoride 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 207975-84-6 2,4-dinitrophenyl-3,4,6-tri-O-acetyl-2-fluoro-2-deoxy-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.